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

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North America Holidays
193554 properties
United States Holidays
149097 properties
Florida Holidays
42192 properties
Villas Key Largo
235 properties
Villas Key West
233 properties
Sugarloaf Key
209 properties
Holiday rentals Islamorada
143 properties
Estates Marathon
137 properties
Key Colony Beach
62 properties
Stock Island
42 properties
Lower Keys
31 properties
Cudjoe Key
21 properties
Long Key
21 properties
Big Pine Key
19 properties
Ramrod Key
13 properties
Matecumbe Key
8 properties
Cottages Sugarloaf
5 properties

Florida Keys

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1,190 Holiday homes

(1) Very Good 

24

Holiday apartment in Tavernier

Key Largo / Tavernier

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £244 / night

£1,709 / week

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Booked 10+ times!

from £244 / night

27

Marathon Shores holiday home rental

Marathon / Marathon Shores

2 7 7 nights min

  • 2 bedrooms
  • sleeps 7
  • 7 nights min
  • Nearest beach 2 km
  • Child friendly
  • Air conditioning

from £141 / night

£982 / week

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Responds fast!
avg. 54 minutes

Booked 20+ times!

from £141 / night

32

Holiday condo in Key Largo

Florida Keys / Key Largo

1 2 28 nights min

  • 1 bedroom
  • sleeps 2
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £57 / night

£398 / week

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Responds fast!
avg. 21 minutes

from £57 / night

(3) Very Good 

41

Holiday apartment in Islamorada

Florida Keys / Islamorada

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £150 / night

£1,050 - £1,581 / week

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Booked 5 times

from £150 / night

(1) Excellent 

17

Yacht rental in Key West

Florida Keys / Key West

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £182 / night

£1,274 / week

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Responds fast!
avg. 1 hour 2 minutes

Booked 100+ times!

from £182 / night

(6) Excellent 

29

Marathon Shores holiday home rental

Marathon / Marathon Shores

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 8 km
  • Child friendly
  • Air conditioning

from £359 / night

£2,511 - £3,023 / week

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Booked 20+ times!

from £359 / night

22

Holiday apartment rental

Florida Keys / Key Largo

6 18 min stay varies

  • 6 bedrooms
  • sleeps 18
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £379 / night

£2,649 / week

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Booked 4 times

from £379 / night

29

Key Largo holiday home rental

Florida Keys / Key Largo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Swimming pool

from £106 / night

£637 - £1,621 / week

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from £106 / night

(1) Very Good 

21

Holiday apartment in Tavernier

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £121 / night

£844 / week

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Booked 8 times

from £121 / night

22

Holiday apartment with swimming pool in Key Largo

Florida Keys / Key Largo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £121 / night

£844 / week

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Booked 4 times

from £121 / night

(29) Excellent 

31

Key West holiday houseboat rental

Florida Keys / Key West

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £304 / night

£2,123 / week

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Responds fast!
avg. 1 hour 2 minutes

Booked 100+ times!

from £304 / night

24

Tavernier holiday apartment rental

Key Largo / Tavernier

6 18 1 night min

  • 6 bedrooms
  • sleeps 18
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £379 / night

£2,649 / week

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Booked 3 times

from £379 / night

(14) Very Good 

15

Holiday condo in Key Largo

Florida Keys / Key Largo

2 7 3 nights min

  • 2 bedrooms
  • sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“Excellent Stay in Key Largo” As regular visitors to the Florida Keys we have stayed in this Apartment many times and have found it to be a great place for relaxing as it has brilliant outside facilities within the complex, including Boat docking, swimming pool, tennis courts,communial indoor area and barbecue area. The Apartment was clean and functional and being in B building, away from any Road noise, it also has easy access to all the complex facilities. Moon Bay is within easy reach of many good Restaurants and Bars. We loved it so much we will be returning this December if Available.

