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 $518 total per night from Dec 8 to Dec 9
$518 total
per night
Dec 8 - Dec 9
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy a day at the beach kayaking, or relax with beach umbrellas. There's no skimping ...
9.4/10 Exceptional! (411 reviews)
always a pleasant stay.

Reviewed on Dec 2, 2025

Opens in a new windowCasa Morada
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $236 total per night from Dec 8 to Dec 9
$236 total
per night
Dec 8 - Dec 9
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! (1,582 reviews)
Great place

Reviewed on Nov 28, 2025

Opens in a new windowChesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $357 total per night from Dec 17 to Dec 18
$357 total
per night
Dec 17 - Dec 18
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. ...
9/10 Wonderful! (1,278 reviews)
Property is beautiful with tons of amenities. The room was very nice and overall we were very happy. Here are a few of the issues we had though for full transparency. The beach is sand, but it's hard in a way that's a bit unnatural and doesn't flow into the water. There were weddings on two nights ...

Reviewed on Dec 3, 2025

Opens in a new windowCheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $282 total per night from Dec 15 to Dec 16
$282 total
per night
Dec 15 - Dec 16
A private beach and a restaurant are featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for ...
8.8/10 Excellent! (1,255 reviews)
Great location right on the ocean

Reviewed on Dec 5, 2025

Opens in a new windowAmara Cay 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 $304 total per night from Dec 16 to Dec 17
$304 total
per night
Dec 16 - Dec 17
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 ...
8.8/10 Excellent! (112 reviews)
Beautiful room, stunning views

Reviewed on Nov 19, 2025

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Drop Anchor

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL
The price is $142 total per night from Dec 8 to Dec 9
$142 total
per night
Dec 8 - Dec 9
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! (1,000 reviews)
The staff was very nice. Thanks

Reviewed on Nov 24, 2025

Opens in a new windowDrop Anchor
Creekside Inn

Creekside Inn

90611 Old Highway Tavernier FL
Fully refundableReserve now, pay when you stay
The price is $201 total per night from Dec 8 to Dec 9
$201 total
per night
Dec 8 - Dec 9
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! (1,002 reviews)
Very basic amenities. Comfortable bed. Friendly staff. Pool clean. Able to use Freebie app to have rides around to restaurants and bars. Right on creek.

Reviewed on Dec 2, 2025

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.
The room was about 90° when we got there and never did cool off for two days we were there. Water pressure in the bathroom was bad. And one of the owners gave us a real bad attitude when we inquired about checking out a little bit late on our last day. We will never go back there again I would not ...

Reviewed on Aug 6, 2018

Opens in a new windowConch On Inn Motel
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More 4 star hotels in Islamorada

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
2,234 hotels
Lowest Price
$142
Highest Price
$518
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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