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Hotels in Islamorada

Choose from 2216 Islamorada Hotel Deals

Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
  • 12 min drive from Theater of the Sea
The price is $386 per night from Jan 8 to Jan 9
$386
includes taxes & fees
Jan 8 - Jan 9, 2025
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,207 reviews)
Wonderful Stay
"Friendly staff, great surrounding and convenient location."

Reviewed on Dec 21, 2024

Amara Cay Resort
Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
  • 22 min walk from Theater of the Sea
The price is $341 per night from Jan 5 to Jan 6
$341
includes taxes & fees
Jan 5 - Jan 6, 2025
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the breakfast and the pool ...
9/10 Wonderful! (1,384 reviews)
"Nice job"

Reviewed on Dec 22, 2024

Chesapeake Beach Resort
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
  • 8 min drive from Theater of the Sea
The price is $449 per night from Jan 16 to Jan 17
$449
includes taxes & fees
Jan 16 - Jan 17, 2025
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,003 reviews)
"Beautiful property and outstanding service easy check in check out and lots of on property amenities as well as lots to do off property. The only extremely minor things were the drinks were not very strong (always a red flag when floaters are offered on the menu), the internet was at times spotty ..."

Reviewed on Dec 22, 2024

Cheeca Lodge & Spa
La Siesta Resort & Villas
La Siesta Resort & Villas
4 out of 5
80241 Overseas Highway, Islamorada, FL
  • 11 min drive from Theater of the Sea
The price is $319 per night from Jan 7 to Jan 8
$319
includes taxes & fees
Jan 7 - Jan 8, 2025
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
8.6/10 Excellent! (1,000 reviews)
"Great resort!!"

Reviewed on Dec 14, 2024

La Siesta Resort & Villas
Islander Resort
Islander Resort
4 out of 5
82100 Overseas Highway, Islamorada, FL
  • 7 min drive from Theater of the Sea
The price is $354 per night from Dec 24 to Dec 25
$354
includes taxes & fees
Dec 24 - Dec 25
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,001 reviews)
"The space is currently ongoing construction but don’t let that stop you from staying. Beautiful location and friendly staff from the initial security guard interaction onward. Would love to come back when the construction is complete"

Reviewed on Dec 16, 2024

Islander Resort
Hadley Resort and Marina
Hadley Resort and Marina
3.5 out of 5
82749 Overseas Hwy, Islamorada, FL
  • 5 min drive from Theater of the Sea
The price is $232 per night from Jan 21 to Jan 22
$232
includes taxes & fees
Jan 21 - Jan 22, 2025
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
7.8/10 Good! (1,002 reviews)
"Good place to stay."

Reviewed on Dec 15, 2024

Hadley Resort and Marina
Breezy Palms Resort
Breezy Palms Resort
2.5 out of 5
80015 Overseas Highway, Islamorada, FL
  • 12 min drive from Theater of the Sea
The price is $221 per night from Jan 12 to Jan 13
$221
includes taxes & fees
Jan 12 - Jan 13, 2025
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
8.4/10 Very Good! (378 reviews)
"Nice pool snd beach area.our unit had no hot water for five minutes atfer turning on shower or sink"

Reviewed on Dec 20, 2024

Breezy Palms Resort
Drop Anchor
Drop Anchor
3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
  • 8 min walk from Theater of the Sea
The price is $207 per night from Jan 13 to Jan 14
$207
includes taxes & fees
Jan 13 - Jan 14, 2025
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,000 reviews)
"Amazing place! Beautiful area with great amenities. Only thing was really stiff beds. But if you like very firm mattresses…it’s a 5 star. That aside …we will definitely be back!!"

Reviewed on Dec 6, 2024

Drop Anchor
Fisher Inn Resort & Marina
Fisher Inn Resort & Marina
3.5 out of 5
84951 Overseas Hwy, Islamorada, FL
  • 6 min walk from Theater of the Sea
The price is $261 per night from Jan 19 to Jan 20
$261
includes taxes & fees
Jan 19 - Jan 20, 2025
Stay at this 3.5-star beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.6/10 Good! (1,000 reviews)
"Great location in the Middle Keys and close to all of the cool hang-outs! Also very clean, has a nice pool and my room had the best balcony view ever!!!"

Reviewed on Dec 17, 2024

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina
Coconut Cove Resort and Marina
2.5 out of 5
84801 Overseas Highway, Islamorada, FL
  • 2 min walk from Theater of the Sea
The price is $258 per night from Jan 9 to Jan 10
$258
includes taxes & fees
Jan 9 - Jan 10, 2025
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
7.4/10 Good! (684 reviews)
"I like it"

Reviewed on Dec 6, 2024

Coconut Cove Resort and Marina
Sunset Inn
Sunset Inn
3 out of 5
82200 Overseas Hwy, Islamorada, FL
  • 6 min drive from Theater of the Sea
The price is $203 per night from Jan 20 to Jan 21
$203
includes taxes & fees
Jan 20 - Jan 21, 2025
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,000 reviews)
"Great location. Walking distance to a couple nice places. Lorelei's is a great place in walking distance. Room was clean and had everything you needed. Pool was heated."

Reviewed on Dec 12, 2024

Sunset Inn
La Jolla Resort
La Jolla Resort
2.5 out of 5
82216 Overseas Highway, Islamorada, FL
  • 6 min drive from Theater of the Sea
The price is $196 per night from Jan 22 to Jan 23
$196
includes taxes & fees
Jan 22 - Jan 23, 2025
Stay at this hotel in Islamorada. Enjoy free WiFi, a private beach, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,002 reviews)
"A lovely gem in Islamorada"

Reviewed on Dec 20, 2024

La Jolla Resort
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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