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

Find Hotels with a Pool in Stock Island, FL

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Stock Island Hotels with a Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
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 marina with boats docked, a swimming pool, and palm trees.
A modern living room with a flat-screen TV, wooden cabinet, grey sofa, and a coffee table.
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
$184 total
Oct 26 - Oct 27
Total with taxes and fees
The Perry Hotel & Marina Key West
A pool with clear water, surrounded by palm trees and lounge chairs.
A restaurant with multiple tables, hanging pendant lights, and a view of the outdoors.
An outdoor bar with wicker chairs and a long wooden bench, overlooking a marina with boats.
A marina with boats docked, a swimming pool, and a building with a flat roof.

2. 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 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.
A bedroom with a bed, a dresser, a door leading to a balcony with a view of water, and a ceiling fan.

3. Docked in Paradise

Docked in Paradise
Stock Island
$569 nightly
$632 total
Oct 29 - Oct 30
Total with taxes and fees
Docked in Paradise
Room
A beachside resort with a wooden deck, palm trees, and a sunset view.
Room
A dining area with a round table and chairs, a potted plant, and a view of the ocean through large windows with shutters.

4. 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 kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a toaster.
A beach with lounge chairs, palm trees, and a water body.
A gym with treadmills, elliptical machines, free weights, and exercise balls.

5. 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
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 living room with a sofa, armchair, coffee table, and a cabinet with decorative items.
A two-story building with a balcony, a visible number '33', and a small porch area.

6. 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
$465 nightly
$516 total
Oct 21 - Oct 22
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 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.
A gym with treadmills, ellipticals, and weight benches.

7. Key West Sailboat Getaway

Key West Sailboat Getaway
Stock Island
$193 nightly
$214 total
Oct 28 - Oct 29
Total with taxes and fees
Key West Sailboat Getaway
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 compact galley kitchen with a built-in refrigerator, a sink, and a window above the counter.
A marina with boats, a lifeguard tower, and a sign for 'The Little Dipper Ice Cream Shop' during sunset.

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
$508 nightly
$564 total
Oct 21 - Oct 22
Total with taxes and fees
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
A modern building with a wooden deck overlooking a body of water, with palm trees and boats in the background.
A modern boat with a wooden exterior, a covered deck, and a view of the marina.
A bedroom with a bed, bedside lamp, window, and a view of the outside.
A modern kitchen with a large island, a seating area with a sofa and chairs, and large windows with a marina view.

9. Waterfront & Heated Pool - Away Awai Floating Villa

Waterfront & Heated Pool - Away Awai Floating Villa
Stock Island
$564 nightly
$627 total
Oct 27 - Oct 28
Total with taxes and fees
Waterfront & Heated Pool - Away Awai Floating Villa
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.
A two-story building with a balcony on the second floor, a covered front porch, and a staircase leading to the entrance.
A modern kitchen with white cabinets, a wooden dining table, and green chairs.
A corner shower with white tiles and a hexagonal floor pattern.

10. Spacious 3-bedroom townhome on Stock Island with resort style pool.

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
$530 nightly
$589 total
Oct 25 - Oct 26
Total with taxes and fees
Spacious 3-bedroom townhome on Stock Island with resort style pool.
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
"Had a great time guest service was amazing"
Jesus 1-night trip
Posted less than an hour ago
Blue Flamingo Resort Key West
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"We had no issues. Room clean, restaurant good!"
Michael 4-night trip
Posted 7 hours ago
Opal Key Resort & Marina, Key West
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
"Wonderful hotel"
Jacob 1-night trip
Posted 7 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

8/10 Good
"Great location on the water"
Jaime 3-night trip
Posted 19 hours 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

8/10 Good
"Pros: great location, nice pool area, clean room, price good for the area, friendly staff. Cons: ice machine near our room broken, one of the elevators was out of order, bed uncomfortably firm, despite the website saying they had dinner inside the only food choices were from the poolside bar. Still waiting on the itemized bill, believe we were overcharged on “extras”."
Lisa 2-night trip
Posted 1 day 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
"Limpio .buena atención. Transporte rápido para el centro y playa parqueo incluido para muchos carros"
rene 2-night trip
Posted 1 day ago
DoubleTree Resort by Hilton Grand Key - Key West
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 2 days ago
Pier House Resort & Spa
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Todo maravillosamente genial"
Yurianay 1-night trip
Posted 3 days ago
Ibis Bay Beach Resort
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"This is a great place just minutes away from Key West proper. The rooms are nice (at least, ours was), the staff was very pleasant and helpful, and the property is well-maintained. Parking is in a gravel lot adjacent to the buildings and very close to the lobby, elevators, and restaurants. We did not use any of their resort amenities, so I will not opine on their quality. I will note that you need to add the daily resort fee to your room charge and tax to estimate the daily rate for staying there."
Eliot 2-night trip
Posted 4 days ago
The Perry Hotel & Marina Key West

Explore a world of travel with Expedia