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Islamorada Rentals

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Islamorada Rentals

About Islamorada

159 house rentals

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

Islamorada house

5 bedrooms / 6 bathrooms / Sleeps 12

Responds fast! avg. 1 hour 6 minutes

$714

1 / 31

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

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$150

1 / 14

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / Sleeps 6

$229

1 / 21

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 5

$81

1 / 25

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

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 0 minutes

$132

1 / 33

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 3 hours 13 minutes

$300

1 / 25

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$76

1 / 24

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$106

1 / 21

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 31 minutes

$256

1 / 16

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / Sleeps 8

$375

1 / 65

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

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$216

1 / 14

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 2 hours 54 minutes

$1,498

1 / 21

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 20 minutes

$279

1 / 25

Beautiful Bayside View

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 6

$415

1 / 39

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

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 4

$129

1 / 19

Newly Renovated Townhome In Tropical Paradise

Islamorada townhouse

2 bedrooms / 2 bathrooms / Sleeps 6

$117

1 / 23

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

$214

1 / 18

Completely Updated Corner Lot home

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 10

$217

1 / 16

Windy Cove #3

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 6

$171

1 / 14

Southern Diversion Islamorada see our fall special

Islamorada house

5 bedrooms / 4 bathrooms / Sleeps 16

$856

1 / 30

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

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$457

1 / 26

BEACON REEF 501

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$110

1 / 25

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

$260

1 / 18

PALMS 301

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$73

1 / 24

Summer Seas #418

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 4

$133

1 / 19

Futura Yacht Club 205

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 4

$129

1 / 13

111 Bayview Isle

Islamorada house

4 bedrooms / 5 bathrooms / Sleeps 8

$233

1 / 22

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 1 hour 44 minutes

$264

1 / 20

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$171

1 / 40

**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

Responds fast! avg. 3 hours 54 minutes

$100

1 / 25

BLUE WATER RETREAT

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

“Blue Water = Everything that you want” This place delivers. You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of all the hous

$183

1 / 26

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$100

1 / 25

4 Bedroom Main House

Islamorada house

4 bedrooms / 2 bathrooms / Sleeps 8

$540

1 / 10

102 Columbus

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 4

$110

1 / 22
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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