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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Stock Island holiday homes

Property grounds

1. 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 HK$2,353
HK$7,604 total
includes taxes & fees
9 Aug - 10 Aug
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Outdoor pool

2. 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 HK$2,353
HK$4,710 total
includes taxes & fees
1 Sept - 2 Sept
Gone Coastal
Pool

3. 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 HK$2,040
HK$4,421 total
includes taxes & fees
4 Aug - 5 Aug
Slice of Paradise
Pool

4. 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 HK$2,580
HK$5,141 total
includes taxes & fees
1 Sept - 2 Sept
Paradise found
Pool

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 HK$2,110
HK$4,664 total
includes taxes & fees
15 Aug - 16 Aug
Another Day in Paradise
Pool

6. 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 HK$2,322
HK$4,723 total
includes taxes & fees
9 Aug - 10 Aug
Spacious 3-bedroom townhome on Stock Island with resort style pool.
Property grounds

7. Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach

Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
Stock Island
10.0 out of 10, Exceptional, (413 reviews)
"Great location - owner was flexible on check in/out. Would highly recommen."
United States
joe t.
The price is HK$4,228
HK$7,754 total
includes taxes & fees
5 Aug - 6 Aug
Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
Interior

8. 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 HK$3,578
HK$8,511 total
includes taxes & fees
10 Aug - 11 Aug
3-bedroom townhome in Key West with fitness room, WiFi
Outdoor dining

9. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (68 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
Poolside Cottage #411
Outdoor dining

10. 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 HK$1,451
HK$2,560 total
includes taxes & fees
1 Sept - 2 Sept
Poolside Cottage #412
Interior

11. Aug.-Sept. Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.

Aug.-Sept. Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.
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 HK$1,012
HK$2,479 total
includes taxes & fees
31 Aug - 1 Sept
Aug.-Sept. Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.
Terrace/patio

12. 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, (20 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is HK$1,441
HK$3,948 total
includes taxes & fees
4 Aug - 5 Aug
Road's End | Prime Old Town Location! Updated Home w/ Pool
Beach towels

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 HK$1,529
HK$4,664 total
includes taxes & fees
10 Aug - 11 Aug
Luxury two floor apartment in prime location of famous Duval Street
Beach nearby

14. Patio Lounge w/ Hot Tub • 1 Block to Duval St | Casita de Catherine by AvantStay

Patio Lounge w/ Hot Tub • 1 Block to Duval St | Casita de Catherine by AvantStay
Old Town Key West
9.8 out of 10, Exceptional, (63 reviews)
"great couples getaway for a first time visit to Key West!!"
United States
Joe C.
Patio Lounge w/ Hot Tub • 1 Block to Duval St | Casita de Catherine by AvantStay
A heated pool

15. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is HK$1,235
HK$4,338 total
includes taxes & fees
1 Sept - 2 Sept
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Exterior

16. SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is HK$1,561
HK$3,915 total
includes taxes & fees
20 Aug - 21 Aug
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
4 bedrooms, Internet

17. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is HK$8,179
HK$14,733 total
includes taxes & fees
9 Aug - 10 Aug
Capmar House by Brightwild Huge Home Pool
Coffee/tea maker, fridge, microwave, oven

18. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (125 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
The price is HK$1,708
HK$4,201 total
includes taxes & fees
9 Aug - 10 Aug
Kelly's Kabin - Adorable Private Summerland Key Cottage
A heated pool

19. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very good, (3 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is HK$1,359
HK$4,493 total
includes taxes & fees
1 Sept - 2 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Coffee/tea maker, fridge, microwave, oven

20. 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, (51 reviews)
"Great location, easy check-in/check-out process, house was clean and spacious, and the host was very communicative!"
United States
Lindsey R.
The price is HK$2,490
HK$7,294 total
includes taxes & fees
9 Aug - 10 Aug
Sea Esta Suite | Located On Iconic Duval w/ Pool
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"We had such a wonderful time at this property. It’s in a great location in front of the water and has an nice restaurant and bar. The pool was great and fun to be around. They only drawback is that there was so much seaweed in the little beach area that we weren’t able to sit by the water. But that wasn’t the properties fault at all. It’s just the way it is right now. The rooms were huge and very clean. I would definitely stay here again next time when I go to Key West."
tania 3-night trip
Posted less than an hour ago
Southernmost Beach Resort and Guesthouses

Find out more about Stock Island

Stock Island Vacation Homes information

Number of reviews
1,075
Accommodation
881 Vacation Homes
Lowest Price
HK$2,479
Highest Price
HK$14,733

Explore a world of travel with Expedia