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

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Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 Dec

Our top choices for Islamorada resorts

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

1. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,319 reviews)
"Super clean resort."
United States
Danielle
The price is AED 477
AED 805 total
includes taxes & fees
20 Oct - 21 Oct
Amara Cay Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,474 reviews)
"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"
United States
Morgan
The price is AED 614
AED 959 total
includes taxes & fees
21 Oct - 22 Oct
Cheeca Lodge & Spa
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

3. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (289 reviews)
"Great place to stay!"
United States
Liosbel
The price is AED 840
AED 1,213 total
includes taxes & fees
18 Oct - 19 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Terrace/patio

4. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,536 reviews)
"Beautiful location, great amenities, and comfortable rooms"
United States
Michael
The price is AED 455
AED 677 total
includes taxes & fees
13 Oct - 14 Oct
Lime Tree Bay Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

5. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
United States
Brianne
The price is AED 617
AED 963 total
includes taxes & fees
8 Nov - 9 Nov
La Siesta Resort & Villas
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

6. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (172 reviews)
"A very peaceful place."
United States
angel
The price is AED 493
AED 554 total
includes taxes & fees
13 Oct - 14 Oct
Matecumbe Resort
A wooden deck with a view of the ocean and a palm tree.

7. Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.6 out of 10, Excellent, (1,182 reviews)
"Clean room, nice sandy beach, great location, my dog was supper happy, I will return every year."
United States
juan
The price is AED 1,021
AED 1,351 total
includes taxes & fees
20 Oct - 21 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
An aerial view of a resort with a large pool, palm trees, and a beach.

8. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,003 reviews)
"Clean room excellent staff good location recommend"
United States
Tania
The price is AED 966
AED 1,289 total
includes taxes & fees
1 Nov - 2 Nov
Playa Largo Resort & Spa, Autograph Collection
A resort pool with palm trees and lounge chairs, surrounded by a beachfront.

9. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
4.0 star property
Marathon
8.0 out of 10, Very good, (233 reviews)
"Amazing service. It was an unexpected experience."
United States
Gabriela
The price is AED 2,016
AED 2,496 total
includes taxes & fees
30 Oct - 31 Oct
Villas At Hawks Cay Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Islamorada Hotel Reviews

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

10/10 Excellent
"Caloosa Cove is well located for exploring both Islamorada as well as the lower keys. The room was clean and spacious and had a very usable kitchen. The balcony in the room offered unobstructed views of the ocean and pool area. The pool was large and also had a great view of the ocean. The only criticism I have is that they had few of the resort amenities I've seen at other properties such as kayaks, bicycles, or hammocks, but I knew that in advance. There's really no sunrise view from the property, but that's a geographic limitation they can't really do anything about."
Kenneth 6-night trip
Posted 12 hours ago
Caloosa Cove Resort by CoolVacay

Frequently asked questions

What can I expect from a resort vacation in Islamorada?
Longing for a relaxing getaway? You deserve all the comforts of a resort, where you can find everything you want for your stay from tasty food and drink options to activities and entertainment. Check out the 25 resorts in Islamorada and discover the one that's best for you, whether you envision yourself kicking back in a luxury suite or heading to the spa for a deep-tissue massage.
What's a favorite resort in Islamorada?
Cheeca Lodge & Spa - Luxury resort. Features 3 outdoor pools, 3 restaurants, and 2 poolside bars. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort - Beach resort. Has 3 outdoor pools, 4 restaurants, and a private beach. Amara Cay Resort - Beach resort. Highly rated for its pool. Enjoy the 2 restaurants, private beach, and 3 bars. La Siesta Resort & Villas - Beach resort. Amenities include a private beach, a marina, and a terrace. Spacious rooms feature pillowtop beds and premium bedding. Matecumbe Resort - Beach resort. Access to a private beach, a garden, and free self parking.
How many resorts can I expect to find in Islamorada?
Choose among Expedia's 25 resort hotels in Islamorada where you'll find fun for all the family, spacious guest rooms, and more.
What can I do in Islamorada?
Travelers come to Islamorada to try fishing and other popular water activities, and also speak highly of the entertainment choices. Get some time by the water at Anne's Beach, or discover the shopping possibilities at Rain Barrel Village. Additional attractions in the area include Bud n' Mary's Dive Center and Robbie's of Islamorada.
What's the seasonal weather like in Islamorada?
The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.
What's the best way to get to and around Islamorada?
Fly into Marathon, FL (MTH-Florida Keys Marathon), which is located 30 mi (48.2 km) away from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

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