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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Stock Island vacation homes

A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

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 ￥51,902
￥99,125 total
includes taxes & fees
Oct 7 - Oct 8
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
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 ￥42,466
￥85,227 total
includes taxes & fees
Oct 6 - Oct 7
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A clear swimming pool with lounge chairs and palm trees.

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.
The price is ￥42,324
￥87,723 total
includes taxes & fees
Sep 30 - Oct 1
Another Day in Paradise
A kitchen with white cabinets, a dishwasher, a coffee maker, and a window with blinds.

4. Poolside Paradise

Poolside Paradise
Stock Island
The price is ￥46,571
￥97,553 total
includes taxes & fees
Sep 27 - Sep 28
Poolside Paradise
A clear swimming pool with lounge chairs and palm trees.

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 ￥49,402
￥93,503 total
includes taxes & fees
Oct 7 - Oct 8
Slice of 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, (39 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
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, (16 reviews)
"Great place for 3 couples. "
United States
Emily F.
The price is ￥74,315
￥163,032 total
includes taxes & fees
Oct 1 - Oct 2
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, (70 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 ￥26,187
￥45,877 total
includes taxes & fees
Sep 27 - Sep 28
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, (37 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is ￥28,594
￥48,584 total
includes taxes & fees
Oct 10 - Oct 11
Poolside Cottage #412
A building with a red door, a covered porch, and a bamboo plant in the foreground.

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 ￥22,145
￥66,411 total
includes taxes & fees
Sep 27 - Sep 28
Road's End | Prime Old Town Location! Updated Home w/ Pool
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

11. 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 ￥30,670
￥87,881 total
includes taxes & fees
Sep 28 - Sep 29
Luxury two floor apartment in prime location of famous Duval Street
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 ￥34,256
￥117,278 total
includes taxes & fees
Oct 26 - Oct 27
Sea Esta Suite | Located On Iconic Duval w/ Pool
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (97 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is ￥20,479
￥61,516 total
includes taxes & fees
Sep 29 - Sep 30
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

14. 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 ￥94,211
￥217,460 total
includes taxes & fees
Sep 27 - Sep 28
Capmar House at Lunara Bay
A patio area with wicker furniture and a grill.

15. 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 ￥46,366
￥139,970 total
includes taxes & fees
Oct 4 - Oct 5
Southernmost Retreat | On Duval! With Hot Tub, Patio

16. 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 ￥24,772
￥67,760 total
includes taxes & fees
Sep 27 - Sep 28
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

17. 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 ￥94,211
￥217,303 total
includes taxes & fees
Sep 28 - Sep 29
The Seagate Estate at Lunara Bay
A wooden deck with a railing, wicker chairs, and a view of greenery.

18. 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 ￥34,399
￥96,116 total
includes taxes & fees
Sep 30 - Oct 1
Starlight Serenity - Hideaway w Stunning Views

19. Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"Loved the property and the location!! It was perfect for me and the family. Short commute to everything we needed and wanted. I can't wait to go back for the next visit!!"
United States
Chris H.
The price is ￥94,211
￥217,460 total
includes taxes & fees
Sep 27 - Sep 28
Aquaria House at Lunara Bay

20. 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 ￥94,211
￥217,460 total
includes taxes & fees
Sep 28 - Sep 29
Spindrift House 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.
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Top Stock Island Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"We loved the resort except the largest pool was closed for the first three days of our stay. That made the others two smaller pools very very crowded."
Maria 4-night trip
Posted 1 hour ago
Southernmost Beach Resort and Guesthouses

Find out more about Stock Island

Stock Island Vacation Homes information

Number of reviews
747
Accommodation
892 Vacation Homes
Lowest Price
￥45,877
Highest Price
￥217,460

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