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Cheap Islamorada Hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
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
1.23 mi from city center
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
Amara Cay Resort

Amara Cay Resort

4 out of 5
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
2.41 mi from city center
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
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$364 nightly
The price is $410 total per night
$410 total
Dec 19 - Dec 20
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.62 mi from city center
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
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
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
1.82 mi from city center
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
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
$178 nightly
The price is $200 total per night
$200 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
0.29 mi from city center
With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum.
On private beach
Pool
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
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
2.53 mi from city center
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 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
0.3 mi from city center
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

La Siesta Resort & Villas

4 out of 5
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
2.05 mi from city center
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
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
$294 nightly
The price is $331 total per night
$331 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
4.16 mi from city center
With a stay at Treasure Harbor in Islamorada, you'll be within a 10-minute walk of Rain Barrel Village and Founders Park.
Pool
Parking included
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$199 nightly
The price is $224 total per night
$224 total
Dec 19 - Dec 20
Total with taxes and fees
2.38 mi from city center
With a stay at Coconut Cove Resort and Marina in Islamorada, you'll be on the waterfront, just steps from Windley Key Fossil Reef Geological State Park and a 3-minute drive from History of Diving Museum.
Pool
Breakfast included
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
$171 nightly
The price is $193 total per night
$193 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
0.15 mi from city center
With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & Discovery Center.
Pool
Pet friendly
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$145 nightly
The price is $163 total per night
$163 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
0.07 mi from city center
With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 10 minutes by foot from Keys History & Discovery Center.
On private beach
Pool
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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
2,221 hotels
Lowest Price
$163
Highest Price
$410
Popular hotels
Chesapeake Beach Resort, Amara Cay Resort, Cheeca Lodge & Spa, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Hadley Resort and Marina, Fisher Inn Resort & Marina, Islander Resort, La Siesta Resort & Villas, Treasure Harbor, Coconut Cove Resort and Marina, Sunset Inn, La Jolla Resort

Most Recent Islamorada Hotel Reviews

Chesapeake Beach Resort

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
Chesapeake Beach Resort