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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

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$107

1 / 21

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / Sleeps 10

$785

1 / 29

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

Islamorada house

5 bedrooms / 6 bathrooms / Sleeps 12

$714

1 / 32

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / Sleeps 6

$229

1 / 21

4 Bedroom Main House

Islamorada house

4 bedrooms / 2 bathrooms / Sleeps 8

$540

1 / 10

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$300

1 / 25

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 8

$198

1 / 25

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$77

1 / 24

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / Sleeps 6

$279

1 / 25

PALMS 201

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$127

1 / 16

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

$1,500

1 / 21

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$257

1 / 16

Executive Bay G5

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$100

1 / 35

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'

$171

1 / 39

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$421

1 / 24

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

Islamorada villa

1 bedroom / 1 bathroom / Sleeps 3

$125

1 / 22

PALMS 417

Islamorada apartment

1 bedroom / 2 bathrooms / Sleeps 4

“Paradise on the ocean” We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay side with amazing sunsets. P

$67

1 / 25

RIOLO VILLA

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

$117

1 / 25

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

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 4

$146

1 / 19

LITTLE BAY - Lower Duplex

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

“Beautiful House in the heart of Islamorada” My kids and I stayed on the property and rented the lower duplex. We had an amazing time and the dock for our boat was perfect. The kids and I went paddleboarding right off the back of our house and the dog

$357

1 / 23

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$147

1 / 25

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$143

1 / 9

Luxury 3 BR condo, boatslip, easy accces to ocean

Islamorada condo

3 bedrooms / 6 bathrooms / Sleeps 8

$300

1 / 20

MATECUMBE JEWEL

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 6

“Our Lobster Trip to the Keys” My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could not have asked for better accomodations wh

$150

1 / 25

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$100

1 / 25

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 6

$264

1 / 20

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$300

1 / 24

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$142

1 / 18

Private home and boat dock oceanside gated community

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$371

1 / 26

SUNSHINE PLACE

Islamorada villa

1 bedroom / 1 bathroom / Sleeps 3

“a jewel worth the search” Dog friendly, spacious location for relaxing or as a base for exploring the upper/middle keys. The property is shoehorned between two resorts, but surprising quiet and even secluded, in a way. Plenty of people-watching avai

$157

1 / 23

LITTLE BAY - Upper Duplex

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

“Classic Islamorada - Amazing Property” Little Bay was a perfect property for us! The setting is idyllic and classic keys - Huge backyard on the Bay with excellent dock area, hammocks and view of the bay. Covered porch was the full width of the house

$357

1 / 25

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / Sleeps 8

$10

1 / 16

141 Ocean Lane

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 6

$183

1 / 24

100' Private Beach Front Ocean Front Estate

Islamorada house

4 bedrooms / 4 bathrooms / Sleeps 12

$1,000

1 / 43

WEST LAKE PLAZA

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 5

$133

1 / 23

**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

$145

1 / 25

BEACON REEF 501

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$110

1 / 25
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