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

Find Hotels with a Pool in Stock Island, FL

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Check availability on Stock Island Hotels with a Pool

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Stock Island hotels with a pool

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A marina with boats docked, a swimming pool, and palm trees.
A multi-story hotel with balconies, palm trees, and a pool area.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

1. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
  • Dive into aquatic bliss with two poolside bars and waterfront dining at this Key West retreat.
$156 nightly
$178 total
Nov 2 - Nov 3
Total with taxes and fees
The Perry Hotel & Marina Key West
A waterfront hotel with a pool, palm trees, and a wooden dock.
A marina with numerous boats docked, a swimming pool, and palm trees.
A clear view of turquoise ocean water and a blue sky with clouds.
A hotel room with a large bed, a view of the ocean, a balcony with a chair, and a painting of coconuts.

2. Hilton Key West Resort & Marina

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.
$174 nightly
$196 total
Oct 25 - Oct 26
Total with taxes and fees
Hilton Key West Resort & Marina
A pool with clear water, surrounded by palm trees and lounge chairs.
An outdoor bar with wicker chairs and a long wooden bench, overlooking a marina with boats.
A restaurant with multiple tables, hanging pendant lights, and a view of the outdoors.
A marina with boats docked, a swimming pool, and a building with a flat roof.

3. Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West

Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Stock Island
$381 nightly
$423 total
Oct 26 - Oct 27
Total with taxes and fees
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
A boat deck with a Yamaha outboard motor, a white railing, and a view of the water and distant shoreline.
A bedroom with a bed, a dresser, a door leading to a balcony with a view of water, and a ceiling fan.
A modern kitchen with a wooden countertop, grey cabinets, and a built-in microwave.
A compact living space with a kitchenette, a sofa, and a dining area.

4. Docked in Paradise

Docked in Paradise
Stock Island
$455 nightly
$505 total
Oct 29 - Oct 30
Total with taxes and fees
Docked in Paradise
Room
A waterfront property with a large building featuring balconies, a pool area, and boats docked in the water.
Room
A beachside resort with a wooden deck, palm trees, and a sunset view.

5. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
Stock Island
$510 nightly
$574 total
Oct 28 - Oct 29
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
A swimming pool with lounge chairs, a covered area, and a building with multiple balconies.
A bedroom with a wooden four-poster bed, a nightstand, a dresser, a television, and a ceiling fan.
A beach with lounge chairs, palm trees, and a water body.
A kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a toaster.

6. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
$507 nightly
$563 total
Oct 26 - Oct 27
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.
A bar with a signboard listing various destinations.
A two-story building with a balcony, a visible number '33', and a small porch area.
A living room with a sofa, armchair, coffee table, and a cabinet with decorative items.

7. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
$495 nightly
$549 total
Oct 20 - Oct 21
Total with taxes and fees
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
An aerial view of a resort with a central swimming pool surrounded by palm trees and sun loungers.
A compact kitchen with a microwave, sink, and refrigerator.
A marina with boats, a lifeguard tower, and a sign for 'The Little Dipper Ice Cream Shop' during sunset.
A compact galley kitchen with a built-in refrigerator, a sink, and a window above the counter.

8. Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West

Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
Stock Island
$485 nightly
$539 total
Oct 20 - Oct 21
Total with taxes and fees
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
A swimming pool with lounge chairs and palm trees.
A marina with numerous boats docked, a clear blue sky, and a distant view of the coastline.
A gym with treadmills, ellipticals, and weight benches.
A sailboat docked at a marina with a cabin, helm station, and a 'Blown Away' sign.

9. Key West Sailboat Getaway

Key West Sailboat Getaway
Stock Island
$397 nightly
$441 total
Oct 26 - Oct 27
Total with taxes and fees
Key West Sailboat Getaway
A modern building with a wooden deck overlooking a body of water, with palm trees and boats in the background.
A modern bathroom with a marble sink, wooden cabinets, and a glass shower enclosure.
A parking lot with various vehicles, including cars and a truck, and palm trees.
A mirror reflecting a room with a wooden cabinet, a window, and a white pillow.

10. Waterfront & Heated Pool - Away Awai Floating Villa

Waterfront & Heated Pool - Away Awai Floating Villa
Stock Island
$598 nightly
$664 total
Oct 27 - Oct 28
Total with taxes and fees
Waterfront & Heated Pool - Away Awai Floating Villa
View all properties

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

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Stock Island Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Great place. Lots of activities, nice bar and food. Staff was amazing."
Dan 1-night trip
Posted less than an hour ago
Blue Flamingo Resort Key West
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"We had an amazing stay. Check in was easy and everyone on the property was helpful and friendly. Our room was clean and comfortable and loved the updated bathroom. Loved the private pool and happy hour complete with visits from wildlife. It was in a wonderful location but far enough away from any loud craziness. Overall no complaints"
Dana 3-night trip
Posted 1 hour ago
The Southernmost Inn - Adults Only
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Excelente íbamos por 1 noche y terminamos solicitando otra."
JESUS ALDIBER 1-night trip
Posted 2 hours ago
Hilton Garden Inn Key West / The Keys Collection
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"I would like to Thank the evening staff for always being helpful, the front desk espically."
sandra 2-night trip
Posted 2 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"This is the third of the historic inn group properties I have stayed at, and it was fabulous, amazing property with beautiful pools and landscaping, and the rooms are so charming and clean and luxurious we loved it!"
Daniel 1-night trip
Posted 3 hours ago
Winslow's Bungalows - Key West Historic Inns
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Great place for families!!"
Anna 2-night trip
Posted 3 hours ago
Parrot Key Hotel & Villas
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Everything was exceptional at Pier House. Breakfast by the water every morning great music and drinks from the bar, well maintained property and beach! Staff went out of their way and were very kimd. Our room with lanai was fantastic! Thank you Pier House!"
Steven 3-night trip
Posted 3 hours ago
Pier House Resort & Spa
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"The hotel was in a great location. The staff was helpful. The room was spacious and clean."
Geraldine 1-night trip
Posted 4 hours ago
Opal Key Resort & Marina, Key West
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"The resort offers shuttle service into town which made it very easy to explore Key West."
Sophia 6-night trip
Posted 5 hours ago
Beachside Resort & Residences

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