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

Find Hotels with Bar in Islamorada, FL from CA $244

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Check availability on Islamorada Hotels with Bar

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Islamorada hotels with a bar

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,800 reviews)
"Nice beach walkable property Great breakfast made to order"
United States
kent brian
The price is CA $198
CA $302 total
includes taxes & fees
Nov 4 - Nov 5
Chesapeake Beach Resort
A bathroom with a large bathtub, a view of the sea, and a pier with boats.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,487 reviews)
"Beautiful resort"
United States
Patricia
The price is CA $224
CA $355 total
includes taxes & fees
Nov 1 - Nov 2
Cheeca Lodge & Spa
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,153 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is CA $262
CA $397 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
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.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"Great location as well."
United States
Amir
The price is CA $221
CA $351 total
includes taxes & fees
Nov 16 - Nov 17
Amara Cay Resort
Terrace/patio

5. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,560 reviews)
"Very nice place the view and sunsets are amazing there is also a restaurant on the property that has great food and drinks we would definitely stay again"
United States
Christopher Michael
The price is CA $161
CA $244 total
includes taxes & fees
Nov 29 - Nov 30
Lime Tree Bay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

6. 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, (304 reviews)
"Great place to stay!"
United States
Liosbel
The price is CA $290
CA $428 total
includes taxes & fees
Nov 29 - Nov 30
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
United States
Brianne
The price is CA $216
CA $346 total
includes taxes & fees
Nov 16 - Nov 17
La Siesta Resort & Villas
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

8. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,003 reviews)
"We have stayed here multiple times and always have a good stay."
United States
Michael
The price is CA $267
CA $378 total
includes taxes & fees
Nov 16 - Nov 17
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.

9. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (34 reviews)
"Very friendly staff"
United States
Maria
The price is CA $261
CA $293 total
includes taxes & fees
Nov 1 - Nov 2
The Ocean View Inn & Pub
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

10. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"
United States
Brian
The price is CA $317
CA $459 total
includes taxes & fees
Nov 2 - Nov 3
Bayside Villas by Islander 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.
View all properties

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"We loved the pools and hot tub. Tiki bar was a huge plus."
Jane 2-night trip
Posted 11 hours ago
Chesapeake Beach 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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