from £148 / night

£747 / week

Enquire View

from £148 / night

27

Holiday apartment with swimming pool in Key Largo

Florida Keys / Key Largo

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £242 / night

£1,693 / week

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from £242 / night

22

Holiday apartment in Tavernier

Key Largo / Tavernier

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £114 / night

£798 / week

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from £114 / night

38

Holiday apartment in Tavernier

Key Largo / Tavernier

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £125 / night

£803 - £2,367 / week

Book View

from £125 / night

37

Apartment letting in Tavernier

Key Largo / Tavernier

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £125 / night

£803 - £2,367 / week

Book View

from £125 / night

39

Holiday apartment in Tavernier

Key Largo / Tavernier

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £137 / night

£879 - £2,537 / week

Book View

from £137 / night

36

Holiday apartment in Tavernier

Key Largo / Tavernier

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £125 / night

£803 - £2,367 / week

Book View

from £125 / night

48

Tavernier holiday apartment rental

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £150 / night

£960 - £2,867 / week

Book View

from £150 / night

38

Holiday apartment in Tavernier

Key Largo / Tavernier

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £138 / night

£886 - £2,557 / week

Book View

from £138 / night

44

Holiday apartment in Tavernier

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £150 / night

£962 - £2,889 / week

Book View

from £150 / night

37

Holiday apartment in Tavernier

Key Largo / Tavernier

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £126 / night

£810 - £2,386 / week

Book View

from £126 / night

39

Tavernier holiday apartment rental

Key Largo / Tavernier

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £137 / night

£879 - £2,537 / week

Book View

from £137 / night

40

Holiday apartment in Tavernier

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £137 / night

£879 - £2,619 / week

Book View

from £137 / night

39

Holiday apartment in Tavernier

Key Largo / Tavernier

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £137 / night

£879 - £2,537 / week

Book View

from £137 / night

39

Holiday apartment in Tavernier

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £137 / night

£878 - £2,618 / week

Book View

from £137 / night

44

Tavernier holiday apartment rental

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £137 / night

£879 - £2,619 / week

Book View

from £137 / night

47

Holiday apartment in Tavernier

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £150 / night

£960 - £2,867 / week

Book View

from £150 / night

48

Holiday apartment in Tavernier

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £150 / night

£960 - £2,867 / week

Book View

from £150 / night

11

Holiday home in Sugarloaf

Florida Keys / Sugarloaf

5 9 28 nights min

  • 5 bedrooms
  • sleeps 9
  • 28 nights min
  • Child friendly
  • Pet friendly

from £214 / night

£1,497 / week

Book View

Booked 3 times

from £214 / night

44

Holiday apartment in Tavernier

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £137 / night

£879 - £2,619 / week

Book View

from £137 / night

(59) Very Good 

Certificate of Excellence

11

Apartment rental in Key West

Florida Keys / Key West

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary

Certificate of Excellence

from £250 / night

£1,746 / week

Book View

Booked 150+ times!

from £250 / night

(30) Very Good 

Certificate of Excellence

17

Holiday apartment in Key West

Florida Keys / Key West

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

Certificate of Excellence

from £214 / night

£1,494 / week

Book View

Booked 100+ times!

from £214 / night

(2) Excellent 

22

Holiday home letting

Florida Keys / Marathon

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 2 km
  • Swimming pool
  • Child friendly

from £345 / night

£2,295 / week

Book View

from £345 / night

(7) Very Good 

26

Holiday home in Sugarloaf Key

Florida Keys / Sugarloaf Key

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from £169 / night

£1,178 / week

Book View

from £169 / night

30

Home rental in Tavernier

Key Largo / Tavernier

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning

from £96 / night

£670 / week

Book View

from £96 / night

(28) Very Good 

Certificate of Excellence

12

Holiday apartment in Key West

Florida Keys / Key West

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 2 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £122 / night

£842 - £2,137 / week

Book View

Booked 100+ times!

from £122 / night

(4) Excellent 

45

Holiday home in Marathon

Florida Keys / Marathon

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £417 / night

£3,715 - £3,954 / week

Book View

Responds fast!
avg. 17 minutes

Booked 50+ times!

from £417 / night

44

Holiday home in Sugarloaf Key

Florida Keys / Sugarloaf Key

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from £117 / night

£814 / week

Book View

Booked 4 times

from £117 / night

Top Destination reviews

OCEANFRONT CONDO WITH ALL AMMENITIES!
Great place

We had 5 days at Ocean Pointe in the apartment which had great views of the ocean. Apartment was clean, comfortable, well equipped and a good size. Ideally situated for exploring the keys. Amenities on site were good. Recommendations on food establishments were good. Could easily have stayed longer and made more use of on site amenities but we're keen to explore the area first and foremost. .see more
Luxurious 3bd/3bth Villa - Your Keys Escape
Marathon memories

We had a great stay at the property we rented in Marathon. It was extremely well equipped with everything we needed for our week. My sister and I were most impressed with the amount of Tupperware, which is always a must with 4 children! The house had plenty of room for two families. The pool was lovely, with shade in the afternoon so not too hot/exposed. We loved to walk down to the end, by the moorings to see the fish & birds. The only downside was the water pressure in 2 of the showers, but there was a third so we used this. It was also a bit of a squeeze to get 8 around the table on the balcony but there was always plenty of space upstairs on the roof, with fabulous views. We loved Marathon-Sombrero beach was our favourite.see more
LAST MINUTE DISCOUNT! 48' Sailing Yacht. Other Yachts & Boats Available!
Great location and boat!

First time for us renting a boat and previous reviews proved accurate. Location in marina at end of pier was nice. Arranged for a captain to take us out for one day (at additional fee) which was a great way to spend a day enjoying the ocean and sun. Tim and Ray very helpful and easy to work with from start to finish. Marina had a nice pool and restaurant. Would recommend using shower facilities at the Marina since boat shower facility very small. Would enjoy doing it again someday.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
KeyWestStay.com
Very good property well placed for Key West

Stopped for two nights. Property just off US1 so easy to reach Key West. However some road noise but really only noticeable on the larger deck. Clean and reasonably well equipped although could do with a few more mugs and Brits would appreciate a kettle. Good communication from owner directions etc. Bobalus bar restaurant in walking distance. Nearest shop at Mobil station had no milk. Publix supermarket an easy drive to Key West along with many restaurants. see more
THIS IS IT! Magnificent Oceanfront Paradise! WE ARE OPEN!!
A great view

Great flat. The photos of the balcony do not do it justice. Ideal situation for seeing the Keys. The apartment was comfortable and well equipped. … see more