Stock Island Vacation Rentals

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Our top choices for Stock Island vacation rentals

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, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$254 nightly
The price is $286
Nov 10 - Nov 11
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

2. Key West Sailboat Getaway

Key West Sailboat Getaway
Stock Island
9.6 out of 10, Exceptional, (4 reviews)
""Blown Away" is a wonderful option for travelers looking for a unique stay near Key West. David was a super helpful host. The boat was the perfect size for my friend and me to stay for the weekend. We really enjoyed the outside area on the boat and all the amenities in the marina. Definitely recommend Portside Bar and Grill for food close by. The shuttle from the front of the hotel was also great for exploring Duval."
United States
Caroline W.
$200 nightly
The price is $224
Nov 16 - Nov 17
Total with taxes and fees
Key West Sailboat Getaway

3. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
$398 nightly
The price is $446
Nov 10 - Nov 11
Total with taxes and fees
Cozy Houseboat

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, (15 reviews)
"6 of us stayed the weekend and it was great. The boat was clean and well stocked with many amenities. The hosts Glen and Abby were amazing. Anything we needed they were quick to oblige. They live on site so they are always there if needed. We are definitely returning next year."
United States
Darren
$258 nightly
The price is $289
Nov 10 - Nov 11
Total with taxes and fees
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

5. 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.
$330 nightly
The price is $369
Nov 11 - Nov 12
Total with taxes and fees
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown

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, (6 reviews)
"Everything was great!"
United States
Terri F.
$354 nightly
The price is $396
Nov 17 - Nov 18
Total with taxes and fees
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West

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

Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle
Stock Island
$313 nightly
The price is $350
Nov 10 - Nov 11
Total with taxes and fees
Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle

8. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (63 reviews)
"Great would definitely stay again "
United States
Zach C.
$463 nightly
The price is $518
Nov 11 - Nov 12
Total with taxes and fees
Living the Dream Key West Style

9. Docked in Paradise

Docked in Paradise
Stock Island
9.2 out of 10, Wonderful, (9 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
$531 nightly
The price is $594
Nov 12 - Nov 13
Total with taxes and fees
Docked in Paradise

10. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (5 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
$482 nightly
The price is $540
Nov 10 - Nov 11
Total with taxes and fees
Slice of Paradise

11. 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.
$556 nightly
The price is $619
Nov 30 - Dec 1
Total with taxes and fees
Waterfront & Heated Pool - Away Awai Floating Villa

12. 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.
$491 nightly
The price is $549
Nov 30 - Dec 1
Total with taxes and fees
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West

13. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (35 reviews)
"Great property but not very walkable but all good"
United States
CAROL K.
$557 nightly
The price is $620
Nov 16 - Nov 17
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo

14. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
$556 nightly
The price is $619
Nov 30 - Dec 1
Total with taxes and fees
Waterfront & Heated Pool - Break Awai Floating Villa

15. Poolside Paradise

Poolside Paradise
Stock Island
$511 nightly
The price is $573
Nov 16 - Nov 17
Total with taxes and fees
Poolside Paradise

16. 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, (9 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.
$518 nightly
The price is $579
Nov 23 - Nov 24
Total with taxes and fees
Spacious 3-bedroom townhome on Stock Island with resort style pool.

17. 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, (139 reviews)
"We had an awesome stay! We enjoyed being able to use the bikes and have covered parking, too. We would definitely stay here again!"
United States
Melanie K.
$502 nightly
The price is $559
Nov 10 - Nov 11
Total with taxes and fees
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

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
$419 nightly
The price is $469
Nov 10 - Nov 11
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

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
$561 nightly
The price is $628
Nov 10 - Nov 11
Total with taxes and fees
3-bedroom catamaran with pool and beach access in amazing Key West!

20. 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
$601 nightly
The price is $676
Nov 16 - Nov 17
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
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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