Islamorada Hotels with Pools

Select your dates to see hotels in Islamorada with a Pools for a refreshing stay.

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Best Islamorada Hotels with Swimming Pools

Check out our selection of Islamorada hotels with Pools

Most Booked

Lowest price

Closest to downtown

Highest Rated

99+

Cheeca Lodge & Spa

Hotels in Islamorada

Featured facilities: Swimming Pool, Exclusive Beach Area, Bar

Great

113 reviews

9.0/10

1 night

From JPY 18,712

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99+

La Jolla Resort

Hotels in Islamorada

Featured facilities: Swimming Pool, Exclusive Beach Area

Great

102 reviews

9.0/10

1 night

From JPY 15,299

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99+

Islander Resort

Hotels in Islamorada

Featured facilities: Swimming Pool, Exclusive Beach Area, Bar

Great

103 reviews

9.2/10

1 night

From JPY 41,614

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99+

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

Hotels in Islamorada

Featured facilities: Swimming Pool, Exclusive Beach Area, Bar

Very Good

102 reviews

8.9/10

1 night

From JPY 33,517

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99+

Amara Cay Resort

Hotels in Islamorada

Featured facilities: Swimming Pool, Exclusive Beach Area, Bar

Very Good

101 reviews

8.5/10

1 night

From JPY 22,713

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Breezy Palms Resort

Hotels in Islamorada

Featured facilities: Swimming Pool, Exclusive Beach Area

Very Good

101 reviews

8.4/10

1 night

From JPY 12,922

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99+

The Islands of Islamorada

Hotels in Islamorada

Featured facilities: Swimming Pool, Exclusive Beach Area, Bar

Amazing

46 reviews

9.4/10

1 night

From JPY 64,045

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99+

Fisher Inn Resort & Marina

Hotels in Islamorada

Featured facilities: Swimming Pool, Exclusive Beach Area

103 reviews

7.5/10

1 night

From JPY 20,030

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99+

Hadley Resort and Marina

Hotels in Islamorada

Featured facilities: Swimming Pool, Exclusive Beach Area

101 reviews

7.4/10

1 night

From JPY 21,607

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99+

Ragged Edge Resort & Marina

Hotels in Islamorada

Featured facilities: Swimming Pool

Amazing

100 reviews

9.6/10

1 night

From JPY 22,407

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See All Hotels with Pools in Islamorada

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.

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:JPY 21,584

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:JPY 22,902

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:JPY 30,787

Frequently Asked Questions

What's the best hotel with Swimming Pools in Islamorada?

Whether your trip to Islamorada is for business or leisure, Cheeca Lodge & Spa (from JPY 17,308) , Amara Cay Resort (from JPY 23,140) and La Siesta Resort & Villas (from JPY 28,949) are popular choices.

Which family-friendly hotels with Swimming Pools in Islamorada are recommended?

Drop Anchor Resort & Marina (from JPY 20,259) is a top choice for families. Enjoy your time with kids and other family members for your stay!

What's the average price for hotels with Swimming Pools in Islamorada?

For hotels with Swimming Pools in Islamorada, the average price is JPY 70,211 on weekdays and JPY 84,537 on weekends (Friday–Saturday).

Which hotels with Swimming Pools in Islamorada have deals?

There are many deals available on Trip.com for both new and loyal users. Please check the promotions page to save your upcoming stays.

What's the best luxury hotel with Swimming Pools in Islamorada?

Islamorada has many luxury hotels with Swimming Pools. Cheeca Lodge & Spa (from JPY 17,308) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from JPY 25,787) are popular choices.