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Featured Islamorada Hotels with Bars

Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
$237 nightly
The price is $266 total per night
$266 total
Sep 14 - Sep 15
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..
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$304 nightly
The price is $342 total per night
$342 total
Sep 22 - Sep 23
Total with taxes and fees
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 4 minutes by foot from Lorelei Restaurant & Cabana Bar.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
$240 nightly
The price is $270 total per night
$270 total
Sep 7 - Sep 8
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.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$214 nightly
The price is $241 total per night
$241 total
Aug 28 - Aug 29
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 steps from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing Co..
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy Islamorada FL
$198 nightly
The price is $223 total per night
$223 total
Aug 31 - Sep 1
Total with taxes and fees
With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 3-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center.
Casa Morada

Casa Morada

3.5 out of 5
82200 overseas HWY Islamorada FL
$194 nightly
The price is $218 total per night
$218 total
Aug 31 - Sep 1
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 6 minutes by foot from Lorelei Restaurant & Cabana Bar.
Creekside Inn

Creekside Inn

2.5 out of 5
90611 Old Highway Tavernier FL
$138 nightly
The price is $155 total per night
$155 total
Sep 8 - Sep 9
Total with taxes and fees
A stay at Creekside Inn places you in the heart of Tavernier, a short 3-minute walk from Florida Keys Dive Center and within 2 minutes by car from Mariners Hospital.
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$237 nightly
The price is $266 total per night
$266 total
Aug 30 - Aug 31
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 a 4-minute walk from Indian Key Historic State Park and 11 minutes by foot from Bud n' Mary's Dive Center.
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
$158 nightly
The price is $178 total per night
$178 total
Aug 30 - Aug 31
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Fisher Inn Resort & Marina, you'll be centrally located in Islamorada, just a 3-minute walk from Windley Key Fossil Reef Geological State Park and 9 minutes by foot from Hog Heaven.
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$217 nightly
The price is $240 total per night
$240 total
Aug 31 - Sep 1
Total with taxes and fees
With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, just a 4-minute walk from Windley Key Fossil Reef Geological State Park and 7 minutes by foot from Hog Heaven.
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
$209 nightly
The price is $235 total per night
$235 total
Aug 30 - Aug 31
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.
The Caribbean Resort

The Caribbean Resort

3.5 out of 5
117 Carroll St Islamorada FL
A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum.
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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.

Islamorada hotels essential information

Accommodation
2,155 hotels
Lowest Price
$155
Highest Price
$342
Popular hotels
Amara Cay Resort, Islander Resort, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Cheeca Lodge & Spa, Pines & Palms Resort, Casa Morada, Creekside Inn, La Siesta Resort & Villas, Fisher Inn Resort & Marina, Drop Anchor, Chesapeake Beach Resort, The Caribbean Resort

Most Recent Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

4 out of 5
Posted 5 hours ago
CheapTickets Verified Review
"We arrived one hour and twenty minutes before check in and were told there were no available rooms, although I am positive there were clean ready rooms. My husband and I went to the pool and enjoyed some music before checking into our room. Room was clean and comfortable. Continental breakfast served the next morning. The attendance were lovely and seemed happy to be at work. Check out soon after."
A verified traveler stayed at Chesapeake Beach Resort
Chesapeake Beach Resort

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