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16 Holiday homes in Florida Keys

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16 Results  |  
19 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £93 /night

£650 - £750 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Enjoy luxury standards at affordable prices during your stay Excellent local activities and facilities. Centrally located to explore the Florida Keys and all the attractions and sights of South Florida, Miami & the Everglades. Contact us if your party has more people, special needs, or plus infants to discuss facilities & assistance  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £111 /night

£777 / week

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Key info:

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

12 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £64 /night

£444 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Genießen Sie Ihre Ferien in unserer 2011 neu eingerichteten und renovierten "Villa Pine Island" mit eigenem beheizbaren Pool und allem Komfort für einen angenehmen und erholsamen Urlaub. Das Haus liegt zentral aber ruhig gelegen in einer Wohnsiedlung mit angenehmer Na  …see more

Featured properties

13 Photos

Villa | 3 Bedrooms | sleeps 8

6 Nights min stay

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from £63 /night

£441 - £634 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Freies NAVI, Großer Pool in Süd/West-Lage, elektrisch beheizt, wunderschöne Gartenanlage mit Obstbäumen, Highspeed-Internet, Kabelfernsehen (HD - HBO), viele Gesellschaftsspiele, umfangreiche Strandausstattung, 100% gemütliche Wohlfühlgarantie, usw.  …see more

24 Photos

House | 3 Bedrooms | sleeps 8

30 Nights min stay

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from £87 /night

£606 / 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

14 Photos

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 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. A boat slip is included in your condo rental and has easy access to BOTH Florida Bay and Atlantic Ocean.  …see more

23 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £94 /night

£653 / week

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Key info:

  • Nearest beach 3 km
  • Not suitable for children
  • Car advised
  • Air conditioning
  • Pets welcome
Find a “Peace of mind” in this beautiful Tropical Paradise. This two bedroom home is conveniently located at Mile Marker 92 in Historical Tavernier, Florida. It is only 69 miles from Miami International Airport, and the residence will truly captivate your mind and help you relax! Want to explore different areas of Florida while you are here? You can head to the Infamous Miami Strip in 90 minutes. Enjoy your day, spend some time touring the area, and go to your Florida Keys Home Rental where it is peaceful, serene, and breathes tranquility. This unique Key-West inspired property is an experience, and you can be at Key West 90 Miles off the coast of Cuba if you would like in just 75 Minutes. There are also local areas that are very enjoyable. Snappers, a Tiki Bar Waterfront Restaurant located at Mile Marker 94.5 is just 5 Minutes away, and they have a great diverse Menu as well as Specialty Drinks. The Tiki Bar at Holiday Isle is another modest location that is hard not to enjoy, and it is conveniently 20 minutes away. Furthermore, If you would perhaps want to enjoy a more sophisticated option, head to the Hilton that is 10 Minutes down the road south to enjoy a massage, their restaurants, and the beautiful scenery. On-Site Amenities: Fruit trees, shaded areas and walking paths cover the large three lot property grounds. The home is equipped with Free Wireless Internet, Flat Screen TV’s, Air-Conditioner, Beautiful Furnishings, and comfortable accommodations. Additionally, CVS, Walgreens, Food Markets, Movie Theater, and Bowling are in the vicinity. This furnished home with safety fenced grounds and screened-in private porches is truly a place you will remember and never forget. With a 2 minute walk, there is a small intimate Sanded Playground perfectly located approximately 50 feet from the Atlantic Ocean for children with swings (both baby and older), slides, and Florida Inspired Playground Animals. The amazing Theater of the Sea is barely 20 minutes away, so you can swim with Dolphins and many more Marine animals during your stay! 'Peace in the Keys is the Place to Be.'  …see more

54 Photos

Cottage | 1 Bedroom | sleeps 4

 

30 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car not necessary
  • Air conditioning
  • Pets welcome
The artist cottage is mainly used as a residence for visiting artist that are in town doing shows at my gallery. The cottage is very quiet and secluded with lots of privacy,situated amongst 100 year old trees and lush tropical foliage. The cottage was built in 1913 and is a true piece of old key west. The property is fenced in and gated and locked. The property is literally a 4 minute walk to Duval st. The cottage is very nice if you like old wood homes . The cottage has a full kitchen and bathroom, two dining areas , one outside on a covered deck next to the hot tub, or cold tub if you want to stay cool in the summer. It has air conditioning with ceiling fans inside , and outside on the covered deck. It is walking distance or biking distance to everything on the island. No taxis necessary .  …see more

