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

Stock Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Stock Island vacation rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$252 nightly
The price is $284
Sep 23 - Sep 24
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
A restaurant with multiple tables, hanging pendant lights, and a view of the outdoors.

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

Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Stock Island
10.0 out of 10, Exceptional, (5 reviews)
"The marina was beautiful boat was quiet, relaxing close to everything but far enough away from the craziness of downtown. Plentyto do close by in and it’s a short drive to Key West my girlfriend said it was by far the best Mother’s Day ever couldn’t be happier. "
United States
Tyler L.
$373 nightly
The price is $414
Sep 23 - Sep 24
Total with taxes and fees
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
A marina with numerous boats docked, a clear blue sky, and a distant view of the coastline.

3. Key West Sailboat Getaway

Key West Sailboat Getaway
Stock Island
9.4 out of 10, Exceptional, (3 reviews)
"This entire boat experience was totally awesome. I had never done anything like this before. Daniel The Host was great. I was able to be in contact with Daniel the whole entire time I was there, which was a week. He did a great job of answering all of my questions. Definitely something I would do again, especially with Daniel's boat."
United States
Thomas
$202 nightly
The price is $224
Sep 29 - Sep 30
Total with taxes and fees
Key West Sailboat Getaway
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

4. 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
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
$464 nightly
The price is $515
Sep 23 - Sep 24
Total with taxes and fees
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a toaster.

5. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (33 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
$511 nightly
The price is $567
Sep 26 - Sep 27
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A resort pool area with lounge chairs and palm trees, surrounded by resort buildings.

6. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (42 reviews)
"Great set up!!!"
United States
Benjamin
$367 nightly
The price is $408
Sep 23 - Sep 24
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
A marina with multiple sailboats docked, clear skies, and calm water.

7. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
$429 nightly
The price is $477
Sep 23 - Sep 24
Total with taxes and fees
Cozy Houseboat
A modern bathroom with a round mirror, a sink, and a bathtub.

8. Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Stock Island
8.4 out of 10, Very good, (13 reviews)
"The host Tina is amazing! "
United States
Denise B.
$288 nightly
The price is $320
Sep 24 - Sep 25
Total with taxes and fees
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
A boat deck with a Yamaha outboard motor, a white railing, and a view of the water and distant shoreline.

9. Docked in Paradise

Docked in Paradise
Stock Island
9.0 out of 10, Wonderful, (8 reviews)
"The houseboat is located in a great marina with a nice place to eat, have a drink, and enjoy a swim. The houseboat is very comfortable and clean. The host has excellent communication. It is only 3 miles away from Duval St but far enough away to be serene."
United States
Michael
$452 nightly
The price is $502
Sep 24 - Sep 25
Total with taxes and fees
Docked in Paradise
A hot tub with a view of a marina and boats during sunset.

10. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (62 reviews)
"Great would definitely stay again "
United States
Zach C.
$347 nightly
The price is $387
Sep 30 - Oct 1
Total with taxes and fees
Living the Dream Key West Style
A marina with boats, a grassy deck with lounge chairs, and a clear sky.

11. Waterfront & Heated Pool - Away Awai Floating Villa

Waterfront & Heated Pool - Away Awai Floating Villa
Stock Island
9.6 out of 10, Exceptional, (5 reviews)
"A unique location with all you need"
United States
Stefanie S.
$536 nightly
The price is $595
Sep 24 - Sep 25
Total with taxes and fees
Waterfront & Heated Pool - Away Awai Floating Villa
A beachside resort with a wooden deck, palm trees, and a sunset view.

12. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
$503 nightly
The price is $566
Sep 27 - Sep 28
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
A clear swimming pool with lounge chairs and palm trees.

13. Another Day in Paradise

Another Day in Paradise
Stock Island
9.6 out of 10, Exceptional, (4 reviews)
"It was perfect for what we were looking for"
United States
Megan A.
$529 nightly
The price is $588
Sep 23 - Sep 24
Total with taxes and fees
Another Day in Paradise
A modern living room with a large window overlooking a marina, a brown leather sofa, a wooden coffee table, and a wicker chair.

14. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
$536 nightly
The price is $595
Sep 23 - Sep 24
Total with taxes and fees
Waterfront & Heated Pool - Break Awai Floating Villa
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

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

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
10.0 out of 10, Exceptional, (7 reviews)
"Perfect for our family trip to Key West. Great location and we enjoyed the pool and nearby restaurants. Easy check in and check out process and clear, timely communication with the owner. "
United States
Samantha P.
$493 nightly
The price is $550
Oct 6 - Oct 7
Total with taxes and fees
Spacious 3-bedroom townhome on Stock Island with resort style pool.
An aerial view of a resort with a central swimming pool surrounded by palm trees and sun loungers.

16. 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
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing time. Would definitely stay there again!"
United States
Andrea S.
$464 nightly
The price is $517
Oct 13 - Oct 14
Total with taxes and fees
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
A wooden deck with a railing, a purple house with white trim, and a palm tree in the background.

17. Poolside Paradise

Poolside Paradise
Stock Island
$588 nightly
The price is $653
Sep 23 - Sep 24
Total with taxes and fees
Poolside Paradise
A clear swimming pool with lounge chairs and palm trees.

18. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
$560 nightly
The price is $623
Oct 4 - Oct 5
Total with taxes and fees
Slice of Paradise
A clear swimming pool surrounded by palm trees and lounge chairs.

19. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (39 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
$587 nightly
The price is $653
Sep 29 - Sep 30
Total with taxes and fees
Paradise found
A bedroom with a bed, bedside tables, a TV, and a door.

20. 3-bedroom catamaran with pool and beach access in amazing Key West!

3-bedroom catamaran with pool and beach access in amazing Key West!
Stock Island
$562 nightly
The price is $625
Sep 24 - Sep 25
Total with taxes and fees
3-bedroom catamaran with pool and beach access in amazing 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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Top Stock Island Hotel Reviews

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Overall an excellent stay. Pool is somewhat small but nice. Staff is overall top notch. Location is about as good as you can get if your plan is to hang in Old Town. Would definitely recommend."
David 5-night trip
Posted 6 hours ago
La Concha Key West, Autograph Collection

Find out more about Stock Island

Everything you need to know about Stock Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stock Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stock Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stock Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stock Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Stock Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $262 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stock Island rentals

At Expedia, we put the best Stock Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stock Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stock Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stock Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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