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: 9/10, based on 114 reviews.
• Convenient to Matecumbe Methodist church, only 0.2 km.
• Price range: $125-$1,620.
2. Amara Cay Resort
• Offers Eco tours, Garden, and Fax/copying service.
• Guest rating: 8.5/10, based on 102 reviews.
• Convenient to Seamonkey's Scuba Diving, only 0.04 km.
• Price range: $148-$1,026.
3. La Siesta Resort & Villas
• Enjoy Fax/copying service, Shuttle service, and Kayaking.
• Rated 8.5/10 based on 98 reviews.
• Convenient to Island Adventures Islamorada, only 0.48 km.
• Nightly rates: $184 to $1,198
All prices shown are for September 30-October 6, as listed on Trip.com.
Find Islamorada hotels with a sprawling Pools.
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Hotel Star Rating
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Guest Rating
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+
Great
113 reviews
9.0/10
1 night
From $116
99+
Great
102 reviews
9.0/10
1 night
From $89
99+
Great
103 reviews
9.2/10
1 night
From $191
99+
Hotels in Islamorada
Featured facilities: Pool, Private beach area, Bar
Very Good
103 reviews
8.9/10
1 night
From $202
99+
Very Good
100 reviews
8.5/10
1 night
From $150
94
Very Good
101 reviews
8.4/10
1 night
From $69
99+
Amazing
46 reviews
9.4/10
1 night
From $415
99+
103 reviews
7.5/10
1 night
From $120
99+
101 reviews
7.4/10
1 night
From $110
99+
Amazing
100 reviews
9.6/10
1 night
From $129
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:$200
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:$145
La Siesta Resort & Villas
8.5/10
Very Good
Posted on Sep 6, 2026|Suite with Multiple Beds and Garden View (Studio Suite Garden View Two Queens)
Guest User
Beautiful resort with a great outdoor pool!
Price per night from:$195
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 $125) , Amara Cay Resort (from $148) and La Siesta Resort & Villas (from $184) 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 $421, and on weekends (Friday–Saturday) is $527.
Which hotels with Swimming Pools in Islamorada are good for families?
Drop Anchor Resort & Marina (from $129) 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 $125) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from $149) are very popular.
Islamorada Hotels with Pools Information
| Total properties | 47 |
|---|---|
| Number of reviews | 2,248 |
| Highest price | $2,777 |
| Lowest price | $221 |
| Weekday Avg. Price | $421 |
| Weekend Avg. Price | $527 |
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