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-$1,618.

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: $147-$1,024.

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: $183 to $1,196

All prices shown are for October 2-October 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

113 reviews

9.0/10

1 night

From $116

Check availability

99+

La Jolla Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area

Great

102 reviews

9.0/10

1 night

From $89

Check availability

99+

Islander Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area, Bar

Great

103 reviews

9.2/10

1 night

From $191

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

103 reviews

8.9/10

1 night

From $202

Check availability

99+

Amara Cay Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area, Bar

Very Good

100 reviews

8.5/10

1 night

From $150

Check availability

Breezy Palms Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area

Very Good

101 reviews

8.4/10

1 night

From $69

Check availability

99+

The Islands of Islamorada

Hotels in Islamorada

Featured facilities: Pool, Private beach area, Bar

Amazing

46 reviews

9.4/10

1 night

From $415

Check availability

99+

Fisher Inn Resort & Marina

Hotels in Islamorada

Featured facilities: Pool, Private beach area

103 reviews

7.5/10

1 night

From $120

Check availability

99+

Hadley Resort and Marina

Hotels in Islamorada

Featured facilities: Pool, Private beach area

101 reviews

7.4/10

1 night

From $110

Check availability

99+

Ragged Edge Resort & Marina

Hotels in Islamorada

Featured facilities: Pool

Amazing

100 reviews

9.6/10

1 night

From $129

Check availability

See More Hotels with Pools in Islamorada

Latest Reviews for Islamorada Hotels

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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:$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 $147) and La Siesta Resort & Villas (from $183) 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 $428, and on weekends (Friday–Saturday) is $528.

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

Drop Anchor Resort & Marina (from $128) 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 $148) are very popular.