Book luxury hotels in Islamorada, FL

Name: Drop Anchor
Price range: CA $287
Rating: 8.8

Top Islamorada Luxury Hotels

Casa Morada

136 Madeira Road, Islamorada, FL

CA $500

CA $619 total

includes taxes & fees

Apr 14 - Apr 15

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 ...

Cheeca Lodge & Spa

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

Free cancellation

Reserve now, pay when you stay

CA $349

CA $487 total

includes taxes & fees

May 13 - May 14

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 ...

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

84001 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $376

CA $515 total

includes taxes & fees

May 12 - May 13

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 ...

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $335

CA $455 total

includes taxes & fees

Apr 29 - Apr 30

Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the breakfast and the pool ...

Islander Resort

82100 Overseas Highway, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $332

CA $461 total

includes taxes & fees

May 4 - May 5

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. ...

Pines & Palms Resort

80401 Old Hwy, Islamorada, FL

CA $470

CA $606 total

includes taxes & fees

Apr 14 - Apr 15

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 $298

CA $428 total

includes taxes & fees

May 14 - May 15

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

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

CA $287

CA $371 total

includes taxes & fees

Apr 15 - Apr 16

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 $266

CA $391 total

includes taxes & fees

May 1 - May 2

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 ...

Creekside Inn Islamorada

90611 Old Highway, Tavernier, FL

Free cancellation

Reserve now, pay when you stay

CA $232

CA $261 total

includes taxes & fees

May 11 - May 12

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. ...

Fisher Inn Resort & Marina

84951 Overseas Hwy, Islamorada, FL

Free cancellation

CA $300

CA $382 total

includes taxes & fees

Apr 28 - Apr 29

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 ...

Conch On Inn Motel

103 Caloosa Street, Tavernier, FL

Get rates

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	2,192 hotels
Lowest Price	CA $232
Highest Price	CA $500
Popular hotels	Cheeca Lodge & Spa, Amara Cay Resort, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Creekside Inn Islamorada, 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

Amara Cay Resort

5 out of 5

Posted 11 hours ago

Travelocity Verified Review

"Lobby was cool. Overall design "

A verified traveller stayed at Amara Cay Resort

Islander Resort

5 out of 5

Posted 4 days ago

Travelocity Verified Review

"Islander Resort is the perfect spot to relax and disconnect. It’s peaceful, beautifully decorated, and has a cozy vibe throughout. The service is great, and the rooms are charming. I loved the on-site restaurants and the included amenities like kayaking and paddleboarding. A true escape from the city!"

A verified traveller stayed at Islander Resort