Compare Fishing Resorts & Hotels in Islamorada

Name: Chesapeake Beach Resort
Price range: $218

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Featured Islamorada Fishing Resorts & Hotels

Islander Resort

82100 Overseas Highway, Islamorada, FL

$270

includes taxes & fees

$240 per night

Dec 1 - Dec 2

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

Cheeca Lodge & Spa

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

$471

includes taxes & fees

$419 per night

Nov 24 - Nov 25

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..

Creekside Inn Islamorada

90611 Old Highway, Tavernier, FL

$116

includes taxes & fees

$103 per night

Dec 1 - Dec 2

With a stay at Creekside Inn Islamorada, you'll be centrally located in Tavernier, within a 15-minute drive of Jimmy Johnson's Big Chill and Florida Keys Dive Center.

Pool

Parking included

Pines & Palms Resort

80401 Old Hwy, Islamorada, FL

$266

includes taxes & fees

$236 per night

Dec 15 - Dec 16

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

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, FL

$221

includes taxes & fees

$196 per night

Dec 18 - Dec 19

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

La Jolla Resort

82216 Overseas Highway, Islamorada, FL

$135

includes taxes & fees

$120 per night

Dec 1 - Dec 2

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

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

84001 Overseas Hwy, Islamorada, FL

$425

includes taxes & fees

$378 per night

Nov 26 - Nov 27

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

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

$232

includes taxes & fees

$210 per night

Nov 23 - Nov 24

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

Fisher Inn Resort & Marina

84951 Overseas Hwy, Islamorada, FL

$189

includes taxes & fees

$168 per night

Dec 1 - Dec 2

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

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

Islander Bayside Villas and Boatslips

81450 Overseas Highway, Islamorada, FL

$324

includes taxes & fees

$288 per night

Dec 1 - Dec 2

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

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

$218

includes taxes & fees

$199 per night

Dec 1 - Dec 2

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	2,217 hotels
Lowest Price	$116
Highest Price	$471
Popular hotels	Islander Resort, Cheeca Lodge & Spa, Creekside Inn Islamorada, Pines & Palms Resort, La Siesta Resort & Villas, La Jolla Resort, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Drop Anchor, Fisher Inn Resort & Marina, Conch On Inn Motel, Islander Bayside Villas and Boatslips, Chesapeake Beach Resort