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Villas in Florida Keys and Holiday rentals - Holiday Lettings - Holiday Rentals Florida Keys

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543 Holiday homes

Holiday condo in Key West

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Full kitchen, extra towels including for the pool, extra blankets if needed.” Ed's apartment was fully stocked with all you need, including pool/beach towels & extra blankets and pillows. Washer and Drier worked well and he supplies you with detergent. Supermarkets near by. Balcony with table and 4 chairs with 2 extra chairs in closet which was great as we were 6. Apartment has 2 full bathrooms! Only complaint was from one of my children who said the double bed she shared with her sister was uncomfortable. Other child slept fine. Thank you Ed - your apartment worked perfect for us.

from £259 / night

£1,606 - £2,462 / week

1 / 20

Home rental in Marathon Shores

Marathon Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £209 / night

£1,458 / week

1 / 13

Holiday boathouse with shared pool in Tavernier

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £204 / night

£1,205 - £2,178 / week

1 / 31

Holiday apartment in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £371 / night

£2,406 / week

1 / 11

Holiday home in Key West

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great Home, Great Location, and everything you need to enjoy KW!” My partner and I and our two good friends have stayed at Casa del Sol for the last three years. Each stay was for three weeks. Casa del Sol is in a GREAT location. Just minutes from the famous Green Parrott and yet in, argueably, the nicest and quietest neighbourhood in KW. We have been doing extended stays in Key West for 6 or 7 years and this location just seems to make everything close whether you are going to Mallory Square for sunsets, Duval street for shopping, Ft Zachry beach to sun and swim or to the Southernmost Point. Everything is an easy walk. And, if walking isn't fast enough the home comes with two well maintained bicycles and locks! The home itself is well equiped, spotlessly clean and Jim and Joanne are always upgrading something to keep the home "A-One". You won't make a mistake choosing this as your vacation rental. As a central location to explore KW OR to just stay in the complex and enjoy the beautiful pool this home will satisfy for sure. We have stayed three times and would not hesitate to stay a fourth!!

from £278 / night

£1,940 - £3,961 / week

1 / 32

Key Largo holiday home accommodation

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £278 / night

£1,805 - £2,314 / week

1 / 22

Key West holiday apartment rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £232 / night

£1,622 / week

1 / 69

Holiday condo in Key Largo

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Place for a Family Get-away” What a wonderful stay we had this past week (December 30, 2012 -January 6, 2013) at Jose and Estella's Condo at Kawama Yacht Club in Key Largo! The condo was so spacious, and extremely clean, which we very much appreciated! Jose and Estella were so very kind and helpful in getting us organized on the front end with all my questions, and then giving us suggestions for what to do when we arrived. I really have to say how very nice these folks are: I truly felt they hoped our stay at their place would be a wonderful experience, and they did all kinds of things to help make that happen. I highly recommend this property as an excellent place for families. We enjoyed the tennis courts, the ocean, the pool, and all the other local activities. So much to do - and then the wonderful home to come back to to unwind and enjoy. Thank you Jose and Estella!

from £255 / night

£1,384 - £1,389 / week

1 / 31

Little Torch Key holiday home rental

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £162 / night

£1,134 / week

1 / 13

Ramrod Key holiday home rental

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £217 / night

£1,515 / week

1 / 19

Key West holiday apartment accommodation

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £603 / night

£4,171 / week

1 / 50

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Perfect family week!!!!” The condo is near everything, and Downtown is not that far away. Loved the pool. The condo was great. We'll visit again!!!!!

from £260 / night

£1,814 / week

1 / 24

Home rental in Cudjoe Key

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

from £502 / night

£4,258 - £5,554 / week

1 / 35

Holiday condo in Marathon

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £124 / night

£863 / week

1 / 17

Key Largo holiday home rental

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £223 / night

£1,555 / week

1 / 29

Holiday caravan/mobile home in Key Largo

Key Largo caravan/mobile home

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £105 / night

£735 / week

1 / 6

Holiday home in Cudjoe Key

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £95 / night

£661 / week

1 / 15

Holiday condo with swimming pool in Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £255 / night

