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: PLN 470-PLN 7,988.

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: PLN 481 to PLN 4,512

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: PLN 515-PLN 3,530.

All prices shown are for September 2-September 8, as listed on Trip.com.

Find Islamorada hotels with a sprawling Pools.

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Top Hotels with Pools in Islamorada

Seek out top Islamorada hotels with proistine Pools.

Most Booked

Lowest price

Closest to downtown

Highest Rated

99+

Cheeca Lodge & Spa

Hotels in Islamorada

Featured facilities: Pool, Private beach area, Bar

Great

111 reviews

9.1/10

1 night

From PLN 418

Check availability

99+

La Jolla Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area

Great

102 reviews

9.0/10

1 night

From PLN 344

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99+

Islander Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area, Bar

Great

103 reviews

9.2/10

1 night

From PLN 807

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Breezy Palms Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area

Very Good

101 reviews

8.4/10

1 night

From PLN 307

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99+

The Islands of Islamorada

Hotels in Islamorada

Featured facilities: Pool, Private beach area, Bar

Amazing

46 reviews

9.4/10

1 night

From PLN 1,345

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99+

La Siesta Resort & Villas

Hotels in Islamorada

Featured facilities: Pool, Private beach area

Very Good

103 reviews

8.4/10

1 night

From PLN 508

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99+

Drop Anchor Resort & Marina

Hotels in Islamorada

Featured facilities: Pool, Private beach area

Very Good

96 reviews

8.6/10

1 night

From PLN 585

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99+

Fisher Inn Resort & Marina

Hotels in Islamorada

Featured facilities: Pool, Private beach area

103 reviews

7.5/10

1 night

From PLN 401

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99+

Amara Cay Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area, Bar

Very Good

103 reviews

8.5/10

1 night

From PLN 654

Check availability

99+

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area, Bar

Very Good

102 reviews

8.9/10

1 night

From PLN 665

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See More Hotels with Pools in Islamorada

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 User

The 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:PLN 525

Chesapeake Beach Resort

9.0/10

Great

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:PLN 540

Hadley Resort and Marina

7.4/10

Posted on Aug 6, 2026|Pool Villa

STOMs

Hadley 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:PLN 472

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 PLN 469) , La Siesta Resort & Villas (from PLN 481) and Amara Cay Resort (from PLN 514) 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 PLN 1,407, and on weekends (Friday–Saturday) is PLN 1,882.

Which hotels with Swimming Pools in Islamorada are good for families?

Drop Anchor Resort & Marina (from PLN 408) 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 PLN 469) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from PLN 473) are very popular.