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Watersports Holidays in Florida Keys - Holiday Lettings

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290 properties with watersports onsite or nearby

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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 £85 / night

£596 - £1,890 / week

1 / 35

Apartment rental in Key West

Key West apartment

1 bedroom • 1 bathroom • sleeps 6

from £257 / night

£1,798 / week

1 / 17

Holiday apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 3

from £211 / night

£1,263 - £1,305 / week

1 / 66

Holiday yacht with shared pool in Key West

Key West yacht

3 bedrooms • 3 bathrooms • sleeps 7

from £1,460 / night

£9,445 / week

1 / 16

Ski home to rent in Marathon

Marathon house

3 bedrooms • 2 bathrooms • sleeps 6

from £387 / night

£2,706 / 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

£859 - £1,375 / 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 £387 / night

£2,706 / week

1 / 38

Key Largo holiday private room rental

Key Largo private room

1 bedroom • 1 bathroom • sleeps 2

from £91 / night

£542 / week

1 / 57

Holiday apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 4

from £103 / night

£722 / week

1 / 22

Holiday home with golf nearby in Marathon

Marathon house

4 bedrooms • 3 bathrooms • sleeps 10

from £559 / night

£3,909 / week

1 / 29

Holiday home rental

Key Colony Beach house

2 bedrooms • 2 bathrooms • sleeps 6

from £160 / night

£1,117 / week

1 / 25

Little Torch Key holiday cottage rental

Little Torch Key cottage

2 bedrooms • 1 bathroom • sleeps 6

from £213 / night

£1,492 / week

1 / 17

Holiday villa rental

Marathon Shores villa

2 bedrooms • 2 bathrooms • sleeps 6

from £370 / night

£2,577 / week

1 / 14

Islamorada holiday condo rental

Islamorada condo

2 bedrooms • 2 bathrooms • sleeps 4

from £146 / night

£1,017 / week

1 / 39

Holiday apartment with shared pool in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 4

from £68 / night

£475 / week

1 / 31

Home rental in Key Largo

Key Largo house

2 bedrooms • 1 bathroom • sleeps 4

from £228 / night

£1,366 - £1,450 / week

1 / 61

Duck Key holiday villa rental

Duck Key villa

2 bedrooms • 2 bathrooms • sleeps 6

from £354 / night

£2,478 / week

1 / 41

Holiday condo in Islamorada

Islamorada condo

1 bedroom • 1 bathroom • sleeps 5

from £111 / night

£776 / week

1 / 15

Holiday townhouse in Key Largo

Key Largo townhouse

2 bedrooms • 3 bathrooms • sleeps 6

from £344 / night

£1,976 / week

1 / 25

Holiday apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 4

from £103 / night

£722 / week

1 / 27

Condo rental in Key West

Key West condo

2 bedrooms • 1 bathroom • sleeps 4

from £295 / night

£2,063 / week

1 / 42

Islamorada holiday condo let

Islamorada condo

2 bedrooms • 2 bathrooms • sleeps 6

from £155 / night

£1,143 / week

1 / 23

Holiday home in Marathon

Marathon house

2 bedrooms • 2 bathrooms • sleeps 6

from £250 / night

£1,744 / week

1 / 27

Holiday apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 2

from £125 / night

£748 / week

1 / 48

Holiday home in Key Largo

Key Largo house

6 bedrooms • 5 bathrooms • sleeps 16

from £1,547 / night

£11,741 - £12,583 / week

1 / 90

Holiday apartment in Marathon Shores

Marathon Shores apartment

1 bedroom • 1 bathroom • sleeps 4

from £154 / night

£1,077 / week

1 / 28

Holiday boathouse in Tavernier

Tavernier boathouse

1 bedroom • 2 bathrooms • sleeps 5

from £301 / night

£2,105 / week

1 / 64

Home rental in Key Largo

Key Largo house

4 bedrooms • 4 bathrooms • sleeps 10

from £430 / night

£3,007 / week

1 / 38

Apartment rental in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 2

from £211 / night

£1,263 / week

1 / 62

Islamorada holiday townhouse accommodation

Islamorada townhouse

2 bedrooms • 3 bathrooms • sleeps 6

from £249 / night

£1,738 / week

1 / 34

Key Largo holiday home rental

Key Largo house

3 bedrooms • 2 bathrooms • sleeps 6

from £169 / night

£1,181 / week

1 / 29

Cudjoe Key holiday home rental

Cudjoe Key house

3 bedrooms • 2 bathrooms • sleeps 6

from £120 / night

£841 / week

1 / 12

Holiday apartment in Marathon Shores

Marathon Shores apartment

2 bedrooms • 2 bathrooms • sleeps 8

from £300 / night

£2,099 / week

1 / 28

Holiday apartment in Key West

Key West apartment

1 bedroom • 1 bathroom • sleeps 2

from £249 / night

£1,738 / week

1 / 16

Holiday home in Big Pine Key

Big Pine Key house

2 bedrooms • 2 bathrooms • sleeps 6

from £215 / night

£1,289 / week

1 / 19

Holiday townhouse rental

Islamorada townhouse

2 bedrooms • 2 bathrooms • sleeps 8

from £115 / night

£802 / week

1 / 38

Holiday apartment rental

Key Largo apartment

2 bedrooms • 2 bathrooms • sleeps 4

“Amazing Vacation!!!” This was our first time visiting the keys and we had such a good time. I'm not sure if it was beginners luck on choosing this condo but we honestly could have not imagined better. We had four total in our party as we went with my wife's parents. This vacation appealed to both of our age groups. The condo was very colorful and fun with it's decorations. The appliances were all top of the line and worked beautifully. We enjoyed the pool and other amenities the resort had to offer as well. There are plenty of local restraints with great reviews within just a few miles, as well as a grocery store if your the cook/grill it yourselfers. We had a blast snorkeling the reef and seeing the underwater Christ in the corals. Key west was only an he and a half drive and was fun as well. I would definatley recommend this condo to anybody looking to stay in the area. I don't currently have the pictures with me to download but please feel free to contact us if your interested. Happy Traveling

from £249 / night

£1,628 / week

1 / 36

Holiday home with indoor pool, golf nearby in Key Colony Beach

Key Colony Beach house

4 bedrooms • 3 bathrooms • sleeps 8

from £385 / night

£2,500 - £4,871 / week

1 / 38

Holiday home in Marathon

Marathon house

4 bedrooms • 5 bathrooms • sleeps 10

from £816 / night

£5,713 / week

1 / 47

Key West holiday condo rental

Key West condo

1 bedroom • 1 bathroom • sleeps 3

from £228 / night

£1,594 / week

1 / 26

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