Explore 16 Luxury Hotels in Islamorada
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Best Luxury Hotels in Islamorada
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $275 total per night from May 10 to May 11
$275 total
May 10 - May 11
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! (1,323 reviews)
Incredible. Everyone was so nice. We will be back.
Reviewed on May 6, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$238 nightly
The price is $268 total per night from Jun 1 to Jun 2
$268 total
Jun 1 - Jun 2
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! (1,720 reviews)
excellent breakfast included. large comfortable rooms
Reviewed on May 5, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $330 total per night from Jun 1 to Jun 2
$330 total
Jun 1 - Jun 2
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! (192 reviews)
Clean updated room, great view and balcony! Loved the property and amenities.
Reviewed on Apr 25, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$247 nightly
The price is $277 total per night from May 20 to May 21
$277 total
May 20 - May 21
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 ...
8.8/10 Excellent! (1,269 reviews)
Great staff
Reviewed on May 5, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$206 nightly
The price is $227 total per night from May 7 to May 8
$227 total
May 7 - May 8
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 ...
8.8/10 Excellent! (1,002 reviews)
Our room was comfortable and clean. The grounds and pool were really nice. The entire staff were awesome. It was really cool having the kayaks on the property. We had a great stay.
Reviewed on Apr 26, 2026
Creekside Inn
90611 Old Highway Tavernier FL
Fully refundableReserve now, pay when you stay
$433 nightly
The price is $487 total per night from May 7 to May 8
$487 total
May 7 - May 8
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! (1,005 reviews)
Lovely stopover for Journey down the Keys. Room was literally Creekside. Great views watching the wildlife & boats passing by! Room & staff perfect
Reviewed on May 6, 2026
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
136 Madeira Road Islamorada FL
$357 nightly
The price is $401 total per night from Jun 1 to Jun 2
$401 total
Jun 1 - Jun 2
Total with taxes and fees
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 ...
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
The Sanctuary Islet by Florida Keys Luxury Rentals
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5 star hotels in Islamorada
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$244 nightly
The price is $275 total per night from May 10 to May 11
$275 total
May 10 - May 11
Total with taxes and fees
9.2/10 Wonderful! (1,323 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 | 2,205 hotels |
|---|---|
Lowest Price | $227 |
Highest Price | $487 |
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
Islander Resort
5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"The property was beautiful and the room was great. We had a double queen room with partial ocean view, but we couldn't see one bit of water. The bathroom was pretty small but the shower was amazing. Unfortunately it rained quite a bit so we were in the room and found that the TV was awful. But we will definitely be staying there again!"
A verified traveler stayed at Islander Resort
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