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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

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$257

1 / 16

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / Sleeps 10

$785

1 / 29

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / Sleeps 6

$229

1 / 21

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

Islamorada house

5 bedrooms / 6 bathrooms / Sleeps 12

$714

1 / 32

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

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 5

$129

1 / 15

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 6

$264

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'

$171

1 / 39

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

Islamorada villa

1 bedroom / 1 bathroom / Sleeps 3

$125

1 / 22

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

Islamorada apartment

1 bedroom / 1 bathroom / Sleeps 4

$175

1 / 9

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

$1,500

1 / 21

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$300

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

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$142

1 / 18

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 8

$198

1 / 25

Sunny Haven Islamorada

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 7

$475

1 / 9

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

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 4

$146

1 / 19

Executive Bay G5

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$100

1 / 35

Florida Keys Beautiful 2B 2B Townhouse

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

$260

1 / 18

HOUSE DORADO

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

$617

1 / 25

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$77

1 / 24

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

$243

1 / 25

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$100

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

$157

1 / 23

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$107

1 / 21

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$300

1 / 24

Private home and boat dock oceanside gated community

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$371

1 / 26

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / Sleeps 6

$279

1 / 25

PALMS 301

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$73

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

$100

1 / 25

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

GULFVIEW GETAWAY

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 10

$317

1 / 24

PALMS 201

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$127

1 / 16

PALMS 402

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$80

1 / 25

WEST LAKE PLAZA

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 5

$133

1 / 23

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / Sleeps 6

$375

1 / 15

Bay Harbour C312

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 6

$285

1 / 30
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