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

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Check availability on Islamorada Luxury Hotels

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Islamorada luxury hotels

1. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
NT$11,383
NT$14,776 total
includes taxes & fees
Aug 30 - Aug 31
The Islands of Islamorada

2. Islander Resort

Islander Resort
Matecumbe
  • Beachfront luxury awaits at Florida Keys haven with private shores, poolside bars, and lavish lanai rooms.
NT$7,715
NT$10,814 total
includes taxes & fees
Sep 22 - Sep 23
Islander Resort

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
  • Beach luxury reimagined at Key Largo resort with private sands, refreshing pools, and coastal dining.
NT$7,493
NT$10,173 total
includes taxes & fees
Sep 28 - Sep 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton

4. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
  • Beachfront luxury awaits at this Key Largo resort with spa treatments and ocean views.
NT$7,829
NT$10,556 total
includes taxes & fees
Sep 21 - Sep 22
Playa Largo Resort & Spa, Autograph Collection

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
  • Seaside elegance awaits at this Islamorada resort with 3 pools, diverse dining, and a marina.
NT$5,540
NT$8,544 total
includes taxes & fees
Sep 7 - Sep 8
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

6. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Experience seaside opulence with private beach access, three outdoor pools, and oceanfront dining at this beachfront Matecumbe resort.
NT$4,711
NT$7,612 total
includes taxes & fees
Sep 7 - Sep 8
Cheeca Lodge & Spa

7. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Florida Keys resort offers private beach paradise with upscale rooms, coastal activities, and luxurious relaxation.
NT$4,674
NT$7,571 total
includes taxes & fees
Sep 2 - Sep 3
Amara Cay Resort

8. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
NT$4,247
NT$7,090 total
includes taxes & fees
Aug 31 - Sep 1
La Siesta Resort & Villas

9. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
Marathon
  • Indulge in oceanfront splendor at this Florida Keys resort with 5 pools, private beach, and full-service spa treatments.
Villas At Hawks Cay Resort

10. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
NT$6,925
NT$9,055 total
includes taxes & fees
Aug 30 - Aug 31
Reefhouse Resort & Marina
View all properties

Find out more about Islamorada

Islamoradaand its attractions for luxury travelers

Islamorada, known as the "Sport Fishing Capital of the World," offers luxury travelers an array of high-end experiences. Start your day with a private charter fishing excursion in the pristine waters of the Florida Keys, where you can reel in tarpon or sailfish with top guides catering to your every need. For those who prefer relaxation, indulge in a spa day at the luxurious Cheeca Lodge, where treatments use fresh local ingredients and the ocean provides a soothing backdrop. Explore the vibrant underwater world with a private scuba diving or snorkeling trip, discovering coral reefs filled with marine life, or take a sunset cruise on a yacht, complete with champagne and hors d'oeuvres. If you’re a culinary enthusiast, don’t miss dining at the acclaimed Pierre’s, where you can savor gourmet dishes featuring local seafood while overlooking the breathtaking bay. For accommodations, the luxurious Ocean House offers beachfront suites with private balconies, perfect for enjoying the stunning sunsets after a day of adventure. Here, attentive service ensures that your every wish is catered to, making your stay as relaxing as it is exhilarating.

Find the best luxury hotels and resorts in Islamorada

Islamorada offers a stunning backdrop for a luxurious retreat, where travelers can indulge in high-end amenities and breathtaking views. Here are some top hotels that epitomize luxury in this beautiful destination.Chesapeake Beach Resort

  • Why it's great for a luxury retreat: For travelers seeking a luxurious escape, Chesapeake Beach Resort offers an exquisite blend of comfort and elegance, a remarkable guest review rating of 9.2. Guests can unwind in stylish accommodations featuring designer toiletries and breathtaking resort views, while enjoying the private white sand beach that enhances the experience of tropical living.
  • Other amenities: Additional features include a refreshing outdoor pool, complimentary breakfast, and convenient concierge services. Guests can explore boat tours or indulge in nearby snorkeling adventures. The hotel also provides air conditioning for comfort, along with daily housekeeping to ensure a pristine stay.
  • Neighborhood: Matecumbe
  • Nearby attractions: History of Diving Museum - 0.56 miles, Theater of the Sea - 1.08 miles, Windley Key Fossil Reef Geological State Park - 1.11 miles

Islander Resort

  • Why it's great for a luxury retreat: Islander Resort is a luxurious haven for travelers, providing a perfect blend of elegance and seaside charm, reflected in its impressive guest review rating of 9.2. With a prime beachfront location, guests can enjoy stunning ocean views while indulging in champagne service or relaxing in poolside cabanas under the sun.
  • Other amenities: Noteworthy amenities include an outdoor swimming pool, a concierge service for personalized experiences, and evening entertainment to enhance the stay. Offering premium bedding, bathrobes, and private beach access, this resort ensures a comfortable and lavish experience. Guests can also enjoy watersports equipment and nearby scuba diving to explore the vibrant marine life.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.53 miles, Islamorada Brewery & Distillery - 0.51 miles, Keys History & Discovery Center - 0.09 miles

