A beach with white lounge chairs, a covered pavilion, and palm trees.

Luxury Hotels & Resorts in Islamorada from AU$240

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Check availability on Islamorada Luxury Hotels

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov

Our top choices for Islamorada luxury hotels

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,802 reviews)
"Nice beach walkable property Great breakfast made to order"
United States
kent brian
The price is AU$302
includes taxes & fees
3 Nov - 4 Nov
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

2. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,157 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is AU$475
includes taxes & fees
1 Nov - 2 Nov
Islander Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

3. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,003 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
The price is AU$240
includes taxes & fees
2 Nov - 3 Nov
La Jolla Resort
A bathroom with a large bathtub, a view of the sea, and a pier with boats.

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,491 reviews)
"Beautiful resort"
United States
Patricia
The price is AU$361
includes taxes & fees
1 Nov - 2 Nov
Cheeca Lodge & Spa
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (305 reviews)
"Great place to stay!"
United States
Liosbel
The price is AU$435
includes taxes & fees
29 Nov - 30 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

6. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"
United States
Brian
The price is AU$471
includes taxes & fees
3 Nov - 4 Nov
Bayside Villas by Islander Resort
A balcony with a view of a beach, a pool, and a thatched-roof structure.

7. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
The price is AU$275
includes taxes & fees
15 Nov - 16 Nov
Hadley Resort and Marina
Terrace/patio

8. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,555 reviews)
"Very nice place the view and sunsets are amazing there is also a restaurant on the property that has great food and drinks we would definitely stay again"
United States
Christopher Michael
The price is AU$262
includes taxes & fees
2 Nov - 3 Nov
Lime Tree Bay Resort
A beach with lounge chairs, palm trees, and a view of the water.

9. Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (833 reviews)
"Excellent Stay!"
United States
Annette
The price is AU$282
includes taxes & fees
3 Nov - 4 Nov
Atlantic Bay Resort
A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

10. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (34 reviews)
"Very friendly staff"
United States
Maria
The price is AU$298
includes taxes & fees
1 Nov - 2 Nov
The Ocean View Inn & Pub
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

11. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,197 reviews)
"cute nice place in an incredible spot. Will visit there again for sure."
United States
keith
The price is AU$144
includes taxes & fees
15 Nov - 16 Nov
Rock Reef Resort
A wooden bridge leading to a beach area with palm trees and a yellow kayak.

12. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (263 reviews)
"This may be my favorite place I've stayed in the Keys! So quaint and the location and breakfast were amazing. We kayaked to the mangroves, ate at the wonderful restaurant across the street (Ballyhoos), and thoroughly enjoyed the beach area"
United States
Brittany
The price is AU$217
includes taxes & fees
2 Nov - 3 Nov
Seafarer Key Largo
A balcony with a view of the sea, a beach, and a thatched hut.

13. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,004 reviews)
"Very nice clean hotel with friendly staff."
Canada
Alexey
The price is AU$194
includes taxes & fees
29 Nov - 30 Nov
Sunset Cove Beach Resort
A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

14. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is AU$184
includes taxes & fees
3 Nov - 4 Nov
Breezy Palms Resort
A bedroom with a wooden bed, a nightstand, a lamp, and a view of the outdoors through large windows.

15. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,002 reviews)
"Excellent location"
United States
kelly
The price is AU$147
includes taxes & fees
3 Nov - 4 Nov
Drift Hotel
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

16. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (180 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is AU$400
includes taxes & fees
2 Nov - 3 Nov
Treasure Harbor
A beach with a thatched-roof hut, lounge chairs, and a swimming area.

17. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,004 reviews)
"Loved the location and the staff were very friendly"
United States
SUSAN
The price is AU$160
includes taxes & fees
22 Nov - 23 Nov
The Pelican Key Largo Cottages
An aerial view of a resort with a large pool, palm trees, and a beach.

18. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,002 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is AU$499
includes taxes & fees
29 Nov - 30 Nov
Playa Largo Resort & Spa, Autograph Collection
A pool area with palm trees and a building with a white roof.

