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81 Results   |  

Excellent 5/5 

24 Photos

Florida / Florida Keys

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

7 Nights min stay

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from £77 / night

£539 - £894 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
ocean views beaches fishing heated outdoor swimming pool private beach tennis courts large balcony fully equipped apartment and kitchen WiFi secure location undercover car parking space gym boat slip new televisions. lettings of a month (or thereabouts) or more availabl  …see more


5 Jan 2015

5/5

"A Beautiful Place"

This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and sunrise. The owner of the … More

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Excellent 5/5 

23 Photos

Florida Keys / Islamorada

House / 2 Bedrooms / sleeps 6

Excellent 5/5 

28 Nights min stay

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Pricing unknown

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offe  …see more


13 Aug 2014

5/5

"Fishing Vacation"

Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.… More

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Very Good 4/5 

24 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 8

Very Good 4/5 

30 Nights min stay

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from £208 / night

£1455 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury house 10 minutes from Duval Street, pool, dock, pool bar, hot tub. Home owner association tennis courts and private beach on exclusive gated community island.  …see more


30 Jul 2015

4/5

"Enjoyable holiday on the Keys"

I stayed on Shark Key with my Mum, aged 82, husband and niece. We had an enjoyable stay using both the pool area, the lagoon and the kayaks. Firstly the house, the kitchen had a lot of equipment… More

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Featured properties

24 Photos

Florida Keys / Key Largo

House / 4 Bedrooms / sleeps 10

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: 1 MONTH Exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. Open concept living area on the middle level of the home offers a formal dining with 8 chairs and 3 bar stools at the kitchen c  …see more

Excellent 5/5 

26 Photos

Florida Keys / Key West

House / 2 Bedrooms / sleeps 6

Excellent 5/5 

29 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
CAYO HUESO SUNSHINE: 2-bedroom, den, 3-bath home. Secluded location near Smathers Beach. Kitchen island countertop is a perfect spot for casual meals. Glass doors open to a private yard, outside dining and your own pool. Upstairs bedrooms feature king size beds wit  …see more


3 Aug 2014

5/5

"Perfect Home for Key West"

This place has all the amenities you need! It was our first time renting a home and it couldn't have been more perfect! Quiet neighborhood, but not too far from the action of Duval.… More

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Very Good 4/5 

25 Photos

Key Largo / Tavernier

House / 4 Bedrooms / sleeps 10

Very Good 4/5 

27 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: 29 DAYS NEW RENTAL OPPORTUNITY! This magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable and extremely inviting living environment. This  …see more


26 Dec 2014

4/5

"Great property but poor experience with realtor"

We rented for the month of November with 9 people in our party. The property and home are beautiful but we unfortunately did not have a very good experience withKeys Holiday rental department. One of … More

As in most cases there are two sides to this story as well. We are truly sorry that this guest feels that they have been so inconvenienced that they have chosen to publish their frustration and attempt to destroy our reputation – one we have spent years building. They have the distinct privilege of being the first and only guest out of the 100’s of guests we have served over the past 9 years to write such a scathing review. For this reason I feel that it is necessary to let readers “hear” the other side of the story. Two weeks prior to their arrival we were notified by the owners that the davits had been inspected and were told that they were no longer safe. Because the owners are planning to install a boat lift they chose to have the davits promptly removed to prevent any accidental use of them. They put three large “bumpers” at the dock to prevent any potential damage to a boat tied up at the dock. The also installed a ladder at the dock for easy access on and off a boat. We notified the guest of the change. They were not pleased with this turn of events but accepted the bumpers and moved forward with their reservation. The guests stored their boat in a nearby marina when they were away from the property for a week or so. We paid the fee for the storing their boat at the marina - $443.98. The guest is correct when they said that there were two broken lounge chairs. These lounge chairs had been removed from the pool area and placed out of the way away along the side of the storage shed by the owner because they were broken. The guest failed to mention that the owners had two very high end wooden lounge chairs with 4” mattresses brought down from the master suite balcony for use by the pool. They also failed to mention that there is a large round table by the pool area and 10 Adirondack plastic chairs stacked in this area for guest use. Also during their stay they failed to mention that somehow a living room side table was damaged and a one end of a pair of mermaid bookends went missing. The books were restacked so that it was not readily obvious that the bookend was missing. The owners noticed it immediately upon their return. The guest did not mention either of these items to us before they departed and when we called to ask if they knew anything about these things they were offended. Later they called back to say that one of the children had accidentally broken the book end. Why was this accident not reported to us when it occurred? The owner provided us with receipts for replacement of the damaged items and the accidental damage Insurance covered the cost - $201.21. The $50 charge deducted from the guests’ security deposit was for the additional cleaning required by the cleaning service because of the condition the home was left in upon their departure. They failed to mention that they left the house with a broken tile on the access panel to the whirlpool tub (not sure why it was removed at all); smelly trash; food stains on the ping pong table; a torn sheet; and a ton of laundry. Accidental damage insurance does not cover excess cleaning charges. We invite you to view our other properties listed on FlipKey and read the reviews left by our other previous guests. You can also visit our website, KeysHolidayRentals.com. All the reviews are very positive and many mention how everyone at Keys Holiday Rentals goes out of our way to accommodate guests’ needs. There was no pleasing this guest. We wish them well in future house rentals. Keys Holiday Rentals

