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

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North America Holidays
208220 properties
United States Holidays
163455 properties
Florida Holidays
49107 properties
Villas Key Largo
239 properties
Villas Key West
221 properties
Sugarloaf Key
206 properties
Estates Marathon
148 properties
Holiday rentals Islamorada
148 properties
Key Colony Beach
65 properties
Stock Island
49 properties
Lower Keys
36 properties
Big Pine Key
23 properties
Cudjoe Key
21 properties
Long Key
17 properties
Ramrod Key
13 properties
Matecumbe Key
10 properties
Villas Duck Key
6 properties
Cottages Sugarloaf
5 properties

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1,216 Holiday homes

33

Holiday apartment rental

Key Largo / Tavernier

6 18 min stay varies

  • 6 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £379 / night

£2,649 / week

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from £379 / night

(7) 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 £363 / night

£2,542 - £3,061 / week

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from £363 / night

(14) Very Good 

15

Key Largo - condo with a very good review rating | wi-fi & sauna | walking holidays

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 £149 / night

£753 / week

Enquire View

from £149 / night

31

Key Largo 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 £398 / night

£2,780 / week

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from £398 / night

34

Apartment in Key Largo with sea view | beach or lakeside relaxation, water sports & fishing | From £244/night

Florida Keys / Key Largo

4 12 min stay varies

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

from £244 / night

£1,707 / week

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from £244 / night

(2) Very Good 

31

Holiday accommodation in Tavernier with great reviews | air conditioning, wi-fi | tennis in town

Key Largo / Tavernier

4 12 min stay varies

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

from £244 / night

£1,707 / week

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from £244 / night

(1) Excellent 

27

Private house with 2 bedrooms in Marathon Shores | air conditioning, wi-fi and more

Marathon / Marathon Shores

2 7 7 nights min

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

from £142 / night

£990 / week

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Responds fast!
avg. 54 minutes

from £142 / night

15

Yacht in Stock Island with solarium / roof terrace from £191/night - Perfect for water sports, fishing & city breaks

Florida Keys / Stock Island

4 10 2 nights min

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

from £191 / night

£1,338 / week

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Responds fast!
avg. 1 hour 30 minutes

from £191 / night

31

Enjoy water sports and tennis in town in Tavernier at this apartment from £114/night

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

(1) Excellent 

19

Fantastic rental in Key West, Florida Keys - Great for water sports and fishing | sea view

Florida Keys / Key West

2 6 2 nights min

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

from £172 / night

£1,204 / week

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Responds fast!
avg. 1 hour 30 minutes

from £172 / night

32

Grab a bargain holiday rental in Key Largo | Holiday condo from £57/night | Sleeps 2

Florida Keys / Key Largo

1 2 28 nights min

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

from £58 / night

£402 / week

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Responds fast!
avg. 21 minutes

from £58 / night

(4) Very Good 

41

Holiday rental in Islamorada with beach / lakeside relaxation, swimming pool, swimming pool

Florida Keys / Islamorada

3 6 14 nights min

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

from £151 / night

£1,052 - £1,584 / week

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from £151 / night

31

Experience a home from home at this apartment in Key Largo | wi-fi & balcony / terrace

Florida Keys / Key Largo

2 6 min stay varies

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

from £122 / night

£851 / week

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from £122 / night

(30) Excellent 

31

Top rated holiday houseboat in Key West | pet friendly | Sleeps 10 | child friendly

Florida Keys / Key West

4 10 min stay varies

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

from £306 / night

£2,140 / week

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Responds fast!
avg. 1 hour 30 minutes

from £306 / night

(3)  

30

Holiday apartment with 2 bedrooms and sea view 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 £122 / night

£851 / week

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from £122 / night

29

Affordable house rental in Florida Keys – 2 bedrooms from £106/night

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

39

Tavernier self-catering apartment from £136/night. Pet friendly with air conditioning / tennis in town

Key Largo / Tavernier

1 4 min stay varies

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

from £136 / night

£875 - £2,527 / week

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Responds fast!
avg. 2 hours 56 minutes

from £136 / night

48

Comfortable apartment in Key Largo. Sleeps 6 in Tavernier

Key Largo / Tavernier

2 6 min stay varies

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

from £149 / night

£957 - £2,856 / week

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Responds fast!
avg. 2 hours 56 minutes

from £149 / night

40

Apartment with 2 bedrooms in Tavernier, Key Largo | swimming pool, balcony / terrace & air conditioning

Key Largo / Tavernier

2 6 min stay varies

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

from £136 / night

£875 - £2,609 / week

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Responds fast!
avg. 2 hours 56 minutes

from £136 / night

11

Child friendly accommodation in Sugarloaf with balcony / terrace, sleeps 9, fishing

Florida Keys / Sugarloaf

5 9 28 nights min

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

from £216 / night

£1,509 / week

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from £216 / night

36

Holiday apartment in Tavernier, Key Largo, from £124/night. With air conditioning, balcony / terrace and much more!

