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Check availability on Islamorada Luxury Hotels

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Luxury Hotels in Islamorada

Private beach, sun-loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5.0 star property
Matecumbe
  • On private beach
  • Beachfront dining
  • Full-service spa
  • 2 poolside bars
  • Concierge services
9.2 out of 10, Wonderful, (1278)
Immersed in luxury, this five-star resort captivates with beachfront massages and seven spa treatment rooms. Guests indulge in championship golf, relax at poolside bars, and enjoy Champagne service while surrounded by stunning ocean vistas and lush tropical gardens.
The price is S$390
includes taxes & fees
15 Dec - 16 Dec
Cheeca Lodge & Spa
Exterior
Amara Cay Resort

Amara Cay Resort

4.0 star property
Matecumbe
  • On private beach
  • Ocean-view dining
  • Poolside bar
8.8 out of 10, Excellent, (1269)
Savour beachfront serenity at this Islamorada luxury haven. Egyptian cotton sheets adorn pillowtop beds while ocean adventures beckon outside. After snorkelling or kayaking, unwind at 3 stylish bars or dine at waterfront restaurants as stunning sunsets paint the horizon.
The price is S$307
includes taxes & fees
1 Dec - 2 Dec
Amara Cay Resort
Beach/ocean view
Drop Anchor

Drop Anchor

3.0 star property
Islamorada
  • Near private beach
  • Outdoor pool
8.8 out of 10, Excellent, (1004)
Waterfront elegance defines this Art Deco retreat where ocean adventures begin. Paddleboarding, motor boating, and sunbathing on beach loungers create perfect days in paradise. Individually furnished rooms with premium bedding provide a luxurious sanctuary after days spent by the sea.
The price is S$167
includes taxes & fees
30 Nov - 1 Dec
Drop Anchor
Private beach, sun-loungers, beach towels, scuba diving
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

3.5 star property
Islamorada
  • On private beach
  • 4 restaurants
  • 24-hour gym
  • Poolside bar
9.0 out of 10, Wonderful, (112)
Seaside luxury awaits at this Art Deco resort with a private beach. Savour delectable cuisine at 4 restaurants, unwind at 3 bars, or dive into the crystal-clear pools. Marina access provides perfect launching points for snorkelling adventures while attentive staff ensures a memorable Florida Keys escape.
The price is S$382
includes taxes & fees
1 Dec - 2 Dec
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Water view
Creekside Inn

Creekside Inn

2.5 star property
Tavernier
  • Near the beach
  • 2 outdoor pools
8.0 out of 10, Very good, (1009)
Seaside sophistication awaits at this newly renovated Florida Keys retreat. Featuring 2 sparkling outdoor pools, marina access, and Egyptian cotton sheets, this Tavernier haven combines ocean proximity with upscale amenities for a refined coastal escape.
The price is S$183
includes taxes & fees
1 Dec - 2 Dec
Creekside Inn
Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 star property
Matecumbe
  • On private beach
  • 2 outdoor pools
  • Concierge services
9.2 out of 10, Wonderful, (1587)
288
The price is S$276
includes taxes & fees
1 Dec - 2 Dec
Chesapeake Beach Resort
Property entrance
Conch On Inn Motel

Conch On Inn Motel

2.0 star property
Indian Waterways
  • Concierge services
7.6 out of 10, Good, (488)
Situated in peaceful Indian Waterways, this intimate 8-room retreat delivers island luxury through attentive concierge assistance and serene garden surroundings. BBQ facilities enhance the laid-back Florida Keys atmosphere while being just minutes from diving adventures and Founders Park.
Conch On Inn Motel
Beach nearby, white sand, sun-loungers, beach umbrellas
Casa Morada

Casa Morada

3.5 star property
Matecumbe
  • Near the beach
  • Poolside bar
  • Concierge services
  • Adults-only
9.4 out of 10, Exceptional, (411)
Seaside indulgence awaits at this adults-only Florida Keys hotel where plush bedding meets beachfront serenity. Massage treatments, a tranquil pool with bar service, and complimentary bicycles create a sophisticated coastal escape just steps from azure waters.
The price is S$611
includes taxes & fees
7 Dec - 8 Dec
Casa Morada
Exterior
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 star property
Islamorada
  • On private beach
  • Outdoor pool
  • Concierge services
8.2 out of 10, Very good, (1014)
Situated on a pristine private beach, this luxurious Islamorada retreat captivates with stunning ocean panoramas. Guests savour complimentary breakfast before exploring via kayaks and paddleboards. After snorkelling adventures, the heated pool beckons for relaxation amid palm-fringed tranquility.
The price is S$165
includes taxes & fees
18 Dec - 19 Dec
Fisher Inn Resort & Marina
Exterior
Islander Resort

Islander Resort

4.0 star property
Matecumbe
  • On private beach
  • Beachfront dining
  • 24-hour gym
  • Poolside bar
  • Concierge services
9.2 out of 10, Wonderful, (1019)
Shoreline sophistication awaits at this Islamorada retreat where 2 sparkling pools, 3 restaurants, and pristine beach cabanas create an exclusive escape. Savour ocean-view dining, explore via complimentary bicycles, or unwind on your private lanai after a day of seaside luxury.
The price is S$416
includes taxes & fees
4 Dec - 5 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.
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Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David were our poolside attendants, and Jessica at the front desk was very helpful. "
Callie 4-night trip
Posted 19 hours ago
Cheeca Lodge & Spa

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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.