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

Book a Islamorada Resort

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27

Our top choices for Islamorada resorts

A bathroom with a large bathtub, a view of the sea, and a pier with boats.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,491 reviews)
"Beautiful resort"
United States
Patricia
The price is ￥24,753
￥39,365 total
includes taxes & fees
Nov 1 - Nov 2
Cheeca Lodge & Spa
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.

2. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,327 reviews)
"Pool side bar On the ocean Very clean and friendly"
United States
Ronald
The price is ￥25,146
￥39,806 total
includes taxes & fees
Nov 15 - Nov 16
Amara Cay Resort
Terrace/patio

3. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,557 reviews)
"Very nice place the view and sunsets are amazing there is also a restaurant on the property that has great food and drinks we would definitely stay again"
United States
Christopher Michael
The price is ￥18,196
￥27,558 total
includes taxes & fees
Oct 28 - Oct 29
Lime Tree Bay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

4. 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, (301 reviews)
"Great place to stay!"
United States
Liosbel
The price is ￥37,672
￥53,898 total
includes taxes & fees
Nov 3 - Nov 4
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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, (1,001 reviews)
"Great place to stay!"
United States
Brianne
The price is ￥23,852
￥38,351 total
includes taxes & fees
Nov 17 - Nov 18
La Siesta Resort & Villas
A compact kitchen with wooden cabinets, a refrigerator, and a window with curtains.

6. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (181 reviews)
"A very peaceful place."
United States
angel
The price is ￥22,678
￥25,513 total
includes taxes & fees
Oct 28 - Oct 29
Matecumbe Resort
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

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
8.8 out of 10, Excellent, (1,195 reviews)
"We loved this place. Will definitely stay there again."
United States
Alan
The price is ￥38,613
￥52,121 total
includes taxes & fees
Nov 9 - Nov 10
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)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is ￥47,719
￥62,367 total
includes taxes & fees
Nov 10 - Nov 11
Playa Largo Resort & Spa, Autograph Collection
An aerial view of a resort with a central pool, multiple buildings, and a marina.

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 ￥72,288
￥91,069 total
includes taxes & fees
Nov 16 - Nov 17
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islamorada Hotel Reviews

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Clean rooms. Beautiful views"
Timothy 4-night trip
Posted 3 hours ago
Amara Cay Resort

Find out more about Islamorada

Islamorada Resorts information

Number of reviews
1,508
Accommodation
12 Resorts
Lowest Price
￥25,513
Highest Price
￥91,069

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.

Explore a world of travel with Expedia