Explore 16 Luxury 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
Best Luxury Hotels in Islamorada
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $214 total per night from Nov 10 to Nov 11
$214 total
Nov 10 - Nov 11
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 ...
9.4/10 Exceptional! (1,811 reviews)
"We stayed for 2 nights at the Chesapeake Bay resort. Great location, Our room was clean and property was well maintained. The front desk staff was very welcoming and helpful. Easy check in and out. Beautiful views of the ocean from our balcony. Great amenities, breakfast each morning was delicious. ..."
Reviewed on Nov 8, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$234 nightly
The price is $263 total per night from Dec 1 to Dec 2
$263 total
Dec 1 - Dec 2
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! (1,514 reviews)
"The suite had an odor like humidity not nice , I paid for a room with view they didn’t give that, anyway it was a nice suite but the odor killed the experience for me"
Reviewed on Nov 8, 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 Nov 29 to Nov 30
$306 total
Nov 29 - Nov 30
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! (311 reviews)
"Rooms were clean, property is bea"
Reviewed on Nov 9, 2026
Creekside Inn
90611 Old Highway Tavernier FL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $147 total per night from Dec 10 to Dec 11
$147 total
Dec 10 - Dec 11
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! (1,023 reviews)
"It’s honestly not a 5 star Ritz Carlton, but for the price, the location, and everything, we enjoyed our stay! Room was clean and very big. We arrived super late but the grounds felt very safe. Would come back!"
Reviewed on Nov 8, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$222 nightly
The price is $250 total per night from Nov 17 to Nov 18
$250 total
Nov 17 - Nov 18
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 ...
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$163 nightly
The price is $178 total per night from Nov 10 to Nov 11
$178 total
Nov 10 - Nov 11
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 ...
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.
Casa Morada
82200 overseas HWY Islamorada FL
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $241 total per night from Nov 16 to Nov 17
$241 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers ...
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
The Islands of Islamorada
82779 Old Hwy Islamorada FL
$754 nightly
The price is $848 total per night from Nov 29 to Nov 30
$848 total
Nov 29 - Nov 30
Total with taxes and fees
9.6/10 Exceptional! (83 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 | 2,118 hotels |
|---|---|
Lowest Price | $147 |
Highest Price | $848 |
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
4 out of 5
Posted 15 hours ago
Travelocity Verified Review
"The suite had an odor like humidity not nice , I paid for a room with view they didn’t give that, anyway it was a nice suite but the odor killed the experience for me"
A verified traveler stayed at Cheeca Lodge & Spa
More Ways To Wander Islamorada
Flights to Islamorada
The best fares to get you there
Islamorada Hotels
Islamorada Vacation Rentals
Great Deals on Alternative Accommodations
Islamorada Car Rentals
Affordable cars to get you around town
Islamorada Vacations
Save more by combining flights, hotels and cars
Things to do in Islamorada
Discover events, experiences & tours