19. Bahia Bay Resort

Bahia Bay Resort
2.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (205 reviews)
"This is our best kept secret! We love it here! We have stayed multiple times and will be back!!"
United States
Patricia
The price is AU$526
includes taxes & fees
3 Nov - 4 Nov
Bahia Bay Resort
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

20. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"Great location as well."
United States
Amir
The price is AU$354
includes taxes & fees
15 Nov - 16 Nov
Amara Cay Resort
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.
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Find out more about Islamorada

Islamoradaand its attractions for luxury travelers

Islamorada, often referred to as the ‘Sportfishing Capital of the World,’ offers an enticing blend of adventure and luxury for discerning travellers. For those inclined towards aquatic pursuits, a private charter fishing excursion can yield not only a trophy catch but also a taste of the local marine life. The stunning waters provide ideal conditions for snorkelling and diving, with the nearby Pennekamp Coral Reef State Park showcasing a kaleidoscope of vibrant corals and tropical fish. Land-based activities are equally appealing; exploring the lush trails of the Indian Key Historic State Park allows for a peaceful retreat into nature, offering stunning views and a chance to encounter exotic wildlife. For a taste of local culture, the Morada Way Arts and Cultural District hosts monthly art walks, where travelers can mingle with local artists while enjoying gourmet bites and fine wines. As for accommodation, the luxurious Cheeca Lodge & Spa stands out with its private beach, world-class spa, and exquisite dining options, creating a perfect base for relaxation after a day of exploration. The experience of unwinding in a beautifully appointed room, complete with ocean views, while enjoying attentive service, ensures that every moment spent in Islamorada feels both special and rejuvenating.

Find the best luxury hotels and resorts in Islamorada

For those seeking a luxurious escape in the picturesque setting of Islamorada, Florida, these hotels offer a blend of opulence and comfort. Each hotel provides a unique experience with top-tier amenities designed for discerning travellers.

Chesapeake Beach Resort

  • Why it's great for a luxury retreat: Chesapeake Beach Resort is an exquisite choice for luxury travellers, with a glowing review rating of 9.2. With designer toiletries and resort views, travelers can truly indulge in a relaxing experience. The private beach access and attentive concierge service ensure a personalised stay that caters to all your needs.
  • Other amenities: Guests can enjoy an outdoor pool for leisurely afternoons, complimentary breakfast to start the day right, and a variety of water activities, including boat tours and snorkeling nearby. The resort features air conditioning for comfort, a patio for serene outdoor moments, and beach towels for those sunny days by the shore. Enjoy ocean views from select rooms and other conveniences like a kitchenette and daily housekeeping.
  • Neighborhood: Matecumbe
  • Nearby attractions: History of Diving Museum - 0.9 km, Theater of the Sea - 1.7 km, Windley Key Fossil Reef Geological State Park - 1.8 km

Cheeca Lodge & Spa

  • Why it's great for a luxury retreat: Cheeca Lodge & Spa stands out as a premier luxury destination with a remarkable review rating of 9.2. This resort offers a beachfront dining experience, a private hot tub, and 24-hour room service, providing travelers with the ultimate in relaxation and indulgence. The exquisite attention to detail, from premium bedding to designer toiletries, is perfect for luxury seekers.
  • Other amenities: In addition to its luxurious accommodations, travelers can enjoy on-site tennis courts, a full-service spa with treatment rooms for massages, and recreational activities such as golf and kayaking. The resort also offers evening entertainment, a poolside bar for refreshing drinks, and a concierge service to assist with planning memorable experiences. The stunning resort structure and lush surroundings create an inviting atmosphere for relaxation and rejuvenation.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.1 km, Florida Keys Brewing Co. - 0.4 km, MoradaWay Arts & Cultural District - 0.6 km

Islander Resort

  • Why it's great for a luxury retreat: With a stellar review rating of 9.2, Islander Resort is a top choice for luxury travellers looking for a beachfront paradise. This resort offers premium bedding, bathrobes, and champagne service, ensuring a lavish experience. Guests can enjoy the private beach access and the relaxing ambiance that complements the serene surroundings of Islamorada.
  • Other amenities: The resort features a restaurant with ocean views, evening entertainment for a vibrant nightlife experience, and a poolside bar for leisurely afternoons. Additional luxuries include a concierge service, beach sun loungers, and cabanas for ultimate relaxation. Guests can also take advantage of on-site water sports equipment, including kayaking and snorkeling, as well as complimentary beach towels and a fitness centre for those who wish to stay active.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.9 km, Keys History & Discovery Center - 0.1 km, Islamorada Brewery & Distillery - 0.8 km

