Find short term rentals in Winter Garden, FL at the best prices
85 available short term rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Short term and Weekly rentals in Winter Garden, FL
9.9 19 reviews
Winter Garden, FL
26/06 – 02/07
$316/nighttotal: $1896 (6 )
Trailside Montverde
1 5
apartment , Montverde
This Montverde holiday home is situated near Montverde Academy and an 8-minute (approximately 13 km) drive from Bella Collina, offering easy access to Orlando's theme parks (around 64 km away). Sleeping up to six guests, the three-bedroom, one-bathroom property features a kitchen with freezer and microwave, air conditioning, Wi-Fi, parking, a spacious yard, and allows pets.
Winter Garden, FL
26/06 – 02/07
$222/nighttotal: $1332 (6 )
Orlando Comfort Close To Top Universal's Attractions
1 5
apartment , Orlando
This one-bedroom flat is situated in Orlando's International Drive District, a mere 965 metres from Universal Studios and between 3.5 to 4 kilometres from Disney Parks. This suite accommodates up to five guests with two queen beds and a sofa bed, offering a fully equipped kitchen, complimentary parking, and access to a swimming pool and gym, with paid shuttle services available for theme park transport.
9.0 2 reviews
Winter Garden, FL
26/06 – 02/07
$442/nighttotal: $2652 (6 )
Vista Cay - Cosy 3 Bedroom Condo
3 5
apartment , Williamsburg
This Williamsburg apartment offers a superb location, conveniently situated near major attractions. The 126 square metre property boasts three bedrooms, two bathrooms, sleeps twelve guests, and includes a swimming pool, jacuzzi, and fitness centre.
9.2 10 reviews
Winter Garden, FL
29/07 – 31/08
$143/nighttotal: $4719 (33 )
All-you-need Studio Apartment Near Downtown
1 2
apartment , Winter Garden
This flat is located in Historic Downtown Winter Garden, within 100 metres of local businesses, the popular farmers market, and the Winter Garden bike trail, with easy access to major motorways. This accommodation sleeps two guests and offers a Queen bed, a compact kitchenette, a modern bathroom, complimentary WiFi, and free off-street parking for one vehicle.
10 17 reviews
Winter Garden, FL
29/07 – 31/08
$306/nighttotal: $10098 (33 )
1921 Bungalow In Historic Downtown Winter Garden
2 2
apartment , Winter Garden
This 1920s bungalow offers accommodation in downtown Winter Garden, situated one block from Plant Street and approximately 19 kilometres from Walt Disney World. This pet-friendly dwelling accommodates up to six guests and includes a kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning, Wi-Fi, and parking, with outdoor amenities such as a sunroom, large garden, and firepit.
10 8 reviews
Winter Garden, FL
26/06 – 02/07
$256/nighttotal: $1536 (6 )
Cottage-pvt Lake & Pool Access Near Disney W/porch
2 5
apartment , Clermont
This Clermont lakeside property is situated within 1.6km of Legends Golf & Country Club and Kings Ridge Driving Range, and under 3.2km from Kings Ridge Golf Club and Lake Louisa State Park. This 91 square metre holiday home boasts two bedrooms, two bathrooms, sleeps six, and features a fully equipped kitchen, swimming pool, jacuzzi, and free Wi-Fi; enjoy on-site water park access and serene lake views.
9.3 389 reviews
Winter Garden, FL
29/07 – 31/08
$143/nighttotal: $4719 (33 )
Superb Renovated Suite, Amazing Water View Best Location To Disney And Universal
1 2
apartment , Orlando
This waterfront flat is ideally situated in Orlando, within a short walk of Pirate's Dinner Adventure and CoCo Key Water Resort, and just a mile from Universal Orlando Resort and The Wheel at ICON Park™. It has consistently received excellent ratings for location, cleanliness, and user experience. This self-catering property can accommodate up to four guests and comes with a fully equipped kitchen, a balcony, and a washing machine. Enjoy the on-site swimming pool, Jacuzzi, and fitness centre, as well as the nearby attractions and family-friendly atmosphere.
