Find short term rentals in Winter Garden, FL at the best prices
85 available short term rental offers
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Best Short term and Weekly rentals in Winter Garden, FL
10 51 reviews
Winter Garden, FL
29/07 – 31/08
$321/nighttotal: $10593 (33 )
Emerald Grove - Close To Disney
1 2
apartment , Winter Garden
This Winter Garden apartment, situated on Plant Street, offers easy access to Winter Garden's downtown area and is approximately 32km from Walt Disney World. The two-bedroom, two-bathroom flat sleeps four guests and features a fully equipped kitchen with stainless steel appliances, a swimming pool, fitness centre, and free on-site parking; nearby attractions include the Plant Street Market and West Orange Trail.
9.9 33 reviews
Winter Garden, FL
29/07 – 31/08
$124/nighttotal: $4092 (33 )
Private Room Close To Disney
1 2
apartment , Winter Garden
This charming bed and breakfast is situated in Winter Garden, just 16-20 kilometres from Disney parks, making it a great base for exploring the attractions and the vibrant town centre. It has consistently received excellent ratings for its cleanliness, location, and overall experience. The guest room is located on the ground floor, offering privacy and easy access. It can accommodate up to two guests and features a private bathroom and a shared kitchen. Guests can enjoy access to a swimming pool, parking, and free Wi-Fi, as well as a spacious living room.
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.
10 2 reviews
Winter Garden, FL
29/07 – 31/08
$273/nighttotal: $9009 (33 )
Luxury Stay | Pool + Gym + Fast Wi-fi
1 2
apartment , Winter Garden
This Winter Garden flat offers convenient access, situated approximately 19-21 kilometres from major attractions such as Camping World Stadium, Universal Studios, and The Wizarding World of Harry Potter, and is 32 kilometres from Orlando International Airport. This 83 square metre apartment, accommodating up to seven guests, features a private swimming pool, an on-site fitness centre, a fully equipped kitchen, and complimentary high-speed Wi-Fi.
9.7 75 reviews
Winter Garden, FL
29/07 – 31/08
$178/nighttotal: $5874 (33 )
16 Mi To Disney: Cottage W/ Deck In Winter Garden
1 2
house , Winter Garden
This modern cottage is located in Winter Garden, Florida, just 26 kilometres from Walt Disney World and close to other attractions like Camping World Stadium, Amway Center, and Church Street Station. The cottage has received excellent ratings for location, cleanliness, and overall experience. The cottage has one bedroom and one bathroom, covering 49 square metres and accommodating up to four guests. Amenities include a fully equipped kitchen, a private patio, air conditioning, free Wi-Fi, and a washer and dryer, making it a comfortable and convenient choice for travellers.
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.
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.
9.4 26 reviews
Winter Garden, FL
29/07 – 31/08
$259/nighttotal: $8547 (33 )
Dtwn Winter Garden Home: 12 Mi To Disney!
3 2
apartment , Winter Garden
This charming cottage is located just 800 metres from Winter Garden's bustling downtown area, offering easy access to the farmers market, restaurants, and shops. It is also less than 24 kilometres from Walt Disney World, making it ideal for those looking to explore the magic of Orlando. The cottage receives consistently excellent user ratings for its location, cleanliness, and overall experience. The cottage has three bedrooms and two bathrooms, comfortably accommodating up to seven guests. Enjoy a fully equipped kitchen, a private yard, and amenities like air conditioning, free Wi-Fi, and off-street parking for two vehicles.
9.8 168 reviews
Winter Garden, FL
29/07 – 31/08
$146/nighttotal: $4818 (33 )
Stay A While
1 2
apartment , Winter Garden
This one-bedroom flat in Winter Garden is located just 40 kilometres from Orlando International Airport and a 25-minute drive from theme parks and nightlife. The apartment is rated excellent for location, cleanliness, and user experience. The flat has a spacious, open layout and comfortably accommodates up to five guests. Amenities include a shared swimming pool, a garden, dedicated parking, and a kitchen with a fridge and microwave.
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.
9.8 44 reviews
Winter Garden, FL
29/07 – 31/08
$292/nighttotal: $9636 (33 )
Winter Garden Charm, Near Disney
1 2
apartment , Winter Garden
This Winter Garden apartment, situated on Plant Street, offers easy access to downtown Winter Garden's restaurants and boutiques, and is less than 3km from the West Orange Trail. The two-bedroom, two-bathroom flat sleeps four guests and boasts a fully equipped kitchen with stainless steel appliances, a private balcony, and access to a swimming pool, fitness centre, and parking.
8.8 5 reviews
Winter Garden, FL
29/07 – 31/08
$249/nighttotal: $8217 (33 )
Stylish 2br • Pool & Gym • Minutes To Disney
1 2
apartment , Winter Garden
This two-bedroom flat is centrally located in Downtown Winter Garden, a short walk from the historic Winter Garden Theatre and Plant Street Market, and 1.3 kilometres from the West Orange Trail. This property offers a swimming pool, fitness centre, and parking, with accommodation for up to five guests and modern amenities including air conditioning and internet.
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
9.4 110 reviews
Winter Garden, FL
29/07 – 31/08
$245/nighttotal: $8085 (33 )
4814 Cayview Avenue #401
3 2
apartment , Williamsburg
This three-bedroom apartment is situated in Williamsburg, a vibrant district in Orlando, Florida, just 2.9 kilometres from the Orange County Convention Center and 3.4 kilometres from The Wheel at ICON Park Orlando. The 116 square metre property features a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a fitness centre and parking on site.
