Compare Boutique Hotels in Islamorada

Name: Drop Anchor
Price range: $219

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Featured Islamorada Boutique Hotels

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

$248

includes taxes & fees

$220 per night

Nov 17 - Nov 18

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

Casa Morada

136 Madeira Road, Islamorada, FL

$521

includes taxes & fees

$471 per night

Dec 10 - Dec 11

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.

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

$219

includes taxes & fees

$199 per night

Nov 15 - Nov 16

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

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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	2,209 hotels
Lowest Price	$219
Highest Price	$521
Popular hotels	Amara Cay Resort, Casa Morada, Drop Anchor

Most Recent Islamorada Hotel Reviews

Chesapeake Beach Resort

5 out of 5

Posted 3 days ago

CheapTickets Verified Review

"Amazing property! We had a reservation at a different place and were not happy with it so decided to push on. We couldn’t be happier. The staff is amazing, breakfast is great and there is a private beach. We are so happy we extended our stay."

A verified traveler stayed at Chesapeake Beach Resort