Find short term rentals in Stock Island, FL at the best prices
104 available short term rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Short term and Weekly rentals in Stock Island, FL
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.
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.
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.
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.
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.
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.
9.6 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.
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.
9.0 2 reviews
Stock Island, FL
19/09 – 18/12
$259/nighttotal: $23310 (90 )
Tropical Tee-time: 2br Townhome In Key West Golf Club With Two Shared Pools, Fitness Center, Dogs Ok
2 2
apartment , Key West
This Key West pet-friendly holiday home is conveniently located near the Key West Golf Club and a two-minute drive (approximately 1.6km) from the Key West Tropical Forest and Botanical Garden. The 75 square metre property offers two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, laundry facilities, Wi-Fi, air conditioning, a swimming pool, and a terrace – perfect for enjoying Key West's outdoor lifestyle.
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.
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
$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.
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
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.
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.
Best Stock Island, FL lodging with a balcony
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.
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
$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.
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.
Frequently Asked Questions about short term rentals in Stock Island, FL
What are the best short term rentals in Stock Island, FL?
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.
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
$294/nighttotal: $26460 (90 )
Cozy 2br 2ba W/pool - Parking - Close To Beaches
1 2
apartment , Key West
This Key West flat offers excellent access to Roosevelt Boulevard, placing it a short drive from Smathers Beach and Higgs Beach, with convenient links to US-1. This property accommodates four guests with two bathrooms, featuring a private balcony, a dedicated workspace, in-unit laundry, air conditioning, a communal swimming pool, and all-inclusive utilities.
Best Stock Island, FL lodging with laundry available
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.
9.6 5 reviews
Stock Island, FL
19/09 – 18/12
$435/nighttotal: $39150 (90 )
**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.
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.
9.6 4 reviews
Stock Island, FL
19/09 – 18/12
$288/nighttotal: $25920 (90 )
Renovated 2br/2ba Condo Pool Spa Tennis Walk To Smathers Beach!
2 2
apartment , Key West
This newly renovated two-bedroom, two-bathroom Key West condo is situated in the Salt Ponds community, a 1.6km walk from Smathers Beach and a short drive from Old Town, Ernest Hemingway Home and Museum, and Fort Zachary Taylor Historic State Park. The apartment, sleeping four guests, boasts a terrace, garden access, swimming pool, parking, and a fully equipped kitchen including a fridge, microwave, and dishwasher; this new listing offers a reduced rate.