6 Photos

House | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £80 /night

£556 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
The "Casa de Addison" is a vacation rental, townhouse style, and is located in Marathon, Florida...in the heart of the Florida Keys. The unequaled Key islands are connected to the mainland by the way of the overseas highway and feature the aquamarine seas of the Atlantic Ocean to the southeast and the gulf of Mexico to the northwest. The Keys provide some of the best fishing in the world, unsurpassed diving from the coral reefs, and excursions by land and boating at their best. Our townhouses consist of covered parking on the ground level; a living room/kitchen, laundry area, and a one-half bath on the second level, and two bedrooms and a full bath on the third level. There are balconies on the 2nd and 3rd level which overlook the basin and the Sombrero golf course.  …see more

6 Photos

House | 3 Bedrooms | sleeps 10

30 Nights min stay

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Pricing unknown

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Key info:

  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • Pets welcome
Right off Key Largo Mile Marker 96 1/2 ... Very relaxing & spacious home with private park at the end of the block (5 houses down from the property). This property is close to everything parks: Founders Park MM 87, John Pennekamp Coral Reef State Park MM 102.5, Harry Harris Park MM 93.5 also Theatre of the Sea MM 84.5, & Tiki Bar MM 84 etc. Restaurants: Waffle House MM 100, Subway MM 91, D' Hooker Sports Bar & Grill MM 102, The Marlin Restaurant MM 102, Paradise Pub MM 102, The Fish House Encore MM 102.3, Tower of Pizza MM 100, Papa John's Pizza MM 98, Doc's Diner MM 99.6, Hobo's Cafe MM 101, Arby's MM 101, Rib Daddy's Steak & Seafood MM 102, Num Thai Restaurant & Sushi Bar MM 103, Coconuts Restaurant & Night Club MM 100, Jimmy Johnson's Big Chill MM 104,The Buzzards Roost Grill & Pub MM 106.5, Sundowner MM 104, Calypso's Seafood Grill MM 99.5, Ballyhoo's Historic Seafood Grille MM 97, Key Largo Conch House MM 100.2 etc., supermarkets/stores: (Publix Supermarket MM 101, Winn Dixie MM 105, Kmart MM 101), shopping stores, thrift stores, Family Dollar MM 99 & 105, etc ... Diving: Sea Dwellers Dive Center MM 99, Garden Cove Dive Center MM 100, Scuba Quest Outlet MM 106, Keys Diver Snorkel & Scuba Center MM 99 Unit 1, Nail Salon: Asia Nails MM 99. Ice cream: Mr C's Gourmet Italian Ice Cream MM 98, Dairy Queen MM 92  …see more

40 Photos

House | 10 Bedrooms | sleeps 24

3 Nights min stay

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from £1331 /night

£9317 - £10870 / week

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Key info:

  • Ask owner if suitable for children
  • Air conditioning
  • Pets welcome
The Lost Pelican Fish Camp is the perfect Florida Keys destination for family reunions, corporate events, and just the perfect place for a family vacation where there is room for the entire family. Located close to mile marker 28.5 and close to just about anything you will want to do or can do while on vacation in the beautiful Florida Keys. This is the only property designed around the Keys Lifestyle with two new Keys elevated homes connected by a sky bridge. Each has 8 bedrooms, 8 bathrooms, plenty of living space, and plenty of outdoor patio space to enjoy the fantastic sunsets and sunrises only experienced in the Florida Keys. This property is the only vacation rental that has a total of 10 bedrooms and 11 bathrooms with 4- King beds 4- Queen beds 4-Twin Beds plus an assortment of other sleeping arrangements. New, clean, and unique is what you can expect in a vacation rental at the Lost Pelican Fish Camp. RENTAL OPTIONS: 1. Budget Minded- you can rent the Pelican Cottage from $450 per night 2. Bigger Budget - you can rent the Pelican Guest House from $1,200 per night 3. Not on a Budget - you can rent the Pelican Main House from $1,500 per night 4. NO BUDGET - you can rent the entire Fish Camp from $2,900 per night Discounts available for weekly, monthly, and returning guests. Minimum Rental Period is 3 nights. (Friday to Sunday). Rates increase during specific dates such as mini-lobster season, Fantasy Fest, and the Holiday Weekends. Add 10% for Holiday Dates. Rates subject to change without notice. For the Best Rate- Call Richard Sr. at. Fishing, boating, diving, and just about anything else that can be done on vacation in the Florida Keys is all available and very close by when you rent the Lost Pelican Fish Camp and there is plenty of room for you to bring your own boat, RV, or camper to enhance the family gathering at the Lost Pelican Fish Camp. Minimum Rental Period is 3 days and weekly rentals get booking priority. Every weekly rental comes with a FREE BAHAMAS PENTHOUSE VACATION BONUS( One Week in the Bahamas) Rents are always higher during peak events like mini-lobster season, lobster season, and of course, Key West Fantasy Fest. There is nothing average about this fantastic vacation rental and the price is as above average as the quality and construction of this one of a kind Keys Vacation Rental. This rental is for those who demand something other than average. Visit for more details Additional amenities include: coffee maker, secluded, nearby bank, nearby internet cafe, ice maker, near beach, outlet shopping, nearby medical services, nearby fedex, nearby grocery, cookware, nearby post office, close to town, nearby atm, golf course, movie theatres, washer & dryer, ironing board.  …see more