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Very Good 4.5/5 

14 Photos

Florida Keys / Key Largo

Condo / 2 Bedrooms / sleeps 7

Very Good 4.5/5 

Min stay varies

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Pricing unknown

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
A view of the pool off your patio and the Florida Bay sunset glows at your front door. Tropical breezes and gardens grace the gated condo community. Only a one hour drive from the airport, you have all the comforts of home with the convenience of Keys activities nearby.  …see more


2 Jun 2015

5/5

"Great place to explore the keys"

My wife and I recently rented from Mr. Stallard. We had a great trip and everything about the condo was perfect. Had a great screened-in porch. The pool area was beautiful. Wi-fi all over the grou… More


10 Aug 2014

5/5

"perfect"

had a great time in key largo, the condo was great, had everything you need as a home from home, good sized rooms ,great working air con, all mod cons you need, very clean, plenty of towels for house … More


15 Apr 2013

5/5

"Just perfect"

We have had a wonderful holiday in Moon Bay. Condo was larger than we were expecting. Both bedrooms large and clean. Lovely patio to sit out on. The complex itself had everythine we could need and… More

So pleased you had a great time have owned apartment (condo)fore 25 years still the Best place to explore the everglades Miami and the Keys all the best Mr A P Stallard

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24 Photos

Key Largo / Tavernier

House / 3 Bedrooms / sleeps 6

28 Nights min stay

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Pricing unknown

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: 30 DAYS NEW HOME (2013) Spend the fall or winter in the Florida Keys! You will love this wonderful 2013 built stilt home. Features include an open living area with gourmet kitchen, stainless steel appliances, including a wine refrigerator and granite  …see more

16 Photos

Florida Keys / Islamorada

House / 3 Bedrooms / sleeps 7

27 Nights min stay

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Pricing unknown

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunr  …see more

Excellent 5/5 

15 Photos

Florida Keys / Islamorada

Apartment / 1 Bedroom / sleeps 4

Excellent 5/5 

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and  …see more


15 Apr 2014

5/5

"Paradise on the ocean"

We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay … More

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Excellent 5/5 

18 Photos

Florida Keys / Key Largo

Apartment / 3 Bedrooms / sleeps 6

Excellent 5/5 

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Exceptional 3 story townhouse located in a quiet oceanfront complex with heated pool and marina. Inspiring ocean views from two balconies and a ground level patio to BBQ. Protected marina and deeded boat slip easily accommodates a boat up t  …see more


18 Dec 2014

5/5

"Perfect Stay"

This place is a perfect place to check in for a stay in the Keys for. Dock with easy access to the channel for a day of fishing or diving. Easy clean up. Nice pool to take a break in. Views are sp… More


27 Jul 2013

5/5

"Private gated condos with boat parking, pool and tennis court"

This condo was spacious, well maintained and included a host of community amenities. There was a pool, tennis and basketball court. It was centrally located to Key Largo, but far enough off the path… More

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27 Photos

Key Largo / Tavernier

House / 2 Bedrooms / sleeps 4

28 Nights min stay

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Pricing unknown

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
Minimum Stay 1 Month. "Beba's Reef House" will capture your imagination the moment you enter the home and rise to the main living level through the reef painted on the walls of the stair well and the photos of fish captured by the owner during numerous dives here in the  …see more

