Book luxury hotels in Islamorada, FL

Name: Drop Anchor
Price range: CA $467
Rating: 8.8

Top Islamorada Luxury Hotels

Casa Morada

136 Madeira Road, Islamorada, FL

CA $569

CA $748 total

includes taxes & fees

26 Mar - 27 Mar

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 $623

CA $798 total

includes taxes & fees

9 Apr - 10 Apr

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 ...

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $446

CA $583 total

includes taxes & fees

12 Mar - 13 Mar

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 $530

CA $687 total

includes taxes & fees

6 Apr - 7 Apr

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 $547

CA $695 total

includes taxes & fees

19 Mar - 20 Mar

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

CA $473

CA $628 total

includes taxes & fees

24 Mar - 25 Mar

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 $467

CA $576 total

includes taxes & fees

12 Mar - 13 Mar

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

CA $432

CA $582 total

includes taxes & fees

30 Mar - 31 Mar

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 ...

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

84001 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $561

CA $726 total

includes taxes & fees

13 Mar - 14 Mar

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 ...

Creekside Inn Islamorada

90611 Old Highway, Tavernier, FL

CA $241

CA $272 total

includes taxes & fees

31 Mar - 1 Apr

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

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 ...

Fisher Inn Resort & Marina

84951 Overseas Hwy, Islamorada, FL

Free cancellation

CA $361

CA $453 total

includes taxes & fees

12 Mar - 13 Mar

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 ...

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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	2,242 hotels
Lowest Price	CA $241
Highest Price	CA $623
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 18 hours ago

Travelocity Verified Review

"I was pleasantly surprised that part of the package involved in staying at Amara Cay included use of two of the sister resorts in the area. Our room overlooked the outdoor dining area and we were treated to evening entertainment sitting on our balcony. The pool was marvelous! "

A verified traveller stayed at Amara Cay Resort

Chesapeake Beach Resort

5 out of 5

Posted 3 days ago

Travelocity Verified Review

"We found our perfect peaceful and quiet getaway! We started each day with waffles or omelets. We loved the private beach with plenty of shade. It was nice to hear the water and birds instead of music or people. The bar was just steps away from the beach or pool. We walked to dinner at Wahoo's every night. I highly recommend Chesapeake for a low key, quiet stay. "

A verified traveller stayed at Chesapeake Beach Resort