Compare Hotels with Pools in Islamorada

Name: Chesapeake Beach Resort
Price range: $547

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Featured Islamorada Hotels with Pools

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

$445

includes taxes & fees

$396 per night

Feb 23 - Feb 24

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 13 minutes by foot from Indian Key Historic State Park.

On private beach

Pool

Islander Resort

82100 Overseas Highway, Islamorada, FL

$330

includes taxes & fees

$293 per night

Feb 23 - Feb 24

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.

On private beach

Pool

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, FL

$403

includes taxes & fees

$358 per night

Feb 23 - Feb 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.

On private beach

Pool

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

$449

includes taxes & fees

$399 per night

Feb 23 - Feb 24

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..

On private beach

Pool

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

$361

includes taxes & fees

$325 per night

Feb 20 - Feb 21

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

$639

includes taxes & fees

$568 per night

Feb 23 - Feb 24

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

$437

includes taxes & fees

$388 per night

Mar 3 - Mar 4

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.

On private beach

Pool

Fisher Inn Resort & Marina

84951 Overseas Hwy, Islamorada, FL

$347

includes taxes & fees

$308 per night

Mar 2 - Mar 3

Free Cancellation

Reserve now, pay when you stay

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

Islander Bayside Villas and Boatslips

81450 Overseas Highway, Islamorada, FL

$486

includes taxes & fees

$432 per night

Mar 2 - Mar 3

Free Cancellation

Reserve now, pay when you stay

With a stay at Islander Bayside Villas and Boatslips, 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

$343

includes taxes & fees

$305 per night

Feb 18 - Feb 19

With a stay at Coconut Cove Resort and Marina in Islamorada, you'll be on the Strip, 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.

Pool

Hot Tub

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

$547

includes taxes & fees

$486 per night

Mar 4 - Mar 5

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.

On private beach

Pool

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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.

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Islamorada hotels essential information

Accommodation	2,234 hotels
Lowest Price	$330
Highest Price	$639
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, Islander Bayside Villas and Boatslips, Coconut Cove Resort and Marina, The Caribbean Resort, Chesapeake Beach Resort