9.6 223 reviews
Winter Garden, FL
26/06 – 02/07
$512/nighttotal: $3072 (6 )
4 Bedroom Plus, Lake View Condo, Vista Cay | 1008
4 5
apartment , Williamsburg
This Williamsburg apartment, ideal for families, is excellently located near Shingle Creek, a 15-minute walk from the Shingle Creek Conference Centre and Golf Course, and under 5 kilometres from the Orange County Convention Center and ICON Park™. This spacious 214-square-metre property boasts four bedrooms, two bathrooms, and sleeps eight, offering a swimming pool, jacuzzi, spa, fitness centre, tennis court, and parking, alongside a fully equipped kitchen and free Wi-Fi.
9.9 27 reviews
Winter Garden, FL
29/07 – 31/08
$138/nighttotal: $4554 (33 )
Winter Garden 1st. Floor Apartment, 1bedr - 1bath
1 2
apartment , Winter Garden
This Winter Garden apartment is conveniently located near Orlando International Airport, approximately 30km away, and a short distance from Winter Garden's town centre, offering easy access to local parks and a brewery. The self-contained flat comprises one bedroom, one bathroom, and sleeps two guests, featuring a kitchen, air conditioning, internet access, and on-site parking.
Winter Garden, FL
26/06 – 02/07
$181/nighttotal: $1086 (6 )
Comfortable Suite Near Disney W Pool And Hot Tub
1 5
apartment , Orlando
This Comfortable Suite Near Disney is conveniently located approximately 18 kilometres from Orlando International Airport, offering easy access to Walt Disney World. The 50-square-metre apartment features one bedroom, one bathroom, and sleeps up to seven guests, boasting a fully equipped kitchen, private patio, hot tub, swimming pool access, and a fitness centre.
9.9 25 reviews
Winter Garden, FL
29/07 – 31/08
$169/nighttotal: $5577 (33 )
Winter Garden Butterfly Retreat
1 2
apartment , Winter Garden
This Winter Garden flat is located just 160 metres from the West Orange Trail and a short walk to the historic downtown area, offering independent access and parking for two cars. This private two-room suite accommodates two guests and features a bedroom, a full bathroom, a living area with a kitchenette and pullout sofa, air conditioning, and is cleaned with fragrance-free products.
10 13 reviews
Winter Garden, FL
29/07 – 31/08
$271/nighttotal: $8943 (33 )
Dtwn Winter Garden Home: 12 Mi To Disney!
3 2
cottage , Winter Garden
This Winter Garden holiday home is situated less than 1km from Winter Garden's town centre, offering easy access to the farmers' market and restaurants, and within 24km of Walt Disney World Resort and 23km of Universal Studios Florida. The 111 square metre property sleeps seven guests across three bedrooms and two bathrooms, boasting a private garden, spa, Wi-Fi, and a well-equipped kitchen with dishwasher, plus off-street parking.
Best family friendly Winter Garden, FL Short term rentals
Among the 85 accommodations in Winter Garden, FL, here are the 4 best family friendly rentals
10 8 reviews
Winter Garden, FL
26/06 – 02/07
$412/nighttotal: $2472 (6 )
Lakefront Getaway! Close To Everything!
1 5
apartment , Oakland
This three-bedroom, two-bathroom flat is located in Oakland, offering lakefront living with direct access to paddleboarding and a lakeside fire pit, just 1.6 kilometres from the West Orange Trail and under 1.6 kilometres from Costco and local shops. This property accommodates up to eight guests and features air conditioning, internet, a kitchen, parking, and a barbecue grill, with daily views of Disney fireworks.
9.8 5166 reviews
Winter Garden, FL
29/07 – 31/08
$266/nighttotal: $8778 (33 )
Vcr4-308 - Deluxe Condo - Convention Center
4 2
apartment , Williamsburg
This family-friendly apartment is located in Williamsburg, just a short distance from the bustling city centre, offering easy access to local attractions and amenities. The property consistently receives excellent ratings for its location, cleanliness, and overall guest experience. The apartment comfortably accommodates families or groups with its three bedrooms, spanning 135 square metres. It offers a range of amenities, including a swimming pool, jacuzzi, terrace, garden, spa, fitness centre, tennis court, and parking facilities, ensuring a relaxing and enjoyable stay.
9.2 76 reviews
Winter Garden, FL
29/07 – 31/08
$264/nighttotal: $8712 (33 )
Vista Cay 3 Bedroom Just Across From Epic!!
