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. La Siesta Resort & Villas
• Offers Fax/copying service, Shuttle service, and Kayaking.
• Rated 8.4/10 based on 102 reviews.
• Only Island Adventures to 0.48 km.
2. Islander Resort
• Guests particularly enjoy the Garden, Dry cleaning, and Eco tours.
• With a rating of 9.1/10 from 102 reviews.
• Only Keys History & Discovery Center to 0.14 km.
3. Cheeca Lodge & Spa
• Rated 9.1/10 based on 109 reviews.
• Convenient to Clearly Unique Charters, only 0.15 km.
The above hotel prices are based on Trip.com for July 26-August 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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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
102 reviews
9.1/10
1 night
From THB 8,118
67
Hotels in Islamorada
With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & Discovery Center. This hotel is 0.5 mi (0.9 km) from Matecumbe United Methodist Church and 0.8 mi (1.3 km) from History of Diving Museum.
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills.
Featured amenities include luggage storage and a safe deposit box at the front desk. Free self parking is available onsite.
Make yourself at home in one of the 30 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and bidets. Conveniences include laptop-compatible safes and blackout drapes/curtains, and housekeeping is provided daily.
"Its decent but its not easy to find in the evening or night when its dark. Would help if it has a bright sign for the Inn.
It has a pool at the back and you can hear the noise if people are partying out there but it seems to quiet down fortunately for us for the day we were there."
Very Good
102 reviews
8.6/10
1 night
From THB 4,904
99+
Great
109 reviews
9.1/10
1 night
From THB 11,972
99+
Very Good
103 reviews
8.5/10
1 night
From THB 5,446
99+
Great
84 reviews
9.3/10
1 night
From THB 6,978
56
Very Good
101 reviews
8.4/10
1 night
From THB 2,596
99+
Great
104 reviews
9.1/10
1 night
From THB 6,750
99+
Hotels in Islamorada
Featured facilities: Private beach area, Bar, Gym
Very Good
102 reviews
8.9/10
1 night
From THB 8,237
99+
102 reviews
7.5/10
1 night
From THB 3,546
99+
Great
102 reviews
9.0/10
1 night
From THB 4,049
Latest Reviews for Islamorada Hotels
See all
Read genuine traveler ratings & reviews to find your perfect stay.
Ragged Edge Resort & Marina
9.4/10
Amazing
Posted onMar 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:THB 7,302
La Siesta Resort & Villas
8.4/10
Very Good
Posted onJun 30, 2026
Guest User
Check in super easy. Nice resort.
Price per night from:THB 5,287
FAQs
Where is the best place for a stay with Swimming Pools in Islamorada?
Whether you are traveling to Islamorada for business or fun, La Siesta Resort & Villas (from THB 6,432) , Cheeca Lodge & Spa (from THB 5,696) and Islander Resort (from THB 8,467) 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 THB 12,173, and the average price on weekends (Friday–Saturday) is THB 16,260.
What’s the best family hotels with Swimming Pools in Islamorada?
Drop Anchor Resort & Marina (from THB 5,049) 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 THB 5,696) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from THB 6,273) 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 | 40 |
|---|---|
| Number of reviews | 2,348 |
| Highest price | THB 34,131 |
| Lowest price | THB 7,043 |
| Weekday Avg. Price | THB 12,173 |
| Weekend Avg. Price | THB 16,260 |
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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 IslamoradaNEW! Waterfront, 3 Bedroom, 3 Bath. Keys Living, Peaceful RetreatPrivate 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 IslamoradaIconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.Cozy 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 OasisHouse 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