Compare Vacation Rentals & Airbnb in Stock Island, FL
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179 Rentals and Airbnb in Stock Island, FL
10 135 reviews
Stock Island, FL
23/10 – 31/10
$1052/nighttotal: $8416 (8 )
Gorgeous Ocean View In Paradise, Close To Key West
3 2
apartment , Stock Island
This Stock Island apartment, offering ocean and mangrove sunrise views from a private balcony, is conveniently located near Key West's downtown area, allowing easy access to its shops, restaurants, and historical sites. The 125 square metre (1352 sq ft) property features three bedrooms, two bathrooms, and a full kitchen including a dishwasher, accommodating up to six guests and boasting a shared swimming pool, jacuzzi, and on-site Yellowfin Bar & Kitchen.
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.
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.
8.7 4748 reviews
Stock Island, FL
23/10 – 31/10
$524/nighttotal: $4192 (8 )
Oceans Edge Key West
1 2
resort , Stock Island
Oceans Edge Key West is located on Stock Island, a short 3 km drive from Key West International Airport and 8 km from the Southernmost Point. The resort has received very good ratings for its location, cleanliness and overall experience. The resort offers a range of rooms and suites, all with flat-screen TVs and private bathrooms. Guests can enjoy a variety of amenities, including multiple swimming pools, a waterfront bar and restaurant, a marina, a spa, and a fitness centre.
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.
9.7 57 reviews
Stock Island, FL
23/10 – 31/10
$507/nighttotal: $4056 (8 )
"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.
9.8 42 reviews
Stock Island, FL
23/10 – 31/10
$449/nighttotal: $3592 (8 )
Stella On Stock Island
1 2
barge , Stock Island
This Stock Island houseboat offers waterfront living, conveniently located near Stock Island's attractions; precise distances to specific landmarks require further clarification. The one-bedroom, one-bathroom vessel sleeps four, featuring a fully equipped kitchen, air conditioning, and a private garden; wet slip dockage at 3D Boatyard is available (subject to availability).
Stock Island, FL
23/10 – 31/10
$474/nighttotal: $3792 (8 )
Cozy Houseboat
1 2
houseboat , Stock Island
Stella on Stock Island, a floating home in Key West, offers a tranquil waterfront location within walking distance of the Perry Hotel and its amenities, providing easy access to Stock Island's attractions. This one-bedroom houseboat sleeps four, featuring a queen bed, sofa bed, fully equipped kitchen, modern bathroom, and internet access; nearby attractions include the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
9.8 160 reviews
Stock Island, FL
23/10 – 31/10
$771/nighttotal: $6168 (8 )
Oceanfront Marina Condo With All Luxuries
3 2
apartment , Stock Island
This Stock Island oceanfront condo, near Smathers Beach and a short distance from Key West attractions such as the Ernest Hemingway Home and Museum and Fort Zachary Taylor, offers stunning panoramic ocean views. This 130 square metre (1,400 square foot) property boasts three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, private terrace, swimming pool, jacuzzi, parking, and access to boat slips and water sports rentals.
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.
9.7 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
$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.
Best family friendly Stock Island, FL vacation rentals
Among the 179 accommodations in Stock Island, FL, here are the 4 best family friendly rentals
9.2 2522 reviews
Stock Island, FL
23/10 – 31/10
$442/nighttotal: $3536 (8 )
The Perry Hotel & Marina Key West
1 2
resort , Stock Island
The Perry Hotel & Marina Key West is located on Stock Island, just 8km from Key West's Old Town and 5km from Key West International Airport. It has excellent user ratings, with particularly high marks for cleanliness and location. The hotel has a waterfront setting with two pools and direct marina access. Guests can enjoy a range of amenities, including restaurants, a spa, a fitness centre, tennis courts, and complimentary shuttle service to Old Town.
Stock Island, FL
23/10 – 31/10
$4634/nighttotal: $37072 (8 )
Apartment ∙ 8 Bedrooms ∙ 16 Guests
8 2
apartment , Key West
This detached house is located in a gated community in Key Haven/Stock Island, offering convenient access to public boat ramps and local rentals, with straightforward travel options by car, boat, or plane. This eight-bedroom, eight-bathroom residence accommodates up to sixteen guests, featuring spacious indoor and outdoor living areas, a fully equipped kitchen, private washer/dryer, and is pet-friendly for animals under 18kg, with a dedicated Guest Experience Manager available to arrange private boat excursions and chauffeur services.
Stock Island, FL
23/10 – 31/10
$2621/nighttotal: $20968 (8 )
Apartment ∙ 4 Bedrooms ∙ 10 Guests
4 2
apartment , Key West
Springtide House, a four-bedroom Key West property, is located in a gated community near Key Haven and Stock Island, offering convenient access to public boat ramps. This spacious residence sleeps ten guests, boasting four king-size beds, a sleeper sofa, a fully equipped kitchen, private washer/dryer, high-speed internet, a fenced yard, gated dock access, driveway parking for up to four vehicles and a boat trailer, and complimentary access to the FYT gym; private boat excursions and chauffeur services are also available.
