Hotels with Entertainment in Stock Island
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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 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.

1. 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 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.

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

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

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

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

3. 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

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.

4. 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, (1,065 reviews)

8.6/10

Excellent

(1,065 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 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.'

5. 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 two-story white building with a porch and a sign indicating it is a vacant property named 'Fitch Lodge'.

A waterfront property with a dock, a boat, and a building with a sign reading "Harbor Walk".

A two-story house with a balcony and a small porch.

A poolside area with a lounge chair, a small table, and a pool.

6. Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 star property

Key West Historic District

8.8 out of 10, Excellent, (663 reviews)

8.8/10

Excellent

(663 reviews)

"Will book again"

Joaquin

The price is S$281

S$281

includes taxes & fees

9 Nov - 10 Nov

Fitch Lodge - Key West Historic Inns

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.

7. 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

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.

8. 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 poolside area with lounge chairs, a staircase leading to a balcony, and a pool.

A Southernmost Inn with a porch, a sign indicating vacancy, and a staircase leading to the entrance.

An outdoor patio with tables and chairs, surrounded by trees and a house.

A dining area with round tables and wicker chairs, a ceiling fan, and a bar area in the background.

9. The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3.0 star property

Old Town Key West

8.4 out of 10, Very good, (1,458 reviews)

8.4/10

Very good

(1,458 reviews)

"Very happy with our stay and our time in Key West, thank you!"

Sandra

The price is S$303

S$303

includes taxes & fees

1 Dec - 2 Dec

The Southernmost Inn - Adults Only

A spacious room with a wooden floor, white furniture, and large windows.

A white building with a covered porch, potted plants, and a white picket fence.

A paved pathway surrounded by lush greenery and palm trees.

A covered outdoor area with a table and chairs, surrounded by white railings and green foliage.

10. Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 star property

Old Town Key West

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

9.2/10

Wonderful

(1,001 reviews)

"Convenient location"

William

The price is S$345

S$345

includes taxes & fees

8 Dec - 9 Dec

Paradise Inn Key West - Adults Only

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 Placencia (PLJ) 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. Hilton Garden Inn Key West / The Keys Collection

2. Blue Flamingo Resort Key West

3. Southwinds Motel

4. The Reach Key West, Curio Collection by Hilton

5. Winslow's Bungalows - Key West Historic Inns

6. Fitch Lodge - Key West Historic Inns

7. Hyatt Centric Key West Resort and Spa

8. Southernmost House - Adult Exclusive

9. The Southernmost Inn - Adults Only

10. Paradise Inn Key West - Adults Only

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