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Islamorada Rentals

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Islamorada Rentals

158 house rentals

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$257

1 / 16

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / Sleeps 6

$229

1 / 21

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$125

1 / 14

Private home and boat dock oceanside gated community

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$371

1 / 26

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / Sleeps 10

$785

1 / 29

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 5

$129

1 / 15

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

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 4

$146

1 / 19

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

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

Islamorada house

5 bedrooms / 6 bathrooms / Sleeps 12

$714

1 / 32

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

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 6

$264

1 / 20

PALMS 301

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$73

1 / 24

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

Islamorada villa

1 bedroom / 1 bathroom / Sleeps 3

$125

1 / 22

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$300

1 / 25

4 Bedroom Main House

Islamorada house

4 bedrooms / 2 bathrooms / Sleeps 8

$540

1 / 10

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

$117

1 / 19

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$300

1 / 24

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

Islamorada apartment

1 bedroom / 1 bathroom / Sleeps 4

$175

1 / 9

**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

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

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

$1,500

1 / 21

PALMS 201

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$127

1 / 16

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$142

1 / 18

**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

PALMS 314

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 5

“Wow, what a beautiful view” This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the

$80

1 / 25

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$107

1 / 21

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$100

1 / 25

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$421

1 / 24

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$250

1 / 20

Florida Keys Beautiful 2B 2B Townhouse

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

$260

1 / 18

LITTLE BAY - Cottage

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

$357

1 / 24

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / Sleeps 6

$279

1 / 25

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$147

1 / 25

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$77

1 / 24

Luxury 3 BR condo, boatslip, easy accces to ocean

Islamorada condo

3 bedrooms / 6 bathrooms / Sleeps 8

$300

1 / 20

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 4

$136

1 / 21

Anglers Reef Vacation Home

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 5

$286

1 / 6

Newly Renovated Townhome In Tropical Paradise

Islamorada townhouse

2 bedrooms / 2 bathrooms / Sleeps 6

$117

1 / 23
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