9.8 5 reviews
Stock Island, FL
23/10 – 31/10
$614/nighttotal: $4912 (8 )
Keys Livin - Yacht Rental
1 2
apartment , Stock Island
This Key West apartment is ideally situated less than 0.5 km from Mallory Square and 0.8 km from Duval Street, offering easy access to Key West Aquarium, Mallory Dock, and the Curry Mansion Museum. Sleeping up to 11 guests, this self-catering property boasts one bedroom, four bathrooms, free Wi-Fi, private parking, a fully equipped kitchen including an oven and microwave, and a washing machine; enjoy sea views from the outdoor dining area.
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
9.9 26 reviews
Stock Island, FL
23/10 – 31/10
$678/nighttotal: $5424 (8 )
Casa Caribe 2bed2bath Sleeps 6 Beautiful Decorated
1 2
apartment , Stock Island
This Stock Island apartment, conveniently located in [Insert Specific District/Area of Stock Island, if known; otherwise remove this section], offers a two-bedroom, two-bathroom dwelling sleeping up to six guests. The 2-bedroom flat boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a swimming pool, fitness centre, parking, and internet access; further details on proximity to Stock Island's beaches and marinas are unavailable.
9.2 122 reviews
Stock Island, FL
23/10 – 31/10
$680/nighttotal: $5440 (8 )
Stay At Sunrise Suites 203!
2 2
apartment , Key West
This Key West condo is situated 1.9 km from Smathers Beach and 1.9 km from the Fort East Martello Museum and Gallery, with other attractions such as the Key West Art & Historical Society within a 3.2 km radius. This 74 square metre, two-bedroom, two-bathroom apartment sleeps six, offering a fully equipped kitchen, private balcony, in-unit laundry, swimming pool, jacuzzi, fitness centre and spa access.
10 11 reviews
Stock Island, FL
23/10 – 31/10
$597/nighttotal: $4776 (8 )
Strictly Pleasure | Unique Yacht Stay In The Keys
1 2
barge , Stock Island
This uniquely docked yacht, Strictly Pleasure, is situated at Perry Marina in Stock Island, offering marina views and convenient access to downtown Key West, approximately 8 kilometres away, via the local trolley service. This pet-friendly accommodation provides two bedrooms, two bathrooms, and can host up to four guests, featuring a galley kitchen with a fridge, freezer, and microwave, air conditioning, a swimming pool, garden, and fitness centre, with parking available directly in front of the vessel.
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.
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
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.
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.
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.
8.0 1 review
Stock Island, FL
19/09 – 18/12
$610/nighttotal: $54900 (90 )
A Key West State Of Mind At The Key West Golf Club
3 2
apartment , Key West
This four-bedroom, three-bathroom townhome is located within the gated Key West Golf Club Community, a short 2.2-kilometre drive from the Ernest Hemingway Home and Museum and 2.7 kilometres from the Southernmost Point. This property sleeps eight guests and offers a screened porch, a fully equipped kitchen with a gas grill, air conditioning, Wi-Fi, and access to community swimming pools and a gym.
Best Stock Island, FL vacation rentals with parking
8.8 124 reviews
Stock Island, FL
23/10 – 31/10
$663/nighttotal: $5304 (8 )
Cozy Dog-friendly Condo W/ Shared Pool, Hot Tub, Private Deck & Parking
2 2
apartment , Key West
This Key West condo is located near the sea, approximately 5.6 kilometres from Old Town and Duval Street, and within 6.4 kilometres of Mallory Square and Fort Zachary Taylor. This 72 square metre apartment offers two bedrooms, two bathrooms, and accommodates up to six guests, featuring resort-style amenities including a heated swimming pool, hot tub, tennis courts, and a fitness centre, with a private deck providing tropical views and dog-friendly accommodation available for a nightly fee.
9.8 20 reviews
Stock Island, FL
19/09 – 18/12
$930/nighttotal: $83700 (90 )
3-bedroom Ocean View Condo In Delightful Key West With Wifi, Ac
3 2
apartment , Stock Island
This three-bedroom, two-bathroom apartment in Key West, Stock Island, is situated directly above Oceanside Marina, offering immediate access to wet slip rentals and the Yellowfin Bar and Grill, and is within a few kilometres of Duval Street's nightlife and numerous restaurants. The property sleeps eight guests comfortably, boasting a large balcony, assigned covered parking, a fully equipped kitchen including a microwave and dishwasher, a swimming pool, and excellent guest reviews; nearby attractions include Smathers Beach.
9.3 326 reviews
Stock Island, FL
23/10 – 31/10
$360/nighttotal: $2880 (8 )
Signature King At Beachside Resort
1 2
apartment , Key West
Beachside Resort & Residences, a guesthouse in Key West, Florida, boasts a seven-acre beachfront location on the Gulf of Mexico, offering easy access to Key West's attractions. This self-catering unit features a king-size bed, private bathroom, and access to a resort pool, hot tub, fitness centre, and on-site restaurants including Tavern N Town and Chicken Walk, accommodating up to two guests.
9.8 111 reviews
Stock Island, FL
23/10 – 31/10
$591/nighttotal: $4728 (8 )
Off Call ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
2 2
apartment , Stock Island
This Stock Island apartment, near mile marker 5, offers easy access to Key West (a short drive away) and the Key West Golf Course (one minute away), with three marinas also conveniently close by. The 105 square metre (1130 square feet) property boasts three bedrooms, three bathrooms, sleeps six, and includes a swimming pool, terrace, parking for two cars, and a fully equipped kitchen; resort amenities are also available.