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Hersha Hospitality in Islamorada
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
1.23 mi from city center
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.
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
2.41 mi from city center
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..
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
0.62 mi from city center
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..
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
1.82 mi from city center
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.
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
$160 nightly
The price is $180 total per night
$180 total
Dec 16 - Dec 17
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.29 mi from city center
With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum.
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
0.3 mi from city center
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.
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
$265 nightly
The price is $298 total per night
$298 total
Dec 14 - Dec 15
Total with taxes and fees
4.16 mi from city center
With a stay at Treasure Harbor in Islamorada, you'll be within a 10-minute walk of Rain Barrel Village and Founders Park.
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
2.53 mi from city center
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.
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
2.05 mi from city center
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.
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$159 nightly
The price is $179 total per night
$179 total
Dec 17 - Dec 18
Total with taxes and fees
2.38 mi from city center
With a stay at Coconut Cove Resort and Marina in Islamorada, you'll be on the waterfront, just steps from Windley Key Fossil Reef Geological State Park and a 3-minute drive from History of Diving Museum.
Sunset Inn
82200 Overseas Hwy Islamorada FL
$148 nightly
The price is $166 total per night
$166 total
Dec 16 - Dec 17
Total with taxes and fees
0.15 mi from city center
With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & Discovery Center.
La Jolla Resort
82216 Overseas Highway Islamorada FL
$134 nightly
The price is $151 total per night
$151 total
Dec 18 - Dec 19
Total with taxes and fees
0.07 mi from city center
With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 10 minutes by foot from Keys History & Discovery 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 | 2,230 hotels |
|---|---|
Lowest Price | $151 |
Highest Price | $446 |
Popular hotels | Chesapeake Beach Resort, Amara Cay Resort, Cheeca Lodge & Spa, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Hadley Resort and Marina, Islander Resort, Treasure Harbor, Fisher Inn Resort & Marina, La Siesta Resort & Villas, Coconut Cove Resort and Marina, Sunset Inn, La Jolla Resort |
Most Recent Islamorada Hotel Reviews
Islander Resort
5 out of 5
Posted 2 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
