Find Luxury Hotels in Islamorada, FL

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Compare Islamorada Luxury Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Cheeca Lodge & Spa
Pool

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1005)
"Excellent vacation resort"
The price is SAR 988
SAR 1,366 total
includes taxes & fees
8 Jan - 9 January 2025
Cheeca Lodge & Spa
Amara Cay Resort
Outdoor pool

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1209)
"Good stop on the way to kw."
The price is SAR 1,562
SAR 2,006 total
includes taxes & fees
26 Dec - 27 Dec
Amara Cay Resort
Drop Anchor
Exterior

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1001)
"The location was beautiful, rooms should be updated. My biggest complaint is a paid for two rooms, same price for both, but one was very much smaller than the other and no balcony in that same room either ?!?!"
The price is SAR 480
SAR 671 total
includes taxes & fees
23 Dec - 24 Dec
Drop Anchor
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior

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

3.0 star property
8.0 out of 10, Very Good, (1008)
"Excellent and amazing property. I love this resort. Will be back"
The price is SAR 1,458
SAR 1,889 total
includes taxes & fees
5 Jan - 6 January 2025
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Creekside Inn Islamorada
Outdoor pool

Creekside Inn Islamorada

2.5 star property
8.0 out of 10, Very Good, (1001)
"Nice location on the creek with manatees in the canal"
The price is SAR 603
SAR 679 total
includes taxes & fees
20 Jan - 21 January 2025
Creekside Inn Islamorada
Chesapeake Beach Resort
Beach

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1386)
"Loved it."
The price is SAR 924
SAR 1,228 total
includes taxes & fees
5 Jan - 6 January 2025
Chesapeake Beach Resort
Conch On Inn Motel
Property grounds

Conch On Inn Motel

2.0 star property
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"
Conch On Inn Motel
Casa Morada
Aerial view

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (371)
"Quaint, laid-back boutique hotel and on the water with good facilities including pool, hammocks, etc. Room was nice and included a futon in a separate space for a child. Walking distance to Lorelei restaurant and several shops. "
The price is SAR 2,376
SAR 2,955 total
includes taxes & fees
27 Dec - 28 Dec
Casa Morada
Fisher Inn Resort & Marina
Exterior

Fisher Inn Resort & Marina

3.5 star property
7.6 out of 10, Good, (1004)
"Great location in the Middle Keys and close to all of the cool hang-outs! Also very clean, has a nice pool and my room had the best balcony view ever!!!"
The price is SAR 763
SAR 981 total
includes taxes & fees
8 Jan - 9 January 2025
Fisher Inn Resort & Marina
Islander Resort
Terrace/patio

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1004)
"The space is currently ongoing construction but don’t let that stop you from staying. Beautiful location and friendly staff from the initial security guard interaction onward. Would love to come back when the construction is complete "
The price is SAR 973
SAR 1,331 total
includes taxes & fees
24 Dec - 25 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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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 travelers looking for an elegant place to stay.
How many luxury hotels will I be able to find in Islamorada?
Lie in the lap of luxury during your getaway to Islamorada in one of Expedia’s 8 luxury hotels.
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 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.