Explore 16 Luxury Hotels in Islamorada

Name: Drop Anchor
Price range: $163 total
Rating: 8.6

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Best Luxury Hotels in Islamorada

Casa Morada

136 Madeira Road, Islamorada, FL

$330 nightly

$371 total

Oct 12 - Oct 13

Total with taxes and fees

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 ...

9.2/10 Wonderful! (408 reviews)

"Beautiful"

Reviewed on Aug 18, 2025

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

Fully refundableReserve now, pay when you stay

$151 nightly

$170 total

Oct 6 - Oct 7

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. ...

9/10 Wonderful! (1,207 reviews)

"I love it"

Reviewed on Sep 21, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$161 nightly

$182 total

Sep 30 - Oct 1

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 ...

9/10 Wonderful! (1,534 reviews)

"Everything was perfect and beautiful"

Reviewed on Sep 23, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$223 nightly

$251 total

Sep 29 - Sep 30

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! (1,258 reviews)

"The resort had free kayaking and paddle boarding which was a great addition."

Reviewed on Sep 22, 2025

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

84001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$245 nightly

$276 total

Sep 29 - Sep 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 ...

8.8/10 Excellent! (82 reviews)

"We had a fantastic time here! The room was spotless- clean bed, fresh towels, and a great shower. Room service breakfast was delicious. The resort has everything you need, so no need to leave. We loved all the onsite restaurants, and the tiki bar was a total vibe. Big shoutout to our favorite bartender, ..."

Reviewed on Sep 8, 2025

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

$148 nightly

$163 total

Sep 29 - Sep 30

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 ...

8.6/10 Excellent! (1,004 reviews)

"Beach view"

Reviewed on Sep 11, 2025

Creekside Inn Islamorada

90611 Old Highway, Tavernier, FL

Fully refundableReserve now, pay when you stay

$105 nightly

$119 total

Sep 28 - Sep 29

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! (1,012 reviews)

"We stayed here off season, the price was right. There is decline in the appearance of the property, looks like they may be trying to fix it up. Breakfast and the bar was closed. The office hours are hit or miss, but the ladies are sweethearts. The pool we had all to ourselves and extremely clean. ..."

Reviewed on Sep 24, 2025

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

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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

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5 star hotels in Islamorada

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

$151 nightly

$170 total

Oct 6 - Oct 7

Total with taxes and fees

9/10 Wonderful! (1,207 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	2,228 hotels
Lowest Price	$119
Highest Price	$371
Popular hotels	Cheeca Lodge & Spa, Amara Cay Resort, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Creekside Inn Islamorada, Chesapeake Beach Resort, Conch On Inn Motel, Casa Morada