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Hersha Hospitality in Islamorada

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$249 nightly
The price is $280 total per night
$280 total
May 25 - May 26
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

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$364 nightly
The price is $410 total per night
$410 total
May 3 - May 4
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..
On private beach
Pool

Islander Resort
82100 Overseas Highway Islamorada FL
$263 nightly
The price is $295 total per night
$295 total
May 17 - May 18
Total with taxes and fees
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.
On private beach
Pool

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$289 nightly
The price is $325 total per night
$325 total
May 3 - May 4
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..
On private beach
Pool

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
May 25 - May 26
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

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$253 nightly
The price is $285 total per night
$285 total
May 12 - May 13
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

Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
$164 nightly
The price is $185 total per night
$185 total
May 5 - May 6
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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
84951 Overseas Hwy Islamorada FL
$198 nightly
The price is $223 total per night
$223 total
Apr 30 - May 1
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.
On private beach
Pool

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$179 nightly
The price is $201 total per night
$201 total
Apr 30 - May 1
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

Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
$264 nightly
The price is $297 total per night
$297 total
Apr 30 - May 1
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

La Jolla Resort
82216 Overseas Highway Islamorada FL
$224 nightly
The price is $252 total per night
$252 total
May 4 - May 5
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

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$210 nightly
The price is $232 total per night
$232 total
Apr 30 - May 1
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.
Pool
Pet friendly
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 | 2,211 hotels |
|---|---|
Lowest Price | $185 |
Highest Price | $410 |
Popular hotels | Chesapeake Beach Resort, Cheeca Lodge & Spa, Islander Resort, Amara Cay Resort, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, La Siesta Resort & Villas, Hadley Resort and Marina, Fisher Inn Resort & Marina, Coconut Cove Resort and Marina, Treasure Harbor, La Jolla Resort, Drop Anchor |
Most Recent Islamorada Hotel Reviews

Amara Cay Resort
5 out of 5
Posted 3 hours ago
CheapTickets Verified Review
"We had the most amazing stay at Amara Cay in Islamorada for our honeymoon! From the moment we arrived, everything felt effortless, relaxing, and truly special. The property is absolutely beautiful—clean, modern, and perfectly captures that laid-back luxury island vibe.
The rooms were comfortable and well-kept, with stunning views that made it hard to leave. The pool area and private beach were highlights for us—plenty of space to unwind, with crystal-clear water and the most peaceful atmosphere. It never felt overcrowded, which made it even more enjoyable.
The staff was incredibly kind and attentive throughout our stay, always going out of their way to make sure we had everything we needed. You can tell they genuinely care about the guest experience.
The location is also perfect—close to everything in Islamorada while still feeling like a private escape. Whether you're looking for a romantic getaway or just a relaxing trip, this place checks every box.
We’ll absolutely be back and couldn’t recommend it more!"
A verified traveler stayed at Amara Cay Resort
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