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

Find Hotels with Bar in Islamorada, FL from CA $241

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Check availability on Islamorada Hotels with Bar

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Islamorada hotels with a bar

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Patricia
CA $229
CA $362 total
includes taxes & fees
Oct 22 - Oct 23
Cheeca Lodge & Spa
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.
A resort pool with palm trees, beach chairs, and umbrellas.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

2. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Ronald
CA $223
CA $355 total
includes taxes & fees
Nov 17 - Nov 18
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A wooden pier leading to a beach with palm trees and a row of beach huts.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.

3. Islander Resort

Islander Resort
Matecumbe
United States
Bryan
CA $242
CA $376 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
A beach with palm trees and lounge chairs.
A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

4. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Dianne
CA $205
CA $310 total
includes taxes & fees
Oct 26 - Oct 27
Chesapeake Beach Resort
Terrace/patio
A spacious living area with a large island, wooden furniture, and a ceiling fan.
A beach with palm trees and a clear view of the ocean.
A resort with a swimming pool, lounge chairs, and palm trees.

5. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
United States
Christopher Michael
CA $175
CA $260 total
includes taxes & fees
Oct 27 - Oct 28
Lime Tree Bay Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A row of colorful beach huts with palm trees in the background.
A resort with a pool surrounded by palm trees and a view of the ocean.

6. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
CA $207
CA $336 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A beach with palm trees, a clear blue sky, and a calm sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A resort with a pool, beach, and ocean view.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Liosbel
CA $337
CA $483 total
includes taxes & fees
Nov 2 - Nov 3
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.
A beach with palm trees, a wooden pier, and beach chairs.
A beachside resort with a pool area, lounge chairs, and palm trees.

8. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
United States
Michael
CA $181
CA $282 total
includes taxes & fees
Oct 21 - Oct 22
Pines & Palms Resort
A beachside lounge with a wooden deck, thatched roof, and tropical plants.
Exterior
A resort with a central swimming pool surrounded by palm trees and a view of the ocean.
A waterfront property with a paved walkway, palm trees, and a white building with a dock.

9. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
United States
Brian
CA $303
CA $444 total
includes taxes & fees
Oct 27 - Oct 28
Bayside Villas by Islander Resort
A poolside area with a water feature, a palm tree, and lounge chairs.
A beach with rows of sun loungers, a thatched hut, and a wooden walkway leading to the water.
A marina with boats docked, a dock, and a building with a blue roof.
A marina with boats docked, a building with a blue roof, and a clear view of the water.

10. Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
Tavernier
United States
Alison and Dan Graziani
CA $186
CA $241 total
includes taxes & fees
Oct 27 - Oct 28
Ocean Pointe Suites at Key Largo
View all properties

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The room we had was exceptional, the view was awesome. The bar area was a nice amenity. Although this is a pet friendly hotel, seems like some people do not feel the need to pick up after their pets, if you know what I mean. So that was why I couldn’t give the grounds a five star."
Christine 2-night trip
Posted 11 hours ago
Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"We've stayed at many places over the years . This place and the room that we had were the best . Waking up in bed to a view of the ocean can't be beat. It is situated on the most luxurious of all the keys.. can't wait to return ."
Tim 3-night trip
Posted 11 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islander Resort

Islander Resort

10/10 Excellent
"We had an incredible stay here. Great views, delicious food, and the staff went above and beyond to make our stay exceptional. We already can’t wait to come back!"
Michaela 1-night trip
Posted 2 days ago
Islander Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Room wash clean, bed and pillows very comfortable and staff was friendly. Lots of little ants on the outdoor walkway and stairs but none in the room."
Janell 1-night trip
Posted 2 days ago
Fisher Inn Resort & Marina
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"We have stayed here multiple times and always have a good stay."
Michael 1-night trip
Posted 2 days ago
Pines & Palms Resort
Casa Morada

Casa Morada

10/10 Excellent
"."
angela 3-night trip
Posted 2 days ago
Casa Morada
The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Muy bien todo excelente servicio"
Rodolfo 4-night trip
Posted 2 weeks ago
The Caribbean 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 850 hotels and other properties, including 31 accommodations with an onsite bar. While you're here, consider a visit to Bud n' Mary's Dive Center and Robbie's of Islamorada.
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. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort: Resort with 4 restaurants. Enjoy the beach bar, poolside bar, 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.
How many hotels with bars should I expect to find in Islamorada?
Expedia has 31 hotels with a bar in Islamorada.
What is there to do in Islamorada?
In the area, you can visit Bud n' Mary's Dive Center, Robbie's of Islamorada, and Anne's Beach, then find a cozy spot for a nightcap. Other places to see include Fiesta Key and Everglades National Park. 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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