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165 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

£536 - £888 / 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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24 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 8

30 Nights min stay

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from £204 / night

£1427 / 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

4 Photos

Florida Keys / Key West

Apartment / 1 Bedroom / sleeps 2

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
NEWTON'S NEST (monthly rental): PLEASE WELCOME THIS NEW MEMBER OF OUR FAMILY; AVAILABLE AS OF SEPTEMBER 20151 bedroom condo with sleeper sofa in the Old Town neighborhood known as The Meadows. Fresh paint, new furnishings, new TVs and lots of comfy additions.Located  …see more

Featured properties

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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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 

15 Photos

Florida Keys / Key Largo

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

7 Nights min stay

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from £87 / night

£603 - £738 / 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 Calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and  …see more


30 Apr 2014

5/5

"Moonbay Condo's Key Largo"

The place was clean and felt like home. A little noisy from a running pump and the exit gate got stuck closed, no outside deck or water view. But all in all it was great, I would stay here again! We h… More


17 Jul 2013

5/5

"A home away from home."

We enjoyed staying at Moon Bay condo in Key Largo,FL. Rental process was easy and all the staff was very accommodating. The condo is beautiful, modern and recently updated. The location is great to… 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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Excellent 5/5 

19 Photos

Florida Keys / Islamorada

Villa / 1 Bedroom / sleeps 3

Excellent 5/5 

1 night min stay

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from £96 / night

£667 - £792 / week

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or  …see more


13 Mar 2015

5/5

"Perfect place for a couple to vacation."

If your looking for the whole package in one this is the place. View, comfortable, privacy and location. Best place I've stayed in the keys, hands down!… More


1 Mar 2014

5/5

"a jewel worth the search"

Dog friendly, spacious location for relaxing or as a base for exploring the upper/middle keys. The property is shoehorned between two resorts, but surprising quiet and even secluded, in a way. Plent… More


8 Jul 2013

5/5

"Awesome place!"

My wife and I just returned from a weeklong stay at this property. I have to say this is far and away the nicest 1 bedroom rental and as far as I'm concerned a hidden jewel in Islamorada. It is the bo… 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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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

19 Photos

Florida Keys / Long Key

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 STAY: 29 DAYS 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 r  …see more

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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Excellent 5/5 

17 Photos

Florida Keys / Islamorada

House / 3 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 Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommoda  …see more


24 Aug 2013

5/5

"Our Lobster Trip to the Keys"

My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could not have asked for be… More

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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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Very Good 4.5/5 

27 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

7 Nights min stay

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from £115 / night

£802 - £1151 / 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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Excellent 5/5 

19 Photos

Florida Keys / Islamorada

Villa / 2 Bedrooms / sleeps 6

Excellent 5/5 

7 Nights min stay

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from £229 / night

£1603 / week

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining are  …see more


28 May 2013

5/5

"A place where memories are made....."

The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for my 9 year old twins … More

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Excellent 5/5 

27 Photos

Florida Keys / Islamorada

Villa / 2 Bedrooms / sleeps 6

Excellent 5/5 

7 Nights min stay

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from £229 / night

£1603 / week

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Key info:

  • Ask owner if suitable for children
  • No pets allowed
Minimum Rental: 7 Nights Lower 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. The units are available for rent by the week, or  …see more


30 Jul 2013

5/5

"Little Bay Fabulous Stay"

We had the pleasure of staying at Little Bay early July...2 couples, 1 pup and our boat. It was fabulous! The view, location, property was exactly what we hoped for. Private but close to restaurant… More


3 Jun 2013

5/5

"Paradise!"

My family and I spent Memorial Day Weekend at this gorgeous property and it was like paradise! Not only was it beautiful inside and out it had a sophisticated charm and inviting ora from the moment y… More

Thank you very much for your kind words. It was a pleasure meeting you and your lovely family. We are delighted that everything exceeded your expectations. We look forward to your return! Andi, Ashely, Kathy & Dick Keys Holiday Rentals


21 Aug 2013

5/5

"Perfect stay!"

