Islamorada Hotels with Pools

Find Islamorada hotels with a sprawling Pools.

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Guest Rating

Amazing 9+Great 8+Good 7+Pleasant 6+

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 €120

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99+

La Jolla Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area

Great

102 reviews

9.0/10

1 night

From €96

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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 €238

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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 €188

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99+

Amara Cay Resort

Hotels in Islamorada

Featured facilities: Pool, Private beach area, Bar

Very Good

100 reviews

8.5/10

1 night

From €153

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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 €73

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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 €466

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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 €136

Check availability

99+

Hadley Resort and Marina

Hotels in Islamorada

Featured facilities: Pool, Private beach area

101 reviews

7.4/10

1 night

From €129

Check availability

99+

Ragged Edge Resort & Marina

Hotels in Islamorada

Featured facilities: Pool

Amazing

100 reviews

9.6/10

1 night

From €128

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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:€184

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:€135

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:€174

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 €110) , Amara Cay Resort (from €143) and La Siesta Resort & Villas (from €165) 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 €405, and on weekends (Friday–Saturday) is €504.

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

Drop Anchor Resort & Marina (from €106) 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 €110) and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from €182) are very popular.