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Cheap Islamorada Hotels

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$336 nightly
The price is $378 total per night
$378 total
Apr 22 - Apr 23
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 steps from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing Co..
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
$269 nightly
The price is $303 total per night
$303 total
May 7 - May 8
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
$334 nightly
The price is $376 total per night
$376 total
Apr 20 - Apr 21
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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..
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$385 nightly
The price is $433 total per night
$433 total
Apr 29 - Apr 30
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.33 mi from city center
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 7 minutes by foot from Islamorada Brewery & Distillery.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

4 out of 5
84001 Overseas Hwy Islamorada FL
$356 nightly
The price is $400 total per night
$400 total
Apr 22 - Apr 23
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.
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$294 nightly
The price is $331 total per night
$331 total
Apr 14 - Apr 15
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.
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
May 6 - May 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
2.52 mi from city center
A stay at Fisher Inn Resort & Marina places you in the heart of Islamorada, a short 3-minute walk from Windley Key Fossil Reef Geological State Park and within 3 minutes by car from Rain Barrel Village.
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
$172 nightly
The price is $194 total per night
$194 total
May 5 - May 6
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.
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$299 nightly
The price is $336 total per night
$336 total
May 3 - May 4
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.
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
$295 nightly
The price is $332 total per night
$332 total
Apr 11 - Apr 12
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.
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
$243 nightly
The price is $274 total per night
$274 total
Apr 29 - Apr 30
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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.
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$420 nightly
The price is $468 total per night
$468 total
Apr 7 - Apr 8
Total with taxes and fees
2.63 mi from city center
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.
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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.

Islamorada hotels essential information

Accommodation
2,210 hotels
Lowest Price
$194
Highest Price
$468
Popular hotels
Cheeca Lodge & Spa, Chesapeake Beach Resort, Amara Cay Resort, Islander Resort, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, La Siesta Resort & Villas, Fisher Inn Resort & Marina, Hadley Resort and Marina, Coconut Cove Resort and Marina, Treasure Harbor, Sunset Inn, Drop Anchor

Most Recent Islamorada Hotel Reviews

Islander Resort

Islander Resort

5 out of 5
Posted 12 hours ago
CheapTickets Verified Review
"⭐⭐⭐⭐⭐ Perfect Stay – Already Want to Go Back! We had an amazing stay at Islander Resort and honestly didn’t want to leave! From the moment we arrived (even with a late check-in), Angela at the front desk set the tone for the entire trip. She was incredibly welcoming, fun, and went above and beyond—giving us a full tour of the property and even personally driving us to our villa since we had no idea where we were going. She immediately put us in vacation mode, and that level of service continued throughout our stay. We stayed in an oceanfront villa, which was absolutely beautiful. The setup was perfect—one king bedroom separate from the living area, plus a pullout couch that would easily work for kids or teens. The view was stunning, and having a front porch lounge area right on the water made it even better. What really stood out about this resort is how it manages to feel both secluded and social at the same time. There are so many little tucked-away lounging areas where you can relax in peace, but also plenty of space for larger groups to gather and enjoy. It’s perfect whether you’re traveling as a couple, with friends, or with kids. Speaking of kids/teens—the amount of activities available is incredible. There’s truly something for everyone, which made it a great fit for our family. Another unexpected highlight was the golf cart taxi service around the property—such a unique and convenient touch. Plus, using the Freebee app to get around Islamorada made everything so"
A verified traveler stayed at Islander Resort
Islander Resort

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