Key Largo / Tavernier

1 4 min stay varies

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

from £125 / night

£800 - £2,358 / week

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Responds fast!
avg. 2 hours 56 minutes

from £125 / night

48

Apartment rental in Tavernier with swimming pool, air conditioning, tennis in town from £149/night

Key Largo / Tavernier

2 6 min stay varies

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

from £149 / night

£957 - £2,856 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £149 / night

44

Stay at this apartment in Tavernier with swimming pool, balcony / terrace & air conditioning from £136/night

Key Largo / Tavernier

2 6 min stay varies

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

from £136 / night

£875 - £2,609 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £136 / night

39

Tavernier apartment great for tennis in town, air conditioning from £136/night

Key Largo / Tavernier

1 4 min stay varies

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

from £136 / night

£875 - £2,527 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £136 / night

37

Apartment in Tavernier from £124/night | 1 bedroom, sleeps 4

Key Largo / Tavernier

1 4 min stay varies

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

from £125 / night

£800 - £2,358 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £125 / night

44

2 bedroom apartment in Tavernier from £135/night | bbq & swimming pool

Key Largo / Tavernier

2 6 min stay varies

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

from £135 / night

£869 - £2,592 / week

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Responds fast!
avg. 1 hour 38 minutes

from £135 / night

39

2 bedroom accommodation in Tavernier

Key Largo / Tavernier

2 6 min stay varies

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

from £136 / night

£875 - £2,609 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £136 / night

37

Ideal apartment in Tavernier from £124/night | 1 bedroom, sleeps 4

Key Largo / Tavernier

1 4 min stay varies

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

from £125 / night

£800 - £2,358 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £125 / night

13

Key West holiday yacht rental

Florida Keys / Key West

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning

from £1,444 / night

£8,508 - £10,634 / week

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from £1,444 / night

38

Apartment in Tavernier with sea view - from £136/night

Key Largo / Tavernier

1 4 min stay varies

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

from £136 / night

£875 - £2,527 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £136 / night

44

Self-catering holiday rental in Tavernier, Key Largo | sea view and swimming pool - pet friendly property

Key Largo / Tavernier

2 6 min stay varies

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

from £148 / night

£951 - £2,856 / week

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Responds fast!
avg. 2 hours 56 minutes

from £148 / night

39

Apartment with air conditioning, bbq, sea view & more in Tavernier

Key Largo / Tavernier

1 4 min stay varies

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

from £135 / night

£869 - £2,510 / week

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Responds fast!
avg. 1 hour 38 minutes

from £135 / night

38

Holiday rental in Tavernier from £124/night. Sleeps 4, 1 bedroom

Key Largo / Tavernier

1 4 min stay varies

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

from £125 / night

£800 - £2,358 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £125 / night

47

Apartment in Tavernier with bbq from £149/night - Great for walking holidays

Key Largo / Tavernier

2 6 min stay varies

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

from £149 / night

£957 - £2,856 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £149 / night

(48) Very Good 

Certificate of Excellence

17

Apartment in Key West that has earned great reviews from travellers from £198/night - Perfect for walking holidays

Florida Keys / Key West

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary

Certificate of Excellence

from £198 / night

£1,386 / week

Book View

Responds fast!
avg. 2 hours 39 minutes

from £198 / night

(5) Excellent 

36

Escape to Key Largo, Florida Keys in this beautiful holiday apartment | Sleeps 6, 2 bedrooms

Florida Keys / Key Largo

2 6 6 nights min

  • 2 bedrooms
  • sleeps 6
  • 6 nights min
  • Child friendly

from £126 / night

£874 - £1,140 / week

Book View

from £126 / night

20

Islamorada holiday apartment rental

Florida Keys / Islamorada

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary

from £190 / night

£1,173 / week

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from £190 / night

(63) Very Good 

Certificate of Excellence

11

Certificate of Excellence apartment in Key West with swimming pool and air conditioning - beach / lakeside relaxation

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 £252 / night

£1,761 / week

Book View

Responds fast!
avg. 2 hours 39 minutes

from £252 / night

(33) Excellent 

Certificate of Excellence

17

Amazing apartment in Key West from £213/night | wi-fi, air conditioning & bbq

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

£1,493 / week

Book View

Responds fast!
avg. 2 hours 39 minutes

from £214 / night

(1) Excellent 

8

Self-catering house in Marathon with satellite tv & air conditioning - Great for beach or lakeside relaxation

Florida Keys / Marathon

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Air conditioning

from £191 / night

£914 / week

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Responds fast!
avg. 2 hours 37 minutes

from £191 / 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