19 Photos

Florida Keys / Long Key

House / 3 Bedrooms / sleeps 7

28 Nights min stay

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Pricing unknown

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY 1 MONTH - You and your entire family will love this serene, quaint part of paradise, in this ultra-charming BEACH HOUSE just footsteps from the SEA. Come and stay in this adorable home located on the crystal clear Atlantic Ocean! The home has plenty of room  …see more

Excellent 5/5 

31 Photos

Florida Keys / Islamorada

Villa / 2 Bedrooms / sleeps 6

Excellent 5/5 

7 Nights min stay

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from £234 / night

£1634 / week

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 7 Nights Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the we  …see more


13 Jan 2015

5/5

"Classic Islamorada - Amazing Property"

Little Bay was a perfect property for us! The setting is idyllic and classic keys - Huge backyard on the Bay with excellent dock area, hammocks and view of the bay. Covered porch was the full width … More


2 Jul 2013

5/5

"I just love it here"

We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area by the water is so nice… More


5 Nov 2012

5/5

"Iguanas, sunshine and the sea in your backyard......."

We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach! The apartment couldn't ha… More

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Excellent 5/5 

23 Photos

Florida Keys / Islamorada

House / 3 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

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Pricing unknown

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Key info:

  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florid  …see more


23 Jan 2013

5/5

"My Paradise from architect's perspective"

My wife and I spend a month at My Paradise and, as an architect, there are certain aspects that bear mention. First, if the weather is mild, you can open the wall of folding glass doors and unite the … More

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Excellent 5/5 

21 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

27 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as  …see more


13 Feb 2015

5/5

"Wow, what a beautiful view"

This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the mas… More

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Excellent 5/5 

24 Photos

Florida Keys / Islamorada

House / 3 Bedrooms / sleeps 8

Excellent 5/5 

27 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost e  …see more


15 Jul 2013

5/5

"Blue Water = Everything that you want"

This place delivers. You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of … More

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Very Good 4.5/5 

24 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

7 Nights min stay

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from £117 / night

£817 - £1174 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the mari  …see more


2 Apr 2014

5/5

"Absolutely Beautiful and convenient for boaters!"

Our family stayed here for a week in late March. We had plenty of room and everything we needed was available. This is a gorgeous condo overlooking the Florida Bay. You get to see an awesome sunset ev… More


24 Mar 2014

5/5

"Fantastic Vacation!"

My family of 5 stayed here for 8 days during early March. Hands down... this is a show up and start relaxing type of rental. The only, and I mean only, thing that was missing from this place was a co… More


1 Jun 2014

4/5

"Fabulous location in the Florida Keys."

Having stayed in other properties at Futura Yacht Club over the years, I can honestly say that this was by far the nicest. The kitchen had been recently renovated with new white goods, and the whole p… More

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32 Photos

Key Largo / Tavernier

House / 4 Bedrooms / sleeps 10

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: 29 DAYS Sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing in the patio and yard area! The patio is spacious  …see more

14 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

29 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Comfortably furnished and ready for you. Conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters, or watch the spectacul  …see more

25 Photos

Florida Keys / Islamorada

House / 2 Bedrooms / sleeps 5

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: 29 DAYS Exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitche  …see more

25 Photos

Florida Keys / Key Largo

House / 4 Bedrooms / sleeps 12

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Enjoy your stay in this gorgeous single family home. You’ll love the convenient location in the Ocean Shores area of Key Largo. There’s easy ocean access from this 90' concrete dock. Water, electricity, fish cleaning station and gas b  …see more

18 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

29 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit provides spectacular ocean views. It is one of the few units that offer spiral stairs to the groun  …see more

20 Photos

Florida Keys / Key Largo

Villa / 3 Bedrooms / sleeps 8

7 Nights min stay

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from £164 / night

£1144 - £1323 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 7 Night Minimum Villa Bella is a fabulous 3 BR/3 BA two-story townhouse. This end unit townhome "lives" on the 2nd floor. The kitchen, dining and living areas are all open to each other in a great room with a gorgeous vaulted ceiling. There are 2 bedr  …see more

18 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panor  …see more

20 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

27 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yours  …see more

15 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

27 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Description….. MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite condo complexes. This unit was recently sold and the new owners are beginning to update some of the décor. You'll love the fantastic panoramic ocean view  …see more

