Explore 16 Luxury Hotels in Islamorada

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Best Luxury Hotels in Islamorada

Casa Morada

Casa Morada

136 Madeira Road Islamorada FL
The price is $307 total per night from Jun 1 to Jun 2
$307 total
per night
Jun 1 - Jun 2
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Enjoy a day at the beach kayaking, or relax ...
9.4/10 Exceptional! (435 reviews)
The meet and great staff is great. The outside bar is currently closed. The bicycles are ok- several with no breaks, seat posts rusted into one height. Our rooms outdoor patio was also shared with maintenance water hose. If you don’t mind your privacy being interrupted… This is a nice quiet location, ...

Reviewed on May 10, 2026

Opens in a new windowCasa Morada
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $318 total per night from May 21 to May 22
$318 total
per night
May 21 - May 22
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! (1,330 reviews)
Exelente service but the room need more clean and attention

Reviewed on May 11, 2026

Opens in a new windowCheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $261 total per night from May 26 to May 27
$261 total
per night
May 26 - May 27
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! (1,742 reviews)
Free, breakfast free, bike rentals great beach, great rooms nice and cool. Honestly, it was a great place.

Reviewed on May 13, 2026

Opens in a new windowChesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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 $359 total per night from Jun 2 to Jun 3
$359 total
per night
Jun 2 - Jun 3
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! (194 reviews)
The resort, staff and facilities are excellent. The location in Islamorada is great either for a few days in the keys or as a stopping point to or from Key West. We didn’t get time to use all of the facilities but there are restaurants on site, kayaks, pools, a lively beach and breakfast so you don’t ...

Reviewed on May 10, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $284 total per night from May 19 to May 20
$284 total
per night
May 19 - May 20
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! (1,284 reviews)
Beautiful location, very helpful staff and just an exquisite experience. Food was excellent. Loved every second.

Reviewed on May 13, 2026

Opens in a new windowAmara Cay Resort
Drop Anchor

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL
The price is $271 total per night from May 17 to May 18
$271 total
per night
May 17 - May 18
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 ...
8.8/10 Excellent! (1,003 reviews)
Excellent

Reviewed on May 10, 2026

Opens in a new windowDrop Anchor
Creekside Inn

Creekside Inn

90611 Old Highway Tavernier FL
The price is $152 total per night from Jun 1 to Jun 2
$152 total
per night
Jun 1 - Jun 2
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! (1,001 reviews)
Clean and everything was great!

Reviewed on May 12, 2026

Opens in a new windowCreekside Inn
Conch On Inn Motel

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.
Opens in a new windowConch On Inn Motel
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5 star hotels in Islamorada

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
2,157 hotels
Lowest Price
$152
Highest Price
$359
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

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