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

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Check prices for these dates

Next weekend
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov

Our top choices for Islamorada resorts

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,441 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
The price is NZ$401
includes taxes & fees
30 Sept - 1 Oct
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, (1,312 reviews)
"Wonderful resort, very friendly staff, would definitely stay again!"
United States
Amy
The price is NZ$405
includes taxes & fees
20 Sept - 21 Sept
Amara Cay Resort
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, (272 reviews)
"Beautiful place Great beds Lots of dining options"
Canada
Eslita
The price is NZ$516
includes taxes & fees
30 Sept - 1 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,498 reviews)
"Would stay again!"
United States
Chadwick
The price is NZ$290
includes taxes & fees
20 Sept - 21 Sept
Lime Tree Bay Resort
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

5. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (162 reviews)
"Worth the money."
United States
paul
The price is NZ$251
includes taxes & fees
30 Sept - 1 Oct
Matecumbe Resort
An aerial view of a resort with a large pool, palm trees, and a beach.

6. 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)
"Super good resorts"
United States
Danilo
The price is NZ$594
includes taxes & fees
30 Sept - 1 Oct
Playa Largo Resort & Spa, Autograph Collection
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, (1,184 reviews)
"Beautiful hotel"
United States
Milagros
The price is NZ$559
includes taxes & fees
30 Sept - 1 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
A resort pool with palm trees and lounge chairs, surrounded by a beachfront.

8. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
4.0 star property
Marathon
8.0 out of 10, Very good, (232 reviews)
"Amazing service. It was an unexpected experience."
United States
Gabriela
The price is NZ$848
includes taxes & fees
20 Sept - 21 Sept
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Everything about the Chesapeake resort is perfect ,had the most incredible time ,will definitely return !!!"
Olga 2-night trip
Posted 13 hours ago
Chesapeake Beach Resort

Find out more about Islamorada

Islamorada Resort information

Number of reviews
3,167
Accommodation
12 Resort
Lowest Price
NZ$251
Highest Price
NZ$848

Frequently asked questions

What can I expect from a resort holiday in Islamorada?
Longing for a relaxing getaway? Treat yourself to the comforts of a resort, where you can find everything you want for your trip—from convenient dining options to activities and entertainment. Choose from 26 resorts in Islamorada and discover the one that's best for you, whether you envision yourself sitting down to fine dining or heading to the spa for a deep-tissue massage.
What's a favourite resort for my stay in Islamorada?
Cheeca Lodge & Spa - Luxury resort. Features 3 outdoor pools, 3 restaurants and 2 poolside bars. Amara Cay Resort - Beach resort. Has 2 restaurants, a private beach and 3 bars. Highly rated for its pool. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort - Beach resort. Enjoy the 3 outdoor pools, 4 restaurants and private beach. 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 from Expedia's 26 resort hotels in Islamorada, where you'll find a selection of great restaurants, beautiful guest rooms and more.
What can I do in Islamorada?
Travellers come to Islamorada to try fishing and other popular water activities, and also speak highly of the entertainment choices. Enjoy 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 Founders Park.
What's the seasonal weather in Islamorada?
The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.
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) from the heart of the city. If you'd like to venture out around the area, you may want a rental car for your journey.