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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

$231

1 / 21

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$259

1 / 16

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$144

1 / 9

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

Islamorada house

5 bedrooms / 6 bathrooms / Sleeps 12

$720

1 / 32

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / Sleeps 10

$791

1 / 29

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

$1,500

1 / 21

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 6

$266

1 / 20

Luxury 3 BR condo, boatslip, easy accces to ocean

Islamorada condo

3 bedrooms / 6 bathrooms / Sleeps 8

$303

1 / 20

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / Sleeps 6

$281

1 / 25

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$143

1 / 18

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$107

1 / 21

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

Islamorada apartment

1 bedroom / 1 bathroom / Sleeps 4

$175

1 / 9

No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

$262

1 / 18

DEC & APRIL DEAL MONTH MINIMUM ENJOY! 9545791140

Islamorada apartment

3 bedrooms / 2 bathrooms / Sleeps 8

$132

1 / 30

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

$117

1 / 19

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

Islamorada villa

1 bedroom / 1 bathroom / Sleeps 3

$126

1 / 22

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$303

1 / 25

Seaside Sanctuary 5 Bedroom Private Pool Home with dockage

Islamorada house

5 bedrooms / 5 bathrooms / Sleeps 16

$720

1 / 15

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$424

1 / 24

**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

$101

1 / 25

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

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 4

$147

1 / 19

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 4

$137

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

$146

1 / 25

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$252

1 / 20

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'

$173

1 / 39

PALMS 201

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$127

1 / 16

BLUE WATER RETREAT

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

“Blue Water = Everything that you want” This place delivers. You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of all the hous

$185

1 / 26

WEST LAKE PLAZA

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 5

$134

1 / 23

MY PARADISE

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 6

“My Paradise from architect's perspective” My wife and I spend a month at My Paradise and, as an architect, there are certain aspects that bear mention. First, if the weather is mild, you can open the wall of folding glass doors and unite the main inte

$245

1 / 25

PALMS 301

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$74

1 / 24

100' Private Beach Front Ocean Front Estate

Islamorada house

4 bedrooms / 4 bathrooms / Sleeps 12

$1,008

1 / 43

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$303

1 / 24

THE PERFECT GETAWAY

Islamorada house

4 bedrooms / 3 bathrooms / Sleeps 10

“The owner was understanding and worked with us” I was scheduled to rent from Dec 29th to Jan 4th and expected 7 friends to join me. For multiple personal reasons four of the seven had to back out and it is not the place you want to be without the full

$360

1 / 14

Newly Renovated Townhome In Tropical Paradise

Islamorada townhouse

2 bedrooms / 2 bathrooms / Sleeps 6

$118

1 / 23

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$101

1 / 25

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

$159

1 / 23

PALMS 402

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$81

1 / 25
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