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Watersports Holidays in Islamorada - Holiday Lettings

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31 properties with watersports onsite or nearby

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Islamorada holiday condo rental

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £184 / night

£1,283 / week

1 / 49

Holiday townhouse with shared pool in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £481 / night

£1,787 / week

1 / 51

Holiday condo rental

Islamorada condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Stay” The condo was very clean and updated! Glenn was very helpful with our stay. We even went fishing on the Reel Sharp and caught a ton of Dolphin! Us college girls will be coming again for Sailfishing season!

from £203 / night

£1,420 / week

1 / 35

Islamorada holiday home rental

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £481 / night

£1,787 / week

1 / 39

Holiday townhouse in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £481 / night

£1,787 / week

1 / 35

Holiday townhouse with shared pool in Islamorada

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £481 / night

£1,787 / week

1 / 31

Home rental in Lower Matecumbe Key

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £279 / night

£1,950 / week

1 / 41

Holiday townhouse with shared pool in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £481 / night

£1,787 / week

1 / 46

Townhouse accommodation in Islamorada with shared pool

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £527 / night

£1,970 / week

1 / 47

Townhouse rental in Islamorada with shared pool

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £527 / night

£1,970 / week

1 / 57

Villa rental in Islamorada

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £284 / night

£1,988 / week

1 / 25

Holiday condo in Islamorada

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £1,191 / night

£8,336 / week

1 / 4

Condo rental in Islamorada

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £126 / night

£882 / week

1 / 19

Holiday townhouse in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £163 / night

£1,136 / week

1 / 52

Holiday home in Islamorada

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £366 / night

£2,559 / week

1 / 2

Holiday home rental

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £302 / night

£2,110 / week

1 / 50

Holiday home in Islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

from £412 / night

£2,659 / week

1 / 42

Holiday condo in Islamorada

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £197 / night

£1,374 / week

1 / 26

Holiday home in Islamorada

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Paradise...” My husband and I were fortunate to find this amazing place to celebrate our 20th anniversary. The property is exactly as it's pictured...and better! It was immaculate, quaint, cozy and had absolutely everything we needed for our week long stay. The rental process was smooth and Ewa provided a detailed email in advance of our stay that was full of precise directions and a list of places and information we'd need to get our stay off on the right foot! The property offers the utmost in privacy and is incredibly peaceful with the most beautiful sunsets over the lagoon! My husband loved catching fish right off the dock and many of our evenings were spent lazily swinging in the hammocks. I would recommend this property to any couple and certainly hope to have the opportunity to visit again!

from £459 / night

£3,209 / week

1 / 28

Islamorada holiday home rental

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,177 / night

£8,244 / week

1 / 20

Holiday townhouse in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,420 / week

1 / 37

Islamorada holiday condo let

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £275 / night

£1,283 - £1,924 / week

1 / 23

Villa letting in Islamorada

Islamorada villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £916 / night

£6,412 / week

1 / 19

Holiday townhouse accommodation

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £129 / night

£898 / week

1 / 33

Home rental in Islamorada

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £326 / night

£2,283 / week

1 / 22

Holiday home in Islamorada

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £916 / night

£6,412 - £10,992 / week

1 / 34

Islamorada holiday townhouse accommodation

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £357 / night

£2,495 / week

1 / 34

Islamorada holiday condo rental

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £313 / night

£2,190 - £3,014 / week

1 / 20

Holiday home in Islamorada

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £413 / night

£2,886 / week

1 / 29

Holiday home in Islamorada

Islamorada house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,701 / night

£11,908 / week

1 / 36

Holiday home in Islamorada

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £229 / night

£1,603 / week

1 / 15

Great rentals within 20 miles that match your search

Home rental in Key Largo

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from £256 / night

£1,791 / week

1 / 15

Key Largo holiday apartment rental

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £184 / night

£1,284 / week

1 / 17

Holiday apartment in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £252 / night

£1,651 / week

1 / 34

Townhouse rental in Key Largo

Key Largo townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £550 / night

£3,847 / week

1 / 57

Townhouse rental in Key Largo with swimming pool

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £321 / night

£1,512 - £3,206 / week

1 / 17

Apartment accommodation in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £321 / night

£1,329 - £2,748 / week

1 / 16

Key Largo holiday apartment rental

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £170 / night

£1,017 - £1,374 / week

1 / 56

Key Largo holiday private room rental

Key Largo private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £115 / night

£687 - £880 / week

1 / 48

Key Largo holiday townhouse rental

Key Largo townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £321 / night

£1,329 - £2,748 / week

1 / 17

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