£1,782 / week

1 / 25

Holiday home in Ramrod Key

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £97 / night

£679 / week

1 / 11

Holiday home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £122 / night

£849 / week

1 / 18

Holiday home in Cudjoe Key

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £116 / night

£811 / week

1 / 14

Holiday home rental

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £335 / night

£2,339 / week

1 / 23

Holiday home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £165 / night

£1,151 / week

1 / 19

Holiday home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £208 / night

£1,453 / week

1 / 19

Home rental in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £157 / night

£1,094 / week

1 / 16

Holiday home in Summerland Key

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £256 / night

£1,792 / week

1 / 12

Holiday home in Summerland Key

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £132 / night

£925 / week

1 / 18

Little Torch Key holiday home rental

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £601 / night

£4,205 / week

1 / 25

Holiday home in Ramrod Key

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £176 / night

£1,226 / week

1 / 12

Holiday home in Cudjoe Key

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £130 / night

£906 / week

1 / 8

Holiday home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £130 / night

£906 / week

1 / 15

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £464 / night

£3,244 / week

1 / 53

Holiday home in Tavernier

Tavernier house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

from £199 / night

£1,393 / week

1 / 41

Holiday home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £153 / night

£1,066 / week

1 / 12

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £309 / night

£2,163 / week

1 / 35

Holiday home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £186 / night

£1,302 / week

1 / 17

Holiday home in Big Pine Key

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £114 / night

£793 / week

1 / 16

Holiday home in Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £119 / night

£830 / week

1 / 17

Holiday home in Summerland Key

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £159 / night

£1,113 / week

1 / 14

Holiday home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £122 / night

£849 / week

1 / 8

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Florida Keys holidays

Florida Keys, FL, including the islands of Key West, Key Largo, Islamorada, Marathon Key and Big Pine Key offers the perfect mix of family beach fun and peaceful holiday relaxation. Spend your days strolling one of the many boardwalks, or swim, snorkel, and kayak in the pristine Gulf. After a long day, retreat back to your holiday rental home at night, escape the crowds, and watch the sunset across the Gulf from your personal porch or deck. With your own private tennis court and pool, luxuries that many rentals offer, you can have a great time without even leaving your holiday home.

Wake up to the sound of waves rolling in and the scent of the salty ocean air, then walk just minutes to the beach for great boardwalk shopping, dining, and entertainment. Truly escape the winter chill by heading to the southernmost point in the United States, Key West, Florida. Take U.S. Highway 1, known to locals as "The Overseas Highway" to get there, and enjoy the breath-taking natural beauty of the ocean scenery and wilderness that borders the road.

Here are a few additional suggestions for your trip to the Florida Keys:

  • Visit the Key West Butterfly & Nature Conservatory: Key West is home to a magnificent array of butterflies from South America, Africa, and Southeast Asia. This Conservatory emphasises the importance of wildlife preservation, offering group tours, unique films, and resident rainforest birds guaranteed to ignight your love for wildlife.
  • Swim with the dolphins: Key West is known for its dolphin friendly environment and facilities that offer guests the opportunity to swim and play with these amazing animals.
  • Explore The Harry S. Truman Little White House: Established in 1890 as a command centre during the Spanish American War, this house was later used as a means of escape during the Cold War. For years, presidents relaxed and restored body and mind here while dealing with war threats. The site is now a living history museum.
  • Sleep under the stars: Spend a night under the legendary stars of Key West. Florida Keys campgrounds are plentiful, and Florida Keys camping can also happen at sea. Charter a boat and drift off with the night sky above and the ocean below.
  • Take a sunset dinner cruise: Gourmet dinner cruises to Florida Keys' destinations are widely available. Nothing is more romantic than raising a glass on a luxury sailboat as the sun sets over the Atlantic.
  • Take a charter fishing trip: An experienced outfitter can provide the boat and equipment you need to pursue deep water species like marlin and swordfish.

Whether you're here for a Florida Keys honeymoon, a family reunion, or a holiday getaway with friends, you'll easily find a perfect holiday rental with all the amenities you need to relax in style. Stay in a charming beach condo close to the restaurants and nightlife or rent an elegant villa with a balcony and stunning views of the ocean. You may also want to make some time during your holiday to visit nearby destinations like Naples or Marco Island.

Top Destination reviews

500 Ocean - Tropical Florida Keys Vacation Home
Fantastic Rental!

Impressed with the cleanliness and well maintained property! Great location and very relaxing porch to enjoy the breeze. Rental is well stocked/supplied with everything you need or may have forgotten to pack. Six people stayed here for 2 weeks very comfortably. We even brought our boat and there was plenty of parking for 2 vehicles and the boat trailer. Will definitely rent this again for future trips. The owners were very helpful and easy to reach with any questions or concerns during our stay.see more
Ocean Vista
Ocean Vista was perfection

Ocean Vista and Roberta (owner) were perfect!! The weather in Key West was a little cooler then we were hoping for but the room was clean, spacious and looked exactly like the pictures. Roberta was amazing!!! She made sure we had all of the information we needed ahead of time and provided us with updates as needed. She was so easy to work with. 10/10 recommend!see more
Islamorada cottage on deep water canal
Amazing house and location

This place has everything you need for a perfect stay in the Florida Keys. Centrally located with a 2 hour drive to Key West as the most far location to visit. Supermarket is 10 min. down the road and has everything you need. At Founders Park (5 min down the road) you have beach access (rare in the Keys) when you show your rental agreement at the gate. This park also has a swimming pool at a few dollars admission. The house itself surprised us. It is so well decorated (we loved all the mosaics) and has everything you possibly need during your stay, from a large kitchen with all the equipment, pots, pans, cutlery, dishwasher, large fridge with icemaker to a large (gas) BBQ outside, garden furniture, sunshade, mosquito netted porch, outside jacuzzi, canoes, sup board. On premise parking spot. Good (relatively quite) air-conditioning. Very cozy sleeping rooms, 2 bathrooms. Quality furniture, good couches in the living room. The canal offers direct access to the water and the bay, you can bring your own boat if it is not to large (the owners have their own boat on a lift), but is leaves enough room for a second boat. The canal has Manatees in it, sharks and dolphins where spotted and the garden has Lagunas and squirrels. Finally the owners are very nice to communicate with and are very flexible and helpful. We had contact via e-mail but the neighbors watch over the house and can always help directly if something is needed.see more
Tropical Island Getaway-Keys
We've stayed here 4 times so far and have booked again for Spring 2017.

Great location, less than an hour away from Miami Airport. Shops and restaurants within walking distance and plenty more choice if you fancy travelling a little further. Great days out on the Keys or Everglades NP. The condo isn't fancy but it's clean and has everything you need and some extras. We love it!see more

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