Compare Hotels with Pools in Islamorada
Secret Bargains - Save an extra 10% or more on select Hotels with Pools
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 Pools
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
The price is $339 per night
$339
includes taxes & fees
$301 per night
Jan 8 - Jan 9, 2025
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
Islander Resort
82100 Overseas Highway, Islamorada, FL
The price is $368 per night
$368
includes taxes & fees
$327 per night
Jan 12 - Jan 13, 2025
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
La Siesta Resort & Villas
80241 Overseas Highway, Islamorada, FL
The price is $319 per night
$319
includes taxes & fees
$283 per night
Jan 7 - Jan 8, 2025
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
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is $357 per night
$357
includes taxes & fees
$317 per night
Jan 8 - Jan 9, 2025
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..
On private beach
Pool
Drop Anchor
84959 Overseas Highway, 222, Islamorada, FL
The price is $195 per night
$195
includes taxes & fees
$177 per night
Jan 8 - Jan 9, 2025
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
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy, Islamorada, FL
The price is $503 per night
$503
includes taxes & fees
$447 per night
Jan 13 - Jan 14, 2025
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
Pines & Palms Resort
80401 Old Hwy, Islamorada, FL
The price is $297 per night
$297
includes taxes & fees
$264 per night
Jan 12 - Jan 13, 2025
With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 5-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center.
On private beach
Pool
Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
The price is $261 per night
$261
includes taxes & fees
$232 per night
Jan 8 - Jan 9, 2025
Free Cancellation
Reserve now, pay when you stay
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.
On private beach
Pool
Islander Bayside Villas and Boatslips
81450 Overseas Highway, Islamorada, FL
The price is $386 per night
$386
includes taxes & fees
$343 per night
Jan 7 - Jan 8, 2025
Free Cancellation
Reserve now, pay when you stay
With a stay at Islander Bayside Villas and Boatslips, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 7 minutes by foot from Florida Keys Brewing Co..
Pool
Pet friendly
Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
The price is $224 per night
$224
includes taxes & fees
$199 per night
Jan 1 - Jan 2, 2025
With a stay at Coconut Cove Resort and Marina in Islamorada, you'll be on the Strip, just steps from Windley Key Fossil Reef Geological State Park and a 3-minute drive from History of Diving Museum.
Pool
Breakfast included
The Caribbean Resort
117 Carroll St, Islamorada, FL
A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum.
Pool
Hot Tub
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
The price is $319 per night
$319
includes taxes & fees
$289 per night
Jan 20 - Jan 21, 2025
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
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 | 2,222 hotels |
|---|---|
Lowest Price | $195 |
Highest Price | $503 |
Popular hotels | Amara Cay Resort, Islander Resort, La Siesta Resort & Villas, Cheeca Lodge & Spa, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Pines & Palms Resort, Fisher Inn Resort & Marina, Islander Bayside Villas and Boatslips, Coconut Cove Resort and Marina, The Caribbean Resort, Chesapeake Beach Resort |
Most Recent Islamorada Hotel Reviews
Drop Anchor
5 out of 5
Posted 21 hours ago
CheapTickets Verified Review
"Very clean. Nice beach area and friendly staff. "
A verified traveler stayed at Drop Anchor
