Book luxury hotels in Islamorada, FL

Name: Drop Anchor
Price range: CA $181
Rating: 8.6

Top Islamorada Luxury Hotels

Casa Morada

136 Madeira Road, Islamorada, FL

CA $556

CA $689 total

Nov 24 - Nov 25

includes taxes & fees

Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $199

CA $303 total

Nov 16 - Nov 17

includes taxes & fees

Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...

Islander Resort

82100 Overseas Highway, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $393

CA $537 total

Dec 1 - Dec 2

includes taxes & fees

Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $276

CA $406 total

Dec 15 - Dec 16

includes taxes & fees

Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...

Pines & Palms Resort

80401 Old Hwy, Islamorada, FL

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Stay at this 3-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $197

CA $315 total

Nov 30 - Dec 1

includes taxes & fees

Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...

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

84001 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $309

CA $441 total

Nov 20 - Nov 21

includes taxes & fees

Stay at this 3.5-star beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

CA $181

CA $253 total

Nov 19 - Nov 20

includes taxes & fees

Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $176

CA $292 total

Dec 3 - Dec 4

includes taxes & fees

Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...

Fisher Inn Resort & Marina

84951 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $157

CA $222 total

Dec 4 - Dec 5

includes taxes & fees

Stay at this 3.5-star beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...

Creekside Inn

90611 Old Highway, Tavernier, FL

Free cancellation

Reserve now, pay when you stay

CA $232

CA $262 total

Nov 16 - Nov 17

includes taxes & fees

Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. ...

Conch On Inn Motel

103 Caloosa Street, Tavernier, FL

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Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Old Road Gallery and Florida Keys Dive Center are ...

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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.

If you’re looking for a luxury vacation in Islamorada, with plush bedding, designer toiletries, world-class concierge staff, and access to the best restaurants and spa treatments, Travelocity has everything you need. You can live it up like the rich and famous in a luxury hotel in Islamorada with discounts and offerings from Travelocity. Now you can have all the luxury perks you want, and stay on the cheap. So live it up! A luxury hotel in Islamorada can whisk you away without breaking the bank.

Islamorada hotels essential information

Accommodation	2,191 hotels
Lowest Price	CA $222
Highest Price	CA $689
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, Fisher Inn Resort & Marina, Islander Resort, Pines & Palms Resort, La Siesta Resort & Villas

Recent Islamorada hotel reviews by fellow wanderers

Chesapeake Beach Resort

5 out of 5

Posted 5 days ago

Travelocity Verified Review

"Our room was beautiful and spotless. The staff was always polite, handling any inquiry or request. The location is ideal, located on the beach with easy access to the main road. They provide a nice breakfast from 6 to 10 every morning with a variety of options to choose from on top of 24-hour coffee."

A verified traveller stayed at Chesapeake Beach Resort

Pines & Palms Resort

5 out of 5

Posted 8 days ago

Travelocity Verified Review

"This was an amazing stay for my birthday weekend. Rooms were very clean. Had everything you need dishes glasses even a dishwasher. The view we had was amazing we received an upgrade for my birthday to a cute cottage. They offer kayaks and bicycles and there are two restaurants within walking distance. Excellent getaway "

A verified traveller stayed at Pines & Palms Resort