Compare Hotels with Air Conditioning in Islamorada
Secret Bargains - Save an extra 10% or more on select Hotels with Air Conditioning
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 Hotels with Air Conditioning
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$328 nightly
The price is $369 total per night
$369 total
Dec 23 - Dec 24
Total with taxes and fees
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
Creekside Inn
90611 Old Highway Tavernier FL
$169 nightly
The price is $190 total per night
$190 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
A stay at Creekside Inn places you in the heart of Tavernier, just a 3-minute walk from Florida Keys Dive Center and within a 5-minute drive of Mariners Hospital.
Pool
Pet friendly
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
$322 nightly
The price is $362 total per night
$362 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$239 nightly
The price is $269 total per night
$269 total
Dec 22 - Dec 23
Total with taxes and fees
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
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
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
$181 nightly
The price is $204 total per night
$204 total
Dec 19 - Dec 20
Total with taxes and fees
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.
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
Islander Resort
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
Angler's Reef Resort by KeysCaribbean
84977 Overseas Highway Islamorada FL
With a stay at Angler's Reef Resort by KeysCaribbean in Islamorada, you'll be within a 5-minute drive of Windley Key Fossil Reef Geological State Park and Rain Barrel Village.
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
$168 nightly
The price is $189 total per night
$189 total
Dec 21 - Dec 22
Total with taxes and fees
With a stay at Breezy Palms Resort in Islamorada (Matecumbe), you'll be within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State Park.
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.
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$384 nightly
The price is $432 total per night
$432 total
Dec 19 - Dec 20
Total with taxes and fees
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..
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 | $189 |
Highest Price | $603 |
Popular hotels | La Siesta Resort & Villas, Creekside Inn, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Chesapeake Beach Resort, Drop Anchor, Fisher Inn Resort & Marina, Amara Cay Resort, Islander Resort, Angler's Reef Resort by KeysCaribbean, Breezy Palms Resort, Casa Morada, Cheeca Lodge & Spa |
Most Recent Islamorada Hotel Reviews
Chesapeake Beach Resort
5 out of 5
Posted 4 days ago
CheapTickets Verified Review
"Idyllic beautiful beach setting, clean comfortable rooms, lovely setting. "
A verified traveler stayed at Chesapeake Beach Resort
Types of Hotels
Top 20 Islamorada Hotels
Hotels Near Islamorada
Top Hotel Brands
Hotels By Star Rating
Cities near Islamorada
More to Explore in Islamorada
Top Picks
Hotels
Flights