Explore 16 Luxury Hotels in Islamorada
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Best Luxury Hotels in Islamorada
Casa Morada
136 Madeira Road Islamorada FL
$488 nightly
The price is $549 total per night from Mar 22 to Mar 23
$549 total
Mar 22 - Mar 23
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Enjoy a day at the beach kayaking, or relax ...
9.4/10 Exceptional! (428 reviews)
Truly a spectacular & stylish hidden gem, almost feels like we have the whole place to ourselves. Plus, pool, gardens, it’s quiet, peaceful with many free activities you can do. Includes paddle boards and kayaks so you can do it for free when you stay with them. Stunning Sunsets at the property phenomenal ...
Reviewed on Mar 3, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$371 nightly
The price is $418 total per night from Apr 12 to Apr 13
$418 total
Apr 12 - Apr 13
Total with taxes and fees
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
9.2/10 Wonderful! (1,298 reviews)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window
Reviewed on Mar 12, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$270 nightly
The price is $304 total per night from Apr 14 to Apr 15
$304 total
Apr 14 - Apr 15
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
9.2/10 Wonderful! (1,667 reviews)
Staff wasn’t very helpful or accommodating.
Reviewed on Mar 15, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$347 nightly
The price is $391 total per night from Apr 15 to Apr 16
$391 total
Apr 15 - Apr 16
Total with taxes and fees
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...
9/10 Wonderful! (170 reviews)
Loved our stay! Beautiful property, comfortable beds. Should've stayed longer honestly. Only thing we'll do different next time is ask for a room in the 21+ area.
Reviewed on Mar 14, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$301 nightly
The price is $339 total per night from Mar 26 to Mar 27
$339 total
Mar 26 - Mar 27
Total with taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...
8.8/10 Excellent! (1,255 reviews)
Desk staff was OK. Bar and restaurant staff seemed slow and overwhelmed even with a small crowd. Cleaning staff wandered around slowly looking at their phones.
Reviewed on Mar 14, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$367 nightly
The price is $409 total per night from Mar 23 to Mar 24
$409 total
Mar 23 - Mar 24
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A business center, a garden, and a picnic area ...
8.8/10 Excellent! (1,007 reviews)
Very pleasantly surprised with the location and quality of this resort. The water view is available throughout the property and this resort is well taken care of. The pool was exceptionally clean and refreshing.
Reviewed on Mar 14, 2026
Creekside Inn
90611 Old Highway Tavernier FL
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $269 total per night from Apr 2 to Apr 3
$269 total
Apr 2 - Apr 3
Total with taxes and fees
This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. ...
7.8/10 Good! (1,002 reviews)
Did not use any facilities. Property does need some repairs and maintenance. Front desk has limited opening hours. Room cleaned daily but room supplies not replenished. Good location though. Manatees and dolphin seem from walkway outside room. Close to main road on one side. Cannot leave curtains ...
Reviewed on Mar 10, 2026
Conch On Inn Motel
103 Caloosa Street Tavernier FL
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, concierge services, and barbecue grills are also on offer.
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.
More 4 star hotels in Islamorada
Serenity by Florida Keys Luxury Rentals
75631 Overseas Highway Islamorada FL
5 star hotels in Islamorada
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$371 nightly
The price is $418 total per night from Apr 12 to Apr 13
$418 total
Apr 12 - Apr 13
Total with taxes and fees
9.2/10 Wonderful! (1,298 reviews)
Islamorada Luxury Hotels
Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the Islamorada luxury hotels are the plush oasis you’ve been looking for.
Choose from the best luxury hotels in Islamorada to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.
We want you to enjoy your next vacation in style and the top luxury resorts in Islamorada will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Islamorada, and plan your next opulent escape.
Islamorada hotels essential information
Accommodation | 2,208 hotels |
|---|---|
Lowest Price | $269 |
Highest Price | $549 |
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 |
Popular Luxury Stays in Islamorada
Recent Islamorada Hotel Reviews By Fellow Wanderers
Islander Resort
4 out of 5
Posted 1 hour ago
Travelocity Verified Review
"The private patio for each room was great perk. Loved the tropical vibe. The food was expensive."
