Search vacation rental in Stock Island, FL from 100+ sites!
179 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in Stock Island, FL
9.8 42 reviews
Stock Island, FL
10/23 – 10/31
$321/nighttotal: $2568 (8 )
Stella On Stock Island
1 2
barge , Stock Island
This Stock Island houseboat offers waterfront living with convenient access to local attractions, though specific distances aren't provided. The one-bedroom, one-bathroom vessel sleeps four guests and features a full kitchen with a fridge, freezer, and microwave, plus air conditioning, a garden, parking, and Wi-Fi.
9.4 3 reviews
Stock Island, FL
09/19 – 12/18
$300/nighttotal: $27000 (90 )
Golf Villa - Indulge Without Overpaying - 2bd/2bath - Large Open Pool
2 2
apartment , Key West
This two-bedroom, two-bathroom condo is located within the Key West Golf Club, offering direct golf course views and is a short drive to Old Town Key West attractions like the Ernest Hemingway Home and Museum. This rental provides a fully equipped kitchen, a private balcony, access to community swimming pools and a fitness center, and requires a minimum 28-day stay for extended Key West immersion.
10 23 reviews
Stock Island, FL
10/23 – 10/31
$694/nighttotal: $5552 (8 )
Tortuga Hammock -2 Bedroom/ 2.5 Bathroom Townhouse With Shared Pool & Parking
2 2
apartment , Stock Island
This Stock Island vacation home is located just a mile from Stock Island Yacht Club & Marina and Clark Maxwell Environmental Habitat, offering easy access to the island's natural beauty and activities. It's also close to Key West Tropical Forest and Botanical Garden, making it a great choice for exploring the area. This vacation rental has received excellent user ratings, ensuring a comfortable and enjoyable stay. The 1,070-square-foot house has two bedrooms and three bathrooms, comfortably accommodating up to four guests. It features a fully equipped kitchen, a refreshing swimming pool, a relaxing terrace, a lush garden, free WiFi, and plenty of parking.
9.7 58 reviews
Stock Island, FL
09/19 – 12/18
$331/nighttotal: $29790 (90 )
"Hemingway" 1 Bedroom At Leo's
1 2
apartment , Stock Island
This one-bedroom apartment rental in Stock Island is conveniently located two blocks from Key West, easily accessible by bicycle, scooter, or golf cart, offering proximity to Key West attractions while maintaining a tranquil setting overlooking a nature preserve. The unit, situated within Leo's RV Park, includes a kitchen with a fridge and microwave, air conditioning, parking, and access to shared amenities such as Tiki huts, ping pong, chess, and billiards, comfortably accommodating two guests.
9.8 5 reviews
Stock Island, FL
10/23 – 10/31
$439/nighttotal: $3512 (8 )
Keys Livin - Yacht Rental
1 2
apartment , Stock Island
Keys Livin offers a one-bedroom apartment in Key West, a short walk from Simonton Street Beach and Duval Street, and less than a mile from the Ernest Hemingway Home and Museum. This Key West rental boasts four bathrooms, sleeps eleven guests, includes free Wi-Fi and private parking, and is conveniently located near the Key West Aquarium, Mallory Dock, and Mallory Square.
9.3 326 reviews
Stock Island, FL
10/23 – 10/31
$258/nighttotal: $2064 (8 )
Signature King At Beachside Resort
1 2
apartment , Key West
Beachside Resort & Residences, a Key West guesthouse, boasts a seven-acre beachfront location on the Gulf of Mexico, offering easy access to Key West's attractions. This one-bedroom, one-bathroom suite features a king bed, mini-fridge, and access to a 24-hour heated pool, hot tub, fitness center, and on-site restaurants like Tavern N Town and Chicken Walk, plus a Guest Experience Manager for booking assistance.
