Updating...

Enter dates for more accurate prices

Islamorada Rentals

Filter

Islamorada Rentals

158 house rentals

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / Sleeps 10

$785

1 / 29

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

$1,500

1 / 21

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

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$257

1 / 16

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

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / Sleeps 6

$279

1 / 25

Luxury 3 BR condo, boatslip, easy accces to ocean

Islamorada condo

3 bedrooms / 6 bathrooms / Sleeps 8

$300

1 / 20

100' Private Beach Front Ocean Front Estate

Islamorada house

4 bedrooms / 4 bathrooms / Sleeps 12

$1,000

1 / 43

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$146

1 / 25

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$250

1 / 20

PALMS 201

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$126

1 / 16

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 6

$264

1 / 20

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

Islamorada villa

1 bedroom / 1 bathroom / Sleeps 3

$126

1 / 22

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$106

1 / 21

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$424

1 / 24

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

Islamorada house

5 bedrooms / 6 bathrooms / Sleeps 12

$714

1 / 32

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$300

1 / 25

PALMS 402

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$80

1 / 25

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$300

1 / 24

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 5

$130

1 / 15

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

Islamorada apartment

1 bedroom / 1 bathroom / Sleeps 4

$175

1 / 9

BEAUTIFUL BAY HARBOUR CONDO W/ BOAT DOCK!

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 8

$357

1 / 14

Private home and boat dock oceanside gated community

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$371

1 / 26

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

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 4

$147

1 / 19

LITTLE BAY - Cottage

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

$357

1 / 24

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

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

$260

1 / 18

RIOLO VILLA

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

$116

1 / 25

**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

Executive Bay G5

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$100

1 / 35

PALMS 301

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$73

1 / 24

Newly Renovated Townhome In Tropical Paradise

Islamorada townhouse

2 bedrooms / 2 bathrooms / Sleeps 6

$117

1 / 23

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

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

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$143

1 / 18

DEC & APRIL DEAL MONTH MINIMUM ENJOY! 9545791140

Islamorada apartment

3 bedrooms / 2 bathrooms / Sleeps 8

$132

1 / 30

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

Gorgeous waterfront home

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 8

$400

1 / 15
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more