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Featured Islamorada 4 Star hotels

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

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

4 out of 5
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $382 per night from Jun 16 to Jun 17
CA $382
CA $506 total
Jun 16 - Jun 17
includes taxes & fees
Book a stay at this beach resort in Key Largo. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,069 reviews)
The room was nice and did have a beautiful view. There are only 2 restaurants..one is ultra expensive, dinner was ok but breakfast was delicious. The other restaurant was good but lacking in variety. I understand we went during the week and there was no entertainment. After dinner, you go to bed. ...

Reviewed on May 14, 2026

Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from May 19 to May 20
CA $258
CA $391 total
May 19 - May 20
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,271 reviews)
Room was clean .some of the staff was really rude. The staff out by paddle board were never around. Better off staying at Three Waters resort . Staff much more accommodating . Nicer and it the sister resort to Amara Cay.

Reviewed on May 14, 2026

Opens in a new windowAmara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $290 per night from May 31 to Jun 1
CA $290
CA $419 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,013 reviews)
Room was spacious but could use better lighting. Bathroom was very small and small vanity with extremely oversized vessel sink resulting nowhere to place anything. Outside shy s and landscaping extremely overgrown but they started trimming day we departed. A big plus was the pool area with plenty ...

Reviewed on May 15, 2026

Opens in a new windowIslander Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $349 per night from Jun 1 to Jun 2
CA $349
CA $494 total
Jun 1 - Jun 2
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (197 reviews)
Great vacation!! Room needed some work such as shower door panel missing and the door didn’t lock. Other than that is was beautiful place It also needs an onsite laundry facility. When you have fishermen you need that badly.

Reviewed on May 15, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $472 per night from May 31 to Jun 1
CA $472
CA $606 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this luxury resort in Key Largo. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,003 reviews)
The staff here is outstanding. They are professional and will go out of their way to accommodate the guest. The resort is amazing and provides a lot of events throughout the days. We will definitely be returning.

Reviewed on May 13, 2026

Opens in a new windowPlaya Largo Resort & Spa, Autograph Collection
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from May 19 to May 20
CA $233
CA $363 total
May 19 - May 20
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
8.6/10 Excellent! (1,002 reviews)
Room was nice with balcony but not what I expected. Thought I was booking the room that was in the picture. All the pictures of my room at time of reservation appeared like the photos shown on the site, but this was not in fact the room we received. Overall the property is pretty nice with bikes, ...

Reviewed on May 14, 2026

Opens in a new windowLa Siesta Resort & Villas
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $793 per night from May 17 to May 18
CA $793
CA $967 total
May 17 - May 18
includes taxes & fees
Book a stay at this beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.6/10 Exceptional! (75 reviews)
The "suite" was a single room with a king and pullout sofa, there was no separation. So if you are traveling with children be aware that this is the same as a double queen at any other hotel room.

Reviewed on Apr 30, 2026

Opens in a new windowThe Islands of Islamorada
Condo in the Keys

Condo in the Keys

4 out of 5
500 Burton Dr Tavernier FL
Book a stay at this beach apartment in Tavernier. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Harry Harris Park and Mangrove Marina ...
8/10 Very Good! (14 reviews)
Nice kitchen. Great view.

Reviewed on Mar 27, 2026

Opens in a new windowCondo in the Keys
The Sanctuary Islet by Florida Keys Luxury Rentals

The Sanctuary Islet by Florida Keys Luxury Rentals

4 out of 5
1565 Ocean Bay Drive Key Largo FL
Book a stay at this beach vacation home in Key Largo. Enjoy free parking and a private beach. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp ...
Opens in a new windowThe Sanctuary Islet by Florida Keys Luxury Rentals
Pineapple Beach by Florida Keys Luxury Rentals

Pineapple Beach by Florida Keys Luxury Rentals

4 out of 5
130 Aregood Lane Islamorada FL
Book a stay at this beach vacation home in Islamorada. Enjoy free parking and a private beach. Popular attractions Old Road Gallery and Founders Park are located ...
Opens in a new windowPineapple Beach by Florida Keys Luxury Rentals
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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.

4 Star Hotels Islamorada

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Islamorada 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Islamorada will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Islamorada, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.

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