Winter Garden, FL vacation rentalscozycozy

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134 Rentals and Airbnb in Winter Garden, FL

Chic Studio Apt #4 By Bike Trail & Historic Downtown Winter Garden - Winter Garden, FL
Winter Garden, FL
1 1
$147/nighttotal: $2940 (20 )

Chic Studio Apt #4 By Bike Trail & Historic Downtown Winter Garden

studio - Winter Garden
This studio apartment in Winter Garden is located within walking distance of the West Orange Trail and the Winter Garden Historic Museum.
This property offers Wi-Fi, air conditioning, a kitchenette with a microwave and fridge, and on-site parking for up to two guests.
2nd Floor Studio Downtown Winter Garden - Winter Garden, FL
9.4 3 reviews
Winter Garden, FL
2 1
$177/nighttotal: $1062 (6 )

2nd Floor Studio Downtown Winter Garden

studio - Winter Garden
This studio apartment is situated in the centre of Downtown Winter Garden, a short 500-metre walk from its main street and the West Orange Trail.
This accommodation offers a main room with a full-size bed, a modern bathroom, air conditioning, WiFi, and a kitchen equipped with a fridge and microwave oven, with parking available and a guest capacity of two people.
Large Studio Apt #8 By Bike Trail & Historic Downtown Winter Garden - Winter Garden, FL
Winter Garden, FL
1 1
$150/nighttotal: $3000 (20 )

Large Studio Apt #8 By Bike Trail & Historic Downtown Winter Garden

studio - Winter Garden
This Winter Garden apartment is located directly opposite the West Orange Bike Trail, a short walk from historic downtown Winter Garden, and approximately 32 kilometres from Walt Disney World and 24 kilometres from Universal Studios.
This pet-friendly studio offers Wi-Fi, air conditioning, a kitchenette with a fridge and microwave, and access to a garden and spa, accommodating up to two guests with a king bed and free parking.
The Laurel In Downtown Winter Garden - Winter Garden, FL
10 11 reviews
Winter Garden, FL
1 2
$240/nighttotal: $4800 (20 )

The Laurel In Downtown Winter Garden

apartment - Winter Garden
This two-bedroom flat is located in the Historic Downtown Winter Garden district, offering convenient access to restaurants, the Winter Garden Farmers Market, and the Splash Pond, all within 500 metres.
This apartment sleeps up to four guests and features a kitchen, air conditioning, parking, and a front porch swing, providing a comfortable base for exploring the area.
Winter Garden D/town 1 Bed/1 Bath 2nd Floor Studio - Winter Garden, FL
9.7 40 reviews
Winter Garden, FL
2 1
$159/nighttotal: $954 (6 )

Winter Garden D/town 1 Bed/1 Bath 2nd Floor Studio

apartment - Winter Garden
This Winter Garden apartment offers convenient access to the downtown area and Winter Garden Village, though precise distances to these locations remain unspecified.
The self-catering flat sleeps two guests and includes a kitchen, air conditioning, parking, and internet access; further details regarding the property's size and specific amenities are unavailable.
Beautiful Deluxe Condo, Vista Cay - 3024 - Winter Garden, FL
9.2 71 reviews
Winter Garden, FL
2 2
$472/nighttotal: $944 (2 )

Beautiful Deluxe Condo, Vista Cay - 3024

apartment - Williamsburg
This two-bedroom apartment is located in Williamsburg, just 3.5 kilometres from the Orange County Convention Center and 3.7 kilometres from SeaWorld Orlando. The 116 square metre apartment offers a range of amenities for guests including a swimming pool, jacuzzi, spa, fitness centre, and a tennis court.
Vista Cay Resort Condo ~ 5 Mi To Universal! - Winter Garden, FL
9.2 45 reviews
Winter Garden, FL
8 3
$456/nighttotal: $5928 (13 )

Vista Cay Resort Condo ~ 5 Mi To Universal!

house - Williamsburg
This Vista Cay Resort condo is situated in Orlando, Florida, approximately 8 kilometres from Universal Studios, 3.2 kilometres from SeaWorld, and 3.4 kilometres from the Orange County Convention Center.
This three-bedroom apartment offers 130 square metres of living space, boasting a fully equipped kitchen, private balcony, and access to resort amenities including a swimming pool, jacuzzi, tennis court, and fitness centre.
Lakeview 2 Suites 6 Min To New Epic Universe - Winter Garden, FL
9.2 35 reviews
Winter Garden, FL
8 2
$591/nighttotal: $7683 (13 )

