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Islamorada Rentals

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Islamorada Rentals

About Islamorada

159 house rentals

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

$1,503

1 / 21

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / Sleeps 6

$238

1 / 21

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$151

1 / 14

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 31 minutes

$259

1 / 16

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

Islamorada house

5 bedrooms / 6 bathrooms / Sleeps 12

Responds fast! avg. 1 hour 11 minutes

$1,500

1 / 31

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 5

$130

1 / 15

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 4

$130

1 / 33

**Summer Promo** Spacious Townhouse with pool at the Executive Bay Club

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$110

1 / 25

Islamorada Tropical Canalfront Paradise

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

$252

1 / 13

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

$126

1 / 22

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$76

1 / 24

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 5

$81

1 / 25

HOUSE DORADO

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

$616

1 / 24

141 Ocean Lane

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 6

$183

1 / 24

PALMS 402

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$80

1 / 25

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$106

1 / 21

Executive Bay G5

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$100

1 / 35

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

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 57 minutes

$262

1 / 18

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

Responds fast! avg. 2 hours 22 minutes

$143

1 / 19

ANTIGUA PLACE

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 6

$173

1 / 25

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 3 hours 12 minutes

$302

1 / 25

Futura Yacht Club 205

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 4

$129

1 / 13

Futura Townhome 708

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 4

$175

1 / 44

GULFVIEW GETAWAY

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 10

$400

1 / 24

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

$100

1 / 25

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$100

1 / 25

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$172

1 / 40

Newly Renovated Townhome In Tropical Paradise

Islamorada townhouse

2 bedrooms / 2 bathrooms / Sleeps 6

$118

1 / 23

164 Plantation Shores Drive

Islamorada house

4 bedrooms / 4 bathrooms / Sleeps 8

$175

1 / 35

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 1 hour 44 minutes

$266

1 / 20

Futura Townhome 731

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 4

$175

1 / 17

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

“Just what the family needed” The accommodations were just what we needed. Chris was a gracious host; she was available for anything we needed. The location and amenities fit our needs perfectly. We were able to swim and kayak in the channel, hang o

$453

1 / 29

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

$359

1 / 14

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$252

1 / 20

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$460

1 / 26

Luxury 3 BR condo, boatslip, easy accces to ocean

Islamorada condo

3 bedrooms / 6 bathrooms / Sleeps 8

Responds fast! avg. 2 hours 40 minutes

$249

1 / 20

PALMS 301

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$73

1 / 24
Viewing 38 of 159

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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