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Luxury Hotels in Islamorada

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Islamorada Hotels

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Featured Islamorada Luxury Hotels

See all 169 Hotels in Islamorada
Harbor Lights

Harbor Lights

84951 Overseas Hwy, Islamorada
2.0 out of 5.0
2.9 out of 5 (320 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
Lime Tree Bay Resort

Lime Tree Bay Resort

68500 Overseas Hwy, Long Key
3.5 out of 5.0
4.1 out of 5 (176 reviews)
Was a very beautiful place and location .. Pool got to be a little crazy with unmanned and unmaintained children. Other than not being able to enjoy the pool did have the ability to use paddle boards, kayaking and bikes.m
  Aug 24, 2017

$109

$109
Pelican Cove Resort & Marina

Pelican Cove Resort & Marina

84457 Overseas Highway, Islamorada
3.0 out of 5.0
3.9 out of 5 (400 reviews)
Nice hotel and great location. I would definitely recommend.
  Aug 2, 2017

$124

$124
La Siesta Resort & Marina

La Siesta Resort & Marina

80241 Overseas Highway, Islamorada
3.0 out of 5.0
3.7 out of 5 (232 reviews)
Super cute, clean and central.Enjoyed our stay. Only draw back, a new A/C unit being installed in outside pool area restaurant at the time.
  Aug 23, 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 (659 reviews)
Hotel was nice ...Though hotel was nice there were too many ants on the beach in the room and on the patio... Also we went to have a drink by the bar in the evening and there was no way to get away from mosquito
  Aug 24, 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 (431 reviews)
Good all rounderWe stayed at the postcard Inn in July. We found the rooms clean and well equipped. The hotel facilities were good, many one criticism would be that it was busy and sometimes difficult to get a beach towel or pool lounger. (There were spare loungers further around the bay but a little out of the way. ...
  Aug 23, 2017

$165

$165
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada
2.5 out of 5.0
3.7 out of 5 (170 reviews)
Honeymoon My husband and I had a great time. The staff was great and friendly at all time of the day. We've been talking about our stay to everyone.
  Aug 15, 2017

$143

$143
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
Creekside Inn Islamorada

Creekside Inn Islamorada

90611 Old Highway, Islamorada
2.5 out of 5.0
3.5 out of 5 (178 reviews)
mom and pop on canalVery clean, comfortable bed. Room is a little small but they do well with what they have. Decent shower, bathroom products. refrigerator. Reasonable off season rates.
  Aug 15, 2017

$98

$98
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Islamorada
4.0 out of 5.0
4.4 out of 5 (653 reviews)
Was the best experience beautiful hotel great staff very clean and accommodating
  Aug 24, 2017

$179

$179
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy, Islamorada
3.5 out of 5.0
4.2 out of 5 (471 reviews)
Nice clean renovated hotel that is hard to find in the middle keys. The additional daily ammeneties charge makes the price for the booking a bit misleading but the hotel is still worth it.
  Aug 23, 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

$119

$119
Drop Anchor Resort and Marina

Drop Anchor Resort and Marina

84959 Overseas Highway, 222, Islamorada
3.0 out of 5.0
4.2 out of 5 (303 reviews)
Beautiful view and quiet try to get grind floor walk out
  Aug 23, 2017

$125

$125
Fiesta Key RV Resort

Fiesta Key RV Resort

70001 Overseas Hwy, Long Key
2.5 out of 5.0
2.8 out of 5 (75 reviews)
Enjoyable stayMy favorite was the restaurant on the water great food & drinks 👍
  Aug 23, 2017

$167

$167
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
Map

Recently booked Luxury Hotels in Islamorada

Islander Resort, a Guy Harvey Outpost
3.0 out of 5.0
Last booking: 3 hours ago
Postcard Inn Beach Resort & Marina
3.0 out of 5.0
Last booking: 7 hours ago
Cheeca Lodge & Spa
4.0 out of 5.0
Last booking: 8 hours ago
Drop Anchor Resort and Marina
3.0 out of 5.0
Last booking: 9 hours ago
Chesapeake Beach Resort
2.5 out of 5.0
Last booking: 9 hours ago
Lime Tree Bay Resort
3.5 out of 5.0
Last booking: 9 hours ago
Pines & Palms Resort
3.0 out of 5.0
Last booking: 9 hours ago
Days Inn Islamorada Oceanfront Resort
2.0 out of 5.0
Last booking: 10 hours ago
Amara Cay Resort
3.5 out of 5.0
Last booking: 10 hours ago

A few days away keeps your stress at bay, especially when you're enjoying a stay in Islamorada. Brilliant activities, scrumptious eats, and chances to capture fantastic photos: these are just some of the reasons to take a trip to Islamorada. You'll devour fabulous eats, eye-guzzle the most popular monuments and landmarks in the region, and enjoy the most sought-after shows. Naturally, you'll stay at a luxury hotel! Anything less than the best is for the birds, so book your luxury hotel in Islamorada on Expedia.com right now and start your trip off on the right (well-dressed) foot.

Book a Luxury Islamorada Vacation

If you need any proof that Islamorada is teeming with marvelous things to do, keep in mind that plenty of folks are happy to have set down roots. No matter what brings you to Islamorada, the destination always delivers. Islamorada is full of comfy hotels on top of appealing attractions, so you can count on a spectacular stay. Crowds have doubled in the last year, and hotel rooms may go fast--book early!

An upscale vacation calls for massages, culture, and activities from your bucket list. When you book your travel on Expedia.com, you can enjoy it all. Thanks to our phenomenal room rates, your bucket list budget will still be intact. After a day of exploring the city, your luxury hotel is waiting with fine dining and impressive amenities. Take advantage of amenities like a concierge or hot tub before the day is over. The luxury accommodations in Islamorada will soothe you into a state of relaxation before you know it.

Find Luxury Islamorada Hotels Now

When you’ve got your heart set on an elegant getaway in Islamorada, Expedia.com is here to save the day. Browse the abundance of real traveler reviews on fabulous 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 gigantic penthouses, while others have tennis courts or salt water pools. Book your dream hotel in Islamorada now, and soon you'll be soaking up luxury in style!