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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
The price is ￥23,938
￥54,236 total
includes taxes & fees
Oct 28 - Oct 29
Aqua Lodges at Hurricane Hole Marina
A modern bathroom with a round mirror, a sink, and a bathtub.

2. 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.
The price is ￥27,032
￥48,175 total
includes taxes & fees
Oct 26 - Oct 27
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
A marina with multiple sailboats docked, clear skies, and calm water.

3. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
The price is ￥31,616
￥79,672 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Houseboat
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.
The price is ￥32,723
￥66,849 total
includes taxes & fees
Oct 26 - Oct 27
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

5. 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
The price is ￥33,434
￥81,560 total
includes taxes & fees
Oct 19 - Oct 20
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
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
The price is ￥28,454
￥61,414 total
includes taxes & fees
Oct 17 - Oct 18
Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle
A boat deck with a Yamaha outboard motor, a white railing, and a view of the water and distant shoreline.

7. 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
The price is ￥39,994
￥79,890 total
includes taxes & fees
Oct 19 - Oct 20
Docked in Paradise
A beach with lounge chairs, palm trees, and a water body.

8. 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.
The price is ￥39,520
￥89,039 total
includes taxes & fees
Oct 26 - Oct 27
Grand Marina Suite - Poolside & Waterfront Condo
A beachside resort with a wooden deck, palm trees, and a sunset view.

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
The price is ￥51,301
￥96,126 total
includes taxes & fees
Oct 26 - Oct 27
Grand Marina Suite by Brightwild Waterfront
A clear swimming pool with lounge chairs and palm trees.

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.
The price is ￥39,694
￥89,394 total
includes taxes & fees
Oct 20 - Oct 21
Slice of Paradise
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.
The price is ￥66,394
￥83,230 total
includes taxes & fees
Oct 21 - Oct 22
Living the Dream Key West Style
A living room with a ceiling fan, a TV mounted on the wall, and a sofa.

12. Poolside Paradise

Poolside Paradise
Stock Island
The price is ￥46,813
￥101,697 total
includes taxes & fees
Oct 18 - Oct 19
Poolside Paradise
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

13. 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.
The price is ￥42,682
￥92,912 total
includes taxes & fees
Oct 27 - Oct 28
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.

14. 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
The price is ￥47,266
￥69,655 total
includes taxes & fees
Oct 26 - Oct 27
Key West Sailboat Getaway
An aerial view of a resort with a central swimming pool surrounded by palm trees and sun loungers.

15. 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.
The price is ￥45,053
￥86,214 total
includes taxes & fees
Oct 19 - Oct 20
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min 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.
The price is ￥48,695
￥106,027 total
includes taxes & fees
Oct 27 - Oct 28
Waterfront & Heated Pool - Away Awai Floating Villa
A resort pool area with lounge chairs and palm trees, surrounded by resort buildings.

17. 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
The price is ￥39,520
￥79,672 total
includes taxes & fees
Oct 17 - Oct 18
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.

18. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
The price is ￥57,865
￥117,924 total
includes taxes & fees
Oct 29 - Oct 30
Waterfront & Heated Pool - Break Awai Floating Villa
A marina with several boats docked, a building with a flat roof, and a clear blue sky.

19. 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
The price is ￥53,067
￥106,809 total
includes taxes & fees
Oct 17 - Oct 18
3-bedroom catamaran with pool and beach access in amazing Key West!
A clear swimming pool with lounge chairs and palm trees.

20. 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.
The price is ￥65,311
￥122,172 total
includes taxes & fees
Oct 18 - Oct 19
Another Day in Paradise
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Staff was awesome."
Peena 1-night trip
Posted 1 hour ago
Southernmost Beach Resort and Guesthouses

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