A sunset over a coastal landscape with a small island surrounded by water.

Search Vacation Homes in Stock Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Stock Island vacation homes

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a building in the background.

1. Gone Coastal

Gone Coastal
Stock Island
9.6 out of 10, Exceptional, (22 reviews)
"Great place , clean and close to everything!"
United States
april
The price is ￥48,027
￥98,236 total
includes taxes & fees
Sep 1 - Sep 2
Gone Coastal
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

2. 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.
The price is ￥43,224
￥92,192 total
includes taxes & fees
Aug 31 - Sep 1
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A covered outdoor seating area with wicker furniture and a white table, overlooking a large tree and lush greenery.

3. TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
10.0 out of 10, Exceptional, (23 reviews)
"Great place nice and clean easy access to the pool short drive to the beach"
United States
Nathan W.
The price is ￥48,027
￥155,228 total
includes taxes & fees
Aug 31 - Sep 1
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
A clear swimming pool with lounge chairs and palm trees.

4. 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 ￥43,224
￥92,192 total
includes taxes & fees
Aug 31 - Sep 1
Slice of Paradise
A clear swimming pool with lounge chairs and palm trees.

5. Another Day in Paradise

Another Day in Paradise
Stock Island
9.4 out of 10, Exceptional, (3 reviews)
"Comfortable homey house."
United States
Wendi T.
The price is ￥47,867
￥101,078 total
includes taxes & fees
Sep 22 - Sep 23
Another Day in Paradise
A clear swimming pool surrounded by palm trees and lounge chairs.

6. 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.
The price is ￥52,670
￥106,220 total
includes taxes & fees
Sep 1 - Sep 2
Paradise found
A dining area with a wooden table, woven placemats, and a chandelier.

7. 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, (15 reviews)
"Great place for 3 couples. "
United States
Emily F.
The price is ￥82,847
￥185,415 total
includes taxes & fees
Aug 31 - Sep 1
3-bedroom townhome in Key West with fitness room, WiFi
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

8. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 reviews)
"We stayed here for our honeymoon and it was perfect. The place was clean and well appointed. The pool right outside was huge and we spent lots of time there. Highly recommend!"
United States
DeAnna Z.
The price is ￥26,655
￥47,337 total
includes taxes & fees
Sep 3 - Sep 4
Poolside Cottage #411
A wooden deck with a large tree, outdoor seating, and a marina in the background.

9. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (36 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is ￥26,655
￥48,298 total
includes taxes & fees
Sep 1 - Sep 2
Poolside Cottage #412
A kitchen with a refrigerator, stove, and two bar stools.

10. Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!

Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
The price is ￥17,146
￥46,026 total
includes taxes & fees
Aug 31 - Sep 1
Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
A building with a red door, a covered porch, and a bamboo plant in the foreground.

11. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (23 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is ￥24,302
￥74,421 total
includes taxes & fees
Aug 31 - Sep 1
Road's End | Prime Old Town Location! Updated Home w/ Pool
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

12. Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (53 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is ￥29,585
￥119,239 total
includes taxes & fees
Sep 1 - Sep 2
Sea Esta Suite | Located On Iconic Duval w/ Pool
An aerial view of a beach with clear turquoise waters, a sandy shore, and a cluster of umbrellas.

13. Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (103 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is ￥31,218
￥95,214 total
includes taxes & fees
Aug 31 - Sep 1
Luxury two floor apartment in prime location of famous Duval Street

14. Spindrift House at Lunara Bay

Spindrift House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (35 reviews)
"Great host!"
United States
Mario C.
The price is ￥95,894
￥229,190 total
includes taxes & fees
Sep 7 - Sep 8
Spindrift House at Lunara Bay
A wooden deck with a hanging hammock and a view of a green landscape.

15. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is ￥34,677
￥94,483 total
includes taxes & fees
Sep 15 - Sep 16
Starlight Serenity - Hideaway w Stunning Views

16. Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The Best VRBO I have stayed in "
United States
Wilbert C.
The price is ￥95,894
￥232,231 total
includes taxes & fees
Aug 31 - Sep 1
Capmar House at Lunara Bay
A patio area with wicker furniture and a grill.

17. Southernmost Retreat | On Duval! With Hot Tub, Patio

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.8 out of 10, Exceptional, (32 reviews)
"Awesome place great location communication with host was great would stay here again next time I’m in key west."
United States
Drew L.
The price is ￥47,371
￥152,135 total
includes taxes & fees
Aug 31 - Sep 1
Southernmost Retreat | On Duval! With Hot Tub, Patio

18. Mastway House at Lunara Bay - Wellness Home

Mastway House at Lunara Bay - Wellness Home
Raccoon Key
9.6 out of 10, Exceptional, (34 reviews)
"Even more beautiful than the pictures! Everything was perfect. "
United States
Elizabeth K.
The price is ￥95,894
￥227,109 total
includes taxes & fees
Sep 10 - Sep 11
Mastway House at Lunara Bay - Wellness Home

19. Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (45 reviews)
"Great communication….we have stayed here several times and will be back! "
United States
james f.
The price is ￥95,894
￥226,628 total
includes taxes & fees
Aug 31 - Sep 1
Aquaria House at Lunara Bay

20. The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (27 reviews)
"Great property, terrific hosts - amazing location!"
United States
Jason T.
The price is ￥95,894
￥226,148 total
includes taxes & fees
Aug 31 - Sep 1
The Seagate Estate at Lunara Bay
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stock Island Hotel Reviews

Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Todo Super bien; el personal que trabaja en la instalación te hacen sentir como en casa muy acogedor; tranquilo y un servicio increíble"
Lenier 1-night trip
Posted 13 hours ago
Ibis Bay Beach Resort

Find out more about Stock Island

Stock Island Vacation Homes information

Number of reviews
759
Accommodation
892 Vacation Homes
Lowest Price
￥46,026
Highest Price
￥232,231

Explore a world of travel with Expedia