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Vacation Rentals & Vacation Rentals in Islamorada

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Vacation Rentals & Vacation Rentals in Islamorada

About Islamorada

452 house rentals

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

1 / 16

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$214

1 / 21

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,499

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 54 minutes

Price per night from

$125

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

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$129

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PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$81

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LITTLE BAY - Cottage

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$357

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Bay Harbour C312

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$286

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PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$76

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 22 minutes

Price per night from

$142

1 / 19

Islamorada Tropical Canalfront Paradise

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$250

1 / 13

**Summer Promo** Modern Executive Bay Club Condo with Pool & Beach

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Great condo, perfect location!” I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and very friendly. The location was close t

Responds fast! avg. 2 hours 27 minutes

Price per night from

$111

1 / 29

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$106

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Executive Bay G5

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$100

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82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$786

1 / 29

OCEANFRONT pool30'DockGatedPrivate7niteMin6ppl max

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 6

“Great Family Vacation Spot” House and property were exactly as represented. Excellent communication by owner and everything went perfectly. Multiple balconies and plenty of areas to soak up the sun or conveniently get out of it for a book or a siest

Price per night from

$465

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Luxury 3 BR condo, boatslip, easy accces to ocean

Islamorada condo

3 bedrooms / 6 bathrooms / sleeps 8

Responds fast! avg. 3 hours 55 minutes

Price per night from

$200

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LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$231

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141 Ocean Lane

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$183

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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

Price per night from

$357

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Beautiful Bayside View

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$799

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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

Price per night from

$357

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Newly Renovated Townhome In Tropical Paradise

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$117

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Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom / 1 bathroom / sleeps 2

“AMAZING!!!!!!!” Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips when we asked. The studio was so well stocked with all

Responds fast! avg. 3 hours 44 minutes

Price per night from

$225

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

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$105

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Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$450

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Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 9 minutes

Price per night from

$264

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PALMS 417

Islamorada apartment

1 bedroom / 2 bathrooms / sleeps 4

“Paradise on the ocean” We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay side with amazing sunsets. P

Price per night from

$66

1 / 25

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$100

1 / 25

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 19 minutes

Price per night from

$300

1 / 25

FALL SPECIAL DISCOUNTED PRICING!!!

Islamorada condo

3 bedrooms / 2 bathrooms / sleeps 6

“The Best Keys Location” My family stayed at this lovely Futura Yacht Club Condo for three weeks this July. We have stayed at many other units in this complex over the years but this unit was one of the nicest we have seen. The unit has been remodel

Responds fast! avg. 3 hours 5 minutes

Price per night from

$114

1 / 35

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

Price per night from

$229

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SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 57 minutes

Price per night from

$171

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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

Price per night from

$80

1 / 25

102 Columbus

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$110

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LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 20 minutes

Price per night from

$279

1 / 25

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$150

1 / 14

ISLAMORADA Waterfront GREEN IVIS PARADISE Min 28 Ngts. Max 10 ppl. 26% Disc >1mo

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$274

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Viewing 38 of 452

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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