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Vacation Rentals & House Rentals in Islamorada

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Vacation Rentals & House Rentals in Islamorada

About Islamorada

474 house rentals

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

Price per night from

$327

1 / 23

75731 Overseas Highway

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. B

Price per night from

$1,142

1 / 32

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$285

1 / 20

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Beautifully appointed, waterside condo!” This property is a beautiful, two bedroom condo, very well appointed, with everything we needed for a great stay! Islamorada is a great middle point to see the other parts of the Keys, and close to great restau

Responds fast! avg. 3 hours 54 minutes

Price per night from

$213

1 / 21

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,494

1 / 21

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

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 47 minutes

Price per night from

$200

1 / 9

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 41 minutes

Price per night from

$342

1 / 43

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$428

1 / 65

164 Plantation Shores Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$200

1 / 35

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

Price per night from

$408

1 / 14

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$229

1 / 40

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

$262

1 / 18

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 11 minutes

Price per night from

$1,384

1 / 17

Dream Escape in Islamorada at Anglers Reef

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 11 minutes

Price per night from

$343

1 / 22

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 55 minutes

Price per night from

$159

1 / 40

Summer Sea #418

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$152

1 / 19

76300 Overseas Highway

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

“76300 overseas highway islamorada” We had a great time. There was plenty of room for our family of six.. The view from the house was absolutely gorgeous. The swimming behind the house was so clear and nice the kids stayed in the water all day. We cou

Price per night from

$196

1 / 25

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

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

“Relax in Luxury” Great Location. Lots of nearby restaurants. Owners were extremely helpful in recommending attractions. A stunningly beautiful home with plenty of room for my large family to spread out. Pool was great. Swimming in warm shallow wa

Responds fast! avg. 3 hours 3 minutes

Price per night from

$1,425

1 / 31

Islamorada Tropical Canalfront Paradise

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 11 minutes

Price per night from

$257

1 / 13

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$343

1 / 25

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$110

1 / 21

Futura Yacht Club 205

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$148

1 / 13

107 San Remo Drive

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$343

1 / 36

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated

Responds fast! avg. 1 hour 51 minutes

Price per night from

$603

1 / 38

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

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

Price per night from

$284

1 / 18

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 the

Responds fast! avg. 2 hours 12 minutes

Price per night from

$257

1 / 28

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 / 24

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 4 minutes

Price per night from

$163

1 / 19

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$85

1 / 25

140 Atlantic Lane

Islamorada house

5 bedrooms / 4 bathrooms / sleeps 10

“Great vacation” We visited over Christmas.All nine of us! The main house and guest house configuration worked out great for our multi- generational group, giving the younger group the opportunity to stay up later and sleep in later. The house had ever

Price per night from

$490

1 / 25

Executive Bay G5

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$115

1 / 35

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$898

1 / 29

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing view! Absolutely gorgeous!” My two teenage daughters and I stayed at this condo and it worked out perfect for us! The view is stunning, and I loved to just sit in the living room and look out at the ocean. The condo was very clean, and reall

Responds fast! avg. 3 hours 51 minutes

Price per night from

$171

1 / 14

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

1 / 25

Bay Harbour C312

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$327

1 / 30

102 Columbus

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$126

1 / 22

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$76

1 / 24

137 LeSerra Lane

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

“The best house we have rented in the keys!” This is the best house we have ever rented in the keys! The furnishings are modern, up-to-date and comfortable, the layout is perfect, the house is well-equipped and well-maintained, and the view is fabulou

Price per night from

$367

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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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