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

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Check availability on Islamorada Hotels with a Bar

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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 balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Yeniaris
£166
includes taxes & fees
30 Aug - 31 Aug
Chesapeake Beach Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
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.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Jessica
£176
includes taxes & fees
7 Sept - 8 Sept
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.
A resort pool with palm trees, beach chairs, and umbrellas.
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
David A
£173
includes taxes & fees
27 Sept - 28 Sept
Amara Cay 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 coastal resort with a marina, clear blue water, and lush greenery.
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.

4. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
United States
Isabel
£164
includes taxes & fees
31 Aug - 1 Sept
Pines & Palms 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 paved pathway leading to a beach with palm trees and a view of the ocean.

5. Islander Resort

Islander Resort
Matecumbe
United States
Sonia
£245
includes taxes & fees
7 Sept - 8 Sept
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 coastal resort with a beach, a swimming pool, and multiple buildings.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Dareen
£198
includes taxes & fees
7 Sept - 8 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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.

7. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
United States
Chadwick
£125
includes taxes & fees
1 Sept - 2 Sept
Lime Tree Bay Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
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.
A beach resort with palm trees, a thatched hut, and a purple building with a window.

8. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
£181
includes taxes & fees
31 Aug - 1 Sept
La Siesta Resort & Villas
A beachside lounge with a wooden deck, thatched roof, and tropical plants.
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
beata
£211
includes taxes & fees
7 Sept - 8 Sept
Bayside Villas by Islander Resort
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A pool area with clear blue water, white lounge chairs, and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

10. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
£333
includes taxes & fees
29 Aug - 30 Aug
The Islands of Islamorada
View all properties

Top Islamorada Hotel Reviews

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Everything was great but the breakfast wasn’t that great and sometimes no one would wait on you but we went out to eat anyway. Bartender was amazing!!"
Deirdre 4-night trip
Posted 5 hours ago
Amara Cay Resort
Casa Morada

Casa Morada

8/10 Good
"The room was updated, clean, and comfortable. The bed and pillows were nice. The location was perfect for us. When it’s all completed it’s going to be a really cool spot for sunsets. Overall worth the money for a one nighter on our way home from the lower keys."
Jeremy 1-night trip
Posted 7 hours ago
Casa Morada
Breezy Palms Resort

Breezy Palms Resort

8/10 Good
"The room was spacious and clean. We were very happy with it. They only provide maid service every 3 days, and that was simply changing sheets and towels. The only issue is the smell from the beach due to dead sea grass and other stink. It made the beach impossible to use, and often was unpleasant anytime you went outside. If you plan to use the private beach, this hotel is not for you."
Sherrill 5-night trip
Posted 1 day ago
Breezy Palms Resort
The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Excellent place to stay!"
Jose 3-night trip
Posted 2 days ago
The Caribbean Resort
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Great spot for a vacation quiet clean spacious on the go breakfast. Also the ability to rent the boat while you’re there is also awesome. I would definitely reserve one beforehand. Other than that will be back again. I highly recommend this place."
Jaimie 3-night trip
Posted 2 days ago
Hadley Resort and Marina
La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Wonderfully magical place that my wife and I enjoyed immensely! The beachfront bungalows were just perfect! Can't wait to see it again soon!"
stuart 4-night trip
Posted 3 days ago
La Siesta Resort & Villas
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
Dareen 3-night trip
Posted 3 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pines & Palms Resort

Pines & Palms Resort

8/10 Good
"Lovely location, beautifully renovated, clean room, close to everything including great restaurants. If you want peace and quiet this is the spot for you. If your idea of the keys includes loud activities this is not for you. The small beach was not accessible due to rotting sargassum. You could not even spend much time at the pool due to the smell. Not the hotels fault obviously but affected our stay negatively."
Arturo 3-night trip
Posted 4 days ago
Pines & Palms Resort
Drop Anchor

Drop Anchor

8/10 Good
"Shower didn’t get super hot & not the best water pressure. Keep blinds closed in summer as the room got very hot and the a/c unit struggled to keep the room cool even at night. Could use a shade for the kitten window to help with this. Full length mirror in the room would’ve been nice as well. Overall nice property but a little older & can use some revamping"
Jacqueline 2-night trip
Posted 6 days ago
Drop Anchor

Frequently asked questions

Searching for hotels with bars in Islamorada?
If you'd like to find a hotel where you can unwind with a late-night cocktail, Islamorada offers 869 hotels and other lodging choices, including 11 accommodation options with an on-site bar. While you're here, consider a visit to Bud n' Mary's Dive Center and Islamorada County Park.
What are the best hotels with bars in Islamorada?
Here's a few 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. Pines & Palms Resort: Enjoy the beach bar, poolside bar and free WiFi. Islander Resort: Hotel with 3 restaurants. Enjoy the beach bar, poolside bar and free WiFi.
How many hotels with on-site bars will I be able to find in Islamorada?
Expedia has 11 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, Islamorada County Park and Founders Park, then find a cosy spot for a nightcap. Other places to see include Robbie's of Islamorada and Anne's Beach. 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 determine the best time for bar-hopping. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.
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, you may want to rent a car for your trip.

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