25 Photos

House | 3 Bedrooms | sleeps 8

28 Nights min stay

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from £259 /night

£1812 - £2407 / week

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Key info:

  • Ask owner if suitable for children
  • Air conditioning
  • Pets welcome
Available Monthly & Seasonally. This Townhouse represents the best Snow Bird Rental at the Southern most tourist destination in the United States. This very upscale unit is available for monthly or seasonal rental to qualified renters who demand and accept nothing but the best. This property is not a transient rental property and their are specific rental restrictions imposed by both the City of Key West and Monroe County Florida making this vacation rental the perfect Snow Bird Rental. You are invited to call us for complete rental options and details. However, if you are shopping price and if you are looking for a cheaper vacation rental in Key West, you can check elsewhere and you will be able to find plenty of them. We respect those seeking a less expensive option, regretfully our unit is not it. We believe that it is important to recognize upfront that the Key West Steamplant is located at the higher end of the rental spectrum in Key West and Unit 214, at the Steamplant, is one of the largest and best choices for a high end Key West vacation rentals. Unit 214 is a breath taking unit available for Monthly or Seasonal rental located at the Key Weststeamplant, the most exclusive address in Key West. This is a two story townhouse with a private elevator and a very private roof top terrace and swimming pool. Unit 214 is a three bedroom rental with a formal dining area and a very large gourmet kitchen. Each bedroom has a king bed and terrace (private patio) that overlooks the water and the harbor area of Old Town Key West. Opulence is a word that describes the lifestyle of the Key West Steamplant and Unit 214 is one of the premier units at the Steamplant. Highly secure building with underground parking. For Rental Options and Specific Information Call Richard Sr Additional amenities include: coffee maker, secluded, nearby bank, nearby internet cafe, ice maker, near beach, outlet shopping, nearby medical services, nearby fedex, nearby grocery, cookware, nearby post office, cd player, symphony orchestra, outdoor shower, close to town, nearby atm, golf course, movie theatres, washer & dryer, ironing board.  …see more

42 Photos

House | 10 Bedrooms | sleeps 20

Very Good 4.5/5 

4 Nights min stay

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from £888 /night

£6212 - £7764 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis court, optional Racket Ball Court, hammocks, paddle boards, bikes , kayaks, basketball court, car parking, 60 foot deep boat dock, and 100 feet shallow dock plus a secondary deep protected from wind and waves boat dock for storms. Close enough to Duval Street/Old Town (a few minutes) to enjoy the fun and quirkness but also in a section of Key West that is quiet and just enough away from the crowds, mopeds, motorcycles, smoke, cruise ships crowds, and noise to appreciate what the KEYS are really all about.THIS PROPERTY IS BY FAR THE BEST KEY WEST HAS TO OFFER!!!!!!! OFF SEASON SPECIALS AVAILABLE. PERFECT FOR LARGE FAMILY GETAWAYS, SMALL BUSINESS RETREATS. Close enough to Duval Street/Old Town (3 miles) to enjoy the fun but also in a section of Key West that is quiet and just enough away from the crowds, mopeds, smoke, cruise ships, and noise to appreciate what the keys are really all about. The house (really a small private resort) is a wonderful place for friends and family (sleeps up to 24) to chill out and enjoy life in the Florida Keys. Lots of activities if you want (tennis, basketball, swimming pool, salt water swimming and fishing, pool table, paddle boards, kayaks, and bikes) or a place just to sit back and watch nature grab a suntan with no cares CALL EARLY AS IT GETS FILLED QUICKLY. THE RESORT COMPOUND CONSISTS OF THE LARGE 8 Bedroom House used by the Real World Key West series and an additional house build around a racket ball court with 2 waterfront bedroom. The additional house is rented as an additional option if wanted.and the price is not in the listing price of 1500 per week night, $2000 per weekend night or $12,000 per week. The prices on this site do not reflect higher prices for certain holiday weeks. The additional house is 400 per night. Please note that to insure the privacy of the Guests of the Main House, the Racket House will not be rented to 3rd parties and is only rented to the Group staying in the big main house. PLEASE NOTE THAT THIS PROPERTY IS ONLY REPRESENTED BY THE OWNER, ANDREW LIPPI AND ANY OTHER PERSON INCLUDING A CRAIGSLIST LISTING IS NOT AUTHORIZED AND PROBABLY A SCAM  …see more

