Villas and Holiday homes in Winter Garden, FL

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Winter Garden, FL holiday homes
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36 Villa rentals in Winter Garden, FL

Search Holiday Homes near the Heart of the City in Winter Garden, FL

Stay near top-rated restaurants and major sights with central holiday homes in Winter Garden, FL city centre.

Enchanted 2 Bedroom Home Near Downtown Winter Garden - Winter Garden, FL
9.6 5 reviews

Enchanted 2 Bedroom Home Near Downtown Winter Garden

house, Winter Garden
This Winter Garden villa is situated near the golf cart district, a 2.4km walk from Plant Street Market, and within a short drive of major attractions such as Disney World (32-40km) and Universal Studios.
The two-bedroom, one-bathroom property sleeps five guests, offering a fully furnished interior with a kitchen including a fridge, microwave, and dishwasher, plus air conditioning, a garden, parking, and excellent internet access; it's close to Crooked Can Brewery and the WG Village Shopping Mall.
Walkable Winter Garden Bungalow: 3 Blocks To Dtwn - Winter Garden, FL
9.8 178 reviews

Walkable Winter Garden Bungalow: 3 Blocks To Dtwn

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.
~ 12 Mi To Disney: Downtown Winter Garden Cottage! - Winter Garden, FL
9.7 175 reviews

~ 12 Mi To Disney: Downtown Winter Garden Cottage!

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.
Fire Pit & Yard: Updated Winter Garden Home! - Winter Garden, FL
10 1 review

Fire Pit & Yard: Updated Winter Garden Home!

house, Winter Garden
This Winter Garden holiday home is situated approximately 19-27 kilometres from major Orlando attractions such as Walt Disney World Resort, Universal Studios Florida, and ICON Park.
The 155 square metre property boasts two bedrooms, two bathrooms, and sleeps up to seven guests, featuring a fully equipped kitchen, a private spa, free Wi-Fi, and a relaxing backyard with a fire pit.

Best family friendly Winter Garden, FL villas and holiday home

Among the 36 accommodations in Winter Garden, FL, here are the 4 best family friendly villas and holiday homes

Perfect Family Two Story Villa 8 Near Seaworld - Winter Garden, FL
9.5 169 reviews

Perfect Family Two Story Villa 8 Near Seaworld

house, Williamsburg
This villa is situated just 5km from Aquatica, the Orange County Convention Center, and Orlando Vineland Premium Outlets, offering a convenient base for exploring the attractions of Orlando. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This two-bedroom, three-bathroom home comfortably accommodates up to six guests. Enjoy a range of amenities, including a private fenced yard, a fully equipped kitchen, a swimming pool, a fitness center, and a bar, making it ideal for a relaxing and enjoyable stay.
Spacious Vista Cay Townhome Newly Furnished - Winter Garden, FL
9.2 235 reviews

Spacious Vista Cay Townhome Newly Furnished

house, Williamsburg
This property is located in Orlando, Florida, just a short distance from popular attractions like SeaWorld and ICON Park. It has consistently received excellent ratings for location, cleanliness and overall user experience.
The home offers a comfortable and well-equipped space for families or groups. It comes with a range of amenities, including a swimming pool, jacuzzi, fitness centre, tennis court, and a bar.
Tropical Treasure - Winter Garden, FL
8.9 87 reviews

Tropical Treasure

house, Williamsburg
Tropical Treasure is situated just 1.9 km from the Orange County Convention Center in Orlando, Florida, offering easy access to the area's attractions. The house has consistently received very good ratings for its location and overall experience, and an excellent rating for cleanliness.
This spacious house offers 116 square meters of living space. The property features a range of amenities, including a swimming pool, jacuzzi, terrace, garden, restaurant, bar, fitness centre, tennis court, and parking.
Charming Villa Near Disney, Pool, 4 Beds, Sleeps 5 - Winter Garden, FL
8.6 4 reviews

