A beach with white lounge chairs, a covered pavilion, and palm trees.

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Check availability on Islamorada Hotels with Bar

Our top choices for Islamorada hotels with a bar

Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,745 reviews)
"Love the place very clean and peaceful"
United States
Elizabeth
The price is CA $205
CA $310 total
includes taxes & fees
Aug 16 - Aug 17
Chesapeake Beach Resort
Balcony

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,339 reviews)
"Great place!!"
United States
David
The price is CA $305
CA $446 total
includes taxes & fees
Aug 6 - Aug 7
Cheeca Lodge & Spa
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,073 reviews)
"Can't wait to stay there again!"
United States
Sarah
The price is CA $404
CA $549 total
includes taxes & fees
Aug 5 - Aug 6
Islander Resort
Room, 1 King Bed with Sofa bed, Oceanfront (Alligator Reef, Lanai) | View from room

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,286 reviews)
"Amazing stay in Amara Cay"
United States
Leidys
The price is CA $238
CA $370 total
includes taxes & fees
Aug 2 - Aug 3
Amara Cay Resort
Room, 1 King Bed, Balcony, Ocean View (Balcony)

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (230 reviews)
"Room was beautiful, just as pictured on the website. It is a lovely place."
United States
CATHY
The price is CA $324
CA $467 total
includes taxes & fees
Aug 5 - Aug 6
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Suite, 1 King Bed with Sofa bed, Ocean View

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,001 reviews)
"Clean quiet and serene. Staff was so helpful and kind!"
United States
Cassandra
The price is CA $245
CA $378 total
includes taxes & fees
Aug 2 - Aug 3
La Siesta Resort & Villas
Restaurant

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (452 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is CA $323
CA $458 total
includes taxes & fees
Aug 13 - Aug 14
Bayside Villas by Islander Resort
Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,389 reviews)
"Amazing we will be staying againn"
United States
JACLYN
The price is CA $171
CA $255 total
includes taxes & fees
Aug 16 - Aug 17
Lime Tree Bay Resort
Oceanfront Three Bedroom Villa

Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Wonderful property and friendly staff. Rooms were lovely and beds very comfortable"
Canada
Jonathan
The price is CA $327
CA $445 total
includes taxes & fees
Aug 4 - Aug 5
Pines & Palms Resort
Balcony view

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (78 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is CA $700
CA $864 total
includes taxes & fees
Aug 2 - Aug 3
The Islands of Islamorada
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.
View all properties

Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"T was so fun and I love all activities you have there. The location was amazing and the views. It has something for everyone in the family. I love how they give you lil surprises outside by the pool. Such great staff checking you in as you come inside. I can’t remember their names. But T really helped out on activities paddle boards , kayaks etc . We Love it and will be back."
Sandy 4-night trip
Posted 3 hours ago
Islander Resort

Frequently asked questions

Searching for hotels with bars in Islamorada?
If you're searching for a hotel where you can enjoy a drink after a day of exploring, Islamorada features 880 hotels and other properties, including 11 accommodations with an onsite bar. While you're here, consider a visit to Everglades National Park.
What are the best hotels with bars in Islamorada?
Here's some of the top Islamorada hotels with bars: Cheeca Lodge & Spa: Resort with 3 restaurants. Enjoy the 2 poolside bars, free parking, and 3 outdoor pools. Chesapeake Beach Resort: Enjoy the bar, free breakfast, and free WiFi. Amara Cay Resort: Resort with 2 restaurants. Enjoy the 3 bars, private beach, and breakfast. Islander Resort: Hotel with 3 restaurants. Enjoy the beach bar, poolside bar, and free WiFi. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort: Resort with 4 restaurants. Enjoy the beach bar, poolside bar, and free WiFi.
How many hotels with bars should I expect to find in Islamorada?
Expedia has 11 hotels with a bar in Islamorada.
What is there to do in Islamorada?
Delight in the outdoors by visiting Everglades National Park, then check out the local bars and enjoy a refreshing drink. Other places to see include Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Islamorada is popular for its entertainment choices and seafood restaurants.
When is the best time to visit Islamorada?
Visiting local bars in Islamorada is better when you know what the weather holds. These rainfall averages and temperatures can help you choose the best time for bar hopping. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.
How can I get to Islamorada and around the area?
Here are some of your transportation choices in and around Islamorada: Fly into Marathon, FL (MTH-Florida Keys Marathon), which is located 30 mi (48.2 km) away from the heart of the city. If you'd like to venture out around the area, consider renting a car to take in more sights.

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