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

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715 Holiday homes

Holiday home in Big Pine Key

Big Pine Key house

3 bedrooms • 2 bathrooms • sleeps 13

from £319 / night

£2,234 / week

1 / 30

Islamorada holiday home rental

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

from £419 / night

£3,349 / week

1 / 21

Holiday apartment in Key Largo

Key Largo apartment

2 bedrooms • 1 bathroom • sleeps 6

from £290 / night

£1,737 / week

1 / 11

Marathon Shores holiday home rental

Marathon Shores house

2 bedrooms • 2 bathrooms • sleeps 7

from £230 / night

£1,605 / week

1 / 29

Holiday home in Marathon

Marathon house

2 bedrooms • 2 bathrooms • sleeps 6

“2020 Mini Season” Great place to stay, extremely clean and comfortable. Updated home with spacious living room, very nice kitchen, and fantastic porch area over looking the water. My Kids loved it to! Perfect location for fishing, diving and catching lobster. Quick boat ride to the reef. Perfect place for a relaxing vacation. The owners have been great with quick responses for even the littlest questions. Thank You Chuck for a awesome trip!!!

from £121 / night

£830 - £1,834 / week

1 / 35

Villa rental in Islamorada

Islamorada villa

2 bedrooms • 2 bathrooms • sleeps 6

from £220 / night

£1,365 - £1,794 / week

1 / 44

Apartment rental in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £224 / night

£1,568 / week

1 / 22

Apartment rental in Key West

Key West apartment

1 bedroom • 1 bathroom • sleeps 6

from £248 / night

£1,736 / week

1 / 17

Marathon Shores holiday home rental

Marathon Shores house

3 bedrooms • 2 bathrooms • sleeps 8

from £1,244 / night

£8,709 - £17,251 / week

1 / 50

Holiday apartment letting

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £375 / night

£2,358 / week

1 / 50

Holiday apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £234 / night

£1,632 / week

1 / 17

Holiday apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 3

from £179 / night

£1,074 - £1,265 / week

1 / 66

Holiday home in Key West

Key West house

5 bedrooms • 4 bathrooms • sleeps 12

“Relaxing with a great location: can't beat it!” The house was exactly you want out of a beach vacation: bright colors, lots of beach themed decorations. Very cute! There was plenty of room for the 10 of us to hang out on both of the great porches, and we had a lot of fun out by the pool. If I ever go back with a large group, I definitely would stay here again!

from £1,418 / night

£9,923 - £10,506 / week

1 / 58

Holiday yacht with shared pool in Key West

Key West yacht

3 bedrooms • 3 bathrooms • sleeps 7

from £1,415 / night

£9,153 / week

1 / 16

Holiday condo in Islamorada

Islamorada condo

2 bedrooms • 2 bathrooms • sleeps 4

from £167 / night

£1,165 / week

1 / 17

Islamorada holiday home rental

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

“Our month of rest and fun!” My husband and I stayed here for the month of January 2012. Weather was great, in fact, perfect. This house was very comfortable, and just a great place to rest. The pool was awesome! This house does need some updating and the pond was in bad shape. We did try to keep the debris off the beach area, but because of location and winds, it was useless. That was very close to the water, we still had clean area to lounge in adirondack chairs. The grounds are beautiful and you are just across the road from bike paths, which we biked many times. The people at Freewheeler were very nice and helpful in any situation. We had a wonderful, restffull, peaceful and fun time at this home! Thank you!

from £891 / night

£5,821 - £7,069 / week

1 / 32

Home rental in Islamorada

Islamorada house

3 bedrooms • 2 bathrooms • sleeps 8

from £333 / night

£2,331 / week

1 / 15

Home rental in Tavernier

Tavernier house

2 bedrooms • 2 bathrooms • sleeps 6

from £125 / night

£875 / week

1 / 28

Ski home to rent in Marathon

Marathon house

3 bedrooms • 2 bathrooms • sleeps 6

from £542 / night

£3,788 / week

1 / 42

Holiday home in Marathon Shores

Marathon Shores house

3 bedrooms • 2 bathrooms • sleeps 8

from £251 / night

£1,757 / week

1 / 42

Holiday condo rental

Islamorada condo

3 bedrooms • 2 bathrooms • sleeps 6

“We hated to leave!” The rental is beautifully decorated and very spacious. The kitchen is very well equipped from dishes, pots and pans and all the gadgets needed for a great vacation. There also is a great swimming pool on the premises. There are some great restaurants in the surrounding area, along with some great fishing. It also is a nice drive to visit the other Keys. I would highly recommend this condo. I know we would stay here again in a heartbeat!

