Explore top 2026 4 Star Hotels in Islamorada
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check prices for these dates
Top Islamorada 4 Star hotels
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is $340 total per night from Aug 17 to Aug 18
$340 total
per night
Aug 17 - Aug 18
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. ...
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $264 total per night from Aug 17 to Aug 18
$264 total
per night
Aug 17 - Aug 18
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! (1,288 reviews)
"It’s nice to have access to there sister properties"
Reviewed on Jul 20, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $306 total per night from Aug 10 to Aug 11
$306 total
per night
Aug 10 - Aug 11
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! (231 reviews)
"The whole staff was discriminating from start to finish. From the moment of check in the staff had a look on their faces like they didn’t want to be there or at least with us. We saw them treat other guests with smiles and pleasantry until it came to us. None of the restaurants or amenities opens ..."
Reviewed on Jul 19, 2026
Playa Largo Resort & Spa, Autograph Collection
97450 Overseas Highway Key Largo FL
Fully refundableReserve now, pay when you stay
The price is $351 total per night from Aug 16 to Aug 17
$351 total
per night
Aug 16 - Aug 17
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! (1,009 reviews)
"Great service."
Reviewed on Jul 19, 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $361 total per night from Aug 12 to Aug 13
$361 total
per night
Aug 12 - Aug 13
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! (1,076 reviews)
"The resort is beautiful and well maintained."
Reviewed on Jul 19, 2026
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $266 total per night from Aug 20 to Aug 21
$266 total
per night
Aug 20 - Aug 21
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! (1,002 reviews)
"Nice place for a short vacation. Many things to do around the area. We requested housekeeping but they never came"
Reviewed on Jul 19, 2026
The Islands of Islamorada
82779 Old Hwy Islamorada FL
The price is $617 total per night from Aug 2 to Aug 3
$617 total
per night
Aug 2 - Aug 3
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! (78 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
Reviewed on Jul 13, 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! (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
Serenity by Florida Keys Luxury Rentals
75631 Overseas Highway Islamorada 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 2 hours ago
Travelocity Verified Review
"We just ended a three night stay here. The property is cute. The rooms were cute and clean. The complementary breakfast was surprisingly delicious. The beach was covered in seaweed and not really raked up. They were doing maintenance on the main pool so unfortunately one of the days we could not use it. It was super noisy in the morning and we were not given a heads up when I sent a text, I got a standard general response, letting me know that a text was sent, but it looked like it never went through. I feel like at check-in. This should’ve been something that was communicated especially when you’re going down for a relaxing peaceful weekend. We spent one of the mornings eating our breakfast listening to loud work being done at the pool directly next to us. Thursday night was cheap but for the price of Friday and Saturday night and how high it was this is something that definitely should’ve been communicated. We were down with family, so there were two other rooms that were booked as well and they all felt the same. When we checked in the two girls didn’t tell us much about the property. My fiancé had asked if he could cut off a band that was on his arm and she looked at him like he had five heads. It was a weird encounter. The food at the tiki hut was extremely expensive and not good whatsoever. However, the drinks were delicious and the guy who made them was wonderful."
A verified traveler stayed at Chesapeake Beach Resort
More ways to wander Islamorada
Explore More Ways to Travel with Travelocity
- 3 Star Hotels in Lower Arsnicker Keys
- 4 Star Hotels in Marathon
- 3 Star Hotels in Tamiami
- Hotels near Founders Park
- Hotels near Florida Keys Dive Center
- 3 Star Hotels in Key Colony Beach
- Hotels with Pools in Venetian Shores
- Venetian Shores Hotels
- 3 Star Hotels in Key Largo
- 4 Star Hotels in Key Largo
- 5 Star Hotels in Key Largo
- 3 Star Hotels in Plantation Key
- 5 Star Hotels in Plantation Key
- Chalets in Plantation Key
- Guest Houses in Plantation Key
- Holiday Park Resorts in Plantation Key
- Aimbridge Hospitality Hotels in Plantation Key
- Beach Resorts & in Plantation Key
- Cheap Hotels in Plantation Key
- Hersha Hospitality Hotels in Plantation Key
- Hotels with Pools in Plantation Key
- Hotels with Free Parking in Plantation Key
- Hotels with Kitchenettes in Plantation Key
- Hotels with smoking rooms in Plantation Key
- Plantation Key Hotels
- Houseboats in Plantation Key
- Hersha Hospitality Hotels in Windley Key
- Villas in Windley Key
- Hotels near Bud n' Mary's Dive Center
- 3 Star Hotels in Pinecrest
- 5 Star Hotels in Pinecrest
- 2 Star Hotels in Bahia Honda Key
- Aimbridge Hospitality Hotels in Lignumvitae Key Botanical State Park
- Lignumvitae Key Botanical State Park Hotels
- 4 Star Hotels in Duck Key
- Matecumbe Hotels
- 5 Star Hotels in Cudjoe Key
- 3 Star Hotels in Elliott Key
- 4 Star Hotels in Coconut Grove
- 5 Star Hotels in Coconut Grove
- 4 Star Hotels in Melody Key
- Lower Matecumbe Beach Hotels
- 3 Star Hotels in The Crossings
- 4 Star Hotels in The Crossings
- 2 Star Hotels in Lower Matecumbe Key
- 4 Star Hotels in Lower Matecumbe Key
- Apartments in Lower Matecumbe Key
- Condos in Lower Matecumbe Key
- Aimbridge Hospitality Hotels in Lower Matecumbe Key
- Lower Matecumbe Key Hotels
- Houseboats in Lower Matecumbe Key
- 3 Star Hotels in Conch Key
- Hotels near Windley Key Fossil Reef Geological State Park
- 4 Star Hotels in Naranja
- 4 Star Hotels in Upper Matecumbe Key
- Extended Stay Hotels in Upper Matecumbe Key
- Holiday Park Resorts in Upper Matecumbe Key
- Aimbridge Hospitality Hotels in Upper Matecumbe Key
- Beach Resorts & in Upper Matecumbe Key
- Hotels with Pools in Upper Matecumbe Key
- Hotels near Sunset Drive Beach
- Hotels near Florida Keys Brewing Co.
- Hotels near Anne's Beach
- Hotels near Matecumbe United Methodist Church
- 3 Star Hotels in Big Pine Key
- 5 Star Hotels in Big Pine Key
- Apartments in Tavernier
- Cabins in Tavernier
- Condos in Tavernier
- Cottages in Tavernier
- Beach Resorts & in Tavernier
- Cheap Hotels in Tavernier
- Fishing Resorts & in Tavernier
- Hotels with Bar in Tavernier
- Hotels with Free Breakfast in Tavernier
- Hotels with Hot Tubs in Tavernier
- Luxury Hotels in Tavernier
- Pet Friendly Hotels in Tavernier
- Hotels on the River in Tavernier
- Tavernier Hotels
- Houseboats in Tavernier
- Motels in Tavernier
- Vacation Homes in Tavernier
- 4 Star Hotels in Florida City
- 5 Star Hotels in Homestead
- 5 Star Hotels in Kendall