Islamorada

Islamorada Hotels with Pools

Select your dates to see hotels in Islamorada with a Pools for a refreshing stay.

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Best Islamorada Hotels with Swimming Pools

Check out our selection of Islamorada hotels with Pools
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area, Bar
Great
112 reviews
9.1/10
1 night
From CAD 160
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99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area
Great
102 reviews
9.0/10
1 night
From CAD 218
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99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area, Bar
Great
103 reviews
9.2/10
1 night
From CAD 302
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88
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area
Very Good
101 reviews
8.3/10
1 night
From CAD 95
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99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area, Bar
Amazing
46 reviews
9.4/10
1 night
From CAD 562
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99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area
Very Good
102 reviews
8.6/10
1 night
From CAD 270
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99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area
Very Good
96 reviews
8.6/10
1 night
From CAD 152
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99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area
102 reviews
7.5/10
1 night
From CAD 189
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99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area, Bar
Very Good
102 reviews
8.5/10
1 night
From CAD 200
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99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area, Bar
Very Good
103 reviews
8.9/10
1 night
From CAD 266
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See All Hotels with Pools in Islamorada

Top rated hotels in Islamorada

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Explore genuine reviews and ratings from real travellers to find the perfect accommodation for your needs.

Ragged Edge Resort & Marina

9.6/10
Amazing
Posted on Mar 18, 2021
Guest User
My husband and I stayed a week at the Ragged Edge Resort & Marina. We were delighted with the spacious apartment especially the two bathrooms. Our apartment had a well equipped kitchen, a counter for eating and a comfortable living area with a sofa and chairs. From the kitchen/living room window we had a beautiful view of the pier and ocean. The pool and pier area provided lots of space and lounge chairs for swimming, fishing and enjoying the sun. In the evening we used the resort's bicycles to tour the neighborhood. The staff at Ragged Edge were wonderful. They made sure we had everything we needed. There were many restaurants nearby but our favorite was ”Lazy Days”. We also took a day trip to Key West which was about 70 miles south of the resort.
Price per night from:CAD 97

Pines & Palms Resort

9.2/10
Great
Posted on Jul 31, 2026|One-Bedroom King Suite with Ocean View
CNGuest User
The hotel is still good, this room type needs to take the stairs to carry luggage and the price is set to be 50% off on the day.
Price per night from:CAD 162

Chesapeake Beach Resort

8.9/10
Very Good
Posted on Aug 22, 2025
Gianny
The place is beautiful and very clean. There were a couple of hiccups but the hotel was quick to fix it. The only part that is upsetting is using on the amenities: fish rod, it kept tangling up. But overall, we will be returning. The breakfast was like no other.
Price per night from:CAD 165

Hadley Resort and Marina

7.4/10
Posted on Aug 6, 2026|Pool Villa
GBSTOMs
Hadley Resort in Islamorada was a fantastic base for our trip. Breakfast was good, seating area outside was lovely, with many options, which made mornings really easy. The staff were genuinely helpful throughout our stay, and our pool villa was very clean, spacious, and perfect for relaxing after long days out. The location couldn’t have been better — ideal for exploring the Keys, and we easily travelled to both Marathon and Key West. Overall, we had a great experience and would definitely stay again.
Price per night from:CAD 189

Frequently Asked Questions

What's the best hotel with Swimming Pools in Islamorada?

Whether your trip to Islamorada is for business or leisure, Cheeca Lodge & Spa (from CAD 173) , La Siesta Resort & Villas (from CAD 257) and Amara Cay Resort (from CAD 204) are popular choices.

Which family-friendly hotels with Swimming Pools in Islamorada are recommended?

Drop Anchor Resort & Marina (from CAD 156) is a top choice for families. Enjoy your time with kids and other family members for your stay!

What's the average price for hotels with Swimming Pools in Islamorada?

For hotels with Swimming Pools in Islamorada, the average price is CAD 536 on weekdays and CAD 683 on weekends (Friday–Saturday).

Which hotels with Swimming Pools in Islamorada have deals?

There are many deals available on Trip.com for both new and loyal users. Please check the promotions page to save your upcoming stays.

What's the best luxury hotel with Swimming Pools in Islamorada?

Islamorada has many luxury hotels with Swimming Pools. Cheeca Lodge & Spa (from CAD 173) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from CAD 186) are popular choices.

Islamorada Hotels with Pools Information

Total properties44
Number of reviews2,315
Highest priceCAD 790
Lowest priceCAD 264
Weekday Avg. PriceCAD 536
Weekend Avg. PriceCAD 683