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Best Vacation rentals and Airbnb offers in Stock Island, FL
Stock Island, FL
09/19 – 12/18
$228/nighttotal: $20520 (90 )
Ocean Oasis At Sunset Marina-2 Bed 2 Bath Oceanfront Condo W/boat Slip Rental
2 2
apartment , Key West
This oceanfront Key West condo is a short walk from the Key West Golf Club and Lower Keys Medical Center, and within a mile of the Florida Keys Community College Library and Key West Tropical Forest & Botanical Garden. This 1170-square-foot, two-bedroom, two-bathroom rental sleeps four and boasts a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and on-site laundry facilities.
9.7 57 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.
10 3 reviews
Stock Island, FL
09/19 – 12/18
$244/nighttotal: $21960 (90 )
Perfectly Poolside In Kwgolfclub
1 2
apartment , Key West
This townhome is located within the gated Key West Golf Club, offering convenient access to the golf course and a short distance to Old Town Key West. This fully furnished 2-bedroom, 2.5-bathroom condo accommodates up to 6 guests and features direct access to a lagoon-style pool with a waterfall, plus in-unit amenities like air conditioning, internet, and a full kitchen.
Stock Island, FL
09/19 – 12/18
$239/nighttotal: $21510 (90 )
Mariner's Oasis At Sunset Marina- 2bed 2 Bath Condo W/boat Slip For Rent
2 2
apartment , Key West
This Key West condo boasts a waterfront location, a short walk from the Key West Golf Club and Lower Keys Medical Center, and within a mile of the Florida Keys Community College Library and Key West Tropical Forest & Botanical Garden. This 1170-square-foot apartment features two bedrooms, two bathrooms, accommodates four guests, and includes a fully equipped kitchen, private balcony, in-unit jetted tub, and access to a swimming pool, jacuzzi, and concierge services.
9.6 4 reviews
Stock Island, FL
09/19 – 12/18
$206/nighttotal: $18540 (90 )
Renovated 2br/2ba Condo Pool Spa Tennis Walk To Smathers Beach!
2 2
apartment , Key West
This Key West apartment rental is conveniently located 1.4 miles from the Fort East Martello Museum and 2.1 miles from Smathers Beach, offering easy access to Key West's historical sites and beaches. The two-bedroom, two-bathroom condo sleeps four guests and features a fully equipped kitchen, private balcony, free Wi-Fi, swimming pool, jacuzzi, and parking; nearby attractions include the Key West Tropical Forest and Botanical Garden and the Key West Art and Historical Society.
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.
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.
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.
9.2 10 reviews
Stock Island, FL
09/19 – 12/18
$324/nighttotal: $29160 (90 )
A Palm Tree Paradise @ The Key West Golf Club
2 2
apartment , Key West
This Key West apartment is located on a private golf course, just a short drive from the lively downtown area and its famous attractions. The apartment has excellent user ratings and is perfect for a relaxing getaway. This two-bedroom, two-bathroom unit comfortably accommodates four guests. Enjoy access to two community pools, a gym, ample parking, and a screened-in porch where you can relax and soak up the tropical atmosphere.
9.0 2 reviews
Stock Island, FL
09/19 – 12/18
$186/nighttotal: $16740 (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 Stock Island townhome, located within the gated Key West Golf Club community, is five miles from Duval Street and four miles from Smathers Beach. The 810-square-foot property features two bedrooms, one bathroom, and accommodates four guests, offering a private patio with a propane grill, access to two community pools, and a fully equipped kitchen.
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.
10 22 reviews
Stock Island, FL
09/19 – 12/18
$483/nighttotal: $43470 (90 )
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.
Best Stock Island, FL vacation rentals with a balcony
10 1 review
Stock Island, FL
09/19 – 12/18
$355/nighttotal: $31950 (90 )
Island Time On The Green At Key West Golf Club
2 2
apartment , Key West
This Key West townhome is located within the prestigious Key West Golf Club, offering immediate access to community pools and a short drive of less than 1 mile to Historic Old Town, Duval Street, and Mallory Square. This 900-square-foot residence accommodates up to 4 guests with 2 bedroom suites, each featuring queen beds and en-suite bathrooms, and includes a fully equipped kitchen, high-speed wireless internet, and an oversized porch with a gas grill.
9.6 5 reviews
Stock Island, FL
09/19 – 12/18
$311/nighttotal: $27990 (90 )
**Sunset Dreams @ Sunset Marina** Condo / Pool & Spa + Last Key Services...
3 2
apartment , Key West
This Key West apartment is located near the Key West Golf Club, just a short walk away, and within a 4 km drive to Smathers Beach. The apartment has excellent user ratings, making it a popular choice for travelers. This 3-bedroom, 2-bathroom apartment offers 1660 square feet of space, accommodating up to 8 guests. Amenities include a fully equipped kitchen, a spa tub, a swimming pool, and free WiFi, ensuring a comfortable and enjoyable stay.
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
This waterfront condo in the private gated community of Sunset Marina is a short drive from Old Town, Key West, offering proximity to landmarks like Ernest Hemingway Home and Museum and Southernmost Point, while being secluded with stunning Florida Bay and Gulf of Mexico views. This 1020 square foot residence features 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests, boasting a full kitchen, a spacious balcony, and access to a community pool, Jacuzzi, tennis court, and concierge services, with an optional boat slip available.
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.
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.
9.8 9 reviews
Stock Island, FL
09/19 – 12/18
$242/nighttotal: $21780 (90 )
The Guava Duff - Beautiful Kw Home With Space To Chill & Lots Of Free Parking!!
