Book luxury hotels in Islamorada, FL

Wander Wisely with exceptional service, 24/7 support

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Islamorada Luxury Hotels

Casa Morada

Casa Morada

3.5 out of 5
136 Madeira Road, Islamorada, FL
The price is CA $303 per night
CA $303
CA $375 total
Aug 14 - Aug 15
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 ...
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $212 per night
CA $212
CA $332 total
Aug 14 - Aug 15
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 ...
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $208 per night
CA $208
CA $311 total
Aug 12 - Aug 13
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

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $286 per night
CA $286
CA $415 total
Aug 18 - Aug 19
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. ...
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy, Islamorada, FL
Get rates
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

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $231 per night
CA $231
CA $351 total
Sep 1 - Sep 2
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

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

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $268 per night
CA $268
CA $393 total
Sep 8 - Sep 9
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

Drop Anchor

3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
Get rates
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

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $193 per night
CA $193
CA $309 total
Sep 10 - Sep 11
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

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $204 total
Aug 12 - Aug 13
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 Islamorada

Creekside Inn Islamorada

2.5 out of 5
90611 Old Highway, Tavernier, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $172 per night
CA $172
CA $194 total
Sep 7 - Sep 8
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

Conch On Inn Motel

2 out of 5
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 ...
Don't see what you're looking for?
See all available properties in Islamorada
View all properties
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.

About Islamorada Luxury Hotels

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
2,180 hotels
Lowest Price
CA $141
Highest Price
CA $303
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Great all around!"
A verified traveller stayed at Cheeca Lodge & Spa
Cheeca Lodge & Spa