Find short term rentals in Stock Island, FL at the best prices

104 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Stock Island, FL short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Stock Island, FL

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

Rare For Kw, Beautiful 3-bedroom House On Swimmable Water + Pool - Stock Island, FL
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.
Tortuga Hammock -2 Bedroom/ 2.5 Bathroom Townhouse With Shared Pool & Parking - Stock Island, FL
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

Paradise Point By Avantstay | Golf Course Living - Stock Island, FL
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.
Seaside Escape- 2 Bed/2 Bath Condo With Shared Pool & Parking - Stock Island, FL
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.
Poolside Suite With Direct Pool Access - Stock Island, FL
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.
Ocean Oasis At Sunset Marina-2 Bed 2 Bath Oceanfront Condo W/boat Slip Rental - 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.

Frequently Asked Questions about short term rentals in Stock Island, FL

Destinations nearby

Best Stock Island, FL lodging with a kitchen

Joan's Caribbean Hideaway - Stock Island, FL
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.
Golf Villa - Indulge Without Overpaying - 2bd/2bath - Large Open Pool - Stock Island, FL
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.
Pool View Suite | Beachside Resort - Stock Island, FL
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.
Cozy 2br 2ba W/pool - Parking - Close To Beaches - Stock Island, FL
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

"Hemingway" 1 Bedroom At Leo's - Stock Island, FL
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.
**Sunset Dreams @ Sunset Marina** Condo / Pool & Spa + Last Key Services... - Stock Island, FL
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.
Ocean Memories Condo- 2 Bedroom, 2 Bath Oceanfront W/ Pool & Hot Tub - Stock Island, FL
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.
Renovated 2br/2ba Condo  Pool  Spa  Tennis  Walk To Smathers Beach! - Stock Island, FL
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.
©2026 cozycozy.com