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Hersha Hospitality in Islamorada
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$220 nightly
The price is $248 total per night
$248 total
Dec 18 - Dec 19
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.
On private beach
Pool
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$268 nightly
The price is $302 total per night
$302 total
Dec 18 - Dec 19
Total with taxes and fees
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..
On private beach
Pool
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$264 nightly
The price is $297 total per night
$297 total
Dec 18 - Dec 19
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..
On private beach
Pool
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
$298 nightly
The price is $335 total per night
$335 total
Dec 18 - Dec 19
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.
On private beach
Pool
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
$163 nightly
The price is $184 total per night
$184 total
Dec 18 - Dec 19
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.
On private beach
Pool
Islander Resort
82100 Overseas Highway Islamorada FL
$340 nightly
The price is $383 total per night
$383 total
Jan 4 - Jan 5, 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.
On private beach
Pool
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
$265 nightly
The price is $298 total per night
$298 total
Dec 18 - Dec 19
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.
Pool
Parking included
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
$168 nightly
The price is $189 total per night
$189 total
Dec 18 - Dec 19
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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.
On private beach
Pool
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$308 nightly
The price is $347 total per night
$347 total
Dec 18 - Dec 19
Total with taxes and fees
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.
On private beach
Pool
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$159 nightly
The price is $179 total per night
$179 total
Dec 18 - Dec 19
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.
Pool
Breakfast included
Sunset Inn
82200 Overseas Hwy Islamorada FL
$139 nightly
The price is $156 total per night
$156 total
Dec 18 - Dec 19
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.
Pool
Pet friendly
La Jolla Resort
82216 Overseas Highway Islamorada FL
$145 nightly
The price is $163 total per night
$163 total
Jan 13 - Jan 14, 2026
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.
On private beach
Pool
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 | 2,221 hotels |
|---|---|
Lowest Price | $156 |
Highest Price | $383 |
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
Chesapeake Beach Resort
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Idyllic beautiful beach setting, clean comfortable rooms, lovely setting. "
A verified traveler stayed at Chesapeake Beach Resort
