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Holiday rentals in Islamorada and Villas - Holiday Lettings - Holiday Rentals Islamorada

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291 Holiday homes

Holiday apartment in Islamorada

Islamorada apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £196 / night

£1,371 - £1,953 / week

1 / 32

Islamorada holiday home rental

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

“Very good and wonderfully relaxing” Only one thing could be changed. The beach needs to be cleaned from time to time , we do realize it is nature with the seaweed but it becomes a bit smelly. But the rest is a 10!!!

from £892 / night

£5,829 - £7,078 / week

1 / 32

Holiday home in Islamorada

Islamorada house

3 bedrooms • 3 bathrooms • sleeps 8

from £1,256 / night

£8,792 / week

1 / 21

Apartment rental in Islamorada

Islamorada apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £210 / night

£1,297 / week

1 / 20

Holiday apartment in Islamorada

Islamorada apartment

1 bedroom • 1 bathroom • sleeps 4

from £146 / night

£1,020 / week

1 / 10

Islamorada holiday home rental

Islamorada house

4 bedrooms • 3 bathrooms • sleeps 8

from £239 / night

£1,666 - £2,290 / week

1 / 35

Islamorada holiday home rental

Islamorada house

3 bedrooms • 2 bathrooms • sleeps 8

from £320 / night

£2,234 / week

1 / 43

Islamorada holiday condo let

Islamorada condo

2 bedrooms • 2 bathrooms • sleeps 6

from £152 / night

£1,118 / week

1 / 23

Holiday apartment in Islamorada

Islamorada apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £90 / night

£628 / week

1 / 21

Islamorada holiday home rental

Islamorada house

2 bedrooms • 2 bathrooms • sleeps 4

from £114 / night

£791 - £1,249 / week

1 / 13

Home rental in Islamorada

Islamorada house

2 bedrooms • 2 bathrooms • sleeps 4

“Great location and view” While the location and view at this house were spectacular, the house itself needs some TLC. The outdoor furniture needs replacing and the purchase of a grill would enhance the experience greatly. Since the outdoor spaces are so great for enjoying the view, the comfort of some adequate seating would be welcomed. The bed was very comfy in the master and to sleep hearing the waves roll in was awesome. The baths are ok, but could also use a little work- ceiling tiles falling down, etc. It is conveniently located to everything without being in the midst of it all. Love Islamorada! Will come back again especially for the fishing and the great restaurants. Might want to experience a rental bayside next time just to change up the view from sunrise to sunset! Overall, we had a great trip and the house fit our needs. A couple with two kids would easily find this place doable.

from £238 / night

£1,666 - £2,249 / week

1 / 18

Holiday home accommodation

Islamorada house

2 bedrooms • 3 bathrooms • sleeps 6

from £252 / night

£1,765 / week

1 / 25

Holiday home rental

Islamorada house

2 bedrooms • 2 bathrooms • sleeps 5

from £63 / night

£437 / week

1 / 25

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 £187 / night

£1,309 / week

1 / 28

Holiday home with swimming pool in Islamorada

Islamorada house

4 bedrooms • 3 bathrooms • sleeps 10

from £213 / night

£1,485 / week

1 / 25

Islamorada holiday condo rental

Islamorada condo

2 bedrooms • 2 bathrooms • sleeps 4

from £141 / night

£987 / week

1 / 40

Holiday home letting

Islamorada house

2 bedrooms • 3 bathrooms • sleeps 6

from £84 / night

£583 / week

1 / 35

Holiday home in Islamorada

Islamorada house

3 bedrooms • 3 bathrooms • sleeps 8

“Awesome Summer Family Vacation” After hours and hours of surfing the internet to only find that places were unavailable or no one would return your calls I stumbled on Venetian Tropics. What a blessing. The owner actually called me right back. We rented the house for a week. Everything was great. We fished and snorkeled everyday. We caught Mahi Mahi, Wahoo, King Mackerel, and still have some in our freezer. Sure beats a hotel. Hope to return again soon. The property manager was very pleasant as well.