3 2
apartment , Williamsburg
This apartment is located at the Vista Cay resort, just a short distance from the many historical attractions of Williamsburg. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment provides comfortable accommodation for a large group or family, with a king-size bed in the master bedroom, a queen-size bed in the second bedroom, and two double beds in the third bedroom. Guests have access to a wide range of amenities, including a swimming pool, a Jacuzzi, a fitness centre, a concierge service, and a host of other activities for families.
9.8 172 reviews
Winter Garden, FL
29/07 – 31/08
$181/nighttotal: $5973 (33 )
Walkable Winter Garden Bungalow: 3 Blocks To Dtwn
1 2
house , Winter Garden
This modern bungalow is situated in Orlando, just a short drive from Winter Garden, making it ideal for exploring both the vibrant city centre and the charming town. The property has received excellent ratings for its location, cleanliness, and overall user experience. This one-bedroom holiday home, spanning 59 square metres, comfortably accommodates up to four guests. The property features a fully equipped kitchen, a private patio, a gas barbecue, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
Best Winter Garden, FL lodging with a kitchen
9.8 17 reviews
Winter Garden, FL
29/07 – 31/08
$184/nighttotal: $6072 (33 )
Modern Luxury Unit In Beautiful Down Town Winter Garden With Wifi, Cable & Pool
1 2
apartment , Winter Garden
This ground-floor flat is located in Winter Garden's town centre, just 320 metres from local restaurants, entertainment, and the West Orange Trail, and under 48 kilometres from Universal Studios Florida, SeaWorld, and Orlando International Premium Outlets. The 85 square metre apartment accommodates up to four guests with a king bed and a queen mattress, offering a full kitchen, fast WiFi, two televisions, air conditioning, a swimming pool, spa, fitness room, and parking.
Winter Garden, FL
26/06 – 02/07
$225/nighttotal: $1350 (6 )
Orlando Comfort Close To Top Attractions
1 5
apartment , Orlando
This Orlando flat offers convenient access to major attractions, located a 17-minute walk from The Wheel At Icon Park and 3.06 kilometres from Universal Studios' Islands of Adventure. This air-conditioned one-bedroom apartment, covering 50 square metres, accommodates up to nine guests and features a fully equipped kitchen with a dishwasher, complimentary on-site parking, free Wi-Fi, and access to a shared pool.
9.6 37 reviews
Winter Garden, FL
29/07 – 31/08
$350/nighttotal: $11550 (33 )
Fire Pit & Yard: Updated Winter Garden Home!
2 2
apartment , Winter Garden
This Winter Garden holiday home is conveniently located near Winter Garden's town centre, offering easy access to Walt Disney World (around 30km away) and Lake Apopka. The spacious 155 sq m property boasts two bedrooms, two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, and an outdoor area with a gas grill; it comfortably sleeps four guests.
10 32 reviews
Winter Garden, FL
29/07 – 31/08
$142/nighttotal: $4686 (33 )
Winter Garden Guest Suite
1 2
B&B , Winter Garden
This Winter Garden guest suite is situated in a peaceful residential neighbourhood, a short walk (approx. 0.8km) from Winter Garden's downtown area, the West Orange Trail, and about 0.8km from Lake Apopka. The self-catering studio offers a private entrance, sleeps two, includes a kitchenette with fridge and microwave, a small fenced patio, and Smart TV with streaming services; nearby attractions include the Farmer's Market and Music on the Plaza.
Frequently Asked Questions about short term rentals in Winter Garden, FL
What are the best short term rentals in Winter Garden, FL?
Best Winter Garden, FL lodging with laundry available
9.7 147 reviews
Winter Garden, FL
29/07 – 31/08
$273/nighttotal: $9009 (33 )
Luxury Winter Garden Getaway Near Disney And Parks
1 2
apartment , Winter Garden
This newly renovated Winter Garden house is located a short walk (less than 1 km) from local shops, restaurants, and a farmers' market, and within a few minutes' drive (approximately 20-30 km) of Walt Disney World Resort and Universal Orlando Resort. Sleeping eight guests, the property boasts three bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, a spacious living room, a private garden with patio, free high-speed internet, and parking; plus golf cart and bike rentals are available nearby.
