Compare Vacation Rentals & Airbnb in Stock Island, FL
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179 Rentals and Airbnb in Stock Island, FL
10 2 reviews
Stock Island, FL
19/09 – 18/12
$361/nighttotal: $32490 (90 )
One Bedroom Suite | Beachside Resort
1 2
apartment , Key West
This luxury resort in North Key West, situated on seven acres of waterfront, offers direct Gulf of Mexico views and is located 1.6 kilometres from Duval Street, placing it close to Florida Keys Beaches and Smathers Beach. This one-bedroom, two-bathroom apartment accommodates up to four guests and features a fully equipped kitchen with stainless-steel appliances, a private balcony, access to a heated swimming pool and hot tub, and is conveniently located near attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point.
9.7 2 reviews
Stock Island, FL
19/09 – 18/12
$305/nighttotal: $27450 (90 )
Monthly Availability Beginning May 2025
2 2
apartment , Key West
This property is situated in a gated community, a short 24-32 kilometre drive from Duval Street, offering a peaceful escape from the bustling centre of Key West. The property has received excellent ratings for cleanliness, location, and user experience. The two-bedroom home, spanning 92 square metres, comfortably accommodates four guests. The property boasts a range of amenities including a swimming pool, jacuzzi, and a fully equipped kitchen, alongside a fitness centre, parking, and a beautiful landscaped garden.
Stock Island, FL
19/09 – 18/12
$408/nighttotal: $36720 (90 )
The Tipsy Mermaid At Key West Golf Club
3 2
apartment , Key West
This two-storey townhome in the Key West Golf Club community is located directly on the fairway, offering convenient access to the Key West Golf Club and a short drive of approximately 1.6 kilometres to Old Town, the Ernest Hemingway Home and Museum, and the Southernmost Point. This dog-friendly accommodation spans 98 square metres and accommodates up to six guests, featuring three bedrooms, two bathrooms, a kitchen equipped with a fridge, microwave oven, and dishwasher, air conditioning, and access to two community swimming pools and a clubhouse gym, alongside multiple private outdoor spaces including a garden patio with lake views.
9.2 13 reviews
Stock Island, FL
19/09 – 18/12
$378/nighttotal: $34020 (90 )
It's A Salt Life After All At The Golf Club In Key West
2 2
apartment , Key West
This two-bedroom, two-bathroom flat offers convenient accommodation on Stock Island, situated 8 kilometres from the historic Old Town Key West attractions and 3.2 kilometres from local beaches. This property for six guests provides on-site swimming pools, a gym, parking for two vehicles, and a fully equipped kitchen, with washer/dryer facilities, pots, pans, towels, and linens included for a comfortable stay.
10 22 reviews
Stock Island, FL
19/09 – 18/12
$674/nighttotal: $60660 (90 )
Tortuga Hammock -2 Bedroom/ 2.5 Bathroom Townhouse With Shared Pool & Parking
2 2
apartment , Stock Island
This Stock Island holiday home is conveniently located within 2km of the Key West Tropical Forest and Botanical Garden, Lower Keys Medical Centre, and the Stock Island Yacht Club & Marina. This two-bedroom, three-bathroom property offers 99 square metres of living space, a private pool, free Wi-Fi, and parking, comfortably accommodating four guests and featuring a fully equipped kitchen and balcony.
9.5 279 reviews
Stock Island, FL
19/09 – 18/12
$452/nighttotal: $40680 (90 )
Pool View Suite | Beachside Resort
1 2
apartment , Key West
This one-bedroom apartment is situated in a resort complex on a 2.8-hectare site overlooking the Gulf of Mexico in Key West, just a short distance from Duval Street and the Southernmost Point. The apartment offers a king-size bed, a queen sleeper sofa, a fully equipped kitchen, a private washer/dryer, and a private balcony, as well as access to a 24-hour heated pool, hot tub, on-site marina, restaurant, and waterview fitness centre.
9.6 11 reviews
Stock Island, FL
19/09 – 18/12
$510/nighttotal: $45900 (90 )
A Sanctuary Home At The Key West Golf Club In Key West
3 2
apartment , Key West
This Key West holiday home is situated less than 1.6km from the Key West Golf Club and the Key West Tropical Forest & Botanical Garden, and within 1.6km of the Lower Keys Medical Center and Florida Keys Community College Library. The three-bedroom property, sleeping up to six guests with a sofa bed, boasts a private swimming pool, terrace, garden, parking, barbecue facilities, a washer/dryer, and is a smoke-free environment.