Charming Villa Near Disney, Pool, 4 Beds, Sleeps 5

house, Clermont
This lakefront villa in Clermont's Vacation Village neighbourhood is situated within a gated community, offering a 48 kilometre drive to major theme parks such as Magic Kingdom® Park and Walt Disney World® Resort, and is adjacent to Lake Louisa State Park.
This family-friendly holiday home accommodates six guests, featuring two bedrooms, one bathroom, air conditioning, a swimming pool, a jacuzzi, and a kitchen equipped with a fridge, microwave oven, and dishwasher, with community amenities including shuffleboard, tennis, and basketball courts.

Frequently asked questions about villa rentals in Winter Garden, FL

Popular destinations

Best Winter Garden, FL villas and holiday homes with a garden

25-30 Min. Disney, Universal & Downtown Orlando - Winter Garden, FL
9.5 72 reviews

25-30 Min. Disney, Universal & Downtown Orlando

cabin, Ocoee
This mid-century style home is located in a suburban area near Orlando, Kissimmee, and Sanford, just 17 miles from the airport and a 25-minute drive from Disney World and Downtown Orlando. The property has received excellent ratings for location, cleanliness, and user experience.
The house has one bedroom with a queen bed and a twin folding bed, accommodating up to three guests. Guests can enjoy amenities such as a fully equipped kitchenette, air conditioning, a swimming pool, and a garden.
Luxury Paradise In Orlando Best Location - Winter Garden, FL
No reviews

Luxury Paradise In Orlando Best Location

house, Williamsburg
This detached property is situated in Paradiso Grande, Orlando, a short distance from Universal's Epic Universe and conveniently located off International Drive, offering proximity to major attractions, dining, and shopping.
This spacious residence, spanning 212 square meters, accommodates up to 12 guests across five bedrooms, featuring a private heated pool and access to the Aquarius Clubhouse amenities, including a resort-style pool and lazy river.
3br 2bath Condo Balcony 5min Conv Center 1388ft - Winter Garden, FL
9.4 4952 reviews

3br 2bath Condo Balcony 5min Conv Center 1388ft

house, Williamsburg
This 3-bedroom condo is located in Orlando, Florida, just 2 miles from SeaWorld Orlando and 2.1 miles from the Orange County Convention Center, offering easy access to a variety of attractions and activities. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The condo provides ample space for families or groups of friends, with a fully equipped kitchen, a washing machine, and free Wi-Fi. It also features a private balcony, a fitness room, concierge service, a swimming pool, a jacuzzi, a tennis court, and a restaurant and bar on site, ensuring a comfortable and enjoyable stay.
Suíte 2 Quartos Moderna Perto Da Universal - Winter Garden, FL
No reviews

Suíte 2 Quartos Moderna Perto Da Universal

house, Orlando
This modern villa is located in a prime Orlando district, 2.1 kilometres from Universal Islands of Adventure and close to Universal Studios Florida, with The Wheel At Icon Park Orlando just 1.8 kilometres away.
This property offers two bedrooms, two bathrooms, and accommodates up to 15 guests, featuring free WiFi, a garden, and outdoor seating, located 14.9 kilometres from Orlando International Airport.

Best Winter Garden, FL villas and holiday homes with parking

Epic Universe Lakeview Condo, Vista Cay-3032 - Winter Garden, FL
No reviews

Epic Universe Lakeview Condo, Vista Cay-3032

house, Williamsburg
This Orlando condominium is situated in Vista Cay, 2.9 kilometres from Universal Epic Universe and 3.2 kilometres from the Orange County Convention Centre.
This 139 square metre, 3-bedroom apartment accommodates up to 17 guests and features a fully equipped kitchen with a dishwasher, air conditioning, a swimming pool, and Wi-Fi.
Near Pool*balcony*vistacay Convention Ctr & Idrive - Winter Garden, FL
9.7 46 reviews

