Islamorada Hotels with Pools
For travelers seeking relaxation, a hotel with a pool in Islamorada offers the perfect respite. You can take a refreshing swim or lounge poolside without leaving the property. When booking, look for hotels with well-maintained pools to enhance your stay.
Trip.com Featured Hotels with Swimming Pools in Islamorada
1. Cheeca Lodge & Spa
• Offers Dry cleaning, Garden, and Fax/copying service.
• Guest rating: 9.1/10, based on 111 reviews.
• Convenient to Matecumbe Methodist church, only 0.2 km.
• Price range: €108-€1,839.
2. La Siesta Resort & Villas
• Enjoy Fax/copying service, Shuttle service, and Kayaking.
• Rated 8.4/10 based on 100 reviews.
• Convenient to Island Adventures Islamorada, only 0.48 km.
• Nightly rates: €119 to €1,071
3. Amara Cay Resort
• Offers Eco tours, Garden, and Fax/copying service.
• Guest rating: 8.5/10, based on 103 reviews.
• Convenient to Seamonkey's Scuba Diving, only 0.04 km.
• Price range: €135-€962.
All prices shown are for September 7-September 13, as listed on Trip.com.
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Seek out top Islamorada hotels with proistine Pools.
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Great
112 reviews
9.1/10
1 night
From €97
99+
Great
102 reviews
9.0/10
1 night
From €74
99+
Great
103 reviews
9.2/10
1 night
From €140
88
Very Good
101 reviews
8.4/10
1 night
From €71
99+
Amazing
46 reviews
9.4/10
1 night
From €311
99+
Very Good
100 reviews
8.6/10
1 night
From €106
99+
Very Good
96 reviews
8.6/10
1 night
From €112
99+
103 reviews
7.5/10
1 night
From €106
99+
Very Good
101 reviews
8.5/10
1 night
From €109
99+
Hotels in Islamorada
Featured facilities: Pool, Private beach area, Bar
Very Good
102 reviews
8.9/10
1 night
From €154
Latest Reviews for Islamorada Hotels
See all
Read genuine traveler ratings & reviews to find your perfect stay.
Pines & Palms Resort
9.2/10
Great
Posted on Jul 31, 2026|One-Bedroom King Suite with Ocean View
Guest UserThe 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:€171
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:€103
Hadley Resort and Marina
7.4/10
Posted on Aug 6, 2026|Pool Villa
STOMsHadley 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:€109
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 €108) , La Siesta Resort & Villas (from €119) and Amara Cay Resort (from €135) 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 €332, and on weekends (Friday–Saturday) is €430.
Which hotels with Swimming Pools in Islamorada are good for families?
Drop Anchor Resort & Marina (from €155) 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 €108) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from €109) are very popular.
Islamorada Hotels with Pools Information
| Total properties | 43 |
|---|---|
| Number of reviews | 2,314 |
| Highest price | €2,476 |
| Lowest price | €191 |
| Weekday Avg. Price | €332 |
| Weekend Avg. Price | €430 |
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