A verified traveler stayed at Islander Resort
More Ways To Wander Islamorada
Flights to Islamorada
The best fares to get you there
Islamorada Hotels
Islamorada Vacation Rentals
Great Deals on Alternative Accommodations
Islamorada Car Rentals
Affordable cars to get you around town
Islamorada Vacations
Save more by combining flights, hotels and cars
Things to do in Islamorada
Discover events, experiences & tours
Explore More Ways to Travel with Travelocity
- Beach Resorts & in Upper Matecumbe Key
- Hotels with Pools in Upper Matecumbe Key
- Adults Only Resorts & in Brickell
- Convention Center Hotels in Brickell
- Hotels with Bar in Brickell
- Hotels with Childcare in Brickell
- Hotels with Free Breakfast in Brickell
- Hotels with Tennis Courts in Brickell
- Oceanfront Hotels in Brickell
- Ski Resorts and in Brickell
- Golf Resorts & in Coconut Grove
- Hotels with Pools in Venetian Shores
- Adults Only Resorts & in Tavernier
- Beach Resorts & in Tavernier
- Cheap Hotels in Tavernier
- Fishing Resorts & in Tavernier
- Golf Resorts & in Tavernier
- Hotels with Balconies in Tavernier
- Hotels with Bar in Tavernier
- Hotels with Free Breakfast in Tavernier
- Hotels with Hot Tubs in Tavernier
- Luxury Hotels in Tavernier
- Pet Friendly Hotels in Tavernier
- Hotels on the River in Tavernier
- Ski Resorts and in Tavernier
- Spa Resorts & in Tavernier
- Beach Resorts & in Plantation Key
- Cheap Hotels in Plantation Key
- Hotels with Pools in Plantation Key
- Hotels with Free Parking in Plantation Key
- Hotels with Kitchenettes in Plantation Key
- Hotels with smoking rooms in Plantation Key
- Convention Center Hotels in South Beach
- Hotels with Childcare in South Beach
- Hotels with Room Service in South Beach
- Hotels with Tennis Courts in South Beach
- Oceanfront Hotels in South Beach
- Waterpark Hotels and Resorts in South Beach
- Winery Hotels in South Beach
- Kid Friendly Hotels in Layton
- Hotels with Pools in Layton
- Hotels with Bar in Layton
- Luxury Hotels in Layton
- Oceanfront Hotels in Layton
- Pet Friendly Hotels in Layton
- Spa Resorts & in Layton
- Adults Only Resorts & in Miami
- Fishing Resorts & in Miami
- Green Hotels in Miami
- Hotels with Childcare in Miami
- Hotels with a Gym in Miami
- Hotels with Free Airport Shuttle in Miami
- Hotels with Tennis Courts in Miami
- Oceanfront Hotels in Miami
- Adults Only Resorts & in Flamingo
- All Inclusive Resorts & in Flamingo
- Beach Resorts & in Flamingo
- Cheap Hotels in Flamingo
- Kid Friendly Hotels in Flamingo
- Fishing Resorts & in Flamingo
- Hotels with Suites in Flamingo
- Hotels with Hot Tubs in Flamingo
- Hotels with an Indoor Pool in Flamingo
- Hotels with smoking rooms in Flamingo
- Hotels on the Lake in Flamingo
- Oceanfront Hotels in Flamingo
- Pet Friendly Hotels in Flamingo
- Waterpark Hotels and Resorts in Flamingo
- Hotel Wedding Venues Hotels in Flamingo
- All Inclusive Resorts & in Key Biscayne
- Arcade Hotels in Key Biscayne
- Beach Resorts & in Key Biscayne
- Boutique Hotels in Key Biscayne
- Convention Center Hotels in Key Biscayne
- Kid Friendly Hotels in Key Biscayne
- Golf Resorts & in Key Biscayne
- Hotels with Balconies in Key Biscayne
- Hotels with Free Parking in Key Biscayne
- Hotels with Hot Tubs in Key Biscayne
- Hotels with Restaurants in Key Biscayne
- Hotels with Room Service in Key Biscayne
- Luxury Hotels in Key Biscayne
- Oceanfront Hotels in Key Biscayne
- Romantic Getaways & Hotels in Key Biscayne
- Hotels with Shopping in Key Biscayne
- Spa Resorts & in Key Biscayne
- Hotel Wedding Venues Hotels in Key Biscayne
- Historic Hotels in Miami Beach
- Hotels with Suites in Miami Beach
- Hotels with Pools in Miami Beach
- Hotels with an Indoor Pool in Miami Beach
- Hotels with Kitchenettes in Miami Beach
- Hotels with Room Service in Miami Beach
- Romantic Getaways & Hotels in Miami Beach
- Winery Hotels in Miami Beach
- Hotels with a Lazy River in Key Largo
- Hotels with Air Conditioning in Key Largo
- Hotels with an Indoor Pool in Key Largo
- Hotels with Waterslides in Key Largo
- Waterpark Hotels and Resorts in Key Largo