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Islamorada Vacation Rentals

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Islamorada Vacation Rentals

About Islamorada

160 house rentals

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

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

Islamorada house

5 bedrooms / 6 bathrooms / Sleeps 12

Responds fast! avg. 46 minutes

$714

1 / 31

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

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$171

1 / 40

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 3 hours 14 minutes

$300

1 / 25

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 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

$66

1 / 25

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 3 hours 26 minutes

$1,500

1 / 21

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

Islamorada townhouse

2 bedrooms / 2 bathrooms / Sleeps 5

$105

1 / 13

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 5

$81

1 / 25

**Spring Discount** 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. 1 hour 23 minutes

$111

1 / 25

4 Bedroom Main House

Islamorada house

4 bedrooms / 2 bathrooms / Sleeps 8

$540

1 / 10

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

Islamorada apartment

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 2 hours 18 minutes

$175

1 / 9

Newly Renovated Townhome In Tropical Paradise

Islamorada townhouse

2 bedrooms / 2 bathrooms / Sleeps 6

$117

1 / 23

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 4 minutes

$279

1 / 25

Executive Bay G5

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$100

1 / 35

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 1 hour 45 minutes

$264

1 / 20

Futura Yacht Club 205

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 4

$129

1 / 13

Oceanfront 5th Floor End Unit, Pool, Free WiFi, Million Dollar Ocean Views!

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 4

Responds fast! avg. 3 hours 0 minutes

$143

1 / 26

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$106

1 / 21

**Spring Discount** Spacious Townhouse with pool at the Executive Bay Club

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 1 hour 23 minutes

$110

1 / 25

LITTLE BAY - Cottage

Islamorada villa

2 bedrooms / 2 bathrooms / Sleeps 6

$357

1 / 24

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$100

1 / 25

WEST LAKE PLAZA

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 5

$133

1 / 23

THE PERFECT GETAWAY

Islamorada house

4 bedrooms / 3 bathrooms / Sleeps 10

“The owner was understanding and worked with us” I was scheduled to rent from Dec 29th to Jan 4th and expected 7 friends to join me. For multiple personal reasons four of the seven had to back out and it is not the place you want to be without the full

$357

1 / 14

Summer Seas #418

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 4

$133

1 / 19

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

$465

1 / 49

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

Islamorada condo

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 3 hours 41 minutes

$129

1 / 19

ANTIGUA PLACE

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 7

$173

1 / 19

Islamorada Tropical Canalfront Paradise

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 3 hours 22 minutes

$250

1 / 13

**Spring Discount** Ocean Front Keys Home with Private Beach - Great for Kite Su

Islamorada house

4 bedrooms / 3 bathrooms / Sleeps 10

Responds fast! avg. 1 hour 23 minutes

$394

1 / 25

2 Bedroom Keys House

Islamorada house

2 bedrooms / 1 bathroom / Sleeps 4

$270

1 / 20

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$76

1 / 24

164 Plantation Shores Drive

Islamorada house

4 bedrooms / 4 bathrooms / Sleeps 8

$175

1 / 35

**Spring Discount** Sandy Beach & Boat Dock at this Tropical Beachfront Townhous

Islamorada house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 1 hour 23 minutes

$141

1 / 25

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

MY PARADISE

Islamorada house

3 bedrooms / 2 bathrooms / Sleeps 6

“My Paradise from architect's perspective” My wife and I spend a month at My Paradise and, as an architect, there are certain aspects that bear mention. First, if the weather is mild, you can open the wall of folding glass doors and unite the main inte

$243

1 / 25

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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