10 2 reviews
Stock Island, FL
09/19 – 12/18
$246/nighttotal: $22140 (90 )
Island Retreat - Key West
1 2
apartment , Key West
This two-bedroom, two-bathroom condo is located in the Salt Ponds community of Key West, offering a peaceful retreat a 10-minute walk from the beach and a short drive or bike ride to Old Town Key West. This recently renovated apartment accommodates up to four guests and features a full kitchen, air conditioning, a swimming pool, and parking, making it ideal for monthly rentals.
9.8 160 reviews
Stock Island, FL
10/23 – 10/31
$551/nighttotal: $4408 (8 )
Oceanfront Marina Condo With All Luxuries
3 2
apartment , Stock Island
This oceanfront condo rental in Key West, near Stock Island, offers easy access to attractions like the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. The 1400-square-foot property boasts three bedrooms, two bathrooms, sleeps six, and features a renovated kitchen, oceanfront balcony, community pool and Jacuzzi, and nearby water sports rentals.
9.4 17 reviews
Stock Island, FL
09/19 – 12/18
$530/nighttotal: $47700 (90 )
The Flight Deck - 3 Bedroom / 3 Bathroom With Shared Pool & Fitness Center!
3 2
apartment , Stock Island
This 3-bedroom townhouse is located in the Coral Hammock Community on Stock Island, just 4 miles from downtown Key West. The home offers two primary suites, each with a king bed, ensuite bathroom, smart TV and private lanai, along with a large shared pool, fitness center, and covered parking for two vehicles.
10 8 reviews
Stock Island, FL
09/19 – 12/18
$110/nighttotal: $9900 (90 )
Uptown Quiet Cottage Close To Beaches, Restaurant & Shopping.
1 2
cottage , Key West
This charming Key West cottage is located in New Town, a quiet neighborhood just a short distance from the bustling downtown area. The cottage boasts excellent ratings from previous guests, highlighting its comfortable and relaxing atmosphere. This one-bedroom, one-bathroom cottage comfortably accommodates two guests. Enjoy the private pool, garden, and off-street parking, as well as access to a fully equipped kitchen, air conditioning, and Wi-Fi.
Stock Island, FL
10/23 – 10/31
$339/nighttotal: $2712 (8 )
Cozy Houseboat
1 2
houseboat , Stock Island
Stella, a Stock Island houseboat near the Perry Hotel, offers easy access to Key West attractions like the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. This one-bedroom, one-bathroom floating home sleeps four guests and features a fully equipped kitchen, modern bathroom, and convenient access to nearby boat storage at 3D Boatyard.
10 2 reviews
Stock Island, FL
09/19 – 12/18
$258/nighttotal: $23220 (90 )
One Bedroom Suite | Beachside Resort
1 2
apartment , Key West
This 1-bedroom condo is located on seven acres overlooking the Gulf of Mexico in north Key West, approximately a 10-minute drive from Duval Street. This luxury resort condo offers a private balcony, a fully-equipped kitchen with stainless-steel appliances, and access to a resort pool, hot tub, and on-site dining.
Best Stock Island, FL vacation rentals with a balcony
Stock Island, FL
09/19 – 12/18
$319/nighttotal: $28710 (90 )
Cabana At The Golf Club-monthly Rental Charming 2-
2 2
apartment , Key West
This Key West vacation home, located within the Key West Golf Club community, offers easy access to Old Town Key West's attractions, though driving distance isn't specified. The 780-square-foot, two-bedroom, two-bathroom cottage features an open-concept layout, accommodating up to six guests and including a private balcony, fenced backyard, washer/dryer, and access to the resort-style pool and fitness center.
9.6 11 reviews
Stock Island, FL
09/19 – 12/18
$365/nighttotal: $32850 (90 )
A Sanctuary Home At The Key West Golf Club In Key West
3 2
apartment , Key West
This Key West vacation home is conveniently located near the Key West Golf Club and Key West Tropical Forest & Botanical Garden, within a 10-minute walk, and close to Lower Keys Medical Center and the Florida Keys Community College Library (within 1 mile). This three-bedroom, two-and-a-half-bathroom house sleeps six, features a private pool, outdoor barbecue grills, washer/dryer, and a balcony, offering ample space and amenities for a relaxing Key West getaway.
