Compare Hotels with Pools in Islamorada
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Featured Islamorada Hotels with Pools
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
The price is $248 per night
$248
includes taxes & fees
$220 per night
Nov 17 - Nov 18
Free Cancellation
Reserve now, pay when you stay
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.
Islander Resort
82100 Overseas Highway, Islamorada, FL
The price is $262 per night
$262
includes taxes & fees
$232 per night
Nov 20 - Nov 21
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 $260 per night
$260
includes taxes & fees
$231 per night
Nov 19 - Nov 20
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.
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is $267 per night
$267
includes taxes & fees
$237 per night
Nov 17 - Nov 18
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..
Drop Anchor
84959 Overseas Highway, 222, Islamorada, FL
The price is $219 per night
$219
includes taxes & fees
$199 per night
Nov 15 - Nov 16
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.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy, Islamorada, FL
The price is $425 per night
$425
includes taxes & fees
$378 per night
Nov 20 - Nov 21
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.
Pines & Palms Resort
80401 Old Hwy, Islamorada, FL
The price is $308 per night
$308
includes taxes & fees
$274 per night
Dec 15 - Dec 16
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.
Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
The price is $170 per night
$170
includes taxes & fees
$151 per night
Nov 21 - Nov 22
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 $265 per night
$265
includes taxes & fees
$235 per night
Nov 20 - Nov 21
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 $168 per night
$168
includes taxes & fees
$149 per night
Nov 17 - Nov 18
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.
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.
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
The price is $213 per night
$213
includes taxes & fees
$195 per night
Nov 17 - Nov 18
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.
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 | 2,209 hotels |
|---|---|
Lowest Price | $168 |
Highest Price | $425 |
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
Chesapeake Beach Resort
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Amazing property! We had a reservation at a different place and were not happy with it so decided to push on. We couldn’t be happier. The staff is amazing, breakfast is great and there is a private beach. We are so happy we extended our stay."
A verified traveler stayed at Chesapeake Beach Resort
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