Compare Historic Hotels in Islamorada

Secret Bargains - Save an extra 10% or more on select Historic Hotels

Start date: Check-in selected.
To Date
End date: Check-out

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Featured Islamorada Historic Hotels

La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$268 nightly
The price is $301 total per night
$301 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
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
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$340 nightly
The price is $383 total per night
$383 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
Don't see what you're looking for?
See all available properties in Islamorada
View all properties
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.

Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.

Islamorada hotels essential information

Accommodation
2,221 hotels
Lowest Price
$301
Highest Price
$383
Popular hotels
La Siesta Resort & Villas, Islander Resort

Most Recent Islamorada Hotel Reviews

Islander Resort

Islander Resort

5 out of 5
Posted 3 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
Islander Resort

Types of Hotels

Top 20 Islamorada Hotels

Hotels Near Islamorada

Top Hotel Brands

Hotels By Star Rating

Cities near Islamorada