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Featured Islamorada 4 Star hotels

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

97000 Overseas Hwy Key Largo FL

CA $383

CA $509 total

Jul 15 - Jul 16

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! (1,122 reviews)

"Everything was so perfect, easy check in and express check out. Every single employee was super nice and helpful."

Reviewed on Jun 30, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

CA $267

CA $405 total

Jul 8 - Jul 9

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! (1,290 reviews)

"Overall, we had a lovely one-night mother-daughter getaway at Amara Cay and would consider staying again. The resort has a relaxing tropical feel, and all public areas were clean and well maintained. The front desk associate who checked us in was exceptional, friendly, accommodating, and kind. (Don’t ..."

Reviewed on Jul 1, 2026

Playa Largo Resort & Spa, Autograph Collection

97450 Overseas Highway Key Largo FL

Fully refundableReserve now, pay when you stay

CA $430

CA $562 total

Jul 15 - Jul 16

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 ...

9/10 Wonderful! (1,002 reviews)

"The floor of the room was dirty and never vacuumed/ swept during our visit. Other guests were loud and entitled."

Reviewed on Jun 30, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

CA $329

CA $466 total

Jul 19 - Jul 20

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. ...

9.4/10 Exceptional! (1,069 reviews)

"We were only there for one day. Rooms are really nice. Property is also great, with an easy walk to two great pools. Sadly the sargassum was pretty bad while we weee here, so you might want to ask before you come. Swimming in the ocean was not possible. Glad the pools were nice."

Reviewed on Jun 30, 2026

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

CA $276

CA $414 total

Jul 15 - Jul 16

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! (1,000 reviews)

"We love it"

Reviewed on Jun 29, 2026

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

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

CA $361

CA $510 total

Jul 14 - Jul 15

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! (222 reviews)

"Hotel is nice but there is a lot of seaweed!!! so the beach is unusable... We were given a room in Building 7, so far from everything—and had to walk way too much! Some staff are nice and another one rude. There is a lot of thing to do there but sincerely it's not worth the money, no coming ..."

Reviewed on Jun 29, 2026

The Islands of Islamorada

82779 Old Hwy Islamorada FL

CA $907

CA $1,099 total

Jul 6 - Jul 7

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! (76 reviews)

"I am not usually about leaving reviews however this property definitely needs it. Heard a lot about being pampered when I was checked in and that they will bring you anything and to let them know what our needs were. Property does not have any coffee shop or restaurant. We were told we could come ..."

Reviewed on May 18, 2026

Condo in the Keys

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! (15 reviews)

"The owners are great and very quick to respond. We had a couple of things that needed resolving which they did immediately. The beds are not the most comfortable, especially the sleeper sofa, it slants down. The cleaning person could do a better job but overall the owners made up for that."

Reviewed on Jun 22, 2026

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Serenity by Florida Keys Luxury Rentals

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 ...

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Turtle Nest Estate by Florida Keys Luxury Rentals

75971 Overseas Highway Islamorada FL

Book a stay at this beach vacation home in Islamorada. Enjoy free parking and a private beach. Popular attractions Robbie’s of Islamorada and Sunset Drive Beach ...

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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.