Amara Cay Resort

  • Why it's great for a luxury retreat: Amara Cay Resort offers a luxurious retreat with an excellent review rating of 8.8. This resort is designed for those who appreciate elegance, featuring an upscale beachfront restaurant and premium bedding in every room. Guests can unwind in the private beach area and enjoy in-room massages for added indulgence.
  • Other amenities: The resort's additional offerings include a poolside bar, a terrace for scenic views, and complimentary beach towels for a day in the sun. Guests can participate in on-site activities like kayaking and scuba diving, and enjoy the convenience of a fully equipped kitchen in select suites. With air conditioning and Egyptian cotton sheets, comfort is paramount throughout the stay.
  • Neighborhood: Matecumbe
  • Nearby attractions: Bud n' Mary's Dive Center - 0.3 km, Indian Key Historic State Park - 1.1 km, Hurricane Monument - 2.3 km

La Siesta Resort & Villas

  • Why it's great for a luxury retreat: La Siesta Resort & Villas is an idyllic luxury destination with a review rating of 8.6, perfect for discerning travellers. The resort features premium bedding, designer toiletries, and a private beach site, ensuring travelers experience the height of comfort and relaxation.
  • Other amenities: Guests can enjoy a poolside bar, complimentary beach towels, and an outdoor pool for leisurely dips. The resort also offers convenient laundry facilities, self-parking, and easy access to nearby golf courses. With a kitchenette in select rooms and daily housekeeping, every need is catered to for a seamless stay. Additionally, the resort provides an electric car charging station and a range of activities, including kayaking and snorkeling.
  • Neighborhood: Matecumbe
  • Nearby attractions: Bud n' Mary's Dive Center - 0.9 km, Indian Key Historic State Park - 0.5 km, Hurricane Monument - 1.7 km

Top Islamorada Hotel Reviews

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Temp RV staff was great. Beautiful property, a little old school. This place is great, but not for Rich snobs."
Carla 2-night trip
Posted 11 hours ago
Coconut Cove Resort and Marina

Frequently asked questions

What are the top-rated luxury hotels in Islamorada?
Among the top-rated luxury hotels in Islamorada, Cheeca Lodge & Spa, Amara Cay Resort, Islander Resort, and La Siesta Resort & Villas are consistently celebrated for their exceptional quality.

The Cheeca Lodge & Spa, with a 9.2 rating, is distinguished by its private beach, on-site golf course, and tennis facilities. Guests frequently praise the friendly and amazing staff, as well as the beautiful and clean rooms.

The Amara Cay Resort, rated 8.8, offers a private beachfront restaurant and a poolside bar. Reviewers frequently highlight the friendly and amazing staff, and the beautiful location.

The Islander Resort, with a 9.2 rating, provides private beach access and beachfront dining. Customers particularly appreciate the beautiful and big pool, along with the great and amazing service.

The La Siesta Resort & Villas, rated 8.6, features designer toiletries and premium bedding. The staff are consistently praised as friendly and amazing, and the rooms as clean and big.
Which area of Islamorada is best to stay in for luxury hotels?
The best area to stay in Islamorada for luxury hotels is along the Overseas Highway (US-1) between approximately Kilometre Marker 80 and Kilometre Marker 84.

This stretch of the Overseas Highway is where you'll find a collection of high-end resorts and private villas, many of which offer direct access to the ocean or bayside. These properties are typically set back from the main road, providing a sense of seclusion and tranquility. You'll often find amenities like private beaches, extensive tropical gardens, and multiple dining options on-site.

Couples looking for a romantic and exclusive getaway will find this area particularly appealing. The resorts here often cater to adults with features such as serene pool areas, spa services, and fine dining restaurants. Many offer water-based activities directly from their property, like guided fishing charters or paddleboarding, making it easy to enjoy the Florida Keys' natural beauty without venturing far.
Which luxury hotels in Islamorada are good for families?
For families seeking luxury hotels in Islamorada, Cheeca Lodge & Spa, Amara Cay Resort, Islander Resort, and La Siesta Resort & Villas are highly recommended.

The Cheeca Lodge & Spa, with a 9.2 rating, offers an array of amenities suitable for families, including an onsite golf course and tennis facilities. Guests frequently praise the friendly and amazing staff, as well as the beautiful and clean rooms.

The Amara Cay Resort, rated 8.8, provides a comfortable stay with its private beach access and beachfront restaurant. Reviewers often highlight the friendly staff, beautiful location, and clean, comfortable rooms.

Islander Resort, a property with a 9.2 rating, features a beautiful, large pool and evening entertainment. Customers consistently praise the friendly staff and the beautiful, clean rooms and amenities.

