The Best Hotels with a Pool in Stock Island, FL from ₩288,903 in 2026

A sunset over a coastal landscape with a small island surrounded by water.

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Our top choices for Stock Island hotels with a pool

Hyatt Centric Key West Resort and Spa

Key West Historic District

₩552,149 total

includes taxes & fees

Jul 27 - Jul 28

Hyatt Vacation Club at Windward Pointe, Key West

Key West

Oceanfront relaxation awaits with heated pool sanctuary and hot tub retreat, mere steps from Key West's beautiful Smathers Beach.

₩609,527 total

includes taxes & fees

Aug 8 - Aug 9

Outdoor pool, pool umbrellas, sun loungers

Hampton Inn Key West FL

Key West

Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.

₩323,084 total

includes taxes & fees

Jul 13 - Jul 14

The Perry Hotel & Marina Key West

Stock Island

Dive into aquatic bliss with two poolside bars and waterfront dining at this Key West retreat.

₩353,440 total

includes taxes & fees

Jul 26 - Jul 27

6 outdoor pools, free cabanas, pool umbrellas

Hilton Key West Resort & Marina

Stock Island

Float above the Florida Keys in a waterfront paradise with 6 serene pools, a private marina, and breathtaking sunset views.

₩381,594 total

includes taxes & fees

Jul 19 - Jul 20

Grand Marina Suite by Brightwild Waterfront

Stock Island

₩1,066,084 total

includes taxes & fees

Jul 9 - Jul 10

Sugar Loaf Lodge

Summerland Key

Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.

₩288,903 total

includes taxes & fees

Jul 9 - Jul 10

Hyatt Vacation Club at Beach House, Key West

Key West

Bask in tropical bliss with a dip in the outdoor pool and hot tub near Smathers Beach.

₩596,388 total

includes taxes & fees

Aug 4 - Aug 5

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Choose what matters most at hotels with a pool in Stock Island

Breakfast included

4 stars

Top Stock Island Hotel Reviews

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"Had a great stay. Our room was the back top unit with the airport right outside our door. Unit 5134. Even with planes so close they were not an issue. Unit was clean and had everything we needed and had a great view from or balcony. The telescope was nice especially to be able to watch the full moons that were in full view each night. All the staff was great and very helpful. The Abby bartenders were great and made some really good mixed drinks. Air conditioning worked great. I would say the only few issues with the room is some of the plugs in the room don’t seem to work. The plug receptacles in the lamps did not seem to work and were hit and miss. The fan in the second bedroom needs to be looked at because it makes a clanking sound when running. Would also be nice to have a black out curtain installed in the second bedroom. All minor issues. Would definitely not have a problem staying here again and in the same unit."