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Featured Islamorada Luxury Hotels

See all 358 Properties in Islamorada

Estimated price for 1 night/2 adults

Cheeca Lodge & Spa
Cheeca Lodge & Spa
4.0 out of 5.0 81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free Cancellation
4.4/5 (1689 reviews)
$215/ night for 2 guests

Beautiful grounds, clean and upgraded rooms, friendly staff.

Reviewed on Jun 21, 2019
Amara Cay Resort
Amara Cay Resort
3.5 out of 5.0 80001 Overseas Hwy, Islamorada, FL
Free Cancellation
4.3/5 (1698 reviews)
$175/ night for 2 guests

I didn’t know what to expect but found the property to be very comfortable and open. The only complaint I can make is the music playing in the bar area was really boring.

Reviewed on Jun 20, 2019
Drop Anchor
Drop Anchor
3.0 out of 5.0 84959 Overseas Highway, 222, Islamorada, FL
4.3/5 (1175 reviews)
$143/ night for 2 guests

A little bit of paradise, the staff were lovely and very helpful, pool area clean and tidy wonderful sandy area with seating and hammocks (I did manage to get in and out without falling on my face) accommodation has full kitchen also BBQ's on site for customer use.

Reviewed on Jun 23, 2019
Postcard Inn Beach Resort & Marina
Postcard Inn Beach Resort & Marina
3.0 out of 5.0 84001 Overseas Hwy, Islamorada, FL
Free Cancellation
3.8/5 (1365 reviews)
$175/ night for 2 guests

The property feels like a real resort which is hard to find beachside in Islamorada

Reviewed on Jun 25, 2019
Creekside Inn Islamorada
Creekside Inn Islamorada
2.5 out of 5.0 90611 Old Highway, Tavernier, FL
3.7/5 (1012 reviews)
$137/ night for 2 guests

What we wish would be for an on site person to assist with bringing the bags to the room...or an elevator. We’re both in our 60s and in not so great health so the struggle up those stairs was real. Other than that it was a wonderful experience and the room, number 17 exceeded our expectations! Thank ...

Reviewed on Jun 10, 2019
Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5.0 83409 Overseas Hwy, Islamorada, FL
3.5/5 (768 reviews)

Property is under total renovation but hotel notified us of this prior to stay. Review will be different after work completed. Beautiful location but water in lagoon by beach is full of junk.

Reviewed on Jun 25, 2019
Conch On Inn Motel
Conch On Inn Motel
2.0 out of 5.0 103 Caloosa Street, Tavernier, FL
3.7/5 (475 reviews)

Overall great experience & owners were great. Only thing I would offer up is could use some new mattresses but everything else was more than expected! Would (or shouldsay will) stay again someday

Reviewed on Aug 6, 2018
Pelican Cove Resort & Marina
Pelican Cove Resort & Marina
3.0 out of 5.0 84457 Overseas Highway, Islamorada, FL
Free Cancellation
4.0/5 (1241 reviews)
$165/ night for 2 guests

Property was amazing! Very clean and friendly staff. The on site restaurants and bars where amazing and did not disappoint. The rooms are spacious and the beds are comfortable. We will defiantly go back.

Reviewed on Jun 24, 2019
Casa Morada
Casa Morada
3.5 out of 5.0 136 Madeira Road, Islamorada, FL
4.8/5 (102 reviews)
$329/ night for 2 guests

The bed hurt my back badly, but literally everything else was excellent! Could use a little shade over the pool.

Reviewed on Jun 23, 2019
Map

Recently booked Luxury Hotels in Islamorada

Postcard Inn Beach Resort & Marina
3.0 out of 5.0
Last booking: 35 minutes ago
Amara Cay Resort
3.5 out of 5.0
Last booking: 1 hour ago
Cheeca Lodge & Spa
4.0 out of 5.0
Last booking: 1 hour ago
Creekside Inn Islamorada
2.5 out of 5.0
Last booking: 4 hours ago
Islander Resort
3.0 out of 5.0
Last booking: 12 hours ago
Pines & Palms Resort
3.0 out of 5.0
Last booking: 12 hours ago
La Siesta Resort & Marina
3.0 out of 5.0
Last booking: 13 hours ago

A few days away keeps your troubles at bay, so book your getaway to Islamorada and prepare to unwind. Intriguing sites, divine eats, and opportunities to take fantastic photos: these are just some of the benefits of visiting Islamorada. You'll treat yourself to the city's best food, marvel at the most noteworthy monuments and landmarks in the region, and enjoy the most popular performances. Naturally, you'll stay at a luxury hotel! Sampling the finer things in life is just your speed, so book your elegant hotel in Islamorada on Expedia.com today, and your relaxing getaway is off to a great start.

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Luxury Hotels in Islamorada

There's no better time than right now to book your getaway in Islamorada, and Expedia.com is here to save the day. Search through the wealth of ratings and reviews on spectacular hotels to find an accommodation that suits your needs. Luxury accommodations offer amenities like stately suites and VIP services. Some of the city's luxury accommodations even feature impeccable penthouses, while others offer pampering spa treatments. Use our easy booking widget to choose a fabulous 5-star hotel in Islamorada, and prepare for the vacation of your life!