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

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Our top choices for Stock Island vacation 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 AED 1,469
AED 2,762 total
includes taxes & fees
12 Oct - 13 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

2. 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

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.
Slice of Paradise

4. Gone Coastal

Gone Coastal
Stock Island
9.6 out of 10, Exceptional, (22 reviews)
"Great place , clean and close to everything!"
United States
april
Gone Coastal

5. 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.
Spacious 3-bedroom townhome on Stock Island with resort style pool.

6. 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.
Paradise found

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 AED 1,928
AED 4,197 total
includes taxes & fees
12 Oct - 13 Oct
3-bedroom townhome in Key West with fitness room, WiFi

8. Poolside Paradise

Poolside Paradise
Stock Island
Poolside Paradise

9. 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.
Poolside Cottage #411

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.
Poolside Cottage #412

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

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 AED 683
AED 2,722 total
includes taxes & fees
13 Sep - 14 Sep
Sea Esta Suite | Located On Iconic Duval w/ Pool

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 AED 716
AED 2,162 total
includes taxes & fees
28 Sep - 29 Sep
Luxury two floor apartment in prime location of famous Duval Street

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (96 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is AED 474
AED 1,493 total
includes taxes & fees
13 Sep - 14 Sep
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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 AED 579
AED 2,025 total
includes taxes & fees
12 Sep - 13 Sep
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

16. 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 AED 636
AED 2,086 total
includes taxes & fees
13 Sep - 14 Sep
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (111 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is AED 474
AED 1,493 total
includes taxes & fees
13 Sep - 14 Sep
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

18. 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 Seagate Estate at Lunara Bay

19. 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.
Capmar House at Lunara Bay

20. 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.
Southernmost Retreat | On Duval! With Hot Tub, Patio
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

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