Compare Beach Resorts & Hotels in Islamorada
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Featured Islamorada Beach Resorts & Hotels
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.
On private beach
Pool
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$261 nightly
The price is $293 total per night
$293 total
Dec 16 - Dec 17
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..
On private beach
Pool
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.
On private beach
Pool
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$259 nightly
The price is $291 total per night
$291 total
Dec 14 - Dec 15
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..
On private beach
Pool
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.
Pool
Pet friendly
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$308 nightly
The price is $347 total per night
$347 total
Dec 14 - Dec 15
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.
On private beach
Pool
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$192 nightly
The price is $215 total per night
$215 total
Dec 17 - Dec 18
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.
On private beach
Pool
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.
On private beach
Pool
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
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.
On private beach
Pool
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.
Pool
Breakfast included
Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
$330 nightly
The price is $371 total per night
$371 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Bayside Villas by Islander Resort, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 7 minutes by foot from Florida Keys Brewing Co..
Pool
Pet friendly
Sands of Islamorada
80051 Overseas Highway Islamorada FL
$195 nightly
The price is $219 total per night
$219 total
Dec 14 - Dec 15
Total with taxes and fees
Located in Islamorada (Matecumbe), Sands of Islamorada is within a 5-minute drive of Bud n' Mary's Dive Center and History of Diving Museum.
Pool
Pet friendly
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 | 2,230 hotels |
|---|---|
Lowest Price | $129 |
Highest Price | $469 |
Popular hotels | Islander Resort, Amara Cay Resort, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Cheeca Lodge & Spa, Drop Anchor, La Siesta Resort & Villas, Chesapeake Beach Resort, Pines & Palms Resort, Fisher Inn Resort & Marina, Casa Morada, Bayside Villas by Islander Resort, Sands of Islamorada |
Most Recent Islamorada Hotel Reviews
Islander Resort
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"The stay was excellent overall. Only issues we had was our room was full of long white flies and they didn't clean up the prior guests gross cigars on the back patio. "
A verified traveler stayed at Islander Resort
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