20 Photos

Florida Keys / Islamorada

House / 4 Bedrooms / sleeps 10

28 Nights min stay

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Pricing unknown

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) You'll love watching the fabulous sunsets over the tranquil waters in this semi-private lagoon setting. This is a three story single family home and offers two balconies overlooking the water and dock area. There's room to dock one  …see more

16 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 6

27 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be  …see more

14 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from t  …see more

17 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamo  …see more

24 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

29 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month New on the rental market. This is your opportunity to secure your winter getaway at a luxurious oceanfront condo in one of Islamorada's most prestigious condominium communities. Ocean front dockage is available for boats up to 28' in length (s  …see more

26 Photos

Florida Keys / Islamorada

House / 3 Bedrooms / sleeps 4

27 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY 29 DAYS. BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This home was completely remodeled in 2013. There is 936 square feet of living area on the main level with 2 bedrooms, a full bath and an ope  …see more

21 Photos

Florida Keys / Islamorada

Apartment / 3 Bedrooms / sleeps 6

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings creat  …see more

26 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 6

28 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable livi  …see more

Very Good 4.5/5 

27 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

3 Nights min stay

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from £127 / night

£883 - £2023 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
DUVAL BREEZE: 2 bedroom 2.5 bath townhome in Duval Square. 1st floor offers an open floor plan with a well stocked kitchen, spacious living room, dining room, half bath and French doors to your own private balcony. 2nd floor has 2 bedrooms with bath ensuite. Master b  …see more


19 Nov 2008

5/5

"Perfect Location"

Great location on Duval. Owners are very accomodating. Really does feel like home. Would def. stay there again… More


18 Jul 2015

5/5

"Duval Breeze - Great Place"

Great location ! Within easy walking distance of everything on Duval. Parking space available. Safe & secure. Nice, well furnished unit. Very satisfied. … More


23 Jul 2014

5/5

"Great Property!"

The property was neat and clean with great amenities! The owners are considerate and left beach chairs and a fully appointed kitchen! Our family loved the central Old Town location and appreciated t… More

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Very Good 4.5/5 

32 Photos

Florida Keys / Key West

Apartment / 3 Bedrooms / sleeps 6

Very Good 4.5/5 

5 Nights min stay

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from £187 / night

£1308 - £3317 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
KEY WEST CASA: One of only a few 3 bedroom 2 bath condos in the Shipyard complex in Truman Annex. Enter the fully stocked kitchen to the living room to the French doors that open onto the back porch. The downstairs bedroom is just to your left and offers 2 twin beds  …see more


8 Aug 2012

5/5

"Another great stay at Key West Casa"

This is the second time that I've rented this house with a group of friends through at Home Key West. Friendly staff makes reservations and check-in very easy. Six adults can stay comfortably here. Th… More


21 Jun 2012

5/5

"Key West Casa"

I am giving a 5 star rating because overall our experience was excellent however; it was not without minor incidents. The condo is very nice and well appointed, very clean and comfortable and we would… More


8 Sep 2011

5/5

"Perfect location and all the amenities"

We recently stayed at this beautiful condo and were very pleased with everything. The location was within walking distance of all that we required - - Groceries, Restaurants, etc. etc. The rooms wer… More

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Excellent 5/5 

25 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

5 Nights min stay

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from £131 / night

£916 - £1967 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
SHIPYARD TREASURE: 2 bedroom 1 bath Shipyard condo has it all. Located in Truman Annex, there is a shared pool, off street parking and 24 hour security. Shipyard Treasure is a 2nd floor condo with private full-length balconies front and rear. This property has an  …see more


11 Feb 2012

5/5

"Great Location, Gorgeous Condo, Great Experience"

Stayed at this true Shipyard Treasure for 9 nights in January 2012. This condo was perfectly located nearby to Duval Street and all it's fun, Fort Zachary Beach which never fails to be peaceful, and … More


11 Jan 2012

5/5

"Perfect New Year's Trip"

The home was great--even bigger than the pictures made it look, with two huge balconies facing either side of the building. The beds were comfortable, the living room spacious, and a few extra New Ye… More


10 Nov 2011

5/5

"Key West for my Birthday"

This was one of the best vacations (other than being on a cruise)that I have ever had. The condo was located within walking distance of 99% of the activities we chose to do. Although we knew there wer… More

