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 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
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 modern living room with a flat-screen TV, wooden cabinet, grey sofa, and a coffee table.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.
A multi-story hotel with balconies, palm trees, and a pool area.

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.
$164 nightly
$186 total
Oct 26 - Oct 27
Total with taxes and fees
The Perry Hotel & Marina Key West
A waterfront hotel with a pool, palm trees, and a wooden dock.
A clear view of turquoise ocean water and a blue sky with clouds.
A marina with numerous boats docked, a swimming pool, and palm trees.
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 27 - Oct 28
Total with taxes and fees
Hilton Key West Resort & Marina
A pool with clear water, surrounded by palm trees and lounge chairs.
A marina with boats docked, a swimming pool, and a building with a flat roof.
A marina with numerous boats docked, surrounded by palm trees and a clear sky.
An outdoor bar with wicker chairs and a long wooden bench, overlooking a marina with boats.

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

Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Stock Island
$376 nightly
$417 total
Oct 27 - Oct 28
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 compact living space with a kitchenette, a sofa, and a dining area.
A modern kitchen with a wooden countertop, grey cabinets, and a built-in microwave.

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 dining area with a round table and chairs, a potted plant, and a view of the ocean through large windows with shutters.
A waterfront property with a large building featuring balconies, a pool area, and boats docked in the water.
Room

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 kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a toaster.
A beach with lounge chairs, palm trees, and a water body.

6. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
$511 nightly
$567 total
Oct 26 - Oct 27
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
An aerial view of a resort with a central swimming pool surrounded by palm trees and sun loungers.
A compact galley kitchen with a built-in refrigerator, a sink, and a window above the counter.
A compact kitchen with white cabinetry, a black countertop, a microwave, a sink with a mirror, and a stainless steel refrigerator.
A marina with boats, a lifeguard tower, and a sign for 'The Little Dipper Ice Cream Shop' during sunset.

7. 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
$494 nightly
$548 total
Oct 26 - Oct 27
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 a thatched roof structure, surrounded by lush greenery and a brick patio.
A pathway through a lush garden with various plants and trees.
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.

8. 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
$469 nightly
$521 total
Oct 20 - Oct 21
Total with taxes and fees
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A swimming pool with lounge chairs and palm trees.
A restaurant with wooden tables and chairs, hanging pendant lights, and a view through large windows.
A marina with numerous boats docked, a clear blue sky, and a distant view of the coastline.
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
$396 nightly
$440 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 bedroom with a bed, a television mounted on the wall, a window, and a wooden shelf with toiletries.
A modern bathroom with a marble sink, wooden cabinets, and a glass shower enclosure.
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
$594 nightly
$660 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
"This hotel is closer to the Key West airport than it is to downtown. This did not matter since the hotel is like a vacation all on its own. With 2 pools and and outdoor bars as well as games on site there is less of a need to go downtown. I arrived at the hotel before the official check in time and they still provided me a room. The room was a decent size and had all the amenities I expected. There is a free hotel shuttle that will take you downtown at the top of every hour and also bring you back. For breakfast I skipped the options at the outdoor bars and instead went to the Starbucks onsite. I regretted this and next time I will just order from the hotel. Breakfast is not included. In summary, despite breakfast I cannot wait to stay at this hotel again!"
Andrew 2-night trip
Posted 1 hour ago
Blue Flamingo Resort Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Excellent friendly staff! Breakfast should have been included with $400+ per night room🙁!"
Robert 1-night trip
Posted 1 hour ago
DoubleTree Resort by Hilton Grand Key - Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"Resort was nice. Good location and amenities were also in good shape. Only real issue I had is the $50 a day parking fee. Just seems not really necessary and is excessive"
Chris 4-night trip
Posted 1 hour ago
Southernmost Beach Resort and Guesthouses
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Beautiful property, beach was perfect, pools were great. The staff are very helpful and knowledgeable"
Robert 2-night trip
Posted 1 hour ago
Casa Marina Key West, Curio Collection by Hilton
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Excellent service!"
Marcela 1-night trip
Posted 3 hours ago
Hilton Garden Inn Key West / The Keys Collection
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 16 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 17 hours ago
Opal Key Resort & Marina, Key West
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Todo maravillosamente genial"
Yurianay 1-night trip
Posted 2 days ago
Ibis Bay Beach Resort
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

10/10 Excellent
"Staff was friendly and very helpful. Their shuttle to downtown was excellent"
Koreena 1-night trip
Posted 2 days ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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