Lakeview 2 Suites 6 Min To New Epic Universe

apartment - Orlando
This two-bedroom, two-bathroom apartment is situated near Universal Studios Florida (2.7km) and ICON Park (1.9km) in Orlando, offering easy access to major attractions.
The 56 square metre property boasts a fully equipped kitchen, private parking, Wi-Fi, a swimming pool, jacuzzi, fitness centre, tennis court and can comfortably accommodate up to 16 guests.
Funtropicaltinyhomegolfcartlake - Winter Garden, FL
9.2 10 reviews
Winter Garden, FL
4 2
$400/nighttotal: $1600 (4 )

Funtropicaltinyhomegolfcartlake

apartment - Winter Garden
This Winter Garden apartment, a two-bedroom property measuring 93 square metres (approximately 0.09 hectares), is situated 1-2 minutes' drive from Winter Garden's town centre and directly opposite Newton Park.
The self-catering flat sleeps five, includes a fully equipped kitchen with modern appliances, a terrace, garden, parking, and a golf cart (free for monthly rentals, daily rental available), plus nearby access to Lake Apopka and Veterans Memorial Park.
Funtropicaltinyhomegolfcartlake - Winter Garden, FL
8.0 5 reviews
Winter Garden, FL
4 1
$345/nighttotal: $1380 (4 )

Funtropicaltinyhomegolfcartlake

house - Winter Garden
This Winter Garden holiday home, FunTropicalTinyHomeGolfCartLake, is situated approximately 21-24 kilometres from major Orlando attractions including Disney's Magic Kingdom, Camping World Stadium, the Amway Center, and Church Street Station.
The 93-square-metre property offers one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, garden, air conditioning, free Wi-Fi, and a golf cart for exploring the nearby lake.
Modern 3br Near Wekiwa Springs & Orlando - Winter Garden, FL
9.8 144 reviews
Winter Garden, FL
8 3
$528/nighttotal: $6864 (13 )

Modern 3br Near Wekiwa Springs & Orlando

apartment - Apopka
This house is located in Apopka, just 4.3 kilometres from Florida Hospital - Apopka and Rock Springs Run, with Wekiwa Springs State Park and AdventHealth Apopka within a 10 kilometre radius. It has received excellent ratings for location, cleanliness, and user experience, making it a great choice for travellers visiting the area.
The property has three bedrooms and can accommodate up to eight guests. It features a fully equipped kitchen, a garden, a barbecue grill, and a washing machine, ensuring a comfortable and convenient stay for families and groups.
Renovated Condo Near By Convention Center  Vc7 306 - Winter Garden, FL
9.7 228 reviews
Winter Garden, FL
8 3
$563/nighttotal: $7319 (13 )

Renovated Condo Near By Convention Center Vc7 306

apartment - Williamsburg
This Williamsburg apartment, ideal for families, boasts a superb location near Shingle Creek Golf Course (1.4 km) and major Orlando attractions including the Orange County Convention Center (less than 5 km) and Aquatica (less than 5 km).
The 186 square metre property offers three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, swimming pool, terrace, garden, fitness centre, and parking.

Best family friendly Winter Garden, FL vacation rentals

Among the 134 accommodations in Winter Garden, FL, here are the 4 best family friendly rentals

Family-friendly Spacious 4bedroom House In Clermont With Wifi, Ac & Private Pool - Winter Garden, FL
9.4 31 reviews
Winter Garden, FL
4 4
$300/nighttotal: $1200 (4 )

Family-friendly Spacious 4bedroom House In Clermont With Wifi, Ac & Private Pool

apartment - Horizon West
This four-bedroom house, situated in the Orange Tree neighbourhood of Four Corners, Clermont, offers easy access to Disney's Animal Kingdom and Walt Disney World Resort, with Disney Springs and Old Town also nearby.
The property sleeps eight guests across king, queen, and twin beds, boasting three bathrooms (one with a jetted bath), a swimming pool, Jacuzzi, and garden, plus a fully equipped kitchen including a fridge, microwave, and dishwasher.
Luxury Pet Friendly Condo, Near Clubhouse & Pool - Winter Garden, FL
9.4 243 reviews
Winter Garden, FL
8 3
$730/nighttotal: $9490 (13 )

