Islamorada

Islamorada Hotels with Pools

Find Islamorada hotels with a sprawling Pools.

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Amazing 9+Great 8+Good 7+Pleasant 6+

Top Hotels with Pools in Islamorada

Seek out top Islamorada hotels with proistine Pools.
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Hotels in Islamorada
Featured facilities: Private beach area, Bar, Spa
Great
111 reviews
9.1/10
1 night
From €115
Check availability
88
Hotels in Islamorada
Featured facilities: Private beach area
Very Good
101 reviews
8.4/10
1 night
From €81
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99+
Hotels in Islamorada
Featured facilities: Private beach area, Bar, Massage room
Amazing
46 reviews
9.4/10
1 night
From €309
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99+
Hotels in Islamorada
Featured facilities: Private beach area
Great
102 reviews
9.0/10
1 night
From €89
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99+
Hotels in Islamorada
Featured facilities: Private beach area
Very Good
97 reviews
8.6/10
1 night
From €107
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99+
Hotels in Islamorada
Featured facilities: Public beach
Great
85 reviews
9.3/10
1 night
From €150
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99+
Hotels in Islamorada
Featured facilities: Private beach area, Bar, Gym
Great
104 reviews
9.2/10
1 night
From €184
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99+
Hotels in Islamorada
Featured facilities: Private beach area, Bar, Gym
Very Good
86 reviews
8.9/10
1 night
From €183
Check availability
99+
Hotels in Islamorada
Featured facilities: Private beach area
Good
103 reviews
7.6/10
1 night
From €95
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99+
Hotels in Islamorada
Featured facilities: Private beach area, Bar, Gym
Very Good
103 reviews
8.5/10
1 night
From €140
Check availability
See More Hotels with Pools in Islamorada

Latest Reviews for Islamorada Hotels

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Read genuine traveler ratings & reviews to find your perfect stay.

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:€148

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:€170

Chesapeake Beach Resort

9.0/10
Great
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:€130

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

8.9/10
Very Good
Posted on Aug 25, 2025
Guest User
The resort was very beautiful and well maintained. The cottage we stayed in was spacious and we really liked the decor and how soft the beds were. The food was good but a little pricey. We were not impressed with the cabana rental. The cabana was not ready when we arrived. We had to wait for it to be cleaned and set up. The cabana was not labeled and we were confused on which cabana was ours as there were 2 next to each other. We asked when service would start and we were told 10am, then we asked again at 10:45, then went to the front office at 11:30 and when 12pm rolled around with no service we decided to leave and get our money back on the cabana. At that point all we paid for was a chair and towel which did not meet our expectation when spending $250.00 on a cabana for the day. I would recommend several things for the cabana. 1. Number the cabanas so you can clearly see the number. Telling us Cabana 2 does not help when they are beside each other. 2. Stock the min fridge with water. 3. Clearly explain on the cabana rental that food/service will not start until a certain time. We expected to at least get something to drink while in the cabana. 4. Install a call button or app that you can be in contact with someone when you need something. There was a significant delay on getting our refund. And we do appreciate the Manager helping us on Friday get that resolved before we checked out on Saturday morning. All in all, the resort was great. We loved the vibe and updates made to the property. The rooms were comfortable and fresh, and we loved the beds as they were very comfortable, and the sheets were so soft. Everyone was friendly and pleasant. We most enjoyed fish like a local with Patrick. We found that the pool in the middle of the property was less used and felt more quiet and more private therefore we spent our time with a good book. I would give the stay at 4.5 out of 5. Highly recommend trying out Three Waters Resort.
Price per night from:€185

La Siesta Resort & Villas

8.4/10
Very Good
Posted on Jun 30, 2026
Guest User
Check in super easy.  Nice resort.
Price per night from:€112

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:€116

Frequently Asked Questions

What are the best hotels with Swimming Pools in Islamorada?

If you are visiting Islamorada for business or tourism, Cheeca Lodge & Spa (from €109) , La Siesta Resort & Villas (from €125) and Amara Cay Resort (from €130) are popular choices.

How much is a hotel with Swimming Pools in Islamorada?

For hotels with Swimming Pools in Islamorada, the average price on weekdays is €315, and on weekends (Friday–Saturday) is €420.

Which hotels with Swimming Pools in Islamorada are good for families?

Drop Anchor Resort & Marina (from €96) is popular for family travel. Book from Trip.com and enjoy your time with families!

What available deals for hotels with Swimming Pools in Islamorada?

Trip.com always provides various promotions and discounts for both new and loyal users. You can check the promotions page to figure out what promotions are available for your stay.

What are some of the best luxury hotels with Swimming Pools in Islamorada?

There are many luxury hotels with Swimming Pools in Islamorada. Cheeca Lodge & Spa (from €109) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from €134) are very popular.

Islamorada Hotels with Pools Information

Total properties43
Number of reviews2,394
Highest price€656
Lowest price€141
Weekday Avg. Price€315
Weekend Avg. Price€420