Compare Hotels with Pools in Islamorada
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Featured Islamorada Hotels with Pools

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$289 nightly
The price is $325 total per night
$325 total
May 3 - May 4
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

Islander Resort
82100 Overseas Highway Islamorada FL
$270 nightly
The price is $304 total per night
$304 total
May 17 - May 18
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 7 minutes by foot from Islamorada Brewery & Distillery.

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$253 nightly
The price is $285 total per night
$285 total
May 12 - May 13
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

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$336 nightly
The price is $378 total per night
$378 total
May 10 - May 11
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..

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$210 nightly
The price is $232 total per night
$232 total
Apr 26 - Apr 27
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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
$322 nightly
The price is $362 total per night
$362 total
May 25 - May 26
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

Pines & Palms Resort
80401 Old Hwy Islamorada FL
$348 nightly
The price is $392 total per night
$392 total
May 14 - May 15
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.

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
$198 nightly
The price is $223 total per night
$223 total
Apr 28 - Apr 29
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
A stay at Fisher Inn Resort & Marina places you in the heart of Islamorada, a short 3-minute walk from Windley Key Fossil Reef Geological State Park and within 3 minutes by car from Rain Barrel Village.

Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
$294 nightly
The price is $331 total per night
$331 total
May 11 - May 12
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

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$179 nightly
The price is $201 total per night
$201 total
Apr 26 - Apr 27
Total with taxes and fees
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

The Caribbean Resort
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.

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$249 nightly
The price is $280 total per night
$280 total
May 10 - May 11
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.
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 | 2,204 hotels |
|---|---|
Lowest Price | $201 |
Highest Price | $392 |
Popular hotels | Amara Cay Resort, Islander Resort, La Siesta Resort & Villas, Cheeca Lodge & Spa, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Pines & Palms Resort, Fisher Inn Resort & Marina, Bayside Villas by Islander Resort, Coconut Cove Resort and Marina, The Caribbean Resort, Chesapeake Beach Resort |
Most Recent Islamorada Hotel Reviews

Coconut Cove Resort and Marina
1 out of 5
Posted 2 hours ago
CheapTickets Verified Review
"Not a place I would recommend!!"
A verified traveler stayed at Coconut Cove Resort and Marina
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