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Family Friendly Holidays in Florida Keys - Holiday Lettings

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601 family friendly properties

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Holiday home in Big Pine Key

Big Pine Key house

3 bedrooms • 2 bathrooms • sleeps 13

from £344 / night

£2,405 / week

1 / 30

Islamorada holiday home rental

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

from £431 / night

£3,443 / week

1 / 21

Holiday apartment in Key Largo

Key Largo apartment

2 bedrooms • 1 bathroom • sleeps 6

from £302 / night

£1,807 / week

1 / 11

Marathon Shores holiday home rental

Marathon Shores house

2 bedrooms • 2 bathrooms • sleeps 7

from £237 / night

£1,657 / 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 £86 / night

£597 - £1,894 / week

1 / 35

Villa rental in Islamorada

Islamorada villa

2 bedrooms • 2 bathrooms • sleeps 6

from £229 / night

£1,416 - £1,862 / week

1 / 44

Apartment rental in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £232 / night

£1,621 / week

1 / 22

Apartment rental in Key West

Key West apartment

1 bedroom • 1 bathroom • sleeps 6

from £259 / night

£1,807 / week

1 / 17

Marathon Shores holiday home rental

Marathon Shores house

3 bedrooms • 2 bathrooms • sleeps 8

from £1,292 / night

£9,038 - £17,904 / week

1 / 50

Holiday apartment letting

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £389 / night

£2,448 / week

1 / 50

Holiday apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

“Fantastic Location” The location of this unit is fantastic! The parking is near the complex gate, the unit itself is directly across from the elevator. Easy access to the pool and grills. One of the best beaches in Key West is directly across the street. Ocean view and quite at night while being less than ten minutes from Duval Street & downtown. Will definitely visit again.

from £241 / night

£1,679 / week

1 / 17

Holiday apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 3

from £211 / night

£1,266 - £1,308 / 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 £1,468 / night

£10,273 - £10,877 / week

1 / 58

Holiday yacht with shared pool in Key West

Key West yacht

3 bedrooms • 3 bathrooms • sleeps 7

from £1,467 / night

£9,492 / week

1 / 16

Holiday condo in Islamorada

Islamorada condo

2 bedrooms • 2 bathrooms • sleeps 4

from £173 / night

£1,205 / 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 £925 / night

£6,043 - £7,338 / week

1 / 32

Home rental in Islamorada

Islamorada house

3 bedrooms • 2 bathrooms • sleeps 8

from £345 / night

£2,411 / week

1 / 15

Home rental in Tavernier

Tavernier house

2 bedrooms • 2 bathrooms • sleeps 6

from £130 / night

£904 / week

1 / 28

Ski home to rent in Marathon

Marathon house

3 bedrooms • 2 bathrooms • sleeps 6

from £388 / night

£2,712 / week

1 / 42

Holiday home in Marathon Shores

Marathon Shores house

3 bedrooms • 2 bathrooms • sleeps 8

from £259 / night

£1,808 / 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 £123 / night

£861 - £1,378 / 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 £389 / night

£2,720 / week

1 / 38

Holiday apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £394 / night

£2,754 / week

1 / 25

Matecumbe Key holiday home rental

Matecumbe Key house

2 bedrooms • 2 bathrooms • sleeps 4

from £186 / night

£1,252 - £1,900 / week

1 / 19

Key West holiday townhouse rental

Key West townhouse

2 bedrooms • 2 bathrooms • sleeps 4

from £296 / night

£2,066 / week

1 / 12

Home letting in Key Colony Beach with golf nearby

Key Colony Beach house

2 bedrooms • 2 bathrooms • sleeps 4

from £203 / night

£1,416 / week

1 / 86

Studio rental in Marathon

Marathon studio

Studio • 1 bathroom • sleeps 3

from £148 / night

£1,036 / week

1 / 9

Holiday home in Big Pine Key

Big Pine Key house

3 bedrooms • 3 bathrooms • sleeps 6

from £121 / night

£844 / week

1 / 17

Key West holiday apartment rental

Key West apartment

1 bedroom • 1 bathroom • sleeps 4

from £173 / night

£1,166 / week

1 / 69

Holiday villa with shared pool in Marathon

Marathon villa

3 bedrooms • 3 bathrooms • sleeps 8

from £320 / night

£2,236 / week

1 / 78

Holiday apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 4

from £104 / night

£726 / week

1 / 22

Home rental in Summerland Key

Summerland Key house

2 bedrooms • 2 bathrooms • sleeps 6

from £121 / night

£844 / week

1 / 14

Holiday home with golf nearby in Marathon

Marathon house

4 bedrooms • 3 bathrooms • sleeps 10

from £560 / night

£3,917 / week

1 / 29

Holiday condo in Marathon

Marathon condo

1 bedroom • 2 bathrooms • sleeps 4

from £203 / night

£1,421 / week

1 / 13

Home rental in Islamorada with shared pool

Islamorada house

5 bedrooms • 3 bathrooms • sleeps 10

from £740 / night

£4,921 - £6,216 / week

1 / 29

Holiday villa in Conch Key

Conch Key villa

1 bedroom • 1 bathroom • sleeps 3

from £142 / night

£840 / week

1 / 13

Holiday home rental

Key Colony Beach house

2 bedrooms • 2 bathrooms • sleeps 6

from £160 / night

£1,119 / week

1 / 25

Holiday home in Islamorada

Islamorada house

2 bedrooms • 2 bathrooms • sleeps 4

from £101 / night

£707 / week

1 / 37

Little Torch Key holiday cottage rental

Little Torch Key cottage

2 bedrooms • 1 bathroom • sleeps 6

from £214 / night

£1,499 / week

1 / 17

Holiday home in Tavernier

Tavernier house

3 bedrooms • 3 bathrooms • sleeps 12

from £155 / night

£1,085 / week

1 / 41

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