The La Siesta Resort & Villas, holding an 8.6 rating, offers spacious, clean rooms and excellent amenities. Its private beach access and resort structure are noted by guests, who often mention the friendly staff and great location.
What are the best luxury hotels in Islamorada with a pool?
In Islamorada, several luxury hotels offer excellent pool facilities, including Cheeca Lodge & Spa, Amara Cay Resort, and Islander Resort.

The Cheeca Lodge & Spa, with a 9.2 rating, provides a range of pool options, including private pools in some accommodations. Guests frequently praise the friendly and amazing staff, beautiful and clean rooms, and excellent service. The resort also boasts an onsite golf course and tennis facilities.

The Amara Cay Resort, rated 8.8, features a beautiful outdoor pool and a poolside bar. Reviewers often highlight the friendly and amazing staff, the beautiful location, and the comfortable and clean rooms.

Islander Resort, an establishment with a 9.2 rating, offers a beautiful and large pool. Customers consistently praise the friendly and great staff, the beautiful and clean rooms, and the great service.

La Siesta Resort & Villas, a property with an 8.6 rating, also provides an outdoor pool. Guests frequently mention the friendly staff, clean and spacious rooms, and the great location.
Which luxury hotels in Islamorada are good for couples?
For couples seeking a luxurious escape in Islamorada, Cheeca Lodge & Spa, Islander Resort, and Amara Cay Resort offer exceptional experiences.

The Cheeca Lodge & Spa, with a 9.2 rating, is celebrated for its private beach, onsite golf course, and private outdoor hot tubs. Reviewers consistently praise the friendly and amazing staff, along with the beautiful and clean rooms.

The Islander Resort, also with a 9.2 rating, features a beachfront restaurant and champagne service, great for romantic evenings. Customers frequently comment on the beautiful and clean rooms, as well as the beautiful and large pool.

Amara Cay Resort, a property with an 8.8 rating, provides a private beach and a beachfront restaurant. Its suites and premium bedding are often noted by guests, who praise the friendly staff and the beautiful location.
Are there any top luxury hotels near Indian Key Historic State Park?
Near Indian Key Historic State Park, Cheeca Lodge & Spa, Islander Resort, and Amara Cay Resort offer distinguished luxury hotels.

The Cheeca Lodge & Spa, with a 9.2 rating, provides an array of upscale amenities including a private beach, an on-site golf course, and private outdoor hot tubs. Guests frequently praise its friendly and amazing staff, as well as the beautiful and clean rooms.

The Islander Resort, rated 9.2, features a beachfront restaurant and private beach access. Customers often highlight the beautiful and big pool, alongside the great and amazing service.

Amara Cay Resort, a property with an 8.8 rating, offers a private beach, beachfront restaurant, and amenities such as Egyptian cotton sheets. Reviewers consistently praise the friendly and amazing staff, and the beautiful location.
What luxury activities and experiences are there in Islamorada?
The best area to stay in Islamorada for luxury experiences is generally around the Upper Matecumbe Key, particularly along the Overseas Highway (US-1). This area is the heart of Islamorada, known for its high-end resorts and direct access to the water.

Upper Matecumbe Key offers a selection of exclusive resorts with private beaches, marinas, and fine dining. You'll find properties here that provide amenities such as private villas, infinity pools, and personalised concierge services. Many of these establishments are located directly on the ocean side, offering stunning views and immediate access to water activities.

Couples looking for a romantic and indulgent escape will find Upper Matecumbe Key particularly appealing. Resorts in this area often specialise in creating memorable experiences, from private sunset cruises and bespoke fishing charters to spa treatments and gourmet meals prepared by private chefs. The focus is on relaxation and bespoke service, allowing couples to enjoy the natural beauty of the Keys in comfort.

Travellers seeking an active yet luxurious holiday will also appreciate this area. Many resorts offer private charters for deep-sea fishing, fly fishing, or snorkelling and diving excursions to the nearby coral reefs.
Can I cancel my luxury hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right luxury hotel in Islamorada for you.
How can I save on a luxury hotel in Islamorada with Expedia?
There are plenty of ways to save on a luxury hotel in Islamorada. Join One Key™, our free travel rewards program, to unlock Member Prices across a range of hotels. Typically, booking in advance will help you save on hotel bookings. If you're feeling spontaneous, be sure to check for last-minute deals.
How much does a luxury hotel in Islamorada cost?
Luxury hotel prices in Islamorada vary, but you can find a great deal from AU$240 on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates.
Is it cheaper to book a luxury Islamorada hotel and flights as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.

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