Best Luxury Hotels in Islamorada

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Our top choices for Islamorada luxury hotels

Balcony
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,292 reviews)
"Breakfast was fantastic "
Canada
Craig
The price is RM1,102
RM1,537 total
includes taxes & fees
28 Jan - 29 Jan
Cheeca Lodge & Spa
View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,261 reviews)
"Great Location, Friendly Staff"
United States
HECTOR
The price is RM875
RM1,281 total
includes taxes & fees
26 Jan - 27 Jan
Amara Cay Resort
Beach/ocean view
Drop Anchor

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,000 reviews)
"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 RM736
RM970 total
includes taxes & fees
19 Jan - 20 Jan
Drop Anchor
In-room safe, individually decorated, individually furnished
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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, (125 reviews)
"Beautiful chilled out hotel"
United Kingdom
Jacqueline
The price is RM1,208
RM1,630 total
includes taxes & fees
21 Jan - 22 Jan
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
View from property
Creekside Inn

Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,001 reviews)
"It is an awesome experience with wonderful views, the location is a big advantage for this hotel"
United States
Vamsi kalyan
The price is RM687
RM773 total
includes taxes & fees
14 Jan - 15 Jan
Creekside Inn
Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,631 reviews)
"Clean, gorgeous view, amazing free breakfast, loved the robes!"
United States
Devon
The price is RM768
RM1,093 total
includes taxes & fees
28 Jan - 29 Jan
Chesapeake Beach Resort
Property grounds
Conch On Inn Motel

Conch On Inn Motel

Conch On Inn Motel
2.0 star property
Indian Waterways
7.6 out of 10, Good, (488 reviews)
"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
Exterior
Casa Morada

Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (417 reviews)
"always a pleasant stay."
United States
robert
The price is RM1,472
RM1,904 total
includes taxes & fees
14 Jan - 15 Jan
Casa Morada
Exterior
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,005 reviews)
"Beautiful location and staff is amazing. Would definitely recommend!"
United States
Zachary
The price is RM695
RM915 total
includes taxes & fees
19 Jan - 20 Jan
Fisher Inn Resort & Marina
Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,008 reviews)
"Rooms are clean, staff is friendly and the place is beautifull"
United States
James
The price is RM1,312
RM1,751 total
includes taxes & fees
15 Jan - 16 Jan
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The breakfast included was the best we've ever had at a hotel. Fresh omelets made to order with a wide choice of ingredients. Fresh fruit (Strawberries and blueberries ) and more. Fresh delicious muffins. The Staff was very friendly and very helpful. Would definitely recommend a stay here. The views are stunning."
Mary 2-night trip
Posted 4 days 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, 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.

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