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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (199 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$269 nightly
The price is $303
Oct 11 - Oct 12
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)
$433 nightly
The price is $481
Oct 13 - Oct 14
Total with taxes and fees
Cozy Houseboat
A modern bathroom with a round mirror, a sink, and a bathtub.

3. 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.
$290 nightly
The price is $322
Oct 13 - Oct 14
Total with taxes and fees
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
A restaurant with multiple tables, hanging pendant lights, and a view of the outdoors.

4. 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.
$377 nightly
The price is $418
Oct 12 - Oct 13
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.

5. 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
$454 nightly
The price is $504
Oct 14 - Oct 15
Total with taxes and fees
Docked in Paradise
A compact cabin with a wooden interior, a control panel, a seating area with cushions, and a potted plant.

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

Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle
Stock Island
$352 nightly
The price is $391
Oct 11 - Oct 12
Total with taxes and fees
Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

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
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
$469 nightly
The price is $520
Oct 12 - Oct 13
Total with taxes and fees
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A hot tub with a view of a marina and boats during sunset.

8. 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 11 - Oct 12
Total with taxes and fees
Living the Dream Key West Style
A clear swimming pool with lounge chairs and palm trees.

9. 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.
$530 nightly
The price is $589
Oct 11 - Oct 12
Total with taxes and fees
Slice of Paradise
A beachside resort with a wooden deck, palm trees, and a sunset view.

10. 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
$566 nightly
The price is $636
Oct 12 - Oct 13
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
A beach with lounge chairs, palm trees, and a water body.

11. 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.
$569 nightly
The price is $632
Oct 13 - Oct 14
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

12. 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.
$535 nightly
The price is $594
Oct 18 - Oct 19
Total with taxes and fees
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A marina with numerous boats docked, a clear blue sky, and a distant view of the coastline.

13. 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
$397 nightly
The price is $441
Oct 25 - Oct 26
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.

14. 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.
$490 nightly
The price is $544
Oct 13 - Oct 14
Total with taxes and fees
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
A marina with several boats docked, a building with a flat roof, and a clear blue sky.

15. 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
$652 nightly
The price is $724
Nov 9 - Nov 10
Total with taxes and fees
3-bedroom catamaran with pool and beach access in amazing Key West!
Open concept living area

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.
$613 nightly
The price is $681
Oct 27 - Oct 28
Total with taxes and fees
Waterfront & Heated Pool - Away Awai Floating Villa
A kitchen with white cabinets, a dishwasher, a coffee maker, and a window with blinds.

17. Poolside Paradise

Poolside Paradise
Stock Island
$578 nightly
The price is $643
Oct 15 - Oct 16
Total with taxes and fees
Poolside Paradise
A resort pool area with lounge chairs and palm trees, surrounded by resort buildings.

18. 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 11 - Oct 12
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.

19. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
$602 nightly
The price is $668
Oct 14 - Oct 15
Total with taxes and fees
Waterfront & Heated Pool - Break Awai Floating Villa
A dining area with a wooden table, woven placemats, and a chandelier.

20. 3-bedroom townhome in Key West with fitness room, WiFi

3-bedroom townhome in Key West with fitness room, WiFi
Stock Island
9.8 out of 10, Exceptional, (16 reviews)
"Great place for 3 couples. "
United States
Emily F.
$993 nightly
The price is $1,102
Oct 12 - Oct 13
Total with taxes and fees
3-bedroom townhome in Key West with fitness room, WiFi
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

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 $206 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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