Compare Luxury Hotels in Islamorada
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Featured Islamorada Luxury Hotels
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$259 nightly
The price is $291 total per night
$291 total
Dec 16 - Dec 17
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing Co..
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$261 nightly
The price is $293 total per night
$293 total
Dec 17 - Dec 18
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and a 2-minute drive from Florida Keys Brewing Co..
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$118 nightly
The price is $129 total per night
$129 total
Dec 17 - Dec 18
Total with taxes and fees
With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, a 4-minute walk from Windley Key Fossil Reef Geological State Park and a 3-minute drive from Rain Barrel Village.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
$278 nightly
The price is $313 total per night
$313 total
Dec 17 - Dec 18
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
Located in Islamorada, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort is by the ocean, within a 5-minute drive of Windley Key Fossil Reef Geological State Park and History of Diving Museum.
Creekside Inn
90611 Old Highway Tavernier FL
$139 nightly
The price is $156 total per night
$156 total
Dec 17 - Dec 18
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
A stay at Creekside Inn places you in the heart of Tavernier, just a 3-minute walk from Florida Keys Dive Center and within a 5-minute drive of Mariners Hospital.
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$192 nightly
The price is $215 total per night
$215 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park.
Conch On Inn Motel
103 Caloosa Street Tavernier FL
Located in Tavernier (Indian Waterways), Conch On Inn Motel is within a 5-minute drive of Old Road Gallery and Florida Keys Dive Center.
Casa Morada
136 Madeira Road Islamorada FL
$417 nightly
The price is $469 total per night
$469 total
Dec 15 - Dec 16
Total with taxes and fees
With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 9 minutes by foot from Keys History & Discovery Center.
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
$143 nightly
The price is $160 total per night
$160 total
Dec 18 - Dec 19
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
A stay at Fisher Inn Resort & Marina places you in the heart of Islamorada, just a 3-minute walk from Windley Key Fossil Reef Geological State Park and within a 5-minute drive of Rain Barrel Village.
Islander Resort
82100 Overseas Highway Islamorada FL
$396 nightly
The price is $446 total per night
$446 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 9 minutes by foot from Islamorada Brewery & Distillery.
Pines & Palms Resort
80401 Old Hwy Islamorada FL
$248 nightly
The price is $279 total per night
$279 total
Dec 15 - Dec 16
Total with taxes and fees
With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 5-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center.
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$328 nightly
The price is $369 total per night
$369 total
Dec 23 - Dec 24
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center.
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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Islamorada hotels essential information
Accommodation | 2,223 hotels |
|---|---|
Lowest Price | $129 |
Highest Price | $469 |
Popular hotels | Cheeca Lodge & Spa, Amara Cay Resort, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Creekside Inn, Chesapeake Beach Resort, Conch On Inn Motel, Casa Morada, Fisher Inn Resort & Marina, Islander Resort, Pines & Palms Resort, La Siesta Resort & Villas |
Most Recent Islamorada Hotel Reviews
Fisher Inn Resort & Marina
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Great location, room was spotless and perfectly met my needs. I plan to return next year."
A verified traveler stayed at Fisher Inn Resort & Marina
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