Luxury Hotels & Resorts in Islamorada from AU$194

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Islamorada Luxury Hotels

Our top choices for Islamorada luxury hotels

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1269)
"It was awesome, great service, staff members are helpful, clean and tidy room with excellent views!"
United States
Sami
The price is AU$468
includes taxes & fees
18 Dec - 19 Dec
Cheeca Lodge & Spa

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1268)
"Friendly staff and beautiful property !"
United States
ron
The price is AU$404
includes taxes & fees
18 Dec - 19 Dec
Amara Cay Resort

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1000)
"Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! "
United States
Laura
The price is AU$194
includes taxes & fees
18 Dec - 19 Dec
Drop Anchor

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, (116)
"Beautiful place to stay"
United States
Jonathan
The price is AU$487
includes taxes & fees
17 Dec - 18 Dec
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Creekside Inn

Creekside Inn
2.5 star property
Tavernier
8.0 out of 10, Very good, (1004)
"Very comfortable stay Local dining walking distance many amenities close by Room was very clean and AC worked great "
United States
Roy
The price is AU$318
includes taxes & fees
17 Dec - 18 Dec
Creekside Inn

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1595)
"Great breakfast, great location, friendly staff, nice extras."
United States
Gary
The price is AU$300
includes taxes & fees
17 Dec - 18 Dec
Chesapeake Beach Resort

Conch On Inn Motel

Conch On Inn Motel
2.0 star property
Indian Waterways
7.6 out of 10, Good, (488)
"Overall great experience & owners were great. Only thing I would offer up is could use some new mattresses but everything else was more than expected! Would (or shouldsay will) stay again someday"
United States
Anonymous traveller
Conch On Inn Motel

Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (414)
"always a pleasant stay."
United States
robert
The price is AU$635
includes taxes & fees
18 Dec - 19 Dec
Casa Morada

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1004)
"Great location, room was spotless and perfectly met my needs. I plan to return next year."
United States
M
The price is AU$241
includes taxes & fees
18 Dec - 19 Dec
Fisher Inn Resort & Marina

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1005)
"This resort is beautiful and the rooms are decorated so tastefully. I highly recommend The Islander Resort for family fun and couples get aways alike. "
United States
Suzanne
The price is AU$982
includes taxes & fees
22 Dec - 23 Dec
Islander 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.

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

Frequently asked questions

Are you looking for a luxury hotel for your stay in Islamorada?
Known for its ocean views and sunsets, Islamorada also has some interesting things to see and do including Everglades National Park, so you may want to take in the local sights during your visit.
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 travellers 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 temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.
What's there to see and do in Islamorada?
Experience all that Islamorada has to offer when you visit Everglades National Park, Florida Keys Brewing Co. and Bud n' Mary's Dive Center. If you have a bit of extra time while you're in the area, you might want to check out Founders Park and Anne's Beach.

Explore a world of travel with Expedia