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Very Good 4.5/5 

25 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

3 Nights min stay

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from £169 / night

£1177 - £2125 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View condo. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated for your comfort and relaxation. Located on the Atlantic Ocean with views from the living room and  …see more


2 Apr 2014

5/5

"Great place - exactly as described - with one of the best pools"

This was a really great place...it's walkable to the beach, with a fantastic pool. The unit was nice...all tile floors, so bring slippers or extra socks. Very spacious with a great balcony. Be read… More

Thank you for taking the time to review our home. It's always great to know our guests have enjoyed the home and Key West itself. Regarding towels, we supply two of each type towel (washcloth, hand towel, bath towel) for 6 people (max accommodation for this condo) which means there should have been 2 extra sets of them for your group of 4. If that was not the case, a quick call to our office would have remedied that situation. Next time you visit please contact us with any inconveniences; we can usually take care of it immediately so your full attention can be on enjoying your stay.


24 Aug 2015

5/5

"Had A Blast!"

Very convenient and very clean. Only complaint was that the pool closed too early. Otherwise, a very enjoyable relaxing stay.… More


2 Aug 2012

5/5

"Nice apartment with ocean view."

Very nice apartment, with two large bedrooms, and balcony with ocean view. One bed can be moved into the living-room if necessary. Very nice, large swimming pool in a beautiful garden. Although the be… More

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Very Good 4.5/5 

30 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 5

Very Good 4.5/5 

5 Nights min stay

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from £134 / night

£932 - £2118 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
LINGER LONGER: 2 bedroom 1.5 bath townhome in Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on the 2nd floor. Downstairs is an open floor plan with kitchen/dining/living roo  …see more


24 Jul 2014

5/5

"Awesome!"

Great accommodations! My family had a great week here! Right by the pool and the condo had everything you need. Can't wait to stay here again!… More


16 Aug 2015

5/5

"Clean and well provisioned"

Townhouse was centrally located, clean, and all basic household goods (paper towels, laundry detergent etc.) were there to meet our needs for the week. I would definitely recommend this unit. … More


13 Jul 2011

5/5

"descriebe the service you received"

we had a wonderful time like every year there. :-) we are always happy to come back . :-)… More

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Excellent 5/5 

24 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

5 Nights min stay

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from £134 / night

£932 - £2118 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
BAHAMIAN REED: 2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West. Conveniently located near all the reasons you came to Key West: Fort Zachary Taylor State Park , Duval Street shops, galleries, bars and restaurants, and Sunset Celebrat  …see more


6 Nov 2008

5/5

"Absolutely Fantastic -"

Thanks to At Home in Key West we found the perfect location for the 1st Girls Get Away! Everything about this place was great..we really enjoyed the back area patio and cooked out 3 of the nights! Pl… More


13 Jul 2015

5/5

"So relaxing!"

Great location! Within a few minutes, you are at Duvall, Mile Marker 0 and Mallory Square! A little bit further is Ft Zack St Park. It was me, my husband and our two children. It was a great space t… More


27 May 2015

5/5

"Great Girlie Getaway!"

Perfect location and space for friends to gather for a great getaway! Three beds so we all had our own. The Truman Annex location couldn't be better for all things Key West. Delighted with our acco… More

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Very Good 4.5/5 

25 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 4

Very Good 4.5/5 

5 Nights min stay

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from £148 / night

£1030 - £2038 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of Old Town. 2-bedroom 2-bath townhome remodeled from top to bottom. Decorated with Key West flair, this is truly a unique  …see more


1 Aug 2014

5/5

"Nicely Updated and Well Maintained"

My wife and I stayed here in July 14. Windward Park is a small (13 units) gated townhome community convenient to Duvall street, but away from the traffic and noise. Unit has been nicely updated and … More


23 Jan 2014

5/5

"Great relaxing Getaway"

We have rented in the Windward Park before, but this unit was the nicest unit by far. Recently updated and remodeled. Completely supplied with anything you will need.… More


26 Dec 2013

5/5

"Perfect!!!"

