Explore 16 Luxury Hotels in Islamorada

Name: Drop Anchor
Price range: $183 total

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Best Luxury Hotels in Islamorada

Casa Morada

82200 overseas HWY Islamorada FL

Fully refundableReserve now, pay when you stay

$186 nightly

$209 total

Oct 7 - Oct 8

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! (460 reviews)

"It was clean, and the staff were lovely. However it’s advertised as a beach front resort, there are some rooms away from the main property which are on the water but the main property is on the main road and is basically a motel. Not at all how it appears on the pictures. It was expensive but we ..."

Reviewed on Sep 26, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$195 nightly

$219 total

Oct 2 - Oct 3

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! (1,475 reviews)

"The room was a little loud from the A/C unit but great stay"

Reviewed on Sep 30, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$186 nightly

$209 total

Oct 6 - Oct 7

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! (1,795 reviews)

"Great place"

Reviewed on Sep 30, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$208 nightly

$234 total

Oct 5 - Oct 6

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! (1,328 reviews)

"La habitación con peste a humedad debido a que no limpiam ni cambian los filtros del aire,el servicio de limpieza de habitaciones es malo tienes que pedir que te pongan papel de baño, al hotel le falta recreación, en las noches es aburrido y de día en la piscina no ponen música, es aburrido,en fin ..."

Reviewed on Sep 29, 2026

Creekside Inn

90611 Old Highway Tavernier FL

Fully refundableReserve now, pay when you stay

$159 nightly

$179 total

Oct 4 - Oct 5

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! (1,020 reviews)

"We were able to see 2 manatees and a shark from our room door!"

Reviewed on Sep 30, 2026

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL

$167 nightly

$183 total

Oct 5 - Oct 6

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 ...

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$280 nightly

$315 total

Oct 18 - Oct 19

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 ...

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.

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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

Turtle Nest Estate by Florida Keys Luxury Rentals

75971 Overseas Highway Islamorada FL

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5 star hotels in Islamorada

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

$195 nightly

$219 total

Oct 2 - Oct 3

Total with taxes and fees

9.2/10 Wonderful! (1,475 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	2,117 hotels
Lowest Price	$179
Highest Price	$613
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 5 hours ago

Travelocity Verified Review

"The room was a little loud from the A/C unit but great stay"

A verified traveler stayed at Cheeca Lodge & Spa

Amara Cay Resort

4 out of 5

Posted 2 days ago

Travelocity Verified Review

"This resort was absolutely beautiful!! The pool was amazing, a resort style pool. The resort had its own private beach area and a dock. Had plenty of seating everywhere, many cool sitting areas around the property. The only negative thing I could say is that the staff didn’t pick up trash and towels around the pool which seemed odd and it was off season so it wasn’t busy. It’s such a beautiful resort that I would think that would be a priority to keep it clean. Another cool thing is that they have a water taxi and shuttle to their 2 sister resorts which you can utilize all of those amenities as well. They also included bike rentals, paddle boards and kayaking on site which is convenient. You can also bring your private boat there and leave it at the dock for a fee. I would absolutely stay there again!"

A verified traveler stayed at Amara Cay Resort