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Islamorada Rentals

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Islamorada Rentals

158 house rentals

Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$125

1 / 14

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / Sleeps 6

$228

1 / 21

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom / 1 bathroom / Sleeps 4

$174

1 / 9

BAYSIDE CONDO MARINA,POOL,TENNIS AND DOCKAGE

Islamorada apartment

3 bedrooms / 2 bathrooms / Sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I'

$170

1 / 39

Futura Yacht Club Bay View Condo with 36' Deeded Boat Slip (Min. 28 Day Rental)

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$142

1 / 9

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$298

1 / 25

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / Sleeps 6

$277

1 / 25

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$256

1 / 16

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

$117

1 / 19

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / Sleeps 10

$780

1 / 29

Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$418

1 / 24

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 4

$145

1 / 19

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$249

1 / 20

Florida Keys Beautiful 2B 2B Townhouse

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

$259

1 / 18

THIS IS IT! Magnificent Oceanfront Paradise! WE ARE OPEN!!

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$141

1 / 18

4 Bedroom Main House

Islamorada house

4 bedrooms / 2 bathrooms / Sleeps 8

$537

1 / 10

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 5

$128

1 / 15

FLORIDA KEYS OASIS - The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****

Islamorada house

5 bedrooms / 6 bathrooms / Sleeps 12

$709

1 / 32

BEAUTIFUL BAY HARBOUR CONDO W/ BOAT DOCK!

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 8

$355

1 / 14

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 6

$263

1 / 20

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 8

$198

1 / 25

Keys home in Anglers Reef with ocean view, dock, community pool & private beach

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$298

1 / 24

111 Bayview Isle

Islamorada house

4 bedrooms / 5 bathrooms / Sleeps 8

$232

1 / 22

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

$1,490

1 / 21

**Spring Discount** Modern Executive Bay Club Condo with Pool & Beach

Islamorada apartment

3 bedrooms / 2 bathrooms / Sleeps 8

“Great condo, perfect location!” I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and very friendly. The location was close t

$129

1 / 25

Serenity Waterfront-Dock, View, Tiki Hut, spa/hot

Islamorada villa

1 bedroom / 1 bathroom / Sleeps 3

$125

1 / 22

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$77

1 / 24

Oceanfront 5th Floor End Unit, Pool, Free WiFi, Panoramic Ocean Views

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 4

$135

1 / 21

**Spring Discount** Family Friendly Executive Bay Townhome with Beach & Pool

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 6

“So much more than expected” I had been here before their renovations (when it was only a 2 bedroom) and it was great. Now that there are 3 bedrooms, it is so much more convenient when staying with another family. This place has tons of space, is welco

$100

1 / 25

Private home and boat dock oceanside gated community

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$369

1 / 26

Seaside Sanctuary 5 Bedroom Private Pool Home with dockage

Islamorada house

5 bedrooms / 5 bathrooms / Sleeps 16

$709

1 / 15

BEACON REEF 501

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$110

1 / 25

PALMS 201

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$127

1 / 16

Manatee Bay

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$227

1 / 20

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$226

1 / 14

Luxury 3 BR condo, boatslip, easy accces to ocean

Islamorada condo

3 bedrooms / 6 bathrooms / Sleeps 8

$298

1 / 20

Executive Bay G5

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$100

1 / 35

Islamorada Tropical Canalfront Paradise

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

$220

1 / 13
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