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Compare 715 Vacation Homes in Stock Island with updated reviews, rates, and availability.

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Sunny days ahead
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
9.6 out of 10, Exceptional, (28)
"Location was good. No major complaints. Backyard was really nice. We would stay here again."
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
Welcome to island time!
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
9.8 out of 10, Exceptional, (58)
"Great stay minus the 5am rooster wake up calls! :) Overall a great place in an amazing location. "
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Welcome to OFF CALL
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
9.6 out of 10, Exceptional, (74)
"I would try this again "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Cozy living room furnishings
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
9.8 out of 10, Exceptional, (114)
"The cottage was perfect for two couples. Both bedrooms had attached bathrooms. Just a few houses down from Duval Street and a few blocks from the beach."
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Shared pool
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
9.0 out of 10, Wonderful, (66)
"Very quiet, clean, and overall great experience. I’ve been staying at properties in the Keys for over 20 years and this is one of the best experiences I have had."
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Grill up your fresh catch (Kayaks not included)
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
9.0 out of 10, Wonderful, (29)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Exterior
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
9.8 out of 10, Exceptional, (10)
"Property was clean with everything we needed, including linens and beach towels. Kitchen was fully equipped. The upstairs was a little too warm at night, but it was in the 90's every day during our stay, so we could understand this. One of the twin beds has a mattress that was very uncomfortable, and needs replaced. We have a vacation rental of our own and we were well pleased with this property. We would recommend! Thank you for the little longer checkout time, as the hurricane changed...
The price is SAR 2,254
SAR 5,451 total
includes taxes & fees
11 Nov - 12 Nov
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
9.0 out of 10, Wonderful, (183)
"Had a great time. Great location. Doesn’t provide more than one trash bag which was an issue we ran into. "
The price is SAR 1,251
SAR 2,735 total
includes taxes & fees
24 Nov - 25 Nov
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Poolside Cottage #411
Pool
Poolside Cottage #411
10.0 out of 10, Exceptional, (27)
"Nice STAY"
The price is SAR 661
SAR 1,192 total
includes taxes & fees
18 Nov - 19 Nov
Poolside Cottage #411
Poolside Cottage #412
Pool
Poolside Cottage #412
10.0 out of 10, Exceptional, (13)
"Nice place right by the pool."
The price is SAR 661
SAR 1,192 total
includes taxes & fees
18 Nov - 19 Nov
Poolside Cottage #412
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Plush linen
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
9.6 out of 10, Exceptional, (19)
"Absolutely stunning view. You can watch so many fish and other sea creatures just swimming by. Anything from Nurse Sharks to Parrot Fish. Even little Horse Shoe Crabs and blue crabs wonder by. The house is adorable and very cozy. It was perfect for coming home after a long day of fishing and exploring. And the hot tub was so wonderful. If you're looking for a little home by the water, I highly recommend this place. We will definitely come back again."
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
Soak up the island life
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
9.8 out of 10, Exceptional, (200)
"Enjoyed out stay at this beautiful property. I would definitely recommend to others. "
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
9.0 out of 10, Wonderful, (169)
"My sister and I rented the place for ourselves and our 4 young adult kids (ranging from 18-21), and we had a very nice time. The AC is not really "central", has free-standing units in 2 of the bedrooms that vent outside, but they are well installed and do the trick, if a bit tricky to regulate the temperature correctly initially. The place is a typical Key West bungalow that feels like some shoeboxes were nailed together, and the back yard is even smaller than expected. Location is great, we did...
The price is SAR 943
SAR 2,265 total
includes taxes & fees
18 Nov - 19 Nov
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Kelly's Kabin - Adorable Private Summerland Key Cottage
Aerial view of Kelly's Kabin.
Kelly's Kabin - Adorable Private Summerland Key Cottage
9.8 out of 10, Exceptional, (103)
"Fantastic little spot to stay if you want to be away from the Key West mobs but want to be close enough for a quick trip there. Finely equipped cottage with good parking and close to a few good places to eat. Very clean and enjoyable."
The price is SAR 1,033
SAR 2,272 total
includes taxes & fees
1 Dec - 2 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage
20 MINUTES TO KEY WEST , BOATERS PARADISE
Pool
20 MINUTES TO KEY WEST , BOATERS PARADISE
9.6 out of 10, Exceptional, (42)
"We enjoyed our stay. The resort area itself was nice and convenient for our needs. Communication with host was excellent. Any questions were promptly answered, as well as additional info to help us in the area. The property description is accurate. We'd be pleased to stay there again."
20 MINUTES TO KEY WEST , BOATERS PARADISE
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach
Dining Area
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach
9.0 out of 10, Wonderful, (150)
"A lovely, typical property located in Old Town area of Key West. Very comfortable stay, quiet ensuring good sleep. Great location and I did everything either by walking or on the bicycle I hired. Excellent communication with host who replied within a couple of hours if not sooner!!"
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Steps from Duval!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
9.8 out of 10, Exceptional, (168)
"Lively house accommodating the 6 of us very well, with a cozy pool in the backyard. Speedy response for any questions. Clean, comfortable and within a short walk of the Duval St. attractions."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Breathtaking views of our marina!
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
9.6 out of 10, Exceptional, (79)
"The stay was good. It was close enough to wedding venue. Few things wrong when we got there. My husband fixed the closet door because it would not open n shut also a door knob was about to fall off so he tightened it."
The price is SAR 747
SAR 1,868 total
includes taxes & fees
12 Nov - 13 Nov
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Cozy decor
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, (24)
"The coconut telegraph was a beautiful stilted home. It was very clean and decorated very nicely with light beachy colors. The best were very comfortable. Everything in the kitchen was functional. It was a great location. We kept our small boat at the dock The property management was very friendly. We were very happy with it and will stay there again.."
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
Varela St. downstairs front porch
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
9.6 out of 10, Exceptional, (198)
"We always love our stay at this location. Marilyn is a wonderful host and treats her return visitors very well. The place is located just a few blocks from anything you want to do in Key West, very cute and comfortable place, and meets our needs perfectly. We love the friendliness of the neighbors and the home is very well maintained. "
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
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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Other property types in Stock Island

Aqua Lodges at Hurricane Hole Marina
Exterior
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (104)
"Nice for affordable price "
The price is SAR 470
SAR 1,046 total
includes taxes & fees
12 Nov - 13 Nov
Aqua Lodges at Hurricane Hole Marina
40'yacht in Paradise Awaits You!
Miscellaneous
40'yacht in Paradise Awaits You!
9.4 out of 10, Exceptional, (25)
"Yacht was clean and well supplied. Included amenities of the resort which were great & convenient, especially the shuttle to downtown Key West. Will add this location to list of future trips."
40'yacht in Paradise Awaits You!
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Beach
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (13)
"BOOK THIS BOAT!!!’ TOP 10 vacations ever!!! Hannah was so accommodating and onboarded us to The Grand Admiral. Beautiful marina with easy access to The Perry hotel and bar, making it a very very comfortable stay. And then the excursion 😍!! Captain Jeff made our day exceptional. We encountered dolphins, lounged on the sandbar, and grilled while watching a breathtaking sunset. We will be making this an annual trip! Thank you Captain Jeff for the best day ever."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
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.