Near Pool*balcony*vistacay Convention Ctr & Idrive

house, Williamsburg
This Orlando holiday home, near the Vista Cay Convention Centre and International Drive, offers easy access to attractions such as the Orange County Convention Center (1.9 km), ICON Park (3.2 km), and SeaWorld (4 km).
This 116 square metre property boasts three bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, Jacuzzi, fitness centre, and fully equipped kitchen with dishwasher.
Vista Cay 3br Near Universal & Convention - Winter Garden, FL
No reviews

Vista Cay 3br Near Universal & Convention

house, Williamsburg
This 3-bedroom, 2-bathroom property is situated in the Vista Cay Resort in Orlando, 1.3 to 2.2 kilometres from Universal Orlando and 800 metres from International Drive, offering convenient access to theme parks and entertainment.
Guests at this holiday home can enjoy free on-site parking, a fully equipped kitchen, and Smart TVs in every room, with access to resort amenities including two swimming pools, a lazy river, a fitness centre, and sports courts, all within a secure, gated community.
Beautiful Condo - Near Epic Universe - 2027 - Winter Garden, FL
9.0 1 review

Beautiful Condo - Near Epic Universe - 2027

house, Williamsburg
This Orlando condo is located a 30-minute walk from the Orange County Convention Centre and 2.6 kilometres from Universal Epic Universe.
This property offers accommodation for up to nine guests with two bathrooms, a full kitchen, complimentary WiFi, a swimming pool, and a hot tub, all within 177 square metres of living space.

Handpicked Holiday Houses with a Swimming Pool in Winter Garden, FL

Enjoy a swim whenever you like, as these holiday homes in Winter Garden, FL feature excellent on-site pool facilities.

Stylish Vista Cay Townhome Near Conv. Ctr I-dr. - Winter Garden, FL
9.2 31 reviews

Stylish Vista Cay Townhome Near Conv. Ctr I-dr.

house, Williamsburg
Scenic Lakeview Condo W Balcony And Resort Pools - Winter Garden, FL
No reviews

Scenic Lakeview Condo W Balcony And Resort Pools

house, Orlando
Resort Style Family Friendly Vacation Villa - Winter Garden, FL
8.8 16 reviews

Resort Style Family Friendly Vacation Villa

house, Williamsburg
Gorgeous Vista Cay Town Home, Vista Cay - 4002 - Winter Garden, FL
9.6 2 reviews

Gorgeous Vista Cay Town Home, Vista Cay - 4002

house, Williamsburg

Compare Luxury Holiday Homes in Winter Garden, FL

Upscale holiday homes in Winter Garden, FL offer a memorable stay with premium amenities designed for those who appreciate the finer things.

Walk To Dtwn: Winter Garden Home W/ Patio - Winter Garden, FL
9.8 136 reviews

Walk To Dtwn: Winter Garden Home W/ Patio

house, Winter Garden

Check Out Holiday Houses with a Jacuzzi in Winter Garden, FL

A holiday home with a hot tub in Winter Garden, FL is ideal for enjoying a private soak at the end of a busy city day.

Dog-friendly Condo With A Kitchenette, Ac, Pools, Hot Tubs, Tennis, & Gym - Winter Garden, FL
No reviews

Dog-friendly Condo With A Kitchenette, Ac, Pools, Hot Tubs, Tennis, & Gym

house, Orlando
Luxury 5br Home With Game Room - Winter Garden, FL
10 1 review

Luxury 5br Home With Game Room

house, Williamsburg
Luxury 2br Epic Universe Condo At Vista Cay 3029 By Vista Cay Resort - Winter Garden, FL
No reviews

Luxury 2br Epic Universe Condo At Vista Cay 3029 By Vista Cay Resort

house, Williamsburg
Magnificent 2 Bedroom Apartment Vista Cay Resort 107 - Winter Garden, FL
9.0 173 reviews

Magnificent 2 Bedroom Apartment Vista Cay Resort 107

house, Williamsburg
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