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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Stock Island vacation rentals

Front of property

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
$238 nightly
The price is $268
Sep 4 - Sep 5
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Marina

2. Key West Sailboat Getaway

Key West Sailboat Getaway
Stock Island
9.0 out of 10, Wonderful, (2 reviews)
"Definitely a unique property. I would recommend this stay for younger or more agile people. Knowing in advance that you will be stepping off the dock into the boat and going down steep steps to get into the living quarters can be tricky. Great Marina View with Marina amenities."
United States
Julia
$202 nightly
The price is $224
Sep 14 - Sep 15
Total with taxes and fees
Key West Sailboat Getaway
Marina

3. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
$430 nightly
The price is $478
Sep 8 - Sep 9
Total with taxes and fees
Cozy Houseboat
Property grounds

4. 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
$426 nightly
The price is $473
Sep 11 - Sep 12
Total with taxes and fees
Docked in Paradise
Room

5. 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.
$287 nightly
The price is $319
Sep 6 - Sep 7
Total with taxes and fees
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Marina

6. 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, (4 reviews)
"Everything was great!"
United States
Terri F.
$360 nightly
The price is $400
Sep 4 - Sep 5
Total with taxes and fees
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Fitness facility

7. 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.
$508 nightly
The price is $564
Sep 7 - Sep 8
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
Pool

8. 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, (41 reviews)
"Great set up!!!"
United States
Benjamin
$358 nightly
The price is $398
Sep 8 - Sep 9
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
House

9. 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
$490 nightly
The price is $551
Sep 13 - Sep 14
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
Pool

10. 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.
$513 nightly
The price is $570
Sep 13 - Sep 14
Total with taxes and fees
Slice of Paradise
Pool

11. Gone Coastal

Gone Coastal
Stock Island
9.6 out of 10, Exceptional, (22 reviews)
"Great place , clean and close to everything!"
United States
april
$548 nightly
The price is $609
Sep 9 - Sep 10
Total with taxes and fees
Gone Coastal
Pool

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.
$543 nightly
The price is $603
Sep 10 - Sep 11
Total with taxes and fees
Spacious 3-bedroom townhome on Stock Island with resort style pool.
Pool

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
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing time. Would definitely stay there again!"
United States
Andrea S.
$447 nightly
The price is $496
Oct 4 - Oct 5
Total with taxes and fees
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
Pool

14. 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.
$561 nightly
The price is $623
Sep 22 - Sep 23
Total with taxes and fees
Another Day in Paradise
Pool

15. 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.
$475 nightly
The price is $528
Sep 30 - Oct 1
Total with taxes and fees
Living the Dream Key West Style
Interior

16. 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.
$647 nightly
The price is $719
Sep 9 - Sep 10
Total with taxes and fees
Waterfront & Heated Pool - Away Awai Floating Villa
Living area

17. 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
$557 nightly
The price is $618
Sep 7 - Sep 8
Total with taxes and fees
3-bedroom catamaran with pool and beach access in amazing Key West!
Living area

18. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
$651 nightly
The price is $723
Sep 7 - Sep 8
Total with taxes and fees
Waterfront & Heated Pool - Break Awai Floating Villa
Pool

19. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (38 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
$592 nightly
The price is $658
Sep 7 - Sep 8
Total with taxes and fees
Paradise found
Pool

20. 40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6

40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
Stock Island
10.0 out of 10, Exceptional, (1 review)
$908 nightly
The price is $1,009
Sep 4 - Sep 5
Total with taxes and fees
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
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

Southwinds Motel

Southwinds Motel

10/10 Excellent
"Southwinds Motel has to be the absolute best spot I’ve stayed at when it comes to conveniences on site along with an awesome location and proximity to sites and activities. Perfectly located around the Southernmost part of Key West, Southwinds gives you fully stocked bar WITH a built-in liquor store. Super convenient off rip. Bar has live music in the afternoon and evening, a pretty nice pool and deck area and, what I really found most convenient, access to rentals for any means of transportation you need for Key West from bicycles to scooters to full sized golf carts. Rentals are provided by Bone Island rentals who also deliver your mode of moving around to the property and picks it up from the property. A totally ‘Key West’ luxury in my mind. So you’re not staying in the fanciest of shindigs, but you rented a motel because you probably plan to be out and about in beautiful Key West and not cooped up, so you most definitely shouldn’t have grand expectations, but you definitely won’t be disappointed with the digs either. Another thing I really appreciated was after check-in, we were also gifted 2 vouchers for free specialty cocktails from their bar. It was small drinks and only their specialty drinks but still complimentary, so we say thank you and enjoy. They let us combine both tickets for one full sized rum runner my wife enjoyed. Overall 10/10 for comfort, convenience, location and it’s vibe. Will absolutely be going back and 100 percent recommend to all staying in KW"
Juan 4-night trip
Posted 4 hours ago
Southwinds Motel

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 $228 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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