8.0 1 review
Stock Island, FL
19/09 – 18/12
$362/nighttotal: $32580 (90 )
Pool View Suite | Beachside Resort
1 2
apartment , Key West
This one-bedroom flat is located in north Key West, approximately a 10-minute drive from Duval Street and within easy reach of Florida Keys Beaches and Smathers Beach. This luxury resort condo offers accommodation for up to four guests, featuring a fully-equipped kitchen with stainless-steel appliances, a private balcony with resort pool views, and access to on-site amenities including a heated swimming pool and hot tub.
Stock Island, FL
19/09 – 18/12
$318/nighttotal: $28620 (90 )
Ocean Oasis At Sunset Marina-2 Bed 2 Bath Oceanfront Condo W/boat Slip Rental
2 2
apartment , Key West
This Key West oceanfront apartment, a short walk from the Key West Golf Club and Lower Keys Medical Center, and within 1.6km of the Florida Keys Community College Library and Tennessee Williams Fine Arts Center, offers stunning ocean views and easy beach access. This 109 square metre self-catering flat boasts two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, parking, and in-building laundry facilities.
Stock Island, FL
19/09 – 18/12
$289/nighttotal: $26010 (90 )
Joan's Caribbean Hideaway
2 2
apartment , Key West
This two-storey apartment, located in the Key West Golf Club, offers a peaceful setting just 1.6 kilometres from the dining and shopping of Downtown Key West and Duval Street. This accommodation sleeps four guests across two bedrooms, featuring a fully equipped kitchen, in-unit laundry, central air conditioning, and access to two communal swimming pools and a clubhouse.
9.4 3 reviews
Stock Island, FL
19/09 – 18/12
$420/nighttotal: $37800 (90 )
Golf Villa - Indulge Without Overpaying - 2bd/2bath - Large Open Pool
2 2
apartment , Key West
This Key West Golf Club flat offers excellent connectivity, being a short drive from Old Town Key West, the Tennessee Williams Fine Art Centre, and the Lower Keys Medical Centre, with the Ernest Hemingway Home and Museum, Southernmost Point, and Florida Keys Beaches all within easy reach. This two-bedroom, two-bathroom apartment accommodates four guests and boasts a fully equipped kitchen, air conditioning, a private balcony with golf course views, and access to shared amenities including two swimming pools and a fitness centre.
Stock Island, FL
19/09 – 18/12
$334/nighttotal: $30060 (90 )
Mariner's Oasis At Sunset Marina- 2bed 2 Bath Condo W/boat Slip For Rent
2 2
apartment , Key West
This Key West waterfront apartment, a short walk from the Key West Golf Club and Lower Keys Medical Center, and within 1.6km of the Florida Keys Community College Library and Key West Tropical Forest and Botanical Garden, offers stunning views. The 109 square metre property boasts two bedrooms, two bathrooms, sleeps four, and includes a full kitchen, washing machine, private balcony, swimming pool, jacuzzi, and concierge service.
Best family friendly Stock Island, FL vacation rentals
Among the 179 accommodations in Stock Island, FL, here are the 4 best family friendly rentals
Stock Island, FL
19/09 – 18/12
$286/nighttotal: $25740 (90 )
72 M² House ∙ 2 Bedrooms ∙ 4 Guests
2 2
house , Key West
This detached property is located on Stock Island, adjacent to the Key West Golf Club, offering direct views of the course and situated approximately 1.6 to 2.4 kilometres from Key West's main attractions. This family-friendly house accommodates up to four guests across two bedrooms and one bathroom, featuring air conditioning, a fully-equipped kitchen, a private patio, and access to two shared swimming pools, with AvantStay providing 24/7 support and optional services.
10 1 review
Stock Island, FL
19/09 – 18/12
$737/nighttotal: $66330 (90 )
40ft Sailboat, 3 Bdrm, 2 Bath, Sleeps Up To 6
3 2
houseboat , Stock Island
This luxury yacht, docked at Perry Marina on Stock Island, Key West, offers easy access via free shuttle to Key West's attractions such as the Ernest Hemingway Home and Museum and Smathers Beach, with the exact distances not specified. The 12-metre vessel boasts three staterooms, two bathrooms, sleeping up to six guests, and includes a kitchen with a fridge, air conditioning, and access to Perry Marina's pools, restaurants, fitness centre, and free parking.
9.4 17 reviews
Stock Island, FL
19/09 – 18/12
$741/nighttotal: $66690 (90 )
The Flight Deck - 3 Bedroom / 3 Bathroom With Shared Pool & Fitness Center!
3 2
apartment , Stock Island
This three-bedroom townhouse is situated in the Coral Hammock Community on Stock Island, just 6.4 kilometres from the centre of Key West. The property offers a private escape with a garden, a swimming pool, and a terrace, perfect for families or groups of up to six guests.
9.8 9 reviews
Stock Island, FL
19/09 – 18/12
$338/nighttotal: $30420 (90 )
The Guava Duff - Beautiful Kw Home With Space To Chill & Lots Of Free Parking!!
