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

Find Hotels with Bars in Islamorada, FL

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Check availability on Islamorada Hotels with Bars

Tonight
Oct 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Islamorada hotels with a bar

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.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Richard
NT$4,822
NT$7,221 total
includes taxes & fees
Oct 14 - Oct 15
Chesapeake Beach Resort
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.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Morgan
NT$6,034
NT$9,123 total
includes taxes & fees
Oct 13 - Oct 14
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 beach with palm trees, a dock, and lounge chairs.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Danielle
NT$4,935
NT$7,887 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
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.
A wooden pier leading to a beach with palm trees and a row of beach huts.

4. Islander Resort

Islander Resort
Matecumbe
United States
Steven
NT$8,333
NT$11,709 total
includes taxes & fees
Oct 18 - Oct 19
Islander Resort
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 resort with a pool, beach, and ocean view.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Liosbel
NT$7,300
NT$10,547 total
includes taxes & fees
Oct 18 - Oct 19
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Terrace/patio
A beach with palm trees and a clear view of the ocean.
A resort with a swimming pool, lounge chairs, and palm trees.
A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.

6. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
United States
Michael
NT$3,954
NT$5,885 total
includes taxes & fees
Oct 14 - Oct 15
Lime Tree Bay Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach with colorful buildings, kayaks, and lounge chairs.
A resort with a pool surrounded by palm trees and a view of the ocean.
A row of colorful beach huts with palm trees in the background.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
NT$5,366
NT$8,371 total
includes taxes & fees
Nov 8 - Nov 9
La Siesta Resort & Villas
A poolside area with a water feature, a palm tree, and lounge chairs.
A marina with boats docked, a building with a blue roof, and a clear view of the water.
A beach with rows of sun loungers, a thatched hut, and a wooden walkway leading to the water.
A balcony with a view of the sea, a white chair, and two buckets with a red shovel.

8. Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
Tavernier
United States
Arthur
NT$3,913
NT$5,104 total
includes taxes & fees
Oct 18 - Oct 19
Ocean Pointe Suites at Key Largo
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 beachside resort with a pool area, lounge chairs, and palm trees.
A coastal resort with a marina, clear blue water, and lush greenery.

9. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
United States
Colt
NT$5,459
NT$7,902 total
includes taxes & fees
Oct 12 - Oct 13
Pines & Palms Resort
A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.
A hotel room with two beds, each with a different patterned bedspread, a nightstand with a lamp, framed artwork on the wall, and an air conditioning unit.
A bedroom with a bed, a nightstand, a chair, and a door.
A swimming pool with a 5 ft depth marker, surrounded by palm trees and a white picket fence.

10. The Ocean View Inn & Pub

The Ocean View Inn & Pub
Islamorada
United States
Maria
NT$5,948
NT$6,691 total
includes taxes & fees
Oct 12 - Oct 13
The Ocean View Inn & Pub
View all properties

Top Islamorada Hotel Reviews

Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"This fun little place was a great stopover on our way to Key West. This is not a new property, but it has been redone so well. We stayed in a bungalow and were really struck by how well it had been renovated. Great vibe and decor."
Susan 1-night trip
Posted 4 hours ago
Breezy Palms Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Un lugar muy tranquilo y una vista hermosa. Excelente para relajarse, meditar y descansar."
Caridad 2-night trip
Posted 1 day ago
Chesapeake Beach Resort
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"This was an absolute dream vacation for my husband and I. The amenities were fantastic and the property was immaculate. The staff were exceedingly concerned about our comfort and asking if we needed anything. The location couldn’t have been better. We will be back."
Steven Allen 3-night trip
Posted 1 day ago
Pines & Palms Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"This was a lovely hotel in a good location. Rooms were clean the staff was lovely! The only thing I would say was the water pressure wasn’t great and not very hot either. Breakfast was good."
Kristy 3-night trip
Posted 2 days ago
Fisher Inn Resort & Marina
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Very clean resort. The pool was fabulous. The tiki bar was great. Stall friendly and helpful. Truly enjoyed my stay!"
Maureen 2-night trip
Posted 5 days ago
Amara Cay Resort
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Amazing gym, really cool pool with waterfall, beautiful view of the sunrise on a small beach. Overall was super nice."
Heidi 2-night trip
Posted 7 days ago
Coconut Cove Resort and Marina
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Great place for the money!"
Nicholas 2-night trip
Posted 8 days ago
Hadley Resort and Marina
The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Muy bien todo excelente servicio"
Rodolfo 4-night trip
Posted 9 days ago
The Caribbean Resort
Casa Morada

Casa Morada

10/10 Excellent
"always a favorite!"
robert 2-night trip
Posted 2 weeks ago
Casa Morada

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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