9.7 500 reviews
Winter Garden, FL
29/07 – 31/08
$268/nighttotal: $8844 (33 )
Is1-110 - Orlando 3br Condo Near Disney | Sleeps 8
4 2
apartment , Williamsburg
This family-friendly apartment is located in Williamsburg, within easy reach of the Orange County Convention Center, Shingle Creek Golf Course, Aquatica and The Wheel at ICON Park™. The property has received excellent ratings for location, cleanliness, and overall user experience. This three-bedroom apartment offers ample space for families or groups. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, fitness centre, and barbecue grills.
9.2 73 reviews
Winter Garden, FL
29/07 – 31/08
$251/nighttotal: $8283 (33 )
Updated Condo Near Conv Ctr, I-drive & Universal
3 2
apartment , Williamsburg
This apartment is located in Orlando, Florida, approximately 2.7 kilometres from the Orange County Convention Center and 3.2 kilometres from The Wheel at ICON Park Orlando. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment offers three bedrooms and spans 131 square metres, making it suitable for families or groups. It comes equipped with a fully equipped kitchen, a swimming pool, a jacuzzi, a terrace, a garden, a bar, a fitness centre, a tennis court, and parking.
9.4 163 reviews
Winter Garden, FL
29/07 – 31/08
$277/nighttotal: $9141 (33 )
Palm Villa
3 2
house , Williamsburg
Palm Villa is a comfortable house located in Orlando, Florida, just a short distance from popular attractions like The Wheel at ICON Park Orlando and SeaWorld Orlando. The property has received excellent ratings for its location, cleanliness, and overall experience. The house offers a well-equipped kitchen with modern appliances and a bathroom, providing a comfortable and spacious stay. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, tennis court, and a restaurant and bar on site.
Best Winter Garden, FL lodging with a kitchen
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.
9.5 31 reviews
Winter Garden, FL
29/07 – 31/08
$220/nighttotal: $7260 (33 )
Winter Garden 2 Bedrooms/2 Bath Home (Downtown)
1 2
apartment , Winter Garden
This fully renovated two-bedroom, two-bathroom house in Winter Garden's downtown area is a 48km drive from Walt Disney World Resort and Orlando International Airport, and within walking distance of Lake Jennie Jewel. The 4-person property boasts a fully equipped kitchen, air conditioning, parking, and internet access, offering easy access to shops, restaurants and Winter Garden's historic district.
9.9 45 reviews
Winter Garden, FL
29/07 – 31/08
$292/nighttotal: $9636 (33 )
The Garden Luxe Retreat, Near Disney
1 2
apartment , Winter Garden
This Winter Garden apartment is situated on Plant Street, a short walk from Winter Garden's historic downtown area and 2km from the Plant Street Market, offering easy access to the West Orange Trail. The two-bedroom, two-bathroom flat sleeps four guests and boasts a fully equipped kitchen, a private balcony or patio (where applicable), free on-site parking, and a fitness centre and swimming pool, all within easy reach of Walt Disney World, Universal Orlando Resort and Downtown Orlando.
9.8 172 reviews
Winter Garden, FL
29/07 – 31/08
$163/nighttotal: $5379 (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.
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
10 4 reviews
Winter Garden, FL
29/07 – 31/08
$326/nighttotal: $10758 (33 )
The Garden Luxe Retreat
1 2
apartment , Winter Garden
The Garden Luxe Retreat apartment is situated in Winter Garden, Florida, offering convenient access to attractions such as Universal Studios Florida and the Orlando International Premium Outlets. This two-bedroom, two-bathroom self-catering property sleeps four guests and boasts on-site water park access, alongside proximity to the Florida Citrus Bowl Stadium and opportunities for exploring nearby nature reserves.
9.8 60 reviews
Winter Garden, FL
29/07 – 31/08
$223/nighttotal: $7359 (33 )
1921 Winter Garden Home 22 Min From Magic Kingdom
1 2
apartment , Winter Garden
This beautifully renovated 1921 bungalow in Winter Garden is located less than 1.5 kilometres from Plant Street's farmers market, breweries, restaurants, and shops. The two-bedroom, two-bathroom house sleeps five guests and features a fully equipped kitchen with modern appliances, a private garden, and parking; nearby attractions include Winter Garden's main attractions.
9.9 56 reviews
Winter Garden, FL
29/07 – 31/08
$192/nighttotal: $6336 (33 )
Cozy Cottage In Winter Garden
1 2
apartment , Winter Garden
This newly renovated two-bedroom, two-bathroom house is situated near Winter Garden's downtown area, within easy reach of restaurants, cafes, the Winter Garden Farmers Market, and the West Orange Trail (approximately 6.4km from Disney World and Universal Studios). The 4-guest property boasts a fully equipped kitchen, air conditioning, parking, excellent Wi-Fi, and is a convenient base for exploring Winter Garden and Orlando's theme parks.
10 6 reviews
Winter Garden, FL
29/07 – 31/08
$259/nighttotal: $8547 (33 )
Cozy 2 Bedroom Apartment In Winter Garden With Fast Wifi, Pool & Fitness Room
2 2
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.
Best Winter Garden, FL lodging with air conditioning
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.
8.8 3 reviews
Winter Garden, FL
29/07 – 31/08
$326/nighttotal: $10758 (33 )
Winter Garden Charm, Near Disney
1 2
apartment , Winter Garden
This Winter Garden apartment, situated on Plant Street, offers easy access to Winter Garden's historic downtown area, with its restaurants and boutiques, and is within a 32km radius of Walt Disney World. The 1100 square metre (approx. 11840 sq ft) property features a modern two-bedroom, two-bathroom layout, accommodating up to four guests and includes a swimming pool, terrace, parking, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
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.
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.