Stock Island Vacation Rentals

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Vacation Rentals in Stock Island

Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (86)
"Aqualodges was a unique, great experience. Really enjoyed the marine life right at our dock. The accommodations were clean and comfortable. Cant wait to come back! "
The price is CA $244
CA $466 total
includes taxes & fees
May 28 - May 29
Aqua Lodges at Hurricane Hole Marina
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (9)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Outdoor dining
52' Power Catamaran Yacht at Luxury Resort Marina
10.0 out of 10, Exceptional, (11)
"We had a great time about Blue Jeans! Louie is an amazing host, as responsive as possible, also took us out for a cruise around Key West, AC works great! Easy Golf kart ride from the marina to down town key west. Pool at the marina was nice as well."
52' Power Catamaran Yacht at Luxury Resort Marina
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Property grounds
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, (17)
"Great property, great views on the water."
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Property grounds
40'yacht in Paradise Awaits You!
9.6 out of 10, Exceptional, (23)
"We had a really nice couple of days on this boat. We are older (over 60), and we weren't sure if it was going to be our thing. It was good though! The host was amazingly helpful. We loved the private beach and pool right around the corner. We have been to Key West a lot, so we didn't need to do all the tourist stuff. We mostly stayed on Stock Island. It was easy to get Ubers, so we didn't bother with a car or golf cart. If we were staying longer, we probably would have rented a golf cart. The...
40'yacht in Paradise Awaits You!
Fridge, microwave, oven, stovetop
LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!
10.0 out of 10, Exceptional, (75)
"The boat was clean and comfortable for our 3 night stay. The staff was top notch."
LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!
Outdoor pool, a heated pool
Luxury 62' Yacht! In a Beautiful Resort
10.0 out of 10, Exceptional, (6)
"Everything was great and we would love to visit again!"
Luxury 62' Yacht! In a Beautiful Resort
Property grounds
Key West Classic Yacht Charter
9.0 out of 10, Wonderful, (7)
"very cool experience! beautiful boat, surprising amount of room. we only had a brief overnight stay, but it was one of the highlights of our trip."
Key West Classic Yacht Charter
Property grounds
Casa Capri Beautiful Tropical style house with 3 King Suites POOL 2 mi to BEACH
10.0 out of 10, Exceptional, (226)
"beautiful property"
Casa Capri Beautiful Tropical style house with 3 King Suites POOL 2 mi to BEACH
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
The price is CA $189
CA $396 total
includes taxes & fees
Jun 20 - Jun 21
Steps from Duval, Pool & Bikes $129-$299 Night!
Sun loungers, beach towels
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
9.2 out of 10, Wonderful, (227)
"This property is no frills but provides everything you need. The location is great, the two room split provides privacy, pool was great and the bikes provided allow for cruising around the island. Tanya was very responsive. Would stay here again."
The price is CA $407
CA $793 total
includes taxes & fees
Jun 10 - Jun 11
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is CA $294
CA $503 total
includes taxes & fees
Jun 12 - Jun 13
Poolside Cottage #411
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (190)
"The house location was absolutely amazing. Everything was top notch. I would recommend this house over and over again, the back yard is so tranquil and the layouts of the room worked out well for bigger parties."
The price is CA $952
CA $2,071 total
includes taxes & fees
May 22 - May 23
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (102)
"Beautiful property in a great location. I would definitely stay again."
The price is CA $165
CA $381 total
includes taxes & fees
May 22 - May 23
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (258)
"This property and host exceeded all of our expectations. It was spacious, comfortable, and welcoming with its amazing kitchen, breezy rooms, and friendly neighbors. The hosts were a pleasure to work with and easy to reach whenever we wished to communicate with them. 10/10 would return to this property. I highly recommend it!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (25)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Fridge, microwave, coffee/tea maker, dining tables
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, (92)
"We absolutely loved this VRBO. We walked everywhere we wanted to go and it was conveniently located. If we come back to Key West we will try and stay here again. Only downfall--bathroom size. We were never in our room anyway so it was not a big issue"
The price is CA $159
CA $373 total
includes taxes & fees
May 22 - May 23
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
Property grounds
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
9.8 out of 10, Exceptional, (104)
"Excellent top drawer"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Property grounds
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
9.0 out of 10, Wonderful, (214)
"Very enjoyable"
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (199)
"Close to everything but just far enough away to be quiet and relaxing. Cute little house. Very walkable location."
The price is CA $272
CA $668 total
includes taxes & fees
May 22 - May 23
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Don't see what you're looking for?
See all available properties in Stock Island
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.

Stock Island Vacation Rental Travel Info

Other types of properties in Stock Island you may be interested in

View from property
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1506)
"good"
The price is CA $261
CA $373 total
includes taxes & fees
Jun 10 - Jun 11
Oceans Edge Key West Resort, Hotel & Marina
Lobby sitting area
The Perry Hotel & Marina Key West
4.0 star property
9.4 out of 10, Exceptional, (1001)
"Beautiful hotel… Service was great! Really enjoyed our stay. "
The price is CA $300
CA $417 total
includes taxes & fees
May 27 - May 28
The Perry Hotel & Marina Key West
Outdoor pool, sun loungers
Havana Cabana at Key West - Adults Only
4.0 star property
8.8 out of 10, Excellent, (1450)
"We enjoyed our stay at Havana Cabana! Loved the pool and the atmosphere!"
The price is CA $249
CA $368 total
includes taxes & fees
Jun 10 - Jun 11
Havana Cabana at Key West - Adults Only
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Stock Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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