Find Islamorada Boutique Hotels
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Featured Islamorada Boutique Hotels

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$271 nightly
The price is $305 total per night
$305 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a gym. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a meeting room, a terrace, and laundry facilities.
On private beach
Pool

Casa Morada
136 Madeira Road Islamorada FL
$482 nightly
The price is $543 total per night
$543 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Guests of Casa Morada enjoy features like an outdoor pool, free WiFi in public areas, and free use of bicycles. There's free parking if you drive. Front-desk staff can assist with dry cleaning/laundry, tours or tickets, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this adults-only hotel include free newspapers, a terrace, and laundry facilities.
Pool
Breakfast included

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$191 nightly
The price is $210 total per night
$210 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Drop Anchor enjoy an outdoor pool, free WiFi in public areas, and a business center. If you drive, put free parking to good use. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include coffee/tea in a common area, free use of bicycles, and a garden.
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.
Islamorada hotels essential information
Accommodation | 2,220 hotels |
|---|---|
Lowest Price | $210 |
Highest Price | $543 |
Popular hotels | Amara Cay Resort, Casa Morada, Drop Anchor |
Recent Boutique Hotels Reviews

Chesapeake Beach Resort
5/5 Excellent
"It was a great breakfast.... they had everything that i liked in particular. They had healthy options.. not a big place so it didnt seem overwhelmed with options just the right amount of options. Place i staid had an amazing ocean view :) "
A verified traveler stayed at Chesapeake Beach Resort
Posted 13 hours ago


