Explore 16 Luxury Hotels in Islamorada

Name: Drop Anchor
Price range: $212 total
Rating: 8.6

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Best Luxury Hotels in Islamorada

Casa Morada

136 Madeira Road Islamorada FL

$518 nightly

$583 total

Jan 25 - Jan 26

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 ...

9.4/10 Exceptional! (418 reviews)

Friendly staff! Laid back place! We enjoyed our stay here! We will be back!

Reviewed on Jan 18, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$346 nightly

$390 total

Jan 29 - Jan 30

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! (1,292 reviews)

Nice resort

Reviewed on Jan 19, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$275 nightly

$310 total

Jan 26 - Jan 27

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! (1,637 reviews)

Room was clean. Check in was fast and the staff was very friendly and welcoming.

Reviewed on Jan 18, 2026

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

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$398 nightly

$448 total

Jan 29 - Jan 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 ...

9/10 Wonderful! (132 reviews)

All staff members were great!

Reviewed on Jan 16, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$276 nightly

$311 total

Jan 27 - Jan 28

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! (1,263 reviews)

Amazing place to stay. Staff was great

Reviewed on Jan 16, 2026

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL

$192 nightly

$212 total

Jan 29 - Jan 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! (1,005 reviews)

Great stay, better than I even expected from the pictures. Quiet, quaint little place right on the water. The edge is actually a dock, but it looks like it’s right on its own, private, wide beach! The internet was good - I had a half day of doing Zoom work calls and had no problems. It’s quiet, the ...

Reviewed on Jan 21, 2026

Creekside Inn

90611 Old Highway Tavernier FL

Fully refundableReserve now, pay when you stay

$199 nightly

$224 total

Jan 25 - Jan 26

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! (1,000 reviews)

Outside my room was table and chairs where you can sit and enjoy watching the boat go by. Housekeeping was superb My room was spotless. There wasn’t any dust or dirt in any corner. The bathrooms were immaculate. I highly recommend this hotel. They also do not charge the resort fee that all the hotels ...

Reviewed on Jan 20, 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.

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.

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5 star hotels in Islamorada

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

$346 nightly

$390 total

Jan 29 - Jan 30

Total with taxes and fees

9.2/10 Wonderful! (1,292 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	2,223 hotels
Lowest Price	$212
Highest Price	$583
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