Compare Adventure Sport Hotels in Islamorada
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Featured Islamorada Adventure Sport Hotels

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is $410 total per night
$410 total
per night
Dec 19 - Dec 20
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..

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
The price is $419 total per night
$419 total
per night
Jan 4 - Jan 5
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.

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is $361 total per night
$361 total
per night
Jan 4 - Jan 5
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..

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
The price is $369 total per night
$369 total
per night
Dec 23 - Dec 24
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.

Islander Resort
82100 Overseas Highway Islamorada FL
The price is $383 total per night
$383 total
per night
Jan 4 - Jan 5
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.

Casa Morada
136 Madeira Road Islamorada FL
The price is $603 total per night
$603 total
per night
Dec 28 - Dec 29
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.

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.
Pet friendly
Parking included

Pines & Palms Resort
80401 Old Hwy Islamorada FL
The price is $347 total per night
$347 total
per night
Jan 4 - Jan 5
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.

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is $269 total per night
$269 total
per night
Dec 22 - Dec 23
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.

Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
The price is $200 total per night
$200 total
per night
Jan 11 - Jan 12
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.

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
The price is $202 total per night
$202 total
per night
Jan 11 - Jan 12
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.
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 | $190 |
Highest Price | $603 |
Popular hotels | Cheeca Lodge & Spa, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Amara Cay Resort, La Siesta Resort & Villas, Islander Resort, Casa Morada, Conch On Inn Motel, Pines & Palms Resort, Chesapeake Beach Resort, Hadley Resort and Marina, Drop Anchor, Creekside Inn |
Most Recent Islamorada Hotel Reviews

Chesapeake Beach Resort
5 out of 5
Posted 4 days ago
CheapTickets Verified Review
"Idyllic beautiful beach setting, clean comfortable rooms, lovely setting. "
A verified traveler stayed at Chesapeake Beach Resort
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