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Islamorada Rentals

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Islamorada Rentals

About Islamorada

158 house rentals

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

$257

1 / 16

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

$1,500

1 / 21

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

$76

1 / 24

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

$375

1 / 65

LITTLE BAY - Cottage

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

$357

1 / 24

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

2.5 BR 1.5 Bath Townhouse with Beautiful Beach and Boat Slippage!

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 5

$105

1 / 13

Islamorada Tropical Canalfront Paradise

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

$250

1 / 13

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 22 minutes

$142

1 / 19

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

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

$236

1 / 21

132 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

“Fantastic getaway” This is a great vacation rental property for a couple or small groups of 4 or less people. First of all, you can't beat the panoramic view of the water and what's more, the water is just 10 ft away. The front yard is one of the best

$229

1 / 18

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

$106

1 / 21

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

$143

1 / 20

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

$171

1 / 40

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 9 minutes

$264

1 / 20

ANTIGUA PLACE

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

$173

1 / 25

THE PERFECT GETAWAY

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

“The most relaxing vacation ever!!” The weather was beautiful for boating, sunning by the pool or the Jacuzzi. Islamorada is beautiful. Less than a mile from the house you'll find "The Moorings" and their restaurants Pierres Morada Bay and The Beach Ca

$357

1 / 14

All NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 24 minutes

$129

1 / 33

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 20 minutes

$279

1 / 25

164 Plantation Shores Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

$175

1 / 35

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

$100

1 / 25

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

$198

1 / 14

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

Islamorada villa

1 bedroom / 1 bathroom / sleeps 3

“Personal Keys Paradise” We recently stayed at Pam and Charlie's place for 8 days. We came down mainly for the fishing, but due to nasty seas, we weren't able to get out much. I couldn't have picked a better location to make our trip worth while! We ha

$125

1 / 22

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

$450

1 / 29

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 11 minutes

$300

1 / 25

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

$150

1 / 14

76004 Overseas Highway

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

“Wonderful accommodations” Aside from being rainy for the majority of our stay, the accommodations were amazing. We will certainly be going back to this house. This house sleeps 8-10 adults comfortably. Freewheeler Realty was a pleasure to do busine

$286

1 / 23

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

$786

1 / 29

Executive Bay G5

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

$100

1 / 35

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

$100

1 / 25

258 Mohawk Street

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

$127

1 / 24

Luxury 3 BR condo, boatslip, easy accces to ocean

Islamorada condo

3 bedrooms / 6 bathrooms / sleeps 8

Responds fast! avg. 2 hours 48 minutes

$249

1 / 20

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

$81

1 / 25

Futura Townhome 731

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 4

$175

1 / 17

102 Columbus

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

$110

1 / 22

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

$146

1 / 25

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

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

$129

1 / 19
Viewing 38 of 158

About Islamorada

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Islamadora, or "Village of Islands", refers to the collection of islands in the Florida Keys including the Keys of Tea Table, Upper and Lower Matecumbe, Plantation, and Windley. Every destination in Islamadora offers access to the very best of this island paradise. The beautiful beaches, emerald golf courses, luxurious spas, and charming local museums in Islamadora make this the perfect place for a family vacation. Islamadora also offers easy access to Everglades National Park, an ecological destination that draws visitors from all over the world to see its dazzling biodiversity and elusive marine life. Come to Islamadora to play, explore, learn about the culture and history of the Florida Keys or simply relax. After the sun goes down, experience the world-class seafood restaurants and laid back vibe of Islamadora's night life.

Here are a few additional suggestions as you plan your trip:

  • Visit the Theater of the Sea: This place is a nature center, aquarium, and theater all rolled into one. Come here to learn about the marine ecosystems of the Florida Keys and interact with dolphins and sea lions.
  • Explore the wharf: Go fishing, rent a boat, or feed the gigantic tarpon at Robbie's marina. There are also sport fishing marinas in Islamadora where you can schedule charter trips and pursue large game like swordfish.
  • Visit the History of Diving Museum: The interactive displays and extraordinary collection of artifacts at the diving museum provide a great way to learn about maritime history and culture.
  • Take an eco-tour: Explore the Everglades National Park by boat, one of the best ways to see marine plants and animals in their natural habitats.
  • Play on the beach: Annie's Beach offers a clean stretch of beautiful white sand and blue ocean waves, perfect for a relaxing day with children. Go swimming, surfing, parasailing, rent a boat, or just sunbathe with a good book.
  • Visit the Windley Key Fossil Reef Geological State Park: This park is known for its hiking trails but more so for its incredible fossilized coral reefs.

Finding a place to stay will be easy in Islamadora, even if you arrive during the height of the summer. Find a quaint cottage for a romantic getaway, a summer home big enough for your whole family, or a luxury beach villa for you and some friends. No matter what you plan to do while you're here, you'll be able to find the perfect vacation rental to meet your needs.

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