Islamorada Hotels with Pools
If you want a relaxing stay, pick a hotel in Islamorada that has a pool. You can swim or rest by the water anytime you like. Look for places with well-kept pools to improve your experience.
Trip.com Featured hotels with Swimming Pools in Islamorada
1. Cheeca Lodge & Spa
• Rated 9.1/10 based on 113 reviews.
• Convenient to Matecumbe Methodist church, only 0.2 km.
2. La Siesta Resort & Villas
• Offers Fax/copying service, Shuttle service, and Kayaking.
• Rated 8.5/10 based on 98 reviews.
• Only Island Adventures Islamorada to 0.48 km.
3. Amara Cay Resort
• With a rating of 8.5/10 from 101 reviews.
• Seamonkey's Scuba Diving is only 0.04 km away.
The above hotel prices are based on Trip.com for September 25-October 1.
Enter your dates to find hotels with swimming pools in Islamorada where you can swim, relax, and recharge.
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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
Check out our recommended hotels with pools in Islamorada.
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Great
114 reviews
9.1/10
1 night
From €125
99+
Great
102 reviews
9.0/10
1 night
From €83
99+
Great
103 reviews
9.2/10
1 night
From €152
99+
Hotels in Islamorada
Featured facilities: Pool, Private beach area, Bar
Very Good
103 reviews
8.9/10
1 night
From €175
99+
Very Good
101 reviews
8.5/10
1 night
From €118
94
Very Good
101 reviews
8.4/10
1 night
From €60
99+
Amazing
46 reviews
9.4/10
1 night
From €355
99+
102 reviews
7.5/10
1 night
From €91
99+
101 reviews
7.4/10
1 night
From €107
99+
Amazing
100 reviews
9.6/10
1 night
From €93
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 onJul 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:€174
Chesapeake Beach Resort
8.9/10
Very Good
Posted onAug 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:€126
La Siesta Resort & Villas
8.5/10
Very Good
Posted onSep 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:€171
FAQs
Where is the best place for a stay with Swimming Pools in Islamorada?
Whether you are traveling to Islamorada for business or fun, Cheeca Lodge & Spa (from €110) , La Siesta Resort & Villas (from €162) and Amara Cay Resort (from €129) are all preferred hotels.
What’s the typical price for hotels with Swimming Pools in Islamorada?
For hotels with Swimming Pools in Islamorada, the average price on weekdays is €352, and the average price on weekends (Friday–Saturday) is €439.
What’s the best family hotels with Swimming Pools in Islamorada?
Drop Anchor Resort & Marina (from €111) is very suitable for family travel. Enjoy a trip together with your kids and other family members!
What's the best high-end place with Swimming Pools to stay in Islamorada?
There are many luxury hotels with Swimming Pools in Islamorada. Cheeca Lodge & Spa (from €110) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from €130) are very popular.
What are some great hotel promotions for property 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 Pools Information
| Total properties | 44 |
|---|---|
| Number of reviews | 2,251 |
| Highest price | €963 |
| Lowest price | €194 |
| Weekday Avg. Price | €352 |
| Weekend Avg. Price | €439 |
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Off the beaten path in one of Islamorada’s hidden gem of a communityFULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full bathsBeautiful vacation home in the heart of Islamorada , Florida KeysCondo on Islamorada on the beautiful Atlantic Ocean.Come enjoy and relax!Oceanfront Estate on Islamorada, Florida Keys - Ocean Oasis of IslamoradaPrivate Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean viewsDrop Anchor Resort & MarinaTiki Hut and Dockage for Boats - Charming Coastal HavenBungalow #4 - 2 Bed/1 Bath & Pool in IslamoradaBayside Villas by Islander ResortCozy canal in the Keys - leads directly into crystal blue ocean! 🌊Lovely 2-Bedroom House in Ocean Front Resort.Deep Water Canal Access with Dual Kitchens - Charming Cozy OasisOcean Harbor Paradise in IslamoradaHouse in Islamorada, in exclusive Venetian Shores.Luxury vacation home. This is Paradise. Perfect for all family occasions.Casa MoradaFisher Inn Resort & MarinaPARADISE SHORESThe Ocean View Inn