4 2
house , Stock Island
This Stock Island house, located 2.5 miles from Key West International Airport, offers easy access to Key West attractions like the Ernest Hemingway Home and Museum (4.7 miles) and Duval Street (4.8 miles). This 1,130-square-foot home features four bedrooms, two bathrooms, a fully equipped kitchen, free bikes, ample private parking, and a terrace—perfect for families or groups seeking a comfortable Key West getaway.
9.7 56 reviews
Stock Island, FL
09/19 – 12/18
$621/nighttotal: $55890 (90 )
Ocean Views! <Br>luxury Suites
1 2
houseboat , Stock Island
This family-friendly houseboat is situated on the waterfront in Stock Island, just a mile from Robbie's and the Key West Tropical Forest and Botanical Garden. The accommodation has earned excellent ratings for its location, cleanliness, and user experience. The houseboat features one bedroom and can comfortably accommodate up to six guests. It offers a range of amenities including a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a terrace, a garden, parking, and internet access.
8.7 4748 reviews
Stock Island, FL
09/19 – 12/18
$358/nighttotal: $32220 (90 )
Oceans Edge Key West
1 2
resort , Stock Island
Oceans Edge Key West is located on Stock Island, just a short drive from Key West International Airport and a few miles from the famous Southernmost Point. The resort receives very good user ratings for its location and cleanliness, along with an excellent overall rating. The resort has a variety of rooms, suites, and other accommodations. Enjoy multiple swimming pools, a waterfront bar and restaurant, on-site water sports, a marina, complimentary Wi-Fi, and a full range of amenities.
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
Stock Island, FL
09/19 – 12/18
$348/nighttotal: $31320 (90 )
Sunset Dreams By Last Key Realty
3 2
apartment , Key West
This Key West rental is conveniently located 2.5 miles from Key West International Airport and 5 miles from Duval Street, offering easy access to attractions like the Ernest Hemingway Home and Museum and Mallory Square. This 1660-square-foot, three-bedroom condo sleeps up to 15 guests and boasts a fully equipped kitchen, private parking, a swimming pool, jacuzzi, spa, and tennis court.
8.8 5 reviews
Stock Island, FL
09/19 – 12/18
$183/nighttotal: $16470 (90 )
2 Bedroom Town Home In A Gated Community With A Resort Sytle Pool.
2 2
apartment , Key West
This 780-square-foot, 2-bedroom, 2-bathroom townhome, named "2 Bedroom Town Home In A Gated Community With A Resort Style Pool," is located within the Key West Golf Club, offering easy access to downtown Key West and Duval Street, which are less than 1 mile away. This accommodation provides a fully equipped kitchen, a combined living/dining area, air conditioning, internet, a private terrace, and access to community pools, a clubhouse, and a fitness center, accommodating up to 4 guests.
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.
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.
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.
9.7 2 reviews
Stock Island, FL
09/19 – 12/18
$218/nighttotal: $19620 (90 )
Monthly Availability Beginning May 2025
2 2
apartment , Key West
This apartment is located in a premier Key West development next to a golf course, offering convenient access within a 15-20 minute drive to Duval Street, Ernest Hemingway Home and Museum, and Southernmost Point. This 990 sq ft rental accommodates up to 4 guests with 2 bedrooms, a full kitchen, and gated community amenities including two swimming pools and a fitness center, with bikes available for local exploration.
Stock Island, FL
09/19 – 12/18
$205/nighttotal: $18450 (90 )
Paradise Point By Avantstay | Golf Course Living
2 2
apartment , Key West
This Key West vacation home is conveniently located near the Key West Golf Club and the Key West Tropical Forest & Botanical Garden, less than a 10-minute walk from each. This 780-square-foot house features two bedrooms, sleeps four, and includes a fully equipped kitchen with a refrigerator, freezer, and dishwasher, a private balcony, a swimming pool, and free Wi-Fi.
Stock Island, FL
09/19 – 12/18
$233/nighttotal: $20970 (90 )
Salt Ponds | Work & Relax In Key West | Poolside Condo Balcony Near Beach
2 2
apartment , Key West
This 2-bedroom, 2-bathroom condo is located in Key West's Salt Ponds community, offering a quiet residential atmosphere just a short drive from Old Town and Duval Street, and less than 1 mile from Smathers Beach. This fully furnished 780 sq ft condo accommodates up to 4 guests and features a resort-style heated pool, spa, private balcony, in-unit laundry, and is move-in ready for extended stays.
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.
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.
9.8 19 reviews
Stock Island, FL
09/19 – 12/18
$665/nighttotal: $59850 (90 )
3-bedroom Ocean View Condo In Delightful Key West With Wifi, Ac
3 2
apartment , Stock Island
9.0 16 reviews
Stock Island, FL
09/19 – 12/18
$475/nighttotal: $42750 (90 )
The Grand Turk | Spectacular Sunset View, Private
2 2
apartment , Key West
Stock Island, FL
09/19 – 12/18
$434/nighttotal: $39060 (90 )
Salty Pelican- Key Haven Home With Pool And Dock
3 2
apartment , Key West
10 1 review
Stock Island, FL
09/19 – 12/18
$420/nighttotal: $37800 (90 )
Pool View Two Bedroom Residence
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.
Stock Island, FL
09/19 – 12/18
$292/nighttotal: $26280 (90 )
The Tipsy Mermaid At Key West Golf Club
3 2
apartment , Key West
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.
