Islamorada Hotels with Pools
A hotel with a pool in Islamorada offers a refreshing retreat after a day of exploring. Relax in an infinity pool, rooftop pool, or heated indoor swimming pool. Many options provide stunning views 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.
• Rated 9.1/10 based on 113 reviews.
• Convenient to Matecumbe Methodist church, only 0.2km.
• Prices range from MXN$2,163 to MXN$26,714.
2. La Siesta Resort & Villas
• Guests particularly enjoy the Fax/Copying Service, Shuttle Bus Service, and Kayaking.
• Rated 8.5/10 based on 98 reviews.
• Only 0.48km to Island Adventures Islamorada.
• Prices range from MXN$3,200 to MXN$20,650.
3. Amara Cay Resort
• Guests particularly enjoy the Eco Tours, Garden, and Fax/Copying Service.
• With a rating of 8.5/10 from 101 guest reviews.
• Seamonkey's Scuba Diving is only 0.04km away.
• Price range: MXN$2,544-MXN$18,325.
The above hotel prices are based on Trip.com for September 20-September 26.
Hotels in Islamorada with a pool for a refreshing stay
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Hotel Star Rating
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Guest Rating
Amazing 9+Great 8+Good 7+Pleasant 6+Best Islamorada Hotels with Swimming Pools
Check out our selection of Islamorada hotels with Pool
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Great
113 reviews
9.1/10
1 night
From MXN$1,917
99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area
Very Good
98 reviews
8.5/10
1 night
From MXN$3,360
99+
Very Good
101 reviews
8.5/10
1 night
From MXN$2,459
99+
Great
102 reviews
9.0/10
1 night
From MXN$1,595
99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area, Bar
Very Good
88 reviews
8.9/10
1 night
From MXN$3,697
88
Very Good
101 reviews
8.3/10
1 night
From MXN$1,178
99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area, Bar
Great
101 reviews
9.2/10
1 night
From MXN$2,917
99+
Amazing
100 reviews
9.6/10
1 night
From MXN$1,469
99+
Hotels in Islamorada
Featured facilities: Swimming Pool, Exclusive Beach Area, Bar
Very Good
103 reviews
8.9/10
1 night
From MXN$3,463
98
Great
86 reviews
9.3/10
1 night
From MXN$3,682
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.
Islander Resort
9.2/10
Great
Posted on Aug 22, 2023
Guest User
Nice hotel rooms that you can drive up to. Nice amount of space—although the bathroom is very small. Pool area is ok, not enough umbrellas. Didn’t get water everyday despite being told it was included with the resort fee. The access to the sea isn’t great. Yoga was fantastic.
Price per night from:MXN$3,967
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:MXN$2,493
Fisher Inn Resort & Marina
7.5/10
Posted on Apr 18, 2024
Guest User
The reception staff were lovely, so welcoming and helpful. Little heated pool and nice sun loungers, just missing some umbrellas to make it perfect. The outside grill was great to use and clean. Room didn’t get cleaned during our two night stay though… 🤷🏼♀️
Price per night from:MXN$2,210
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:MXN$2,138
Frequently Asked Questions
How much is the average rate for hotels with Swimming Pools in Islamorada?
For hotels with Swimming Pools in Islamorada, the average price on weekdays is MXN$6,973, and the average price on weekends (Friday–Saturday) is MXN$8,640.
Which hotels with Swimming Pools in Islamorada are recommended for travellers with children?
Drop Anchor Resort & Marina (from MXN$2,199) is very suitable for family travel. Enjoy a trip together with your kids and other family members!
Which hotels with Swimming Pools in Islamorada are luxury hotels?
Many hotels with Swimming Pools in Islamorada are luxury hotels. Cheeca Lodge & Spa (from MXN$2,163) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from MXN$2,570) are very popular.
What are the popular hotels with Swimming Pools in Islamorada?
Whether you are travelling to Islamorada for business or tourism, Cheeca Lodge & Spa (from MXN$2,163) , La Siesta Resort & Villas (from MXN$3,200) and Amara Cay Resort (from MXN$2,544) are all preferred hotels.
What promotions are available for hotels with Swimming Pools in Islamorada?
Trip.com provides various promotions and discounts for users all year round. You can check the promotions page to see what promotions are available on Trip.com.
Islamorada Hotels with Pool Information
| Total properties | 46 |
|---|---|
| Number of reviews | 2,198 |
| Highest price | MXN$47,391 |
| Lowest price | MXN$2,583 |
| Weekday Avg. Price | MXN$6,973 |
| Weekend Avg. Price | MXN$8,640 |
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