Explore 16 Luxury Hotels in Islamorada

Name: Casa Morada
Price range: $241 total

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Best Luxury Hotels in Islamorada

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$215 total

per night

Nov 17 - Nov 18

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 ...

9.4/10 Exceptional! (1,827 reviews)

"The room was clean and felt newly renovated. The shower door is farm slide style glass that is very heavy and difficult to use. There is not much sound insulation between the rooms. Our upstairs neighbors were very loud and were up super early which caused us to lose sleep. Not the hotels fault but ..."

Reviewed on Nov 14, 2026

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

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$306 total

per night

Nov 29 - Nov 30

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! (314 reviews)

"Clean room with balcony and water views. Overall this is a very well maintained property. I would only suggest more staffing for quicker check ins and delivery of coffee and condiments for the rooms."

Reviewed on Nov 14, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$252 total

per night

Nov 17 - Nov 18

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! (1,332 reviews)

"If I have one complaint, it would be access to a decent cup of coffee. You would think there would be a quick access coffee shop or station or at least through the bar."

Reviewed on Nov 14, 2026

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL

$180 total

per night

Nov 24 - Nov 25

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)

"They were amazing! Amenities were great fun! Will definitely be back!"

Reviewed on Nov 11, 2026

Creekside Inn

90611 Old Highway Tavernier FL

Fully refundableReserve now, pay when you stay

$148 total

per night

Dec 16 - Dec 17

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! (1,024 reviews)

"The stay was great, only issue was that the bathroom shower didn't have much pressure"

Reviewed on Nov 15, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$281 total

per night

Nov 16 - Nov 17

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. ...

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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Casa Morada

82200 overseas HWY Islamorada FL

Fully refundableReserve now, pay when you stay

$241 total

per night

Nov 16 - Nov 17

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers ...

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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

Serenity by Florida Keys Luxury Rentals

75631 Overseas Highway Islamorada FL

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5 star hotels in Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL

$895 total

per night

Nov 19 - Nov 20

9.6/10 Exceptional! (83 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	2,120 hotels
Lowest Price	$148
Highest Price	$895
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

Chesapeake Beach Resort

4 out of 5

Posted 23 hours ago

Travelocity Verified Review

A verified traveler stayed at Chesapeake Beach Resort

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

4 out of 5

Posted 1 day ago

Travelocity Verified Review

A verified traveler stayed at Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Coconut Cove Resort and Marina

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"This is my second time staying here. It's a laid-back, extremely quiet place, so if you're looking for the party vibe, definitely not for you. The "beach" is really no more than a mangrove swamp, but that's typical of the Keys. For beaches, look elsewhere in Florida. The pool makes up for it, though. It is absolutely beautiful, with a waterfall and a chiller, so the water is always cool and refreshing even at the height of summer. And best of all: the pool is open 24 hours! This place is super safe; I left my sliding glass door unlocked the whole time I was here and had no problems. They offer a free, very basic "grab and go" breakfast in the lobby every morning (toast, muffins, cereal, yogurt, coffee and OJ). There is no restaurant or bar on the premises, but plenty of options nearby. The people who own and run this place are some of the nicest, most helpful people you will ever meet. A friend of mine who joined us midway through our stay had booked his room for the wrong date (totally his fault), and they helped him straighten everything out and got him a room at no extra charge!"

A verified traveler stayed at Coconut Cove Resort and Marina