My wife, youngest daughter and I spent 8 days at the Leeward Isle unit of Windward Park on Truman ave.in Key West just before Christmas in 2013. Since we vacation several times a year, we have experie… More

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Very Good 4.5/5 

27 Photos

Florida Keys / Key West

Apartment / 3 Bedrooms / sleeps 6

Very Good 4.5/5 

5 Nights min stay

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from £171 / night

£1193 - £2043 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
ALLURING PORCHES – This 2 bedroom 3 bath townhome with den in Truman Annex is the tranquil escape you’ve been looking for. 50% larger than similar homes in the area. First level is the kitchen with all you need, dining room, oversized living room with high-end ele  …see more


24 Aug 2013

5/5

"Great family house"

Spentba week there. Lots of private nooks and crannies. Beautiful and plant lined porches. Great location very clean. Small kitchen. But lots of great restaurants within walkin distance.… More


22 Aug 2013

5/5

"Awesome Experience"

Alluring porches is a beautiful home tucked away in the Truman annex. We had 3 couples staying in the home and the luxury of having 3 full bathrooms was wonderful!!! We all felt as though we had our… More


5 Jul 2013

5/5

"It was great!"

Alluring porches was just like home. It had everything you needed and more. The pool was well taken care of and we used it everyday. At Home in Key West and their employees were very nice to deal wi… More

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Excellent 5/5 

26 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

5 Nights min stay

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from £148 / night

£1030 - £2038 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
ISLAND WIND: 2 bedroom, 2 bath Bahamian-style townhome, with tin roof and white spindled decks. Snuggle into an oh-so-comfy king bed in the Master bedroom upstairs; bathroom is ensuite. Guest bedroom downstairs with 2 twin beds; bathroom ensuite with entrance from t  …see more


7 Oct 2014

5/5

"A great place in Key West"

Everything was great except there was no water in the jacuzzi. But, it was very hot out in late September so the jacuzzi wasn't too inviting anyway. Otherwise, it was a great place and the pool was … More


26 Jul 2013

5/5

"Wonderful"

We had a wonderful time. The place was beautiful, clean, and had all the amenities of home. All we really had to do was buy our food. If we were to stay long term this would be the place. I would reco… More


13 Sep 2012

5/5

"Amazing!"

We stayed in the Island Wind from July 30 - Aug 6 2012. Your townhome is beautiful, with all the amenities anyone could ask for! Our original flight home was delayed (due to weather) and we were extre… More

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Very Good 4.5/5 

26 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 4

Very Good 4.5/5 

5 Nights min stay

Add to shortlist

from £148 / night

£1030 - £2038 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dining area with an open kitchen. A separate private deck just off the dining area complete with BBQ grill and laundry closet.  …see more


18 Jun 2015

5/5

"Great Location and Property"

We were thoroughly pleased with the property. It was exactly as described and pictured. It is close to Duval for everything but secluded enough for quiet relaxation by the pool. And it was well equ… More


14 May 2015

5/5

"Great location!"

Very easy to rent. Beautiful. Pool well kept. Clean. 1 1/2 blocks from Duval and Truman trolley. Plenty of space. Would recommend and would stay there again.… More


14 Jul 2014

5/5

"This property is clean, convenient and safe."

my grown daughter and i visited Key West for some R & R time together. i traveled from Chevy Chase, MD and she from San Francisco. we were not a bit disappointed in our accommodations. my daughter … More

Thank you for taking the time to review our home. We appreciate all the lovely things you said about our home. The mattresses are less than one year old; thankfully it feeling too soft did not impact your visit overall. We look forward to your return!

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Very Good 4.5/5 

25 Photos

Florida Keys / Key West

House / 1 Bedroom / sleeps 4

Very Good 4.5/5 

3 Nights min stay

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from £115 / night

£801 - £1682 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
TRANQUILITY - Charming cottage full of color and creativity.Cozy furnishings in the living area, bright and open kitchen. A half bath and sleeper sofa on the main level allow the extra space for 2 guests to enjoy their own privacy. Upstairs you will find a loft style ma  …see more


1 Aug 2013

5/5

"We'll be back!"

When we arrived, we found the place to be completely adorable, easy to find and within reasonable distance to every location we expected to visit. The staff was amazing and helped us in so many ways. … More


10 Nov 2012

5/5

"Great Fantasy Fest Home Base!"