Our family rented both the upper and lower duplexes and had a wonderful time. The management people were super friendly and had tons of information and ideas/recommendations for anything you could n… More

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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 £229 / night

£1603 / 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 

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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Very Good 4/5 

20 Photos

Florida Keys / Key Largo

Apartment / 2 Bedrooms / sleeps 4

Very Good 4/5 

7 Nights min stay

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from £87 / night

£603 - £706 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: 7 NIGHTS. This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. N  …see more


6 Feb 2015

4/5

"Very Comfortable Condo"

We booked last minute and were pleasantly surprised to find a roomy, cheerful, well-maintained condo waiting for us when we arrived. The kitchen was well-equipped, and the view from the living room … More


20 Mar 2014

4/5

"Great winter getaway!"

We had a wonderful 2 month stay at Moon Bay. The condo was very comfortable and in a great location. We thoroughly enjoyed relaxing by the pool and sitting out on the bay. No problems at all. The Key… 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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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 £161 / night

£1122 - £1297 / 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

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

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

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

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

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

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

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

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

24 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

29 Nights min stay

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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

21 Photos

Florida Keys / Islamorada

Apartment / 3 Bedrooms / sleeps 6

28 Nights min stay

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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

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Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 6

28 Nights min stay

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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

23 Photos

Florida Keys / Islamorada

Apartment / 2 Bedrooms / sleeps 4

28 Nights min stay

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless  …see more

16 Photos

Florida Keys / Islamorada

House / 3 Bedrooms / sleeps 7

27 Nights min stay

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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

27 Photos

Key Largo / Tavernier

House / 2 Bedrooms / sleeps 4

28 Nights min stay

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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

32 Photos

Key Largo / Tavernier

House / 4 Bedrooms / sleeps 10

28 Nights min stay

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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

25 Photos

Florida Keys / Islamorada

House / 2 Bedrooms / sleeps 5

28 Nights min stay

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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

24 Photos

Florida Keys / Key Largo

House / 4 Bedrooms / sleeps 10

28 Nights min stay

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
MINIMUM STAY: 28 DAYS 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 kitche  …see more

Very Good 4/5 

24 Photos

Florida Keys / Key West

Apartment / 1 Bedroom / sleeps 4

Very Good 4/5 

3 Nights min stay

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from £86 / night

£600 - £1464 / week

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Key info:

  • Ask owner if suitable for children
  • Air conditioning
  • Pets welcome
PARADISE PLACE: Ground level 1-bedroom 1-bath condo in the Palm Gardens community just 6 blocks from Duval Street.Completely renovated, this lovely property offers hardwood floors and cabinets, granite kitchen countertop and beautifully tiled bath.Queen size sleeper  …see more


8 Jul 2015

5/5

"Paradise Place "

We stayed at Paradise Place for 6 days and totally enjoyed it. Very clean and plenty of towels, beach towels an other extras. The spa pool was awesome with beautiful palm trees around pool area. Beau… More


3 Oct 2013

5/5

"Quiet and comfortable"

Having never stayed in Key West before, I was pleasently surprise to have a true home on the island. For those concerned over the distance from the craziness of Duval, don't be. The walk is not bad an… More


11 Jul 2013

5/5

"We couldn't ask for a better place to stay for our honeymoon!"

I was beyond impressed with the services provided by @Home Key West. From the first call, as I was frazzled, due to wedding planning, the staff helped me and aided in telling me about their services a… 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 £165 / night

£1154 - £2084 / 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.


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


3 Jun 2012

5/5

"Very Beautiful to wake up to and go to sleep to a great view"

Loved it, they had everything that we needed, well organized, and a very relaxing stay. Great Views… More

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Very Good 4.5/5 

24 Photos

Florida Keys / Key West

House / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

3 Nights min stay

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from £202 / night

£1414 - £3025 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Pets welcome
TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ceilings, new appliances, new furnishings and a true Key West feel. One block from Duval Street , it is close to restaurants, shops, galleries and clubs. The Atlantic  …see more


17 Jul 2015

5/5

"Great House!"

