Find short term rentals in Stock Island, FL at the best prices
104 available short term rental offers
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Best Short term and Weekly rentals in Stock Island, FL
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.
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.
9.6 90 reviews
Stock Island, FL
19/09 – 18/12
$451/nighttotal: $40590 (90 )
One Bedroom Suite | Beachside Resort
1 2
apartment , Key West
This Key West Beachside Resort condo, situated directly on the Gulf of Mexico, offers stunning Gulf views from its private balcony. The one-bedroom apartment, sleeping up to four guests with a king bed and queen sleeper sofa, boasts a fully equipped kitchen, private washer/dryer, and access to a heated pool, hot tub, fitness centre, and on-site marina; bookable sandbar or sunset cruises enhance your stay.
10 7 reviews
Stock Island, FL
19/09 – 18/12
$320/nighttotal: $28800 (90 )
Tropical Townhome On Golf Course
1 2
apartment , Key West
This Key West golf course townhome, situated within the Key West Golf Club, is minutes' drive from Key West's downtown area and beaches. The spacious two-storey property boasts two bedrooms, two bathrooms, and sleeps four guests comfortably, offering a fully equipped kitchen, multiple outdoor living spaces, and stunning 17th fairway views.
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.
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.
10 3 reviews
Stock Island, FL
19/09 – 18/12
$342/nighttotal: $30780 (90 )
Perfectly Poolside In Kwgolfclub
1 2
apartment , Key West
This townhome is located in the Key West Golf Club, a gated community, and is a short walk to the golf course and approximately 3 kilometres from Old Town Key West. This fully furnished apartment accommodates up to six guests and features a lagoon-style swimming pool with a waterfall accessible from the private patio, along with a kitchen equipped with a fridge, freezer, microwave, and dishwasher.
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.
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.
Stock Island, FL
19/09 – 18/12
$360/nighttotal: $32400 (90 )
Poolside Suite With Direct Pool Access
1 2
apartment , Key West
This Key West condo, located in the north of the island, offers direct access to the Gulf of Mexico and is situated just 1.6 kilometres from Duval Street. This one-bedroom apartment accommodates up to four guests and features a private balcony with pool views, a fully-equipped kitchen, air conditioning, internet, and access to an on-site heated swimming pool and hot tub, with complimentary shuttle service to local attractions.
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.
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.
Best family friendly Stock Island, FL Short term rentals
Among the 104 accommodations in Stock Island, FL, here are the 2 best family friendly rentals
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.
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.
Best Stock Island, FL lodging with a balcony
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.
10 1 review
Stock Island, FL
19/09 – 18/12
$497/nighttotal: $44730 (90 )
Island Time On The Green At Key West Golf Club
2 2
apartment , Key West
This townhome is situated within the exclusive Key West Golf Club gated community, offering 24-hour security and direct access to community pools, just minutes from Historic Old Town, Duval Street, and Mallory Square. This 84 square meter residence accommodates four guests in two bedroom suites, boasting a fully equipped kitchen, an oversized porch, and a landscaped backyard with a gas grill, all overlooking the Key West Golf Club.
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.
9.6 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.
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**Sunset Dreams @ Sunset Marina** Condo / Pool & Spa + Last Key Services...
3 2
apartment , Key West
This apartment is located just 1.6km from Key West Golf Club and 4km from Smathers Beach, offering a convenient base for exploring the island. It has received excellent ratings from previous guests. This spacious three-bedroom apartment, covering 154 square metres and accommodating up to eight guests, provides ample space for a comfortable stay. It features a fully equipped kitchen, a private terrace, a swimming pool, a jacuzzi, and a spa, ensuring a relaxing and enjoyable experience.
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.
9.7 57 reviews
Stock Island, FL
19/09 – 18/12
$463/nighttotal: $41670 (90 )
"Hemingway" 1 Bedroom At Leo's
1 2
apartment , Stock Island
This Stock Island apartment, situated two blocks from the Key West entrance, offers easy access to Key West's attractions via bicycle, scooter, or golf cart. The one-bedroom flat, located within Leo's RV Park, sleeps two guests and includes a kitchen with fridge and microwave, air conditioning, parking, and access to on-site recreational facilities such as ping pong, chess, and billiards, plus relaxing Tiki Huts.
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.
Best Stock Island, FL lodging with laundry available
Stock Island, FL
19/09 – 18/12
$286/nighttotal: $25740 (90 )
Paradise Point By Avantstay | Golf Course Living
2 2
apartment , Key West
This Key West holiday home is situated less than 1.6km from both the Key West Golf Club and the Key West Tropical Forest and Botanical Garden. The 72 square metre property offers two bedrooms sleeping four, a fully equipped kitchen with fridge, freezer, and dishwasher, a private balcony, swimming pool, and free Wi-Fi; it's also within a mile of the Lower Keys Medical Center and Florida Keys Community College Library.
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 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.
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.