Compare Boutique Hotels in Islamorada
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Featured Islamorada Boutique Hotels
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$321 nightly
The price is $361 total per night
$361 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
Casa Morada
136 Madeira Road Islamorada FL
$536 nightly
The price is $603 total per night
$603 total
Dec 28 - Dec 29
Total with taxes and fees
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.
Pool
Breakfast included
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$184 nightly
The price is $202 total per night
$202 total
Jan 11 - Jan 12, 2026
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
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 | 2,221 hotels |
|---|---|
Lowest Price | $202 |
Highest Price | $603 |
Popular hotels | Amara Cay Resort, Casa Morada, Drop Anchor |
Most Recent Islamorada Hotel Reviews
Islander Resort
5 out of 5
Posted 2 days ago
CheapTickets Verified Review
"The resort was perfect
Everyone from checking in and during our stay could not have been nicer and helpful"
A verified traveler stayed at Islander Resort
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