4 2
house , Stock Island
This Stock Island house, 4km from Key West International Airport, offers easy access to the Ernest Hemingway Home and Museum (7.6km) and Duval Street (7.7km). The 105 square metre property boasts four bedrooms, two bathrooms, a fully equipped kitchen, a jacuzzi, free bikes, and ample private parking, comfortably accommodating families or groups.
Best Stock Island, FL vacation rentals with a pool
Among the 179 accommodations in Stock Island, FL, here are the 4 best rentals with a pool
Stock Island, FL
19/09 – 18/12
$326/nighttotal: $29340 (90 )
Salt Ponds | Work & Relax In Key West | Poolside Condo Balcony Near Beach
2 2
apartment , Key West
This furnished condominium is located in the Salt Ponds community of Key West, a short drive from Old Town and Duval Street, and approximately 0.5 kilometers from Smathers Beach. This 72 square meter flat offers 2 bedrooms and 2 bathrooms for up to 4 guests, featuring a resort-style heated pool, Jacuzzi, private balcony, in-unit washer and dryer, and is ideal for stays of 28 days or more.
10 2 reviews
Stock Island, FL
19/09 – 18/12
$344/nighttotal: $30960 (90 )
Island Retreat - Key West
1 2
apartment , Key West
This Key West condo, situated in the Salt Ponds community, is a 1.6km walk from the beach and a short drive or cycle ride from Key West's Old Town. The two-bedroom, two-bathroom apartment sleeps four, boasts a newly renovated interior with all new furniture, a swimming pool, and parking, offering a peaceful retreat with a view of the salt ponds.
10 103 reviews
Stock Island, FL
19/09 – 18/12
$882/nighttotal: $79380 (90 )
Ocean Memories Condo- 2 Bedroom, 2 Bath Oceanfront W/ Pool & Hot Tub
2 2
apartment , Stock Island
This waterfront apartment is located on Stock Island, just 3.2 kilometres from the Stock Island Yacht Club & Marina and 4.8 kilometres from Key West Tropical Forest and Botanical Garden. The apartment offers a spacious 139 square metre living space with two bedrooms, two bathrooms, a balcony, and a fully equipped kitchen, comfortably accommodating up to four guests.
9.2 27 reviews
Stock Island, FL
19/09 – 18/12
$480/nighttotal: $43200 (90 )
Key Haven Retreat-4 Bedroom 3 Bath Canal Front Home W/private Pool, Boat Dock
4 2
apartment , Key West
This Key Haven waterfront house, offered as '30 Noches De Estancia Mínima Requisito. Asilo Clave Retreat - 4 Dormitorio Casa', is located in Key West, Florida, close to the Ernest Hemingway Home and Museum and the Southernmost Point. The 168 square metre (1804 sq ft) property features four bedrooms, three bathrooms, sleeping up to ten guests, a private pool, and a dock with boat and trailer parking; amenities include a kitchen with dishwasher, air conditioning, Wi-Fi, and in-unit laundry.
Frequently Asked Questions about vacation rentals in Stock Island, FL
What are some interesting places to visit in or near Stock Island, FL?
Stock Island itself is pretty small, but you're right next to Key West! You can easily visit the Ernest Hemingway Home and Museum, the Key West Butterfly and Nature Conservatory, or even take a sunset cruise. There's also the Southernmost Point of the Continental US, which is a popular photo op.
What are the best Airbnb and vacation rentals in Stock Island, FL?
Which walking or cycling routes are the best in Stock Island, FL?
There's a lovely walk or bike ride along the waterfront on the north side of Stock Island. You can also take the Old Town Trolley from Key West to Stock Island, which is a fun way to see the area.
What are the most popular Airbnbs in Stock Island, FL?
What sports or outdoor activites can visitors enjoy in and around Stock Island, FL?
Stock Island is a great place for fishing, kayaking, and paddleboarding. You can also rent jet skis and go for a spin around the waters. And of course, there's always swimming and sunbathing on the beaches.
What are the best vacation rentals with a pool in Stock Island, FL?
What time of year is best to rent a vacation rental Stock Island, FL?
The best time to visit is during the winter months, from November to April, when the weather is dry and sunny. But, if you want to avoid the crowds, you can visit during the shoulder season, from May to June or September to October.
What are the local dishes in Stock Island, FL region?
The Florida Keys are famous for their fresh seafood. Some local dishes include conch fritters, stone crab claws, and key lime pie. You can also find lots of great Cuban food in the area.
