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

Find 4 Star Hotels in Islamorada, FL from $214

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Check availability on Islamorada 4 Star Hotels

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Islamorada 4-star hotels

A wooden deck with a view of the ocean and a palm tree.
A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.
A beach bar with a thatched roof, palm trees, and a view of the sea.
A modern hotel room with a large bed, a desk with a lamp, a chair, and a view of the ocean.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
United States
Milagros
$315 nightly
$354 total
Oct 1 - Oct 2
Total with taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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.
A resort pool with palm trees, beach chairs, and umbrellas.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

2. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
MICHAEL
$210 nightly
$236 total
Sep 29 - Sep 30
Total with taxes and fees
Amara Cay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A beach with palm trees, a clear blue sky, and a calm sea.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
$264 nightly
$297 total
Sep 30 - Oct 1
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
An aerial view of a resort with a large pool, palm trees, and a beach.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A beach with clear water, a wooden pier, and lounge chairs under a tree.

4. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Tania
$312 nightly
$351 total
Oct 8 - Oct 9
Total with taxes and fees
Playa Largo Resort & Spa, Autograph Collection
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.

5. Islander Resort

Islander Resort
Matecumbe
United States
John
$254 nightly
$285 total
Sep 27 - Sep 28
Total with taxes and fees
Islander Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach with colorful buildings, kayaks, and lounge chairs.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A resort with a pool surrounded by palm trees and a view of the ocean.

6. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
La Siesta Resort & Villas
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A pool area with clear blue water, white lounge chairs, and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

7. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
$504 nightly
$566 total
Oct 1 - Oct 2
Total with taxes and fees
The Islands of Islamorada
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A wooden deck with a thatched-roof structure, a sign indicating no swimming, and a clear view of the ocean.
A spacious living room with a dining area, a sofa, and a coffee table.
A clear blue pool with lounge chairs and umbrellas, surrounded by greenery.

8. Condo in the Keys

Condo in the Keys
Tavernier
United States
Angela
Condo in the Keys

9. Pineapple Beach by Florida Keys Luxury Rentals

Pineapple Beach by Florida Keys Luxury Rentals
Islamorada
Pineapple Beach by Florida Keys Luxury Rentals

10. The Sanctuary Islet by Florida Keys Luxury Rentals

The Sanctuary Islet by Florida Keys Luxury Rentals
Key Largo
The Sanctuary Islet by Florida Keys Luxury Rentals

11. Turtle Nest Estate by Florida Keys Luxury Rentals

Turtle Nest Estate by Florida Keys Luxury Rentals
Matecumbe
Turtle Nest Estate by Florida Keys Luxury Rentals

12. Lime Key by Florida Keys Luxury Rentals

Lime Key by Florida Keys Luxury Rentals
Buccaneer Point
Lime Key by Florida Keys Luxury Rentals

13. Midnight Runner by Florida Keys Luxury Rentals

Midnight Runner by Florida Keys Luxury Rentals
Tavernier
Midnight Runner by Florida Keys Luxury Rentals

14. Serenity by Florida Keys Luxury Rentals

Serenity by Florida Keys Luxury Rentals
Matecumbe
Serenity by Florida Keys Luxury Rentals

15. Bay Beach by Florida Keys Luxury Rentals

Bay Beach by Florida Keys Luxury Rentals
Key Largo
Bay Beach by Florida Keys Luxury Rentals
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Islamorada.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
$190 nightly
$214 total
Oct 4 - Oct 5
Total with taxes and fees
Cheeca Lodge & Spa
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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.

Learn more about Islamorada

The turquoise waters between the Keys offer world-class fishing that even beginners can enjoy with knowledgeable local guides. Spend mornings snorkeling coral reefs teeming with tropical fish, then unwind at waterfront restaurants where chefs cook your fresh catch.

See all hotels in Islamorada
A white two-story house with blue accents, surrounded by palm trees and a sandy area.

Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"Loved the property!!! So quiet and relaxing! Great bar, pools, beaches!!!! Would absolutely stay again!"
Tracy 2-night trip
Posted 1 day ago
Islander Resort
Amara Cay Resort

Amara Cay Resort

8/10 Good
"We had a great stay and overall I would definitely return as it’s a wonderful property. The hotel rooms are spacious and clean. I appreciated the responsiveness of staff and communication via text and ability to make requests via QR code. I would say breakfast was lackluster and the service was extremely slow. Furthermore, I ordered two scrambled eggs and was served powdered eggs which tasted absolutely disgusting. I send that back, and was asked if I would like “hard shell” eggs instead. I thought this was very odd! You wouldn’t expect this at a resort of this level!"
Olga 2-night trip
Posted 1 day ago
Amara Cay Resort

Find out more about Islamorada

The preparation of any vacation starts with picking a splendid spot. Islamorada is a popular choice with travelers because it offers so much. But, "location, location, location" applies to more than just your vacation destination. Now that you got a feel for the town, it is time you to learn a little more about your home for the next few nights.

Hotels as Stunning as the City

Islamorada saw its fair share of visitors last year. Expedia's comment section features reviews that can help you narrow down your choices. When you book a 4-star room you can breathe easy knowing that these properties strive to meet your wishes. You'll never need to search long for to keep up with your exercise schedule, a refreshing dip, or delectable dinner during your stay, thanks to everything these hotels offer. They work hard to make their facilities and grounds hospitable from the time you step onto the property and with each step throughout the hotel. Islamorada has several wonderful accommodations that make for the perfect escape.

Rooms have been furnished to keep you as comfortable as possible, with amenities like designer bathroom products, ultra-comfortable bedding, and in-room tea or coffee. So, sit back and unwind. Moreover, if you find yourself in need of anything else, you can rest assured the staff will work their best to ensure you stay pleased during your time. These properties are so nice that you'll regret the day you have to return home.

Book a 4-Star Hotel in Islamorada Today!

Your vacation to Islamorada should be one where you don't have to worry about the little things. Make sure to book soon. With so few accommodations, and so many people desiring to vacation in Islamorada, you may miss the chance to book the perfect place.

Frequently asked questions

What are the best 4-star hotels in Islamorada?
Expedia travelers highly recommend Cheeca Lodge & Spa. From its handy amenities to its welcoming staff, every feature of this 4-star hotel in Islamorada is designed to offer an incredible vacation experience.
How much does it cost to stay in a 4-star hotel in Islamorada?
To book a 4-star hotel in Islamorada that matches your budget, take advantage of Expedia's sort and search filters. Take a look at what's available during your vacation dates and use our pricing filter to set your limit. You can also sort your results by the most budget-friendly retreat first.
  • Search for the lowest price from $214
What's the difference between 5-star and 4-star hotels in Islamorada?
Treat yourself to luxury living during your Islamorada getaway by staying at a 4-star hotel. As well as featuring upmarket accommodations, these properties are usually filled with amenities such as bathrobes, large beds and plenty more. A 5-star hotel will go the extra mile to make your trip an even more lavish and unforgettable one. 24-hour concierge assistance, elegant furnishings and gourmet dining are just the start of the first-rate conveniences and services you'll likely get access to.

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