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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 $376 per night from Nov 29 to Nov 30
CA $376
CA $501 total
Nov 29 - Nov 30
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 ...
8.8/10 Excellent! (1,199 reviews)
"This was an amazing resort. Highly recommend!"

Reviewed on Nov 14, 2026

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

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $331 per night from Nov 29 to Nov 30
CA $331
CA $477 total
Nov 29 - Nov 30
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. ...
Opens in a new windowIslander Resort
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 $233 per night from Nov 17 to Nov 18
CA $233
CA $366 total
Nov 17 - Nov 18
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! (1,332 reviews)
"If I have one complaint, it would be access to a decent cup of coffee. You would think there would be a quick access coffee shop or station or at least through the bar."

Reviewed on Nov 14, 2026

Opens in a new windowAmara Cay 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 $296 per night from Nov 29 to Nov 30
CA $296
CA $437 total
Nov 29 - Nov 30
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! (314 reviews)
"Clean room with balcony and water views. Overall this is a very well maintained property. I would only suggest more staffing for quicker check ins and delivery of coffee and condiments for the rooms."

Reviewed on Nov 14, 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 $375 per night from Nov 29 to Nov 30
CA $375
CA $501 total
Nov 29 - Nov 30
includes taxes & fees
Book a stay at this luxury resort in Key Largo. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,004 reviews)
"Deseando volver!!!!!"

Reviewed on Nov 14, 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 $221 per night from Nov 17 to Nov 18
CA $221
CA $353 total
Nov 17 - Nov 18
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! (1,003 reviews)
"Great first time experience and lovely property"

Reviewed on Nov 12, 2026

Opens in a new windowLa Siesta Resort & Villas
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 ...
Opens in a new windowCondo in the Keys
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
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 John Pennekamp Coral Reef State Park and Jimmy ...
Opens in a new windowThe Sanctuary Islet by Florida Keys Luxury Rentals
Serenity by Florida Keys Luxury Rentals

Serenity by Florida Keys Luxury Rentals

4 out of 5
75631 Overseas Highway Islamorada FL
Book a stay at this beach vacation home in Islamorada. Enjoy free parking and a private beach. Popular attractions Sunset Drive Beach and Robbie’s of Islamorada ...
Opens in a new windowSerenity 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.

Recent Islamorada hotel reviews by fellow wanderers

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