Islamorada Vacation Homes

A beach with white lounge chairs, a covered pavilion, and palm trees.

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Our top choices for Islamorada holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

1. Little Peace of Haven

Key Largo

Jacob S.

HK$3,467 total

includes taxes & fees

4 Nov - 5 Nov

A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

2. Charming Home in Key Largo

Key Largo

JOHN P.

HK$2,952 total

includes taxes & fees

15 Oct - 16 Oct

A coastal residential area with a marina, modern buildings, and a swimming pool.

3. 1. Key Largo Waterfront Studio | Canal & Ocean

Key Largo

David C.

HK$2,733 total

includes taxes & fees

7 Oct - 8 Oct

A building with a white car parked in front, surrounded by palm trees and gravel.

4. 2. Waterfront Key Largo Studio | Fish & Relax

Key Largo

James G.

HK$2,713 total

includes taxes & fees

5 Oct - 6 Oct

A two-story building with a pool, a boat dock, and a table set for dining.

5. Waterfront / Ocean Access Canal / Kamp Key / Homes

Matecumbe

"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."

Mike H.

HK$7,701 total

includes taxes & fees

26 Oct - 27 Oct

A balcony with a view of the sea, a dining area with chairs and a table, and a ceiling fan.

6. Beach Residence Private Overwater Dock Heated Pool Mahi Key

Matecumbe

HK$18,756 total

includes taxes & fees

14 Oct - 15 Oct

A beach with a wooden structure and a signpost indicating directions to various locations.

7. FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Key Largo

Aaron G.

HK$4,806 total

includes taxes & fees

14 Oct - 15 Oct

A modern indoor space with a pool, white wicker furniture, and a white crib.

8. El Encanto: private saltwater pool & tiki lounge

Key Largo

HK$4,476 total

includes taxes & fees

7 Oct - 8 Oct

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Top Islamorada Hotel Reviews

Hadley Resort and Marina

10/10 Excellent

"Great place for the money!"

Matecumbe Resort

10/10 Excellent

"I had a wonderful stay at Matecumbe Resort in Islamorada, Florida. The efficiency unit was exceptionally clean, comfortable, and tastefully decorated, creating a welcoming and relaxing atmosphere. One of the highlights of the property is its peaceful setting. The resort offers a high level of privacy and tranquility, making it an ideal place to unwind and enjoy the beauty of the Keys. While I had no direct interactions with the staff, their approach was appreciated. They were available if needed but otherwise allowed guests to enjoy their stay without interruption. Since everything was well organized and met my expectations, I had no reason to seek assistance. The resort's location is also very convenient, with excellent restaurants, shopping, and local attractions nearby. To top it all off, the property offers a beautiful view of the sunrise over the Atlantic Ocean, providing the perfect start to each day. Overall, all of my expectations were met, and I would gladly recommend Matecumbe Resort to anyone seeking a clean, comfortable, quiet, and well-located getaway in Islamorada."

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