9.2 13 reviews
Stock Island, FL
09/19 – 12/18
$270/nighttotal: $24300 (90 )
It's A Salt Life After All At The Golf Club In Key West
2 2
apartment , Key West
This Stock Island townhome offers convenient access to Key West attractions, located five miles from Duval Street and Historic Old Town Key West, and two miles from island beaches. This two-bedroom, two-bathroom residence accommodates up to six guests, featuring two community pools, a gym, a butterfly garden, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
8.6 127 reviews
Stock Island, FL
09/19 – 12/18
$405/nighttotal: $36450 (90 )
Resort Suite With Pool, Hot Tub, Tennis & Full Kitchen
2 2
apartment , Key West
This Key West condo, located in the exclusive Sunrise Suites Resort on the east side of the island, is a short drive to Key West International Airport and attractions like the Southernmost Point and Ernest Hemingway Home and Museum. This 800 sq ft condo offers 2 bedrooms and 2 bathrooms, accommodating up to 6 guests with a private balcony, a fully equipped kitchen, free WiFi, and access to a shared lagoon-shaped pool and hot tub, with one dog permitted.
Our Favorite Family-Friendly Vacation Rentals in Stock Island, FL
Find the perfect family vacation rental or Airbnb in Stock Island, FL with plenty of room to spread out near local beaches.
Stock Island, FL
09/19 – 12/18
$547/nighttotal: $49230 (90 )
Rare For Kw, Beautiful 3-bedroom House On Swimmable Water + Pool
3 2
apartment , Stock Island
This Stock Island vacation home offers waterfront living with direct dock access to open water, ideal for swimming, kayaking, and snorkeling, and is located just 5 miles from Old Town Key West's museums, shops, and entertainment. This 3-bedroom, 1-bathroom condo accommodates up to 8 guests and features a private swimming pool, a large stone patio, a pool table, kayaks, a paddleboard, and 2 parking spaces, with shallow water access suitable for boats.
Stock Island, FL
10/23 – 10/31
$702/nighttotal: $5616 (8 )
Seas The Breeze, Poolside Condo Near The Beach
2 2
apartment , Key West
This apartment in Key West is located 0.6 miles from Key West International Airport and approximately 4 miles from Southernmost Point and Duval Street. This family-friendly, 800 square foot apartment features 2 bedrooms, 2 bathrooms, air conditioning, a kitchen, a swimming pool, a jacuzzi, a balcony, and parking for up to 11 guests, with free Wi-Fi available.
Stock Island, FL
10/23 – 10/31
$3315/nighttotal: $26520 (8 )
Apartment ∙ 8 Bedrooms ∙ 16 Guests
8 2
apartment , Key West
This estate is located in Key Haven, Florida Keys, offering proximity to public boat ramps on Key Haven and Stock Island, and a short drive to Key West attractions. This luxurious villa accommodates 16 guests with eight king bedrooms, each with an ensuite bathroom, featuring expansive indoor/outdoor living spaces, a pool, grilling and dining areas, a fully equipped kitchen, and private boat excursions.
10 150 reviews
Stock Island, FL
10/23 – 10/31
$522/nighttotal: $4176 (8 )
'Oceanside Oasis' Direct Ocean Views & 3 Br's
3 2
apartment , Stock Island
This Stock Island condo boasts a waterfront location less than a mile from the Stock Island Yacht Club & Marina and Boca Chica Nude Beach, with Key West Tropical Forest and Botanical Garden and Key West Golf Club within two miles. This 1,470-square-foot rental features three bedrooms, two bathrooms, and accommodates six guests, offering a swimming pool, Jacuzzi, terrace, and fully equipped kitchen including a dishwasher; on-site barbecue grills are available for guest use.
