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

Holiday 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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Stock Island holiday homes

1. 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, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is €460
includes taxes & fees
27 Sept - 28 Sept
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

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 €485
includes taxes & fees
6 Oct - 7 Oct
Spacious 3-bedroom townhome on Stock Island with resort style pool.

3. 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.
Another Day in Paradise

4. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (39 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is €582
includes taxes & fees
29 Sept - 30 Sept
Paradise found

5. 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 €561
includes taxes & fees
4 Oct - 5 Oct
Slice of Paradise

6. Poolside Paradise

Poolside Paradise
Stock Island
Poolside Paradise

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, (16 reviews)
"Great place for 3 couples. "
United States
Emily F.
The price is €942
includes taxes & fees
27 Sept - 28 Sept
3-bedroom townhome in Key West with fitness room, WiFi

8. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is €265
includes taxes & fees
25 Sept - 26 Sept
Poolside Cottage #411

9. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is €276
includes taxes & fees
18 Oct - 19 Oct
Poolside Cottage #412

10. 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, (24 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is €396
includes taxes & fees
26 Sept - 27 Sept
Road's End | Prime Old Town Location! Updated Home w/ Pool

11. 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 €665
includes taxes & fees
2 Oct - 3 Oct
Sea Esta Suite | Located On Iconic Duval w/ Pool

12. 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.
Luxury two floor apartment in prime location of famous Duval Street

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (96 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is €345
includes taxes & fees
27 Sept - 28 Sept
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

14. 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 €398
includes taxes & fees
25 Sept - 26 Sept
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

15. 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 €1,271
includes taxes & fees
27 Sept - 28 Sept
Capmar House at Lunara Bay

16. 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 €1,406
includes taxes & fees
7 Oct - 8 Oct
Capmar House by Brightwild Huge Home Pool

17. 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 €422
includes taxes & fees
26 Sept - 27 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.6 out of 10, Exceptional, (33 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 €830
includes taxes & fees
28 Sept - 29 Sept
Southernmost Retreat | On Duval! With Hot Tub, Patio

19. Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate at Lunara Bay | Wellness Home
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
The price is €1,224
includes taxes & fees
30 Sept - 1 Oct
Evershore Estate at Lunara Bay | Wellness Home

20. The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (28 reviews)
"Great property, terrific hosts - amazing location!"
United States
Jason T.
The price is €1,271
includes taxes & fees
28 Sept - 29 Sept
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Stock Island Hotel Reviews

Find out more about Stock Island

Stock Island Holiday Homes information

Number of reviews
600
Accommodation
892 Holiday Homes
Lowest Price
€265
Highest Price
€1,406

Explore a world of travel with Expedia