Destinations nearby
Best Stock Island, FL vacation rentals with a balcony
Stock Island, FL
19/09 – 18/12
$764/nighttotal: $68760 (90 )
Rare For Kw, Beautiful 3-bedroom House On Swimmable Water + Pool
3 2
apartment , Stock Island
This Stock Island holiday let offers oceanfront living, with Old Town Key West's museums and shops a mere 5-minute drive (approximately 8 kilometres) away. This spacious 3-bedroom house, accommodating up to 8 guests, boasts a private swimming pool, direct safe open water access from a private dock for swimming and watersports, and a separate den/rec room, with kayaks and a paddleboard provided.
9.4 3 reviews
Stock Island, FL
19/09 – 18/12
$566/nighttotal: $50940 (90 )
Seaside Escape- 2 Bed/2 Bath Condo With Shared Pool & Parking
2 2
apartment , Key West
This two-bedroom, two-bathroom condominium in the Sunrise Suites complex is located approximately 3.2 kilometres from Old Town Key West, offering a peaceful base near Smathers Beach and Key West International Airport. This third-floor end unit provides private lanai views of the tennis courts and access to a communal swimming pool, fitness facility, and on-site convenience store, accommodating up to six guests with a fully equipped kitchen and en-suite bathrooms.
Stock Island, FL
19/09 – 18/12
$446/nighttotal: $40140 (90 )
Cabana At The Golf Club-monthly Rental Charming 2-
2 2
apartment , Key West
This Key West Golf Club holiday home, a short drive from Key West's Old Town and its attractions including the Ernest Hemingway Home and Museum, offers a peaceful retreat. The 72-square-metre (775 sq ft) property features two bedrooms, two bathrooms, and sleeps six, boasting a private balcony, swimming pool access, and a fully equipped kitchen with modern appliances.
8.0 1 review
Stock Island, FL
19/09 – 18/12
$408/nighttotal: $36720 (90 )
Painted Sky~2 Br/2 Ba Waterfront Condo At Sunset Marina W/ Pool & Boat Slip!
2 2
apartment , Key West
This Key West seaside condo is situated a short walk from the Key West Golf Club and Lower Keys Medical Center, and within 1.6km of the Florida Keys Community College Library and the Tennessee Williams Fine Arts Center. This 95 square metre apartment sleeps six guests and boasts two bedrooms, two bathrooms, a fully equipped kitchen, private balcony, free Wi-Fi, swimming pool, Jacuzzi, tennis court, and concierge service.
Best Stock Island, FL vacation rentals with parking
Stock Island, FL
19/09 – 18/12
$655/nighttotal: $58950 (90 )
Waterfront Boater's Paradise On Deep Water Canal, Boat Dock, Ocean Access
4 2
apartment , Stock Island
This Stock Island waterfront bungalow, a 15-minute (24 km) drive from Key West's city centre, offers direct ocean access via a deep-water canal with a private dock. The four-bedroom, two-bathroom houseboat sleeps eight guests and features kayaks, paddleboards, a barbecue, and outdoor shower; enjoy easy access to local shops and restaurants.
9.2 10 reviews
Stock Island, FL
19/09 – 18/12
$452/nighttotal: $40680 (90 )
A Palm Tree Paradise @ The Key West Golf Club
2 2
apartment , Key West
This two-bedroom apartment is situated on the only 18-hole golf course in the Florida Keys, just a short drive from Key West’s famous attractions like Ernest Hemingway Home and Museum, Fort Zachary Taylor Historic State Park, and Smathers Beach. The apartment has received excellent reviews from previous guests, highlighting its peaceful and secluded setting. The apartment features an open-plan living area downstairs, ideal for families or groups of up to four. Guests can enjoy a range of amenities including two swimming pools, a gym, and ample parking, as well as access to the golf course.
8.8 5 reviews
Stock Island, FL
19/09 – 18/12
$256/nighttotal: $23040 (90 )
2 Bedroom Town Home In A Gated Community With A Resort Sytle Pool.
2 2
apartment , Key West
This two-storey townhouse, part of the '2 Bedroom Town Home In A Gated Community With A Resort Style Pool' offer, is located within the Key West Golf Club, a short drive (a few kilometres) from Key West's Duval Street and its attractions. The 72-square-metre property features two queen-sized bedrooms, two bathrooms, and accommodates four guests; amenities include a fully equipped kitchen, two community pools, a fitness centre, and interim housekeeping.
10 8 reviews
Stock Island, FL
19/09 – 18/12
$154/nighttotal: $13860 (90 )
Uptown Quiet Cottage Close To Beaches, Restaurant & Shopping.
1 2
cottage , Key West
This charming cottage is situated in the New Town neighbourhood of Key West, just a short distance from the lively downtown area and within easy reach of attractions such as the Ernest Hemingway Home and Museum. It has received excellent ratings from previous guests. The cottage has one bedroom and one bathroom, comfortably accommodating two guests. It offers a range of amenities, including a private swimming pool, a garden, and off-street parking, perfect for enjoying a relaxing stay in Key West.