Vacation Rentals & House Rentals in Islamorada

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502 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

$249

Price per night from

$249

(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

$213

Price per night from

$213

(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

(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

(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

$175

Responds fast!
avg. 29 minutes

Price per night from

$175

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

$300

Responds fast!
avg. 2 hours 23 minutes

Price per night from

$300

(4) 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

$321

Price per night from

$321

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

$197

Price per night from

$197

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

$171

Price per night from

$171

(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

$357

Price per night from

$357

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

$145

Price per night from

$145

(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

$249

Price per night from

$249

(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

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

$250

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$250

(3) Excellent 

33

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

$110

Responds fast!
avg. 2 hours 58 minutes

Price per night from

$110

(1) Excellent 

13

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

Florida Keys / Islamorada

Islamorada townhouse

2 5 30 nights min

  • 2 bedrooms
  • sleeps 5
  • 30 nights min
  • Child Friendly

Price per night from

$105

Price per night from

$105

(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

$1,128

Price per night from

$1,128

28

Dog-friendly, waterfront home w/ a private pool, hot tub, & private beach

Florida Keys / Islamorada

Islamorada house

4 14 7 nights min

  • 4 bedrooms
  • sleeps 14
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$858

Responds fast!
avg. 3 hours 2 minutes

Price per night from

$858

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

$422

Price per night from

$422

(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

(10) 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
“Love this place!” We stayed here august 2011 with 2 other couples and fell in love with this place. We are here again now! This has plenty of room for the 6 of us. It is very clean. The furnishings are not luxurious, but we are still very comforta
…see more

Price per night from

$193

Price per night from

$193

(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
…see more

Price per night from

$257

Price per night from

$257

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

$150

Price per night from

$150

(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

$1,250

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$1,250

56

Islamorada Oceanfront Estate, Pool, Beach Cottages-- Sea Ranch -- Florida Keys

Florida Keys / Islamorada

Islamorada house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,169

Price per night from

$1,169

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

$112

Price per night from

$112

(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

(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

$369

Price per night from

$369

(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

(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

$884

Price per night from

$884

(31) 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

$224

Responds fast!
avg. 3 hours 18 minutes

Price per night from

$224

(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

$248

Responds fast!
avg. 1 hour 36 minutes

Price per night from

$248

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

$300

Price per night from

$300

(8) Very Good 

25

140 Atlantic Lane

Florida Keys / Islamorada

Islamorada house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
“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
…see more

Price per night from

$482

Price per night from

$482

(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

$142

Responds fast!
avg. 3 hours 4 minutes

Price per night from

$142

(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

$338

Price per night from

$338

(2) Excellent 

25

PALMS 314

Florida Keys / Islamorada

Islamorada apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Ask about children
“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
…see more

Price per night from

$80

Price per night from

$80

(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

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.