from £487 / night

£3,403 / week

1 / 38

Holiday home in Islamorada

Islamorada house

3 bedrooms • 2 bathrooms • sleeps 6

from £275 / night

£2,082 - £2,498 / week

1 / 36

Holiday apartment rental

Islamorada apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £166 / night

£1,160 - £1,670 / week

1 / 25

Islamorada holiday home rental

Islamorada house

5 bedrooms • 6 bathrooms • sleeps 12

from £4,497 / night

£31,478 - £58,292 / week

1 / 44

Islamorada holiday villa rental

Islamorada villa

2 bedrooms • 2 bathrooms • sleeps 6

from £312 / night

£2,182 / week

1 / 25

Holiday condo in Islamorada

Islamorada condo

1 bedroom • 1 bathroom • sleeps 5

from £108 / night

£752 / week

1 / 15

Holiday home in Islamorada

Islamorada house

3 bedrooms • 3 bathrooms • sleeps 6

from £286 / night

£1,999 - £2,665 / week

1 / 34

Holiday apartment rental

Islamorada apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £59 / night

£408 / week

1 / 25

Home rental in Islamorada with shared pool

Islamorada house

5 bedrooms • 3 bathrooms • sleeps 10

from £714 / night

£4,747 - £5,996 / week

1 / 29

Holiday home with swimming pool in Islamorada

Islamorada house

2 bedrooms • 2 bathrooms • sleeps 6

from £85 / night

£594 / week

1 / 22

Holiday home in Islamorada

Islamorada house

2 bedrooms • 2 bathrooms • sleeps 6

from £374 / night

£2,618 / week

1 / 29

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 £114 / night

£795 - £1,339 / week

1 / 35

Islamorada holiday home rental

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

from £419 / night

£3,349 / week

1 / 21

Islamorada holiday villa rental

Islamorada villa

2 bedrooms • 2 bathrooms • sleeps 6

from £312 / night

£2,182 / week

1 / 23

Holiday home in Islamorada

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

from £417 / night

£4,664 / week

1 / 22

Islamorada holiday condo rental

Islamorada condo

3 bedrooms • 3 bathrooms • sleeps 6

from £225 / night

£1,574 / week

1 / 20

Holiday home in Islamorada

Islamorada house

3 bedrooms • 3 bathrooms • sleeps 4

from £153 / night

£1,067 / week

1 / 22

Islamorada holiday villa rental

Islamorada villa

2 bedrooms • 2 bathrooms • sleeps 6

from £312 / night

£2,182 / week

1 / 24

Holiday home in Islamorada

Islamorada house

2 bedrooms • 2 bathrooms • sleeps 4

from £92 / night

£642 / week

1 / 22

Holiday home in Islamorada

Islamorada house

3 bedrooms • 3 bathrooms • sleeps 6

from £239 / night

£1,666 - £2,290 / week

1 / 30

Holiday home in Islamorada

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

from £1,004 / night

£7,028 - £9,204 / week

1 / 46

Islamorada holiday villa rental

Islamorada villa

1 bedroom • 1 bathroom • sleeps 3

from £141 / night

£982 - £1,235 / week

1 / 23

Holiday apartment in Islamorada

Islamorada apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £97 / night

£679 / week

1 / 25

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Islamorada holidays

Islamadora, or "Village of Islands", refers to the collection of islands in the Florida Keys including the Keys of Tea Table, Upper and Lower Matecumbe, Plantation, and Windley. Every destination in Islamadora offers access to the very best of this island paradise. The beautiful beaches, emerald golf courses, luxurious spas, and charming local museums in Islamadora make this the perfect place for a family holiday. Islamadora also offers easy access to Everglades National Park, an ecological destination that draws visitors from all over the world to see its dazzling biodiversity and elusive marine life. Come to Islamadora to play, explore, learn about the culture and history of the Florida Keys or simply relax. After the sun goes down, experience the world-class seafood restaurants and laid back vibe of Islamadora's night life.

Here are a few additional suggestions as you plan your trip:

  • Visit the Theatre of the Sea: This place is a Nature Center, aquarium, and theatre all rolled into one. Come here to learn about the marine ecosystems of the Florida Keys and interact with dolphins and sea lions.
  • Explore the wharf: Go fishing, rent a boat, or feed the gigantic tarpon at Robbie's marina. There are also sport fishing marinas in Islamadora where you can schedule charter trips and pursue large game like swordfish.
  • Visit the History of Diving Museum: The interactive displays and extraordinary collection of artefacts at the diving museum provide a great way to learn about maritime history and culture.
  • Take an eco-tour: Explore the Everglades National Park by boat, one of the best ways to see marine plants and animals in their natural habitats.
  • Play on the beach: Annie's Beach offers a clean stretch of beautiful white sand and blue ocean waves, perfect for a relaxing day with children. Go swimming, surfing, parasailing, rent a boat, or just sunbathe with a good book.
  • Visit the Windley Key Fossil Reef Geological State Park: This park is known for its hiking trails but more so for its incredible fossilised coral reefs.

Finding a place to stay will be easy in Islamadora, even if you arrive during the height of the summer. Find a quaint cottage for a romantic getaway, a summer home big enough for your whole family, or a luxury beach villa for you and some friends. No matter what you plan to do while you're here, you'll be able to find the perfect holiday rental to meet your needs.

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