Hotels with Entertainment in Stock Island
Florida
United States of America
Hotels with Entertainment
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A sunset over a coastal landscape with a small island surrounded by water.

Hotels with Entertainment in Stock Island

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your current months are November, 2026 and December, 2026.

November 2026

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Our top choices for Stock Island hotels with entertainment

A hotel with a swimming pool, sun loungers, and palm trees.

A spacious living area with a sofa, chairs, a coffee table, and a swing chair.

A beachside resort with palm trees, outdoor seating, and a food truck.

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

1. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4.0 star property

New Town

8.6 out of 10, Excellent, (2,778 reviews)

8.6/10

Excellent

(2,778 reviews)

"Nice resort very family friendly"

Sigrid A

The price is S$253

S$253

includes taxes & fees

15 Nov - 16 Nov

Blue Flamingo Resort Key West

A swimming pool with lounge chairs and palm trees.

A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.

A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

A modern living room with a sectional sofa, a small round table, and a potted plant.

2. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 star property

New Town

8.2 out of 10, Very good, (1,356 reviews)

8.2/10

Very good

(1,356 reviews)

"Room was very comfortable, staff was very helpful and breakfast was good"

Darlene

The price is S$202

S$202

includes taxes & fees

15 Nov - 16 Nov

Hilton Garden Inn Key West / The Keys Collection

A beach with a wooden pier, palm trees, and beach umbrellas.

A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.

An outdoor dining area with tables and chairs, overlooking the ocean.

An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

3. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4.0 star property

Old Town Key West

8.6 out of 10, Excellent, (1,066 reviews)

8.6/10

Excellent

(1,066 reviews)

"Had a great experience to celebrate my birthday here."

Rowena

The price is S$380

S$380

includes taxes & fees

30 Nov - 1 Dec

The Reach Key West, Curio Collection by Hilton

A hotel with a swimming pool, balconies, and a view of the sea.

A balcony with a view of the ocean, a table, chairs, and a railing.

A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

4. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4.0 star property

Key West Historic District

9.2 out of 10, Wonderful, (1,003 reviews)

9.2/10

Wonderful

(1,003 reviews)

"Wonderful property with wonderful staff"

Michael Joseph

The price is S$458

S$458

includes taxes & fees

1 Dec - 2 Dec

Hyatt Centric Key West Resort and Spa

An outdoor bar area with wooden tables and blue stools, a bar counter, and a sign that reads "Liqour Store".

A white decorative sculpture in a garden area with a white fence and a building in the background.

A modern kitchen with a granite countertop, white cabinetry, and a coffee machine.

A motel with a porch, white chairs, and a signboard.

5. Southwinds Motel

Southwinds Motel

2.0 star property

Old Town Key West

8.6 out of 10, Excellent, (1,397 reviews)

8.6/10

Excellent

(1,397 reviews)

"Great place to stay"

becky

The price is S$266

S$266

includes taxes & fees

1 Dec - 2 Dec

Southwinds Motel

An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

A modern hotel with a prominent glass facade, palm trees, and a clear sky.

A couple relaxing by a poolside lounge with a view of palm trees and a clear sky.

A modern hotel room with a bed, sofa, coffee table, and artwork.

6. H2O Suites - Adults Only

H2O Suites - Adults Only

3.5 star property

Old Town Key West

9.8 out of 10, Exceptional, (674 reviews)

9.8/10

Exceptional

(674 reviews)

"Amazing stay! Loved the private pool!"

Kimberly

The price is S$604

S$604

includes taxes & fees

30 Nov - 1 Dec

H2O Suites - Adults Only

A large, ornate hotel with a pool, palm trees, and a view of the ocean.

A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

A large, two-story house with a prominent tower and a covered porch.

A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.

7. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4.0 star property

Old Town Key West

9.4 out of 10, Exceptional, (1,003 reviews)

9.4/10

Exceptional

(1,003 reviews)

"Such a wonderful peaceful place to stay! Great food close by and Duval Street"

Edward Lance

The price is S$464

S$464

includes taxes & fees

16 Nov - 17 Nov

Southernmost House - Adult Exclusive

A two-story building with a covered entrance, palm trees, and a bench outside.

A white picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery.

A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights.

A white building with a sign reading 'Kimpton Key West Winslow's Bungalow.'

8. Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4.0 star property

Old Town Key West

9.2 out of 10, Wonderful, (1,483 reviews)

9.2/10

Wonderful

(1,483 reviews)

"Great location, friendly staff and feels like a private oasis"

Matthew

The price is S$353

S$353

includes taxes & fees

28 Nov - 29 Nov

Winslow's Bungalows - Key West Historic Inns

A pool area with lounge chairs and a cabana.

A balcony with a table set for breakfast, overlooking the sea.

A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.

9. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

4.0 star property

Key West Historic District

9.2 out of 10, Wonderful, (1,001 reviews)

9.2/10

Wonderful

(1,001 reviews)

"Great place to stay!"

Trevor

The price is S$471

S$471

includes taxes & fees

22 Nov - 23 Nov

Ocean Key Resort - A Noble House Resort

A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

A patio area with white metal tables and chairs, surrounded by potted plants and palm trees.

A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.

A pool with a lion head sculpture in the center.

10. Artist House Key West

Artist House Key West

3.5 star property

Key West Historic District

9.8 out of 10, Exceptional, (473 reviews)

9.8/10

Exceptional

(473 reviews)

"We had a wonderful stay at The Artist House! The property is full of charm and fascinating history, and the location is perfect for exploring Key West. The staff was friendly and welcoming throughout our visit. A truly enjoyable experience, and I’d happily stay again!"

Joseph

The price is S$362

S$362

includes taxes & fees

30 Nov - 1 Dec

Artist House Key West

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Flights from Dhahran (DHA) to Key West (EYW)
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Flights from Longview (GGG) to Key West (EYW)
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Flights from Owensboro (OWB) to Key West (EYW)
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Flights from Peppimenarti (PEP) to Key West (EYW)
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Flights from Philadelphia (PHL) to Key West (EYW)
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Flights from Placencia (PLJ) to Key West (EYW)
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Flights from Port Elizabeth (PLZ) to Key West (EYW)
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Flights from Richmond (RIC) to Key West (EYW)
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Flights from Roswell (ROW) to Key West (EYW)
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Flights from Fort Myers (RSW) to Key West (EYW)
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Flights from Sanford (SFM) to Key West (EYW)
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Flights from Shreveport (SHV) to Key West (EYW)
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Flights from Singapore (SIN) to Key West (EYW)
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Flights from San Juan (SJU) to Key West (EYW)
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Flights from Tri-Cities (TRI) to Key West (EYW)
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Flights from St. Augustine (UST) to Key West (EYW)
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Flights from Vopnafjordur (VPN) to Key West (EYW)
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Flights from Trenton (YTR) to Key West (EYW)
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Hotels with Entertainment in Stock Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Stock Island hotels with entertainment

1. Blue Flamingo Resort Key West

2. Hilton Garden Inn Key West / The Keys Collection

3. The Reach Key West, Curio Collection by Hilton

4. Hyatt Centric Key West Resort and Spa

5. Southwinds Motel

6. H2O Suites - Adults Only

7. Southernmost House - Adult Exclusive

8. Winslow's Bungalows - Key West Historic Inns

9. Ocean Key Resort - A Noble House Resort

10. Artist House Key West

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