Cheeca Lodge & Spa

  • Why it's great for a luxury retreat: Cheeca Lodge & Spa stands as a beacon of luxury in Islamorada with a stellar review rating of 9.0. This resort promises an unforgettable experience with its beachfront dining, private hot tubs, and poolside service. Guests can enjoy an exclusive stay with premium bedding and designer toiletries that elevate the comfort level to new heights.
  • Other amenities: Among its luxurious offerings are an onsite golf course, a full-service spa with massage treatments, and tennis courts for active guests. The hotel also features 24-hour room service, couples dining options, and a poolside bar that adds to the resort's charm. For those who appreciate relaxation, the deep soaking bathtubs and massages on the beach create a serene atmosphere.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.06 miles, Florida Keys Brewing Co. - 0.28 miles, MoradaWay Arts & Cultural District - 0.34 miles

Amara Cay Resort

  • Why it's great for a luxury retreat: Amara Cay Resort captures the essence of luxury with its inviting atmosphere and exceptional guest review rating of 8.8. This resort features beachfront dining and in-room massage services, ensuring that every moment is tailored to relaxation and indulgence. Guests will appreciate the climate-controlled accommodations, premium bedding, and the option of private beach access for a serene retreat.
  • Other amenities: The resort also provides a variety of additional amenities, including a poolside bar, complimentary beach towels, and outdoor pools for leisure. Guests can enjoy onsite kayaking or enjoy the stunning views from their balconies. With a focus on comfort and luxury, this resort offers an unforgettable getaway.
  • Neighborhood: Matecumbe
  • Nearby attractions: Bud n' Mary's Dive Center - 0.21 miles, Indian Key Historic State Park - 0.67 miles, Hurricane Monument - 1.4 miles

La Siesta Resort & Villas

  • Why it's great for a luxury retreat: La Siesta Resort & Villas offers a luxurious escape for travelers looking to indulge on their stay in Islamorada, with an excellent review rating of 8.6. The resort features premium bedding, designer toiletries, and a private beach area, creating an upscale environment for relaxation and enjoyment. Guests can enjoy the allure of a poolside bar and breathtaking views from their accommodations.
  • Other amenities: Additional amenities include a fully equipped kitchenette, convenient self-parking, and access to water sports activities. The resort also provides beach towels, outdoor pool options, and stunning beachfront dining experiences to cater to every guest's needs. With its thoughtful features and prime location, La Siesta Resort & Villas ensures a memorable stay.
  • Neighborhood: Matecumbe
  • Nearby attractions: Bud n' Mary's Dive Center - 0.56 miles, Indian Key Historic State Park - 0.31 miles, Hurricane Monument - 1.04 miles

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Check-in went smoothly and the little touch of offering some champagne on arrival made me feel special! Loved the updated room! Beds comfy. Staff accommodating. Breakfast has many great hot /cold choices. Coffee was 👍One of the Pools was a little dirty but front desk had maintenance on it when I informed them .."
Janet 3-night trip
Posted 11 hours ago
Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Absolutely love it here and will definitely return for another stay."
Lisa 2-night trip
Posted 15 hours ago
Cheeca Lodge & Spa
Islander Resort

Islander Resort

10/10 Excellent
"It’s a beautiful property right on the water with very nice pool area and right near everything in Islamorada"
Steven 1-night trip
Posted 17 hours ago
Islander Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Muy bueno nos encantó lo recomiendo al máximo . 👌👌👌👌👌"
Ivet 2-night trip
Posted 17 hours ago
La Siesta Resort & Villas
Casa Morada

Casa Morada

8/10 Good
"The room was updated, clean, and comfortable. The bed and pillows were nice. The location was perfect for us. When it’s all completed it’s going to be a really cool spot for sunsets. Overall worth the money for a one nighter on our way home from the lower keys."
Jeremy 1-night trip
Posted 2 days ago
Casa Morada
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
Dareen 3-night trip
Posted 6 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pines & Palms Resort

Pines & Palms Resort

8/10 Good
"Lovely location, beautifully renovated, clean room, close to everything including great restaurants. If you want peace and quiet this is the spot for you. If your idea of the keys includes loud activities this is not for you. The small beach was not accessible due to rotting sargassum. You could not even spend much time at the pool due to the smell. Not the hotels fault obviously but affected our stay negatively."
Arturo 3-night trip
Posted 6 days ago
Pines & Palms Resort
Drop Anchor

Drop Anchor

8/10 Good
"Shower didn’t get super hot & not the best water pressure. Keep blinds closed in summer as the room got very hot and the a/c unit struggled to keep the room cool even at night. Could use a shade for the kitten window to help with this. Full length mirror in the room would’ve been nice as well. Overall nice property but a little older & can use some revamping"
Jacqueline 2-night trip
Posted 8 days ago
Drop Anchor

Frequently asked questions

Are you looking for a luxury hotel for your stay in Islamorada?
During your visit, you might want to enjoy the ocean views and sunsets which Islamorada is known for.
What's the best luxury place to stay in Islamorada?
Cheeca Lodge & Spa is a luxury resort with a private beach and 3 restaurants, and it's a popular choice for Expedia travelers looking for an elegant place to stay.
When can I expect good weather in Islamorada?
Planning for the weather is an important factor for making your trip to Islamorada a success, especially when you're splurging. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.
What's there to see and do in Islamorada?
Experience all that Islamorada has to offer when you visit Bud n' Mary's Dive Center, Islamorada County Park, and Founders Park. If you have a bit of extra time while you're in the area, you might want to check out Robbie's of Islamorada and Anne's Beach.

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