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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (200 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$258 nightly
The price is $290
Oct 30 - Oct 31
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
A marina with multiple sailboats docked, clear skies, and calm water.

2. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
$431 nightly
The price is $479
Nov 1 - Nov 2
Total with taxes and fees
Cozy Houseboat
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
$396 nightly
The price is $440
Nov 1 - Nov 2
Total with taxes and fees
Key West Sailboat Getaway
A modern bathroom with a round mirror, a sink, and a bathtub.

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

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Stock Island
8.0 out of 10, Very good, (14 reviews)
"This was the best place I have ever stayed! Tina is an amazing host, the energy was magnificent! "
United States
Ashley S.
$279 nightly
The price is $310
Oct 26 - Oct 27
Total with taxes and fees
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
A bedroom with a bed, a small table, a chair, a window, and a view of the water.

5. Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Stock Island
6.8 out of 10, (13 reviews)
"My wife and I have been to Key West many times, and Liam's house boat has to be the coolest place we've stayed yet! "
United States
Mike W.
$228 nightly
The price is $253
Oct 25 - Oct 26
Total with taxes and fees
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
A pool area with lounge chairs and palm trees.

6. 43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown

43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
Stock Island
10.0 out of 10, Exceptional, (7 reviews)
"We loved staying on this beautiful boat and all the amenities of the Perry Marina. Will definitely stay again: highly recommend "
United States
Erin S.
$352 nightly
The price is $390
Oct 26 - Oct 27
Total with taxes and fees
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
A restaurant with multiple tables, hanging pendant lights, and a view of the outdoors.

7. 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, (6 reviews)
"Everything was great!"
United States
Terri F.
$376 nightly
The price is $417
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.

8. 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
$575 nightly
The price is $638
Oct 29 - Oct 30
Total with taxes and fees
Docked in Paradise
A waterfront property with a large building, a dock with boats, and palm trees.

9. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (35 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.
$508 nightly
The price is $564
Oct 25 - Oct 26
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A swimming pool with palm trees and a clear sky.

10. Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle

Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle
Stock Island
$348 nightly
The price is $387
Oct 25 - Oct 26
Total with taxes and fees
Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle
A hot tub with a view of a marina and boats during sunset.

11. 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.
$474 nightly
The price is $527
Oct 25 - Oct 26
Total with taxes and fees
Living the Dream Key West Style
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
$533 nightly
The price is $600
Oct 26 - Oct 27
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
An aerial view of a resort with a central swimming pool surrounded by palm trees and sun loungers.

13. 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
9.4 out of 10, Exceptional, (3 reviews)
"We had an amazing time. Would definitely stay there again!"
United States
Andrea S.
$511 nightly
The price is $567
Oct 26 - Oct 27
Total with taxes and fees
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
A clear swimming pool with lounge chairs and palm trees.

14. 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.
$512 nightly
The price is $569
Oct 26 - Oct 27
Total with taxes and fees
Slice of Paradise
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

15. 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, (137 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
$503 nightly
The price is $558
Oct 26 - Oct 27
Total with taxes and fees
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A modern building with a wooden deck overlooking a body of water, with palm trees and boats in the background.

16. Waterfront & Heated Pool - Away Awai Floating Villa

Waterfront & Heated Pool - Away Awai Floating Villa
Stock Island
9.4 out of 10, Exceptional, (8 reviews)
"A unique location with all you need"
United States
Stefanie S.
$587 nightly
The price is $652
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.

17. 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, (8 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.
$533 nightly
The price is $592
Oct 27 - Oct 28
Total with taxes and fees
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A clear swimming pool with lounge chairs and palm trees in the background.

18. Poolside Paradise

Poolside Paradise
Stock Island
$577 nightly
The price is $642
Oct 28 - Oct 29
Total with taxes and fees
Poolside Paradise
A resort pool area with lounge chairs and palm trees, surrounded by resort buildings.

19. 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
$451 nightly
The price is $501
Oct 25 - Oct 26
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
A marina with multiple boats docked, a floating structure with a green deck and seating, and a building with large windows.

20. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
$639 nightly
The price is $709
Oct 29 - Oct 30
Total with taxes and fees
Waterfront & Heated Pool - Break Awai Floating Villa
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

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

8/10 Good
"Construction underway at the hotel site. Staff and room were fine. Beautiful view."
William 1-night trip
Posted 4 hours ago
Hilton Key West Resort & Marina

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 $219 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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