10 6 reviews
Winter Garden, FL
26/06 – 02/07
$533/nighttotal: $3198 (6 )
Cozy 2 Bedroom Apartment In Winter Garden With Fast Wifi, Pool & Fitness Room
2 5
apartment , Winter Garden
This 109 square metre flat in Winter Garden is situated 27 kilometres from the Kia Centre and 37 kilometres from Magic Kingdom Park, offering convenient access to local attractions. This residence accommodates up to six guests and features two bedrooms, two bathrooms, a fully equipped kitchen with a microwave and dishwasher, air conditioning, and on-site parking.
9.7 170 reviews
Winter Garden, FL
29/07 – 31/08
$276/nighttotal: $9108 (33 )
~ 12 Mi To Disney: Downtown Winter Garden Cottage!
2 2
house , Winter Garden
This Downtown Winter Garden Cottage is located in Winter Garden, Florida, just a short drive from Orlando's main attractions like Disney's Magic Kingdom and Universal Studios. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience. The cottage offers two bedrooms and a bathroom across 81 square metres, comfortably accommodating up to four guests. Guests can enjoy a range of amenities including air conditioning, free Wi-Fi, a fully equipped kitchen, a garden, a spa, and parking.
Winter Garden, FL
26/06 – 02/07
$251/nighttotal: $1506 (6 )
1 Bedroom Apartment Near Disney And Universal
1 5
apartment , Lake Buena Vista
This one-bedroom flat in Lake Buena Vista offers convenient access, being a mere 800 metres from the Disney Parks and Vineland Outlet, and approximately 2.4 kilometres from Universal Studios and International Drive. This spacious suite accommodates up to six guests, featuring two queen beds and a queen sofa bed, a fully equipped kitchen, separate living and sleeping areas with televisions, and complimentary access to the swimming pool and gym.
Best Winter Garden, FL lodging with air conditioning
Winter Garden, FL
26/06 – 02/07
$326/nighttotal: $1956 (6 )
Stylish 2br • Pool & Gym • Minutes To Disney
2 5
apartment , Winter Garden
This two-bedroom flat is situated in Orlando, approximately 19-21 kilometres from prominent attractions such as Camping World Stadium, Universal Studios' Islands of Adventure, and The Wizarding World of Harry Potter. This 104 square metre apartment accommodates up to eight guests and features a fully equipped kitchen with a dishwasher, air conditioning, free WiFi, a garden with a children's playground and outdoor fireplace, a year-round outdoor pool, a gym, and direct access to a terrace and balcony.
10 13 reviews
Winter Garden, FL
26/06 – 02/07
$256/nighttotal: $1536 (6 )
Lilac Loft- Lake, Pool, Pickle Ball, Disney, Fun!
2 5
apartment , Clermont
This two-bedroom, two-bathroom holiday home in Clermont's Vacation Village is situated less than 1.6km from Legends Golf & Country Club and Kings Ridge Driving Range, and under 3.2km from Lake Louisa State Park. The 91 square metre property offers a private pool, free Wi-Fi, a fully equipped kitchen, and accommodates up to six guests, with in-house games and books provided.
Winter Garden, FL
29/07 – 31/08
$139/nighttotal: $4587 (33 )
Luxury 1br • Pool & Gym • Close To Downtown
1 2
apartment , Winter Garden
This Orlando flat is situated 19 kilometres from Camping World Stadium and The Wizarding World of Harry Potter, and 34 kilometres from Orlando International Airport. This 85 square metre apartment accommodates up to 7 guests, featuring 1 bedroom, 1 bathroom, a fully equipped kitchen, air conditioning, a terrace, a swimming pool, a fitness centre, and a children's playground, with free Wi-Fi provided.
10 3 reviews
Winter Garden, FL
26/06 – 02/07
$467/nighttotal: $2802 (6 )
Updated 4/2 Winter Garden Home 20 Min From Disney!
1 5
apartment , Winter Garden
This Winter Garden flat is situated within the town's golf cart district, less than 1 kilometre from the town centre and a 20-minute drive from both Disney World and Universal Orlando Resort. This 4-bedroom, 2-bathroom flat accommodates up to 8 guests with a king bed, two queen beds, and a triple bunk, featuring air conditioning, internet, a fully equipped kitchen with a dishwasher, and optional golf cart hire for local exploration.