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Vacation Rentals & House Rentals in Islamorada

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31 house rentals

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 7 minutes

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Price per night from

$6,183

Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom / 1 bathroom / sleeps 2

“AMAZING!!!!!!!” Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips when we asked. The studio was so well stocked with all the essentials and then even the ones you forgot! It was wonderful to see a manatee swim up past the dock our first morning there. A very magical spot with generous hosts. It had everything we wanted and then some. After a week there and driving around the whole Keys it was 100% the most perfect choice for us. I miss those hammocks!

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Price per night from

$260

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$424

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$587

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$310

Gorgeous waterfront home

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$462

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$376

Beautiful Pool Home with Private Dock with Beach Access

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$401

Islamorada Florida Cozy Cottage

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 2 hours 8 minutes

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Price per night from

$327

Paradise at Islamorada

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$161

3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$274

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$285

Great rentals within 20 miles that match your search

1/1 with Living Room plus Oceanview

Tavernier guest house

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$165

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

Studio / 1 bathroom / sleeps 2

“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.

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Price per night from

$175

Beautiful Private Home with Beach Access.

Key Largo house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$58

Key Largo Beautiful House

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 27 minutes

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Price per night from

$289

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Price per night from

$211

Florida Keys Splendor at Hammer Point

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

“Winter Paradise!” My wife and I stayed at this great place in January 2014 and it was wonderful. It was very clean and well maintained. The canal was great to watch the fish jump and we saw Manatees almost every day. We especially liked the kayak and did a lot of site seeing from the ocean side. Migdy was great to work with and very accommodating. We would highly recommend this place to anyone.

Responds fast! avg. 3 hours 37 minutes

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Price per night from

$133

Sunrise Waterfront Home

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$288

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$287

Private Key Largo Bayside Canalfront home

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$168

Conch Life Haven

Key Largo apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$214

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$404

Cozy Couple Getaway! or Great Family Home

Key Largo house

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$104

Bayfront Vacation Home Villa Rental Bayside Beach View

Key Largo villa

2 bedrooms / 2 bathrooms / sleeps 6

“Lobster season trip” Beautiful villa had everything we needed and the location was perfect. We came to experience the lobster season. Brought our own boat once we found a public ramp at the Caribbean Club we were able dock our boat behind the villa and that made our boat trips so much easier. Absolutely loved Key Largo.

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Price per night from

$230

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$288

Tropical Getaway with Private Beach

Tavernier condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$251

The "Designated Paradise" - let this Bayside Estate take your breath away

Layton house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 7 minutes

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Price per night from

$4,580

Islamorada Waterfront Paradise | 5br | Dock | Pool

Tavernier house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 33 minutes

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Price per night from

$229

Comfortable Clean HouseBoat in an amazing location

Tavernier boathouse

1 bedroom / 2 bathrooms / sleeps 5

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Price per night from

$401

Key Largo Rental Fantastic Views

Key Largo condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 33 minutes

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Price per night from

$344

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