This house is in a good location, walking distance to restaurants and Duval. Our favorite part of this property was the pool area! It's very private and beautifully landscaped.… More


1 May 2014

5/5

"Tropical Dreaming (of returning soon)"

Just back for a completely relaxing getaway at this property. The property is even better than in the photos. Lovely original artwork on the walls made for a very comfortable and homey location for a … More


13 Mar 2014

5/5

"Charming"

This was a very nice and clean rental. The location was perfect and close to Duval but not the hustle and bustle. I would suggest a king bed in the master but that is just a personal preference. Ve… More

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Very Good 4/5 

24 Photos

Florida Keys / Key West

Apartment / 1 Bedroom / sleeps 2

Very Good 4/5 

3 Nights min stay

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from £72 / night

£504 - £1334 / 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
OSPREY: Studio cottage located in The Colony Suites, a compound nestled in Old Town Key West. Osprey offers all the amenities for two who want a larger space than a hotel room. Sunny and bright, sitting area, queen size bed, full bathroom and kitchenette. Fre  …see more


21 Mar 2015

5/5

"Great location"

We walked everywhere and, in fact, never moved our vehicle. The cottage is cozy, clean and comfortable and the pool is great. Having a washer and dryer on the property was convenient. I would suggest … More


26 Oct 2014

5/5

"Will definitely stay here the next time we're in Key West!"

We had a wonderful time staying at Osprey and will reserve this cute little place every time we go to Key West. The location on Olivia St is ideal for getting to all the action on Duval when you want… More


26 Jun 2013

5/5

"Private Oasis"

Osprey is absolutely adorable. It's the perfect size for two people. Everything is brand new and clean. It's about a 5 minute walk from the center of Duval. The cottage has a small porch and is just s… More

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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 £113 / night

£786 - £1650 / 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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Excellent 5/5 

29 Photos

Florida Keys / Key West

House / 5 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

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from £486 / night

£3398 - £7250 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Pets welcome
CASA GRANDE: Located on a quaint lane steps from Duval Street with room to park 2 vehicles off-street.Built for entertaining from the wide open floor plan that encompasses the spacious living room and grand kitchen to the magnificent pool.Master bedroom with bath ensui  …see more


17 Jul 2015

5/5

"Casa Grande- Room For All"

We thoroughly enjoyed our Key West vacation. At the end of a street, 40-yards from Duval, we couldn't believe how quiet Casa Grande actually was. Children, Grandchildren and Grandparents had plenty of… More


6 May 2015

5/5

"Perfect choice for large group"

This was our second year at Casa Grande and I recommend highly if you're a group of 8-12 people. Beautiful location near 1100 block of Duval. Nice large pool in backyard, spacious kitchen/living area,… More

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Very Good 4.5/5 

27 Photos

Florida Keys / Key West

House / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

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
  • Pets welcome
DUVAL ON THE SQUARE: Located at the Duval Square on Duval but above all the hubbub, built on the 2nd and 3rd story of the complex.Nicely decorated with bedding for up to 6 guests. Sleeper sofa and loveseat in the living room are terrific for an afternoon of relaxing o  …see more


9 Apr 2015

5/5

"Very nice place --Great location"

The condo is very well maintained. Furniture is clean and appropriate for the location. We found the location to be excellent as it is away from the hustle and bustle of Duval's lower end but yet ve… More


2 Jun 2015

4/5

"Great Location, clean and close to the pool."

The place was spacious, clean and right on Duval. The only somewhat negative was the noise from the restaurants on the square, but would not stop me from renting this unit again. The pool was great an… More


10 Apr 2013

4/5

"A really good place to stay"

Duval Square is a very good location. Crowd noise is not a problem. However the parrots from the New York restaurant below can get annoying. The inside of the apartment is nicely done. The balcony'… 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

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from £130 / night

£909 - £1999 / 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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