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Find Luxury Hotels in Islamorada from $95

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Travelers Enjoyed These Luxury Hotels

Coconut Cove Resort and Marina
2 out of 5
84801 Overseas Highway, Islamorada, FL
The price is $95 per night
3.3/5 (288 reviews)

"Coconut Cove was the first stop on our trip. It is situated right on the ocean which is an awesome plus! The tiki huts added charm and the property had a great tropical feel."…"

Reviewed on Feb 29, 2020

Coconut Cove Resort and Marina
Casa Morada
3.5 out of 5
136 Madeira Road, Islamorada, FL
The price is $329 per night
4.8/5Exceptional! (141 reviews)

"Very clean and quiet. Simply beautiful. Easy to relax here. Simplicity paired with elegance!"…"

Reviewed on Jun 15, 2020

Casa Morada
Pines & Palms Resort
3 out of 5
80401 Old Hwy, Islamorada, FL
The price is $161 per night
4.5/5Wonderful! (634 reviews)

"We loved our stay at Pines and Palms. Clean with great location. Love Chris at the pool bar and beach is fabulous. Will return!"…"

Reviewed on Aug 3, 2020

Pines & Palms Resort
Amara Cay Resort
3.5 out of 5
80001 Overseas Hwy, Islamorada, FL
Free CancellationReserve now, pay when you stay
The price is $169 per night
4.4/5Wonderful! (979 reviews)

"Beautiful property, great view and the room was fantastic."…"

Reviewed on Aug 8, 2020

Amara Cay Resort
Islander Resort
3 out of 5
82100 Overseas Highway, Islamorada, FL
Free CancellationReserve now, pay when you stay
The price is $146 per night
4.4/5Wonderful! (939 reviews)

"Excellent property. Very clean and updated. Scenic but my only complaint was very slow service at pool. I would of drank a whole lot more if It didn’t take so long to get a beer."…"

Reviewed on Aug 2, 2020

Islander Resort
Drop Anchor
3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
The price is $125 per night
4.4/5Excellent! (977 reviews)

"Loved all the spaced out seating areas right in fro"…"

Reviewed on Aug 5, 2020

Drop Anchor
Cheeca Lodge & Spa
4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free CancellationReserve now, pay when you stay
The price is $132 per night
4.4/5Excellent! (980 reviews)

"The beautiful ocean view, the greenery and the vibe."…"

Reviewed on Jul 30, 2020

Cheeca Lodge & Spa
Postcard Inn Beach Resort & Marina
3 out of 5
84001 Overseas Hwy, Islamorada, FL
Free CancellationReserve now, pay when you stay
The price is $169 per night
4.2/5Excellent! (955 reviews)

"I think this place is doing what they can to create a nice vacation environment given the COVID circumstances."…"

Reviewed on Aug 12, 2020

Postcard Inn Beach Resort & Marina
Pelican Cove Resort & Marina
3 out of 5
84457 Overseas Highway, Islamorada, FL
Free CancellationReserve now, pay when you stay
The price is $143 per night
4.1/5Very Good! (967 reviews)

"Good place, great views, excellent marina for our 22’ boat"…"

Reviewed on Aug 2, 2020

Pelican Cove Resort & Marina
La Siesta Resort & Marina
3 out of 5
80241 Overseas Highway, Islamorada, FL
Free CancellationReserve now, pay when you stay
The price is $169 per night
3.9/5Very Good! (984 reviews)

"Loved the location, hoped the bar was going to be open since both sister hotels had them open. Had some issues with plumbing since the unit was recently remodeled. Place is ideal for Boaters."…"

Reviewed on Aug 10, 2020

La Siesta Resort & Marina
Creekside Inn Islamorada
2.5 out of 5
90611 Old Highway, Tavernier, FL
The price is $106 per night
3.8/5Good! (987 reviews)

"My stay was excellent. Right choice. Everything was great accept the WI-FI"…"

