Explore top 2026 4 Star Hotels in Islamorada
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Top Islamorada 4 Star hotels
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
$302 nightly
The price is $340 total per night from Jul 12 to Jul 13
$340 total
Jul 12 - Jul 13
Total with taxes and fees
A private beach, 2 restaurants, and 2 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
8.6/10 Excellent! (1,094 reviews)
"Excelente servicio y todo muy limpio"
Reviewed on Jun 16, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$243 nightly
The price is $273 total per night from Jul 6 to Jul 7
$273 total
Jul 6 - Jul 7
Total with taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...
8.8/10 Excellent! (1,313 reviews)
"We had a wonderful stay at Amara Cay and recommend it for an unforgettable vacation. We were treated with great kindness, and the place is beautiful."
Reviewed on Jun 15, 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$316 nightly
The price is $356 total per night from Jun 29 to Jun 30
$356 total
Jun 29 - Jun 30
Total with taxes and fees
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...
9.4/10 Exceptional! (1,061 reviews)
"Everything was great, we had a nice & relaxing time."
Reviewed on Jun 16, 2026
Playa Largo Resort & Spa, Autograph Collection
97450 Overseas Highway Key Largo FL
Fully refundableReserve now, pay when you stay
$352 nightly
The price is $396 total per night from Jun 30 to Jul 1
$396 total
Jun 30 - Jul 1
Total with taxes and fees
This luxury resort features a full-service spa, a marina, and 3 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the ...
9/10 Wonderful! (1,001 reviews)
"The service was poor all around and the food was not fresh like you'd expect for the price and at a “resort.” The staff admitted the “fresh squeezed, orange juice“ was not fresh and from a can the guacamole was also from a can and not made out of actual fresh guacamoles. The menu variety was lacking, ..."
Reviewed on Jun 13, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$336 nightly
The price is $378 total per night from Jun 30 to Jul 1
$378 total
Jun 30 - Jul 1
Total with taxes and fees
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...
9/10 Wonderful! (211 reviews)
"Overall our stay was nice. We loved the shores pool, and paid extra for ocean view and balcony, which was ruined by the sargassum(out of resorts control of course). Also the balcony was not a private balcony attached to our room, it was just an extension off the walk way open to anyone really, so ..."
Reviewed on Jun 16, 2026
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $271 total per night from Jul 6 to Jul 7
$271 total
Jul 6 - Jul 7
Total with taxes and fees
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, ...
8.6/10 Excellent! (1,000 reviews)
"The staff was friendly, but the site was not maintained well. We stayed in a Queen suite which was dated and well worn. The shower handle kept falling off. We also stayed in the Villa which was in much better condition that the Queen Suite. My biggest pet peeve was that the garbage cans were overflowing ..."
Reviewed on Jun 16, 2026
The Islands of Islamorada
82779 Old Hwy Islamorada FL
$688 nightly
The price is $774 total per night from Jul 6 to Jul 7
$774 total
Jul 6 - Jul 7
Total with taxes and fees
A marina, 2 outdoor pools, and a 24-hour gym are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach ...
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
The private beach and full-service spa are among the highlights at this apartment. There's fun for all ages with a playground and an arcade/game room, and families ...
8/10 Very Good! (14 reviews)
"Nice kitchen. Great view."
Reviewed on Mar 27, 2026
The Sanctuary Islet by Florida Keys Luxury Rentals
1565 Ocean Bay Drive Key Largo FL
This vacation home features a private beach and free WiFi in public areas. Take advantage of the free self parking.
Pineapple Beach by Florida Keys Luxury Rentals
130 Aregood Lane Islamorada FL
This vacation home features a private beach and free WiFi in public areas. Take advantage of the free self parking.
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
Chesapeake Beach Resort
4 out of 5
Posted 14 hours ago
Travelocity Verified Review
"Breakfast selection each day was excellent. Room was clean, just a little noisy from upstairs kids footsteps in the morning. 2 pools were great although main pool in need of resurfacing and a bit too warm, understandable due to 90+ temps. Love the free kayaks and paddle boards. Staff was very friendly and accommodating. Beautiful views and convenient location."
A verified traveler stayed at Chesapeake Beach Resort
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