Frequently Asked Questions about vacation rentals in Stock Island, FL
What sports or outdoor activites can visitors enjoy in and around Stock Island, FL?
Stock Island and Key West are known for their water sports. You can go snorkeling, diving, fishing, kayaking, paddleboarding, and sailing. There are also plenty of opportunities for hiking, biking, and birdwatching.
What are the best Airbnb and vacation rentals in Stock Island, FL?
What other towns or cities can be easily accessed from Stock Island, FL?
Stock Island is part of Key West, so you're already in the heart of the action. You can easily access other parts of Key West, like Old Town and the Southernmost Point. You can also take a ferry to nearby islands like Marathon and Islamorada.
What are the most popular Airbnbs in Stock Island, FL?
What amenities are commonly available in vacation rentals in Stock Island, FL?
Vacation rentals in Stock Island are often equipped with amenities like kitchens, laundry facilities, and private pools or hot tubs. Many also have balconies or patios with views of the water.
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 Stock Island is during the winter months, from December to April, when the weather is warm and sunny. The summer months can be hot and humid, but there are often special events and festivals.
What are the best rentals for families and kids in Stock Island, FL?
What are the local dishes in Stock Island, FL region?
You'll find plenty of fresh seafood in Key West. Some popular dishes include conch fritters, stone crab claws, and Key lime pie. There are also many restaurants that serve Caribbean and Cuban cuisine.
What are the best rentals or Airbnbs with a jacuzzi in Stock Island, FL?
Best Stock Island, FL vacation rentals with parking
9.2 27 reviews
Stock Island, FL
09/19 – 12/18
$344/nighttotal: $30960 (90 )
Key Haven Retreat-4 Bedroom 3 Bath Canal Front Home W/private Pool, Boat Dock
4 2
apartment , Key West
This Key Haven vacation home, near the Ernest Hemingway Home and Museum and Southernmost Point, offers the "30 Noches De Estancia Mínima Requisito. Asilo Clave Retreat - 4 Dormitorio Casa" rental. The 1810-square-foot house features four bedrooms, three bathrooms, sleeps ten guests, and includes a private pool, boat dock space, and gated parking.
9.5 86 reviews
Stock Island, FL
10/23 – 10/31
$345/nighttotal: $2760 (8 )
Poolside Suite With Direct Pool Access
1 2
apartment , Key West
This luxurious one-bedroom condo at the Beachside Resort in Key West offers direct Gulf of Mexico views and easy access to Key West's attractions. The 1-bedroom, 1-bathroom unit sleeps 4, features a king bed, full kitchen with stainless steel appliances, private balcony with resort pool access, in-unit washer/dryer, and access to resort amenities including a heated pool, hot tub, and the Tavern N Town restaurant.
10 103 reviews
Stock Island, FL
09/19 – 12/18
$631/nighttotal: $56790 (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 two miles from the Stock Island Yacht Club & Marina, Key West Tropical Forest and Botanical Garden, and Key West Golf Club. The 1,500-square-foot apartment features two bedrooms, two bathrooms, and a private balcony, comfortably accommodating up to four guests with amenities including a swimming pool, a jacuzzi, a spa, and parking.
Stock Island, FL
09/19 – 12/18
$469/nighttotal: $42210 (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 drive from Key West's downtown, offers direct ocean access via a private deep-water canal. The four-bedroom, two-bathroom houseboat sleeps eight guests and features kayaks, paddleboards, a grill, and an outdoor shower; nearby attractions include the Ernest Hemingway Home and Museum and the Southernmost Point.
Browse Vacation Rentals with a Pool in Stock Island, FL
A vacation rental with a pool in Stock Island, FL is the perfect amenity to complement your time spent by the water.
