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

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Check availability on Islamorada Luxury Hotels

Tonight
25 Sept - 26 Sept
Tomorrow
26 Sept - 27 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Islamorada luxury hotels

A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.
A gated entrance to a resort with palm trees and a clear sky.

1. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
Rp7.255.980
Rp9.295.717 total
includes taxes & fees
1 Oct - 2 Oct
The Islands of Islamorada
An aerial view of a resort with a large pool, palm trees, and a beach.
A beachside patio with lounge chairs, a table, and a view of the ocean.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

2. 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.
Rp4.711.908
Rp6.288.606 total
includes taxes & fees
11 Oct - 12 Oct
Playa Largo Resort & Spa, Autograph Collection
A wooden deck with a view of the ocean and a palm tree.
A hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious dining area with high ceilings, wicker furniture, and large windows.
A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.

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.
Rp4.672.949
Rp6.239.373 total
includes taxes & fees
29 Sept - 30 Sept
Baker's Cay Resort Key Largo, Curio Collection by Hilton
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A wooden pier leading to a beach with palm trees and a row of beach huts.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.

4. Islander Resort

Islander Resort
Matecumbe
  • Beachfront luxury awaits at Florida Keys haven with private shores, poolside bars, and lavish lanai rooms.
Rp3.869.856
Rp5.663.605 total
includes taxes & fees
7 Oct - 8 Oct
Islander Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A resort with a pool, beach, and ocean view.
A beach with palm trees, a clear blue sky, and a calm sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.

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.
Rp3.712.195
Rp5.486.417 total
includes taxes & fees
15 Oct - 16 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.
A resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.

6. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Florida Keys resort offers private beach paradise with upscale rooms, coastal activities, and luxurious relaxation.
Rp2.769.366
Rp4.425.734 total
includes taxes & fees
27 Sept - 28 Sept
Amara Cay Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.
A tropical resort with a swimming pool, palm trees, and a waterfall.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

7. 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.
Rp2.669.484
Rp4.313.367 total
includes taxes & fees
29 Sept - 30 Sept
Cheeca Lodge & Spa
A resort pool with palm trees and lounge chairs, surrounded by a beachfront.
A modern living room with a sofa, chairs, a dining table, a TV, and a view of the ocean.
A modern kitchen with white cabinetry, a stainless steel oven, and a large island with a bowl of fruit.
A resort with a large pool surrounded by lounge chairs, a beach area, and a building with multiple floors.

8. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
Marathon
  • Indulge in oceanfront splendour at this Florida Keys resort with 5 pools, private beach, and full-service spa treatments.
Rp6.790.164
Rp8.747.666 total
includes taxes & fees
27 Sept - 28 Sept
Villas At Hawks Cay Resort
A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.
A poolside area with blue chairs and a thatched-roof structure.
A spacious living room with large windows, comfortable seating, and decorative plants.
A spacious bar area with high ceilings and large windows, offering views of the ocean.

9. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
Rp3.565.284
Rp4.727.674 total
includes taxes & fees
28 Sept - 29 Sept
Reefhouse Resort & Marina
A wooden deck with a pool and chairs overlooking a beach with palm trees.
A hotel room with a sofa, a desk, a chair, a TV, and a balcony with curtains.
A beach with a wooden walkway leading to the water, palm trees, and a clear sky.
A pool area with palm trees and a view of the ocean.

10. Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club
Marathon
Rp3.136.518
Rp4.388.551 total
includes taxes & fees
25 Oct - 26 Oct
Grassy Flats Resort & Beach Club
View all properties

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"I liked the breakfast. One pool was being worked on and the pool workers helped themselves to the free breakfast. Some of them stood in the coffee and drink area and ate their free breakfast. The tree trimmers took up some of relaxing areas and they were noisy. The cleaning staff and the front desk staff were very good. The breakfast cook was friendly. The spa was hot but no jet action. We probably won’t be coming back. Thanks"
William 3-night trip
Posted 1 hour ago
Chesapeake Beach Resort
Casa Morada

Casa Morada

10/10 Excellent
"always a favorite!"
robert 2-night trip
Posted 5 hours ago
Casa Morada
Drop Anchor

Drop Anchor

10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
Payman 3-night trip
Posted 1 day ago
Drop Anchor
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

8/10 Good
"Room was OK with killer water view!"
Rick 3-night trip
Posted 2 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"This place was the best place to stay I've ever been ever it is wonderful there's nothing not to like about this place the ocean the pool the people the place everybody's so nice and accommodating they will do anything they can to make sure you're happy it's paradise in paradise I would suggest to stay at this place anytime it would be a mistake not to"
Michael 1-night trip
Posted 3 days ago
Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Excellent stay! Love this place and will definitely be back!"
Hailey Ritch and Patrick 3-night trip
Posted 8 days ago
Coconut Cove Resort and Marina

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 travellers looking for an elegant place to stay. Another upscale choice for your holiday is The Islands of Islamorada.
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 Bud n' Mary's Dive Center, Robbie's of Islamorada and Anne's Beach. If you have a bit of extra time while you're in the area, you might want to check out Fiesta Key and Everglades National Park.

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