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

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Our top choices for Islamorada luxury hotels

Balcony view

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (77 reviews)
The price is S$796
includes taxes & fees
2 Aug - 3 Aug
The Islands of Islamorada
Exterior

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,012 reviews)
  • cleanliness
    Beachfront luxury awaits at this Key Largo resort with spa treatments and ocean views.
The price is S$477
includes taxes & fees
2 Aug - 3 Aug
Playa Largo Resort & Spa, Autograph Collection
Exterior

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, (1,135 reviews)
  • cleanliness
    Beach luxury reimagined at Key Largo resort with private sands, refreshing pools, and coastal dining.
The price is S$499
includes taxes & fees
26 Jul - 27 Jul
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,078 reviews)
  • cleanliness
    Beachfront luxury awaits at Florida Keys haven with private shores, poolside bars, and lavish lanai rooms.
The price is S$431
includes taxes & fees
10 Aug - 11 Aug
Islander Resort
Balcony

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,346 reviews)
  • cleanliness
    Experience seaside opulence with private beach access, three outdoor pools, and oceanfront dining at this beachfront Matecumbe resort.
The price is S$337
includes taxes & fees
9 Aug - 10 Aug
Cheeca Lodge & Spa
Premium bedding, in-room safe, individually decorated

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, (226 reviews)
  • cleanliness
    Seaside elegance awaits at this Islamorada resort with 3 pools, diverse dining, and a marina.
The price is S$464
includes taxes & fees
10 Aug - 11 Aug
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
View from room

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,293 reviews)
  • cleanliness
    Florida Keys resort offers private beach paradise with upscale rooms, coastal activities, and luxurious relaxation.
The price is S$346
includes taxes & fees
23 Jul - 24 Jul
Amara Cay Resort
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, (1,011 reviews)
The price is S$348
includes taxes & fees
10 Aug - 11 Aug
La Siesta Resort & Villas
3 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, (218 reviews)
  • cleanliness
    Indulge in oceanfront splendour at this Florida Keys resort with 5 pools, private beach, and full-service spa treatments.
The price is S$1,206
includes taxes & fees
13 Jul - 14 Jul
Villas At Hawks Cay Resort
3 restaurants; breakfast, lunch and dinner served

Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
Key Largo
9.4 out of 10, Exceptional, (1,492 reviews)
The price is S$355
includes taxes & fees
26 Jul - 27 Jul
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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Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"This was a nice place to get away from the urban Key West. The staff was very friendly and solved any issues regardless of the time (noisy neighbor, needed blanket) and the shore was close by. There was staff routinely monitoring the beach and property so it was very secure. The location has easy access to restaurants and shops if you have a car. The large pool had a bar / food and the property has a nice restaurant. The breakfast is cook to order pancakes and omelets, very nice! Pros Great staff everywhere! Ocean view is a real view if you select it We had a suite with a king bed and the teen had a separate fold out couch that was comfortable Microwave and mini-fridge were convenient Bathroom was very nice had a toilet in a separated section with a door A second pool was available with shade making it cooler in the summer Parking was easy and right outside, some covered by the buildings Elevator if you have the ocean view was very convenient Fresh omelet to order with a dozen ingredients, good yogurt options with toppings that were plentiful Balcony was very nice Reasonable price Cons - not much Next to a busy road. We could not hear it from outside the room door but there are two buildings and we were at the far building, so not bad at all for us Not much available without a car I recommend not going in June as the seaweed odor is unpleasant No one went to the beach but it was fine at the pool"
matthew 2-night trip
Posted 13 hours ago
Chesapeake Beach Resort

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, Bud n' Mary's Dive Center 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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