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Our top choices for Islamorada luxury hotels

On the beach, sun-loungers, beach umbrellas, beach towels

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (73 reviews)
The price is £625
includes taxes & fees
14 Apr - 15 Apr
The Islands of Islamorada
Exterior

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Beachfront luxury awaits at this Key Largo resort with spa treatments and ocean views.
The price is £341
includes taxes & fees
3 May - 4 May
Playa Largo Resort & Spa, Autograph Collection
Property grounds

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.6 out of 10, Excellent, (1,035 reviews)
  • cleanliness
    Beach luxury reimagined at Key Largo resort with private sands, refreshing pools, and coastal dining.
The price is £314
includes taxes & fees
22 Apr - 23 Apr
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Balcony

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,316 reviews)
  • cleanliness
    Experience seaside opulence with private beach access, three outdoor pools, and oceanfront dining at this beachfront Matecumbe resort.
The price is £258
includes taxes & fees
3 May - 4 May
Cheeca Lodge & Spa
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,014 reviews)
  • cleanliness
    Beachfront luxury awaits at Florida Keys haven with private shores, poolside bars, and lavish lanai rooms.
The price is £316
includes taxes & fees
3 May - 4 May
Islander Resort
Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,276 reviews)
  • cleanliness
    Florida Keys resort offers private beach paradise with upscale rooms, coastal activities, and luxurious relaxation.
The price is £245
includes taxes & fees
22 Apr - 23 Apr
Amara Cay Resort
In-room safe, individually decorated, individually furnished

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, (181 reviews)
  • cleanliness
    Seaside elegance awaits at this Islamorada resort with 3 pools, diverse dining, and a marina.
The price is £290
includes taxes & fees
22 Apr - 23 Apr
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,009 reviews)
The price is £226
includes taxes & fees
28 Apr - 29 Apr
La Siesta Resort & Villas
5 outdoor pools, pool cabanas (surcharge), pool umbrellas

Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
4.0 star property
Marathon
8.2 out of 10, Very good, (191 reviews)
  • cleanliness
    Indulge in oceanfront splendour at this Florida Keys resort with 5 pools, private beach, and full-service spa treatments.
The price is £617
includes taxes & fees
2 May - 3 May
Villas At Hawks Cay Resort
3 restaurants, breakfast, lunch, dinner served; American cuisine

Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
Key Largo
9.4 out of 10, Exceptional, (1,416 reviews)
The price is £280
includes taxes & fees
20 Apr - 21 Apr
Reefhouse Resort & Marina
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

Nestled in the heart of the Florida Keys, Islamorada is a playground for luxury travellers seeking both adventure and relaxation. Begin your journey with a visit to the stunning Theatre of the Sea, where you can enjoy intimate marine life shows and even swim with dolphins, creating unforgettable memories for the whole family. For those who prefer an oceanic escape, the vibrant coral reefs of the Florida Keys National Marine Sanctuary await, offering world-class snorkelling and diving experiences amidst colourful marine life. Indulge in a private fishing charter with local experts, casting lines for tarpon and bonefish in the crystal-clear waters, or unwind at the exclusive Morada Bay Beach Café, where you can savour gourmet dining with sunset views over the turquoise ocean. For a unique experience, don’t miss the chance to explore the historic African Queen, a restored steamboat that offers leisurely cruises paired with exquisite dining options. When it comes to accommodation, the luxurious resorts along the scenic Overseas Highway provide stunning oceanfront views and exceptional amenities, such as private beaches, personalised concierge services, and exquisite dining experiences, ensuring that every moment of your stay is pampered and memorable.

Find the best luxury hotels and resorts in Islamorada

For those seeking a lavish escape in Islamorada, Florida, these top hotels offer unparalleled luxury, exquisite amenities, and breathtaking views. Each hotel has been meticulously selected to provide an indulgent experience for discerning travellers.