from £113 / night

£788 - £1,327 / week

1 / 35

Holiday apartment rental

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

“Amazing!” We booked this condo last minute for a quick getaway. I would like to say I am so happy I found this place. This is where my family and I will stay anytime we come to key west. The condo was spacious and had everything you could think of. The location was perfect, about a 5 minute drive from Duval St. The amenities at the complex were also very nice. We spent a lot of time in the hot tubs and pool.

from £375 / night

£2,620 / week

1 / 38

Holiday apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £381 / night

£2,663 / week

1 / 25

Key West holiday condo rental

Key West condo

1 bedroom • 1 bathroom • sleeps 2

from £125 / night

£873 / week

1 / 18

Matecumbe Key holiday home rental

Matecumbe Key house

2 bedrooms • 2 bathrooms • sleeps 4

from £179 / night

£1,206 - £1,830 / week

1 / 19

Key West holiday townhouse rental

Key West townhouse

2 bedrooms • 2 bathrooms • sleeps 4

from £286 / night

£1,996 / week

1 / 12

Home letting in Key Colony Beach with golf nearby

Key Colony Beach house

2 bedrooms • 2 bathrooms • sleeps 4

from £195 / night

£1,365 / week

1 / 86

Studio rental in Marathon

Marathon studio

Studio • 1 bathroom • sleeps 3

from £144 / night

£1,004 / week

1 / 9

Holiday home in Big Pine Key

Big Pine Key house

3 bedrooms • 3 bathrooms • sleeps 6

from £117 / night

£815 / week

1 / 17

Key Largo holiday private room rental

Key Largo private room

1 bedroom • 1 bathroom • sleeps 2

from £77 / night

£460 - £525 / week

1 / 57

Key West holiday apartment rental

Key West apartment

1 bedroom • 1 bathroom • sleeps 4

from £167 / night

£1,124 / week

1 / 69

Holiday villa with shared pool in Marathon

Marathon villa

3 bedrooms • 3 bathrooms • sleeps 8

from £308 / night

£2,157 / week

1 / 78

Holiday home in Cudjoe Key

Cudjoe Key house

3 bedrooms • 2 bathrooms • sleeps 6

from £88 / night

£617 / week

1 / 8

Holiday home in Little Torch Key

Little Torch Key house

2 bedrooms • 1 bathroom • sleeps 4

from £75 / night

£525 / week

1 / 12

Holiday apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 4

from £100 / night

£700 / week

1 / 22

Holiday home in Little Torch Key

Little Torch Key house

3 bedrooms • 2 bathrooms • sleeps 6

from £118 / night

£825 / week

1 / 8

Home rental in Summerland Key

Summerland Key house

2 bedrooms • 2 bathrooms • sleeps 6

from £117 / night

£816 / week

1 / 14

Holiday home with golf nearby in Marathon

Marathon house

4 bedrooms • 3 bathrooms • sleeps 10

from £541 / night

£3,784 / week

1 / 29

Holiday home in Big Pine Key

Big Pine Key house

2 bedrooms • 1 bathroom • sleeps 4

from £87 / night

£604 / week

1 / 16

Holiday condo in Marathon

Marathon condo

1 bedroom • 2 bathrooms • sleeps 4

from £195 / night

£1,365 / week

1 / 13

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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 View Penthouse
A fabulous apartment in a great location

This is a fabulous apartment in an excellent area with lovely views of the ocean. Joe is so friendly and helpful. Had a wonderful holiday here and would highly recommend to anyone staying in the Keys. … see more
OCEANFRONT CONDO WITH ALL AMMENITIES!
Condo Stay

Condo is in an excellent location, clean and all amenities needed for a stay. Kim the owner is super responsive. The view is perfect from the patio window. Its family friendly and also has a great pool too with a bar. We also went to the marina to fish and the beach is small but lots of space. You can snorkel too. The only let down for us, and it is not the condo and the owners, more the site Ocean Pointe itself, is the visible sight of plastic waste around the back of the complex, on the paths and down by the ocean. If they spent a day or so cleaning this up it would makes a massive difference. Also there are a tonne of stray cats that could be removed. Like we said, the condo and the owners are great and we had a great stay and wold stay again.see more
Captain Rons Tropical Vacation Hideaway
THE place to stay in the keys if you like peace and quiet!

Captain Rons Tropical Vacation Hideaway is only 30 miles to Key West, but worlds away from the crowds. The home is very clean and comfortable. Captain Ron made the whole process simple and painless. I would without hesitation stay here again and recommend this home to anyone looking to stay in the Keys! 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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