9.5 279 reviews
Stock Island, FL
10/23 – 10/31
$352/nighttotal: $2816 (8 )
Pool View Suite | Beachside Resort
1 2
apartment , Key West
This Key West condo, located at the Beachside Resort on the Gulf of Mexico, offers stunning gulf-front views and easy access to Key West's attractions. The one-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with stainless steel appliances, a king bed, a queen sleeper sofa, a private balcony overlooking the resort pool, and access to resort amenities including a heated pool, hot tub, fitness center, and on-site dining.
10 45 reviews
Stock Island, FL
10/23 – 10/31
$642/nighttotal: $5136 (8 )
Gorgeous Ocean View In Paradise - Three Bedroom Condo - Minutes From Key West!
3 2
apartment , Stock Island
This Stock Island waterfront apartment rental is located within one mile of the Stock Island Yacht Club & Marina and Boca Chica Nude Beach, offering easy access to boating and unique beach experiences. The 1,360-square-foot unit features three bedrooms, two bathrooms, and accommodates six guests, boasting a private fenced yard, a fully equipped kitchen, and access to an on-site pool, hot tub, and tennis court.
10 10 reviews
Stock Island, FL
10/23 – 10/31
$397/nighttotal: $3176 (8 )
Oceanview Condo W/pool, Jacuzzi
1 2
apartment , Key West
This two-bedroom, two-bathroom condo at the La Brisa resort in Key West offers direct ocean views and is located directly across the street from Smathers Beach. The 6-guest unit features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus resort amenities including a pool, jacuzzi, sauna, and parking; enjoy breathtaking ocean views from your private balcony.
9.6 90 reviews
Stock Island, FL
09/19 – 12/18
$323/nighttotal: $29070 (90 )
One Bedroom Suite | Beachside Resort
1 2
apartment , Key West
This one-bedroom Key West condo, part of the Beachside Resort, sits directly on the Gulf of Mexico, offering easy access to water activities. The 1-bedroom unit features a king bed, queen sleeper sofa, full kitchen with stainless steel appliances, private balcony with Gulf views, in-unit washer/dryer, and access to a heated pool, hot tub, fitness center, and on-site restaurants like Tavern N Town and Chicken Walk.
Find the Best Seaside Vacation Rentals in Stock Island, FL
Relax near the shore in these coastal Stock Island, FL vacation rentals, combining comfortable amenities with beautiful seaside scenery just moments away.
9.6 51 reviews
Stock Island, FL
09/19 – 12/18
$492/nighttotal: $44280 (90 )
The Salt Cay | Updated! Stunning Sunset View, Pool
2 2
apartment , Key West
8.0 1 review
Stock Island, FL
09/19 – 12/18
$292/nighttotal: $26280 (90 )
Painted Sky~2 Br/2 Ba Waterfront Condo At Sunset Marina W/ Pool & Boat Slip!
2 2
apartment , Key West
10 1 review
Stock Island, FL
09/19 – 12/18
$387/nighttotal: $34830 (90 )
Two Bedroom Residence
2 2
apartment , Key West
10 1 review
Stock Island, FL
09/19 – 12/18
$341/nighttotal: $30690 (90 )
Dog-friendly, Gulf-front Condo With Pool, Hot Tub & Gorgeous Sunset Views
2 2
apartment , Key West
Top-Rated 5-Star Vacation Rentals in Stock Island, FL
Experience 5-star comfort in a luxury Stock Island, FL vacation rental designed with premium amenities throughout.
9.8 111 reviews
Stock Island, FL
10/23 – 10/31
$423/nighttotal: $3384 (8 )
Off Call ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
2 2
apartment , Stock Island
Best Vacation Rentals with a Steam Room in Stock Island, FL
Relax with an on-site sauna at these vacation rentals in Stock Island, FL, perfect for a steam session after a day by the water.
9.4 3 reviews
Stock Island, FL
09/19 – 12/18
$300/nighttotal: $27000 (90 )
Golf Villa - Indulge Without Overpaying - 2bd/2bath - Large Open Pool