Reviewed on Jul 28, 2020

Creekside Inn Islamorada
Conch On Inn Motel
2 out of 5
103 Caloosa Street, Tavernier, FL
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3.8/5Good! (484 reviews)
Great little place to call home

"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

Conch On Inn Motel
Lookout Lodge Resort
3 out of 5
87770 Overseas Hwy, Islamorada, FL
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3.8/5Good! (78 reviews)

"I had a wonderful stay at Lookout Lodge. The room could be updated but things were good. The staff was so helpful in telling us about things to do."…"

Reviewed on Jan 1, 2018

Lookout Lodge Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Free CancellationReserve now, pay when you stay
The price is $143 per night
3.5/5Good! (878 reviews)

"Very nice room, fully renovated, clean! Staff very seeet, friendly and helpful. Brand new pool. But the beach water was gross, we would dare to go in. I guess that’s what key’s beaches looks like. This hotel is still under construction. No breakfast offered."…"

Reviewed on Aug 7, 2020

Chesapeake Beach Resort
Fisher Inn Resort & Marina
3.5 out of 5
84951 Overseas Hwy, Islamorada, FL
The price is $109 per night
3.2/5 (987 reviews)

"The staff was polite and very helpful with all of our needs. The location was perfect for us and our weekend boating plans. They offer free kayaks and paddle boards to enjoy which was awesome as well as the onsite boat ramp and docking which was immensely convenient."…"

Reviewed on Jul 7, 2020

Fisher Inn Resort & Marina
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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.

Want to find the perfect hotel for your luxury holiday in Islamorada? Use Expedia to help you arrange a flight to Marathon, FL (MTH-Florida Keys Marathon) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are an important consideration when you plan a vacation, so we make it easy to find what you need to make your stay special. If you want a posh hotel that has a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Islamorada offers. During your visit, you might want to enjoy the ocean views and sunsets which Islamorada is known for.

When to Visit Islamorada

This is what you can expect from the weather when you are staying in Islamorada:

  • Hottest months: August, July, June, and September, with an average temperature of 91°F
  • Coldest months: January, December, February, and March, with an average temperature of 65°F
  • Driest months: January, December, February, and April, with an average rainfall of 2.05 inches
  • Rainiest months: September, August, June, and October, with an average rainfall of 6.27 inches

Exploring Islamorada

Enjoy Islamorada and visit History of Diving Museum, Theater of the Sea, and Windley Key Fossil Reef Geological State Park. If you have a little extra time during your trip, you might want to make a stop at Hurricane Monument and Bud n' Mary's Dive Center.

Other things that make Islamorada unique are its:
  • Fishing
  • Diving
  • Entertainment
  • Snorkeling
  • Opera
  • Seafood
  • Theater

Frequently asked questions

Are you looking for a luxury hotel for your stay in Islamorada?
Arrange a flight into Marathon, FL (MTH-Florida Keys Marathon) Airport and then treat yourself to a stay at one of 26 luxurious hotels. Known for its ocean views and sunsets, Islamorada also has some interesting things to see and do including Theater of the Sea, so you may want to take in the local sights during your visit.
What's the best luxury place to stay in Islamorada?
Cheeca Lodge & Spa is a 4-star resort with a private beach and 3 restaurants, and it’s a popular choice for Expedia travelers looking for an elegant place to stay. Another upscale choice for your trip is Playa Largo Resort & Spa, Autograph Collection.
What's the seasonal weather like in Islamorada?
The hottest months are usually August and July with an average temp of 85°F, while the coldest months are January and December with an average of 72°F. Average annual rainfall for Islamorada is 46 inches.
What's there to see and do in Islamorada?
Experience all that Islamorada has to offer when you visit Theater of the Sea, Bud n’ Mary’s Dive Center, and Founders Park. If you have a bit of extra time while you’re in the area, you might want to check out History of Diving Museum and Windley Key Fossil Reef Geological State Park.

Travelers Loved These Luxury Hotels

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