Vacation Rentals & House Rentals in Islamorada

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482 house rentals

20

Oceanfrontparadise: 209

Florida Keys / Islamorada

Islamorada apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$251

Price per night from

$251

(15) Excellent 

21

Islamorada Luxury Waterfront Condo with Boat Slip

Florida Keys / Islamorada

Islamorada apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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
…see more

Price per night from

$215

Price per night from

$215

(2) Excellent 

21

Ocean-Front Caribbean Home.

Florida Keys / Islamorada

Islamorada house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$1,500

Price per night from

$1,500

(3) Excellent 

9

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

Florida Keys / Islamorada

Islamorada apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$202

Responds fast!
avg. 30 minutes

Price per night from

$202

(4) Excellent 

16

Newly refinished condo open water views very nice

Florida Keys / Islamorada

Islamorada condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$200

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$200

(5) Excellent 

23

76004 Overseas Highway

Florida Keys / Islamorada

Islamorada house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
“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
…see more

Price per night from

$328

Price per night from

$328

65

100 Palo De Oro Drive

Florida Keys / Islamorada

Islamorada house

4 8 28 nights min

  • 4 bedrooms
  • sleeps 8
  • 28 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$430

Price per night from

$430

(2) Excellent 

25

MATECUMBE JEWEL

Florida Keys / Islamorada

Islamorada house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet Friendly
“Our Lobster Trip to the Keys” My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could not have asked for better accomodations wh
…see more

Price per night from

$157

Price per night from

$157

40

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Florida Keys / Islamorada

Islamorada condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$197

Price per night from

$197

43

Bay and Beach Beauty

Florida Keys / Islamorada

Islamorada house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 0.01 mi
  • Child Friendly
  • Air conditioning

Price per night from

$345

Responds fast!
avg. 2 hours 14 minutes

Price per night from

$345

13

Futura Yacht Club 205

Florida Keys / Islamorada

Islamorada house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly

Price per night from

$148

Price per night from

$148

(11) Very Good 

25

76300 Overseas Highway

Florida Keys / Islamorada

Islamorada house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
“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
…see more

Price per night from

$196

Price per night from

$196

(3) Excellent 

21

BEACON REEF 310

Florida Keys / Islamorada

Islamorada apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$110

Price per night from

$110

(3) Excellent 

45

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

Florida Keys / Islamorada

Islamorada condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$188

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$188

(6) Very Good 

14

THE PERFECT GETAWAY

Florida Keys / Islamorada

Islamorada house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“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
…see more

Price per night from

$409

Price per night from

$409

(16) Very Good 

18

132 Columbus Drive

Florida Keys / Islamorada

Islamorada house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
“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
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Price per night from

$263

Price per night from

$263

25

Anglers Reef Islamorada Florida Sleeps 6

Florida Keys / Islamorada

Islamorada house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$344

Price per night from

$344

(1) Excellent 

13

Islamorada Tropical Canalfront Paradise

Florida Keys / Islamorada

Islamorada house

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$251

Price per night from

$251

22

Dream Escape in Islamorada at Anglers Reef

Florida Keys / Islamorada

Islamorada villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$288

Responds fast!
avg. 2 hours 14 minutes

Price per night from

$288

(3) Excellent 

25

LITTLE BAY - Upper Duplex

Florida Keys / Islamorada

Islamorada villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children
  • Pet Friendly
“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
…see more

Price per night from

$357

Price per night from

$357

35

164 Plantation Shores Drive

Florida Keys / Islamorada

Islamorada house

4 8 28 nights min

  • 4 bedrooms
  • sleeps 8
  • 28 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$201

Price per night from

$201

19

Summer Sea #418

Florida Keys / Islamorada

Islamorada house

2 4 28 nights min

  • 2 bedrooms
  • sleeps 4
  • 28 nights min
  • Child Friendly

Price per night from

$153

Price per night from

$153

(2) Excellent 

17

Incredible Luxury Home with Waterfront!! Paradise

Florida Keys / Islamorada

Islamorada house

5 12 28 nights min

  • 5 bedrooms
  • sleeps 12
  • 28 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$1,390

Price per night from

$1,390

35

Executive Bay G5

Florida Keys / Islamorada

Islamorada house

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Child Friendly

Price per night from

$115

Price per night from

$115

(28) Excellent 

38

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

Florida Keys / Islamorada

Islamorada house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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
…see more

Price per night from

$608

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$608

(1) Excellent 

24

LYONS LANDING

Florida Keys / Islamorada

Islamorada house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$245

Price per night from

$245

(2) Excellent 

25

PALMS 309

Florida Keys / Islamorada

Islamorada house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$85

Price per night from

$85

(5) Excellent 

31

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

Florida Keys / Islamorada

Islamorada house

5 12 4 nights min

  • 5 bedrooms
  • sleeps 12
  • 4 nights min
  • Nearest beach 4 mi
  • Swimming pool
  • Child Friendly
“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
…see more

Price per night from

$1,437

Responds fast!
avg. 2 hours 28 minutes

Price per night from

$1,437

(5) Excellent 

19

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

Florida Keys / Islamorada

Islamorada condo

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$164

Responds fast!
avg. 3 hours 4 minutes

Price per night from

$164

(8) Very Good 

Certificate of Excellence

14

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

Florida Keys / Islamorada

Islamorada condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$167

Responds fast!
avg. 3 hours 39 minutes

Price per night from

$167

(4) Excellent 

29

82754 Overseas Highway

Florida Keys / Islamorada

Islamorada house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly

Price per night from

$900

Price per night from

$900

(32) Excellent 

28

Islamorada Waterfront Paradise Getaway!

Florida Keys / Islamorada

Islamorada house

1 2 30 nights min

  • 1 bedroom
  • sleeps 2
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Air conditioning
“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
…see more

Price per night from

$258

Responds fast!
avg. 2 hours 52 minutes

Price per night from

$258

51

Islamorada Paradise

Florida Keys / Islamorada

Islamorada house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Price per night from

$690

Price per night from

$690

(7) Excellent 

18

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

Florida Keys / Islamorada

Islamorada villa

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$287

Responds fast!
avg. 1 hour 36 minutes

Price per night from

$287

(7) Very Good 

31

137 LeSerra Lane

Florida Keys / Islamorada

Islamorada house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
“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
…see more

Price per night from

$368

Price per night from

$368

22

102 Columbus

Florida Keys / Islamorada

Islamorada house

2 4 28 nights min

  • 2 bedrooms
  • sleeps 4
  • 28 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$126

Price per night from

$126

(1) Excellent 

36

107 San Remo Drive

Florida Keys / Islamorada

Islamorada house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$344

Price per night from

$344

(5) Excellent 

21

SANCTUARY IN PARADISE

Florida Keys / Islamorada

Islamorada house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We wer
…see more

Price per night from

$502

Price per night from

$502

About Islamorada

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.