The unit was great! We were there 7 days and it was perfect place to call home during Fantasy Fest. 2 blocks to Duvall and you were in the midst of it all. The unit was beautiful inside and out. A gr… More


11 Oct 2012

5/5

"Tranquility is everything the name suggests. And more... :)"

As a former resident of Key West, I am very picky about the places I stay and have high expectations as I know the true gems that exists on the island. Without a doubt, Tranquility tops my list. The… More

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Very Good 4/5 

24 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 5

Very Good 4/5 

5 Nights min stay

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from £178 / night

£1242 - £2465 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
TRUMAN'S HIDEAWAY: Lovely condo in the exclusive Harbour Place condominium complex in Truman Annex. Spacious living/dining room area, fully equipped kitchen, Master bedroom with king bed, guest bedroom with 2 twins, private deck offering sun and shade, and the most s  …see more


30 Aug 2014

5/5

"Great condo - great location"

We had a wonderful 5 nights at Truman Annex. At Home in Key West made sure the rental was ready and made everything very easy for us. The condo was clean and spacious, well-situated to the pool and th… More


7 Jul 2014

5/5

"Great place and Amazing location"

My wife and I had a wonderful stay in 'Truman's Hideaway'. The location of this condo is ideal, walking distance from everywhere we wanted to go during our 5-day stay in Key West. Because of the loc… More


29 May 2013

5/5

"Our Week at Truman's Hideaway"

We were very pleased with the condo we rented for our stay in Key West. It was convenient, spacious, clean, quiet, lovely, and we will ask for that unit again. We loved sitting out on the patio afte… More

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Very Good 4/5 

24 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Very Good 4/5 

3 Nights min stay

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from £124 / night

£867 - £1597 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
BRISA DEL MAR - 2 bedroom, 2 bath condo located oceanfront with a direct view of Atlantic Ocean. Fully equipped kitchen, dining area, and living room that opens to a private balcony with unlimited ocean views. Master bedroom has a full bathroom ensuite and entry to a pr  …see more


8 Jan 2014

5/5

"Amazing"

The condo at Barisa was perfect, lots of space and breath taking views every day. Everything you could possibly need was right there. Not far from old town and all the beaches were easy to get to.the … More


4 Jul 2012

5/5

"Awesome!"

Our recent stay was wonderful-the apartment was even nicer then described-the pool was beautiful-exceptionally clean apartment and environment-the view of the atlantic Ocean from the balcony was well … More


4 Apr 2010

5/5

"Beach Front Paradise!"

We brought our three kids and could not have had a more relaxing week of vacation. This property was located in an ideal location for lounging on the beach and listening to the waves roll in while din… More

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Good 3.5/5 

31 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 4

Good 3.5/5 

5 Nights min stay

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from £134 / night

£932 - £2118 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. An ideal location only 2 blocks from famous Duval Street and the attractions of historic Old Town Key West. You can walk or bike to restaurants, nightlife, en  …see more


7 Dec 2014

5/5

"Great location."

We really enjoyed the condo. It was clean and well kept. It was close to everything in Key West. We had a great time. I would recommend this to anyone. I felt right at home, very comfortable.… More


24 Apr 2014

5/5

"Great vacation place!"

Our stay at the Hemingway House was great! The house was neat and clean, the beds were comfortable and the pool was nice and only a few steps away. We liked that we were only 2 blocks from Duval Stree… More


8 May 2013

5/5

"Wonderful!"

This was a lovely property! Small but cozy and with all the amenities we would want. Great porches outside bedrooms. Gas grill on patio was a plus. Steps away from the pool. Much nicer and cheape… More

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Very Good 4/5 

26 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Very Good 4/5 

5 Nights min stay

Add to shortlist

from £145 / night

£1014 - £2142 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
CROWNER'S JEWEL: Delightful 2 bedroom 2.5 bath Conch-style townhome in the quiet gated community of Truman Annex, surrounded by historic buildings and tropical flora; only a short walk to Duval Street.Master bedroom has small bath ensuite and private balcony (note: bo  …see more


10 Apr 2014

5/5

"Everything I expected and some additional pleasent surprises!"

Immaculate condo with every amenity you will need including beach equipment! Nearby parking made it very convenient with 1/4 mile walk or drive to Fort Zaccary State Park beach and picnic area! Two s… More


17 Feb 2014

5/5

"Fabulous"

What A wonderful place to stay at while vacationing in Key West. Location is one block from Duval Street and very convenient to the beaches. Nestled and cozy in beautiful lush tropical vegetation. Ki… More


12 Dec 2013

5/5

"porter lane"

Place was great, close to ask attractions and you could walk everywhere! Very neat and clean, equipped with anything you'd need! A great choice for us and we have been there yearly for a few yearly s… More

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