Explore 16 Luxury Hotels in Islamorada
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Best Luxury Hotels in Islamorada
Casa Morada
136 Madeira Road Islamorada FL
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $180 total per night from Aug 31 to Sep 1
$180 total
Aug 31 - Sep 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Spend a day at the beach kayaking, or relax with sun loungers and beach ...
9.4/10 Exceptional! (451 reviews)
"The entire experience was a disappointment. Expedia advertised this as CASA MORADA but we were given a room at SUNSET INN. The room as on the street, not on the water or even in the property located at the water. The actual property we stayed at was recently purchased by Casa Morada and we were not ..."
Reviewed on Aug 10, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $241 total per night from Aug 18 to Aug 19
$241 total
Aug 18 - Aug 19
Total with taxes and fees
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
9.2/10 Wonderful! (1,397 reviews)
"The pools and bars were great! Our room was dirty, our toilet base was broken, in room coffee pot was HORRIBLE! The food there is ok, I recommend eating out at least for dinners. The bar service while at the pool was the absolute best part. Butch was the best bartender!"
Reviewed on Aug 17, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $228 total per night from Aug 19 to Aug 20
$228 total
Aug 19 - Aug 20
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
9.2/10 Wonderful! (1,751 reviews)
"We had a wonderful stay! The breakfast was exceptional, and the rooms were beautiful, spacious, and very fresh and comfortable. The staff was extremely friendly, attentive, and professional. Unfortunately, I cannot give the hotel five stars because both swimming pools were very dirty and had visible ..."
Reviewed on Aug 16, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$272 nightly
The price is $306 total per night from Sep 7 to Sep 8
$306 total
Sep 7 - Sep 8
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! (250 reviews)
"Stayed in build 7 and it had a great view restaurant was good the bars where nice and most of all I booked a fishing trip with Whiskey Throttle guide service and Sean put me on a dinosaur of a tarpon and boy was it a beast. If the fishing is slow grab Whiskey Throttle for a great water ..."
Reviewed on Aug 14, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$140 nightly
The price is $153 total per night from Aug 18 to Aug 19
$153 total
Aug 18 - Aug 19
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A business center, a garden, and a picnic area ...
8.6/10 Excellent! (1,003 reviews)
"The room was terrible. The floors were sticky and covered in dirt, not sand, but dirt. My son spilt water on the floor and as we wiped it up with a white towel the towel was completely black. The stove was very dirty as well, when we wiped ups mess on the stove the rag was black. The room was in ..."
Reviewed on Aug 16, 2026
Creekside Inn
90611 Old Highway Tavernier FL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $154 total per night from Aug 18 to Aug 19
$154 total
Aug 18 - Aug 19
Total with taxes and fees
This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. ...
7.8/10 Good! (1,014 reviews)
"Great location. Pet-friendly."
Reviewed on Aug 16, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $248 total per night from Aug 30 to Aug 31
$248 total
Aug 30 - Aug 31
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 ...
Conch On Inn Motel
103 Caloosa Street Tavernier FL
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, concierge services, and barbecue grills are also on offer.
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.
More 4 star hotels in Islamorada
Serenity by Florida Keys Luxury Rentals
75631 Overseas Highway Islamorada FL
5 star hotels in Islamorada
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$214 nightly
The price is $241 total per night from Aug 18 to Aug 19
$241 total
Aug 18 - Aug 19
Total with taxes and fees
9.2/10 Wonderful! (1,397 reviews)
Islamorada Luxury Hotels
Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the Islamorada luxury hotels are the plush oasis you’ve been looking for.
Choose from the best luxury hotels in Islamorada to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.
We want you to enjoy your next vacation in style and the top luxury resorts in Islamorada will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Islamorada, and plan your next opulent escape.
Islamorada hotels essential information
Accommodation | 2,169 hotels |
|---|---|
Lowest Price | $153 |
Highest Price | $306 |
Popular hotels | Cheeca Lodge & Spa, Amara Cay Resort, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Creekside Inn, Chesapeake Beach Resort, Conch On Inn Motel, Casa Morada |
Popular Luxury Stays in Islamorada
Recent Islamorada Hotel Reviews By Fellow Wanderers
Cheeca Lodge & Spa
5 out of 5
Posted 11 hours ago
Travelocity Verified Review
"Beautiful resort with a very polite staff. We will definitely stay here again"
A verified traveler stayed at Cheeca Lodge & Spa
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