16 Photos

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 Enjoy the magnificent ocean views of this wonderful condominium complex. You'll love the newly completed renovations. The kitchen has been totally remodeled with all new cabinets and appliances. The living room furniture is brand new and there's a big flat screen TV on the wall. The baths have been updated and modernized. This affordable unit is located on the second floor with a walkout patio to the terrace. Only 6 units in the entire complex offer this "back door" exit directly from the unit to the terrace level and stairs leading directly to the pool and ocean. The two bedrooms, one with a king bed and the other with twin beds provide comfortable sleeping for 4. The master suite has a dressing area and separate bath. The kitchen is complete in every way - pots and pans, dishes, cooking utensils, flatware and appliances are ready for you to serve up a meal prepared at home or one delivered from a local restaurant. The Palms of Islamorada is one of the most sought after condo complexes in the area. Its ocean front property is conveniently located by Bud and Mary's Marina, Lazy Days Restaurant and the Outback Steakhouse. A swimming pool, hot tub, tiki, lounge chairs by the water's edge, his and hers exercise rooms and manicured grounds combine to provide just the right atmosphere for a great holiday or retreat. Rate Details: Rent is $2100 to $3450/month depending on season. Monthly Rates are calculated from the 1st day of the month to the last day of the month. Additional Charges: $175 departure cleaning fee; $200 processing fee; $45 accidental damage insurance; and 12.5% state and local taxes. Refundable Security Deposit: $500. Utility Caps/Mo: $200 for electricity. Condo Association Charges: There is a required application and a fee of $100. Travel Insurance: This is an optional service we offer through a national travel insurance provider. Plans include valuable medical coverage, trip interruption, emergency travel services and more. Please click on the Travel Insurance tab on our website for more information.
All reservations made on this website are tentative and subject to confirmation by the management company. Rates and fees are subject to change without notice prior to confirmation of reservation. Additional amenities include: beds pull-out queen sleeper sofa, wifi in unit yes, cooling central air, total # of units 84, bed size 2nd rm 2 twins, washer/dryer coin-op - eachfloor, parking space no. #79, bed size 1st/master king, bath tub yes, elevator yes, beach distance 6 miles, beach access founders park, phone-local calls yes, property type condo, club house yes, seawall - concrete yes, boat ramp kayaks/sailing, view ocean, stove/oven elec/gas electric, square footage, est. 1041, micro/dishwash/disp. micro/dw/disp, location islamorada, max # guests 4-6, phone in unit yes, gated entry yes, bldg. complex name palms of islamorada, TVs/VCR/DVD wall flat screen/DVD.  …see more

15 Photos

House | 4 Bedrooms | sleeps 9

Excellent 5/5 

3 Nights min stay

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from £140 /night

£979 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Beautiful canal front, clean, home located on ocean side in Long Key. MM 68. 4 bedrooms 3 baths total: 3 bedroom, 2 bath upstairs, 1 bedroom/bath (studio) downstairs. Great fishing and diving moments away. This is our family's vacation hideaway. Never rented prior to December 2012. Direct TV w HBO, Regional Sports Package, NFL Sunday ticket in three rooms: One HD plasma/DVD in living room, TV/DVD combo in master bedroom, ED plasma downstairs. Two refrigerators, one ice maker. Leather recliner seating in LR. Tasteful keys decor throughout. Board games, dominoes, chess. Relaxing second floor wood porch with rattan chaise seating, wicker rocking chairs. Enjoy the open water view of Florida Bay across the street.  …see more

18 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

2 Nights min stay

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from £111 /night

£777 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
One of the most beautiful Elevated Villas available at Mariner's Club in Key Largo, boasting a panaoramic view of the Atlantic. King Bed in Master Bedroom King Bed in 2nd Bedroom and a Twin Day Bed with a Twin Trundle in the Den area for additional Sleeping Space Full Sized, Fully Equipped Kitchen, including Microwave, Stove/Oven, Refridgerator, Dishwasher, Toaster, Coffee Maker, and Blender. Enjoy Relexation in Luxury.  …see more

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