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Islamorada, FL Luxury Hotels $76

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Islamorada Hotels

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Featured Islamorada Luxury Hotels

See all 103 Hotels in Islamorada
Harbor Lights

Harbor Lights

84951 Overseas Hwy, Islamorada
2.0 out of 5.0
2.9 out of 5 (319 reviews)
Quiet place, close to the beach and other facilit.Small place, nice and very helpful lady in front desk. A few minutes from the Theater of the sea, good food around too.
  Jul 26, 2017

$76

$76
La Siesta Resort & Marina

La Siesta Resort & Marina

80241 Overseas Highway, Islamorada
3.0 out of 5.0
3.7 out of 5 (230 reviews)
Paradise!Beautiful setting, in recently updated resort. This was our second time staying at La Siesta and again provided an atmosphere that was quiet, relaxing, and beautiful. Very family friendly.
  Jul 19, 2017

$136

$136
Islander Resort, a Guy Harvey Outpost

Islander Resort, a Guy Harvey Outpost

82100 Overseas Highway, Islamorada
3.0 out of 5.0
4.2 out of 5 (656 reviews)
Ok hotel. Service was bad. Took us hours to get clean towels to our room. Overpriced in my opinion.
  Aug 8, 2017

$100

$100
Postcard Inn Beach Resort & Marina

Postcard Inn Beach Resort & Marina

84001 Overseas Hwy, Islamorada
3.0 out of 5.0
3.6 out of 5 (428 reviews)
Nice placeWe stayed four nights the second week on July. Great hotel very clean and comfortable. Lots of choice activities and food. Marina on site with dive shop. Only draw back was the water at the beach was stagnet if their was no currents. We would definitely stay again. We had a great stay.
  Jul 25, 2017

$165

$165
Pelican Cove Resort & Marina

Pelican Cove Resort & Marina

84457 Overseas Highway, Islamorada
3.0 out of 5.0
3.9 out of 5 (399 reviews)
Nice hotel and great location. I would definitely recommend.
  Aug 2, 2017

$124

$124
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy, Islamorada
3.5 out of 5.0
4.2 out of 5 (461 reviews)
Great hotel with keys feelFamily and puppy (sandy) had a wonderful week at hotel love the new pool setup and local shuttle, wish we could have experienced the new menu but as with everything else at hotel I am sure it will be great.
  Jul 26, 2017

$155

$155
Pines & Palms Resort

Pines & Palms Resort

80401 Old Hwy, Islamorada
3.0 out of 5.0
4.4 out of 5 (134 reviews)
NO private beach but excelent room & poolThe description of the hotel in Expedia states that "Resort Features: … private sand beach" and that one of the popular property highlights is a "private beach" (This can be seen in the attached picture). In practice, the beach is dirty and rocky and isn’t accessible. No sand beach as promised. This ...
  Jul 19, 2017

$102

$102
Lookout Lodge Resort

Lookout Lodge Resort

87770 Overseas Hwy, Islamorada
2.5 out of 5.0
3.6 out of 5 (22 reviews)
Rundown but Great LocationI have stayed here before, the views and location are amazing. The Staff is exceptional, but the rooms are in dire need of repair and upgrade. I was not thrilled to find out upon check in that the bulk of the property had been reserved for a Private Party on the day of my arrival and would be closed. ...
  Jul 4, 2017

$148

$148
Conch On Inn Motel

Conch On Inn Motel

103 Caloosa Street, Islamorada
2.0 out of 5.0
3.7 out of 5 (145 reviews)
Owners very helpful with local informationWe enjoyed the location and the low-key vibe of the place. We went to the keys to be outside. The Inn's philosophy is very much that, with comfortable seating and outside gathering space. If you are looking for a Keys experience that isn't a carbon copy chain hotel, I recommend Conch on Inn.
  Aug 2, 2017

$99

$99
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Islamorada
4.0 out of 5.0
4.4 out of 5 (646 reviews)
Nice place, need to review policies.Great hotel and location, wait staff is slow in restaurants, amenities (fishing poles, bikes, etc.) have to be returned by 6 pm, so not very accessible for late day use. Overall I was well taken care of.
  Aug 14, 2017

$179

$179
Map

Recently booked Luxury Hotels in Islamorada

Conch On Inn Motel
2.0 out of 5.0
Last booking: 20 minutes ago
Pines & Palms Resort
3.0 out of 5.0
Last booking: 27 minutes ago
Amara Cay Resort
3.5 out of 5.0
Last booking: 30 minutes ago
Days Inn Islamorada Oceanfront Resort
2.0 out of 5.0
Last booking: 33 minutes ago
Casa Thorn
3.0 out of 5.0
Last booking: 1 hour ago
Cheeca Lodge & Spa
4.0 out of 5.0
Last booking: 3 hours ago
Islander Resort, a Guy Harvey Outpost
3.0 out of 5.0
Last booking: 5 hours ago
Postcard Inn Beach Resort & Marina
3.0 out of 5.0
Last booking: 6 hours ago
Drop Anchor Resort and Marina
3.0 out of 5.0
Last booking: 8 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.

Booking Islamorada Vacations

It turns out plenty of folks love Islamorada enough to have set down roots -- how is that for proof that Islamorada is full of wonderful things to do? No matter what brings you to Islamorada, the destination always delivers. Islamorada is full of dreamy hotels in addition to friendly locals, so it's no mystery why travelers come back. Crowds have doubled in the last year, so book early!

Any 5-star getaway is the perfect opportunity to indulge in art, culture, and spa treatments. When you're smart enough to book travel on Expedia.com, the world is your oyster. Thanks to our incredible rates on hotels, you'll still have a healthy budget for the most compelling and captivating things to do. After a day of seeing the sights, your luxury hotel is waiting with fine dining and incredible amenities. Before you go to bed, order a glass of wine to your room and revel in your successful day. The luxury hotels in Islamorada will have you feeling the serenity in the blink of an eye.

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!