Chesapeake Beach Resort

  • Why it's great for a luxury retreat: For travellers looking for a refined beachfront experience, Chesapeake Beach Resort stands out with a remarkable review rating of 9.2. This resort boasts designer toiletries and private beach access, ensuring a tranquil and luxurious stay. Guests can unwind in elegant rooms with air conditioning and spectacular resort views, complemented by dedicated concierge services for a seamless experience.
  • Other amenities: Additional features include a beautiful outdoor pool with sun loungers, complimentary beach towels, and a range of onsite activities such as boat tours and kayaking. Enjoy a leisurely day on the private beach or explore the nearby ocean with snorkelling adventures. The hotel also offers convenient amenities like daily housekeeping and a kitchenette in rooms, perfect for longer stays.
  • 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

Islander Resort

  • Why it's great for a luxury retreat: Islander Resort offers a luxurious retreat with a review rating of 9.2, featuring direct beach access and premium bedding for a restful stay. This resort is designed for relaxation, with a private beach location and concierge services to cater to every need. Guests can enjoy champagne service and an array of dining options, including beachfront restaurants.
  • Other amenities: Additional amenities include a poolside bar, evening entertainment, and beach sun loungers for ultimate comfort. The resort offers water sports equipment, a mini golf course, and a variety of recreational activities like windsurfing and kayaking. With electric car charging stations and self-parking options, the Islander Resort ensures a straightforward experience for all guests.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.9 km, Islamorada Brewery & Distillery - 0.8 km, Keys History & Discovery Center - 0.1 km

Cheeca Lodge & Spa

  • Why it's great for a luxury retreat: Cheeca Lodge & Spa is the epitome of luxury in Islamorada, with an impressive guest rating of 9.0. This lavish retreat features a stunning beachfront restaurant, private hot tubs, and exceptional concierge service. The resort offers unmatched amenities such as a golf course and tennis courts, ensuring guests indulge in both relaxation and recreation.
  • Other amenities: Additional amenities include 24-hour room service, premium bedding, and a full-service spa that provides massages on the beach. Guests can enjoy poolside cabanas, couples dining options, and the luxury of deep soaking bathtubs in their rooms. With evening entertainment and supervised childcare, Cheeca Lodge & Spa caters perfectly to all aspects of a luxury getaway.
  • 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

Amara Cay Resort

  • Why it's great for a luxury retreat: Amara Cay Resort is a luxurious haven with a guest review rating of 8.8, offering a perfect blend of relaxation and adventure. With its stunning beachfront location, guests can enjoy in-room massages and high-end amenities such as premium bedding and air conditioning. The resort’s restaurant serves exquisite cuisine with beautiful ocean views, making it a delightful dining experience.
  • Other amenities: Additional offerings include an outdoor pool, beach towels, and a terrace for sun-soaked relaxation. Guests can enjoy onsite kayaking or explore nearby snorkeling opportunities. The resort features a poolside bar, fitness facilities, and complimentary beach sun loungers, ensuring every aspect of a luxurious stay is covered.
  • 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 presents a luxurious experience with a solid review rating of 8.6. Guests can indulge in premium bedding and designer toiletries, alongside private beach access for a serene getaway. The resort features a poolside bar and offers evening entertainment for a perfect blend of relaxation and fun.
  • Other amenities: Additional amenities include beach sun loungers, a kitchenette in select rooms, and an outdoor pool accessible for all guests. There’s also a fitness centre nearby, ensuring health-conscious travellers can maintain their routines. With complimentary beach towels, electric car charging stations, and convenient self-parking, La Siesta Resort & Villas is designed to provide a seamless luxury experience.
  • 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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Breakfast was great, views were awesome, nice little private beach (rare in the keys) perfect location with plenty of night life walking distance and near by! Would stay again for sure!"
Kenneth 3-night trip
Posted 2 hours ago
Chesapeake Beach Resort

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 5-star 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 4-star 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 4-star 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 4-star 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 Mile Marker 80 and Mile 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.
How much does a luxury hotel in Islamorada cost?
Luxury hotel prices in Islamorada vary, but you can find a great deal from £179 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.
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 5-star 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 4-star 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 4-star 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 4-star 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 5-star 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 4-star 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, a 4-star 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 4-star 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 5-star 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 4-star 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 4-star 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 5-star 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 4-star 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 4-star 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.
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 programme, 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.
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.
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.

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