Luxury Pet Friendly Condo, Near Clubhouse & Pool

apartment - Williamsburg
This eco-friendly condo is located in Orlando, just 1.2 miles from the Orange County Convention Center, making it a convenient choice for those attending events or exploring the area. The apartment has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The property offers three bedrooms and two bathrooms, providing ample space for families or groups of friends, with a total floor area of 131 square metres. Guests can enjoy a range of amenities including a swimming pool, Jacuzzi, terrace, garden, restaurant, bar, fitness centre, tennis court, and parking, offering a variety of activities and comforts for a relaxing and enjoyable stay.
Lofty Lodge - Winter Garden, FL
9.5 193 reviews
Winter Garden, FL
8 3
$644/nighttotal: $8372 (13 )

Lofty Lodge

house - Williamsburg
Lofty Lodge is a comfortable house situated in Orlando, just 2.2 miles from the Orange County Convention Center and SeaWorld Orlando, offering easy access to a variety of attractions. This property has received excellent reviews for its location, cleanliness, and overall experience.
The house has 3 bedrooms and spans 116 square metres, providing ample space for families or groups. Guests can enjoy a range of amenities, including a swimming pool, Jacuzzi, terrace, garden, bar, fitness centre, tennis court, and parking.
Vista Cay 3 Queen Beds 1 King Master Conservation - Winter Garden, FL
9.9 75 reviews
Winter Garden, FL
4 3
$590/nighttotal: $2360 (4 )

Vista Cay 3 Queen Beds 1 King Master Conservation

apartment - Williamsburg
This Williamsburg apartment, ideal for families, boasts a superb location offering easy access to local attractions.
The 116 square metre (1248 square foot) property features three bedrooms, two bathrooms, and accommodates up to six guests, complete with a swimming pool, Jacuzzi, and private terrace.

Best Winter Garden, FL vacation rentals with parking

Executive 3 Bedroom Villa At Universal,convention Center, Vista Cay - Winter Garden, FL
9.5 370 reviews
Winter Garden, FL
8 3
$633/nighttotal: $8229 (13 )

Executive 3 Bedroom Villa At Universal,convention Center, Vista Cay

apartment - Williamsburg
This three-bedroom apartment is conveniently located in Williamsburg, just a short distance from the city's main attractions. It has consistently received excellent ratings for its location, user experience, and cleanliness.
The apartment offers 186 square metres of space, comfortably accommodating up to eight guests. Amenities include a swimming pool, jacuzzi, terrace, garden, fitness centre, tennis court, and parking, as well as a fully equipped kitchen, a restaurant, and a bar.
Spacious Garage Apartment In Winter Garden - Winter Garden, FL
9.9 80 reviews
Winter Garden, FL
1 2
$271/nighttotal: $5420 (20 )

Spacious Garage Apartment In Winter Garden

house - Winter Garden
This Winter Garden guest house, situated a short walk or cycle from the downtown area and West Orange Trail, offers convenient access to Winter Garden's attractions and Orlando's theme parks.
The self-contained property, sleeping four guests in two bedrooms and one bathroom, features a spacious layout with large windows, a fully equipped kitchen including dishwasher, shared laundry facilities, and the use of two bicycles (liability applies).
Private Pool, Spa And Games Room - 16009 - Winter Garden, FL
9.7 13 reviews
Winter Garden, FL
8 5
$446/nighttotal: $5798 (13 )

Private Pool, Spa And Games Room - 16009

apartment - Horizon West
This five-bedroom, four-bathroom holiday home in Horizon West, Florida, is conveniently located approximately 3.4 kilometres from Lake Louisa State Park and within 9.7 kilometres of Northeast Regional Park and Lake Davenport.
This spacious 206-square-metre property boasts a private pool, on-site water park, spa tub, and arcade, accommodating up to ten guests and offering easy access to nearby water parks such as Surfari Water Park and Island H2O Live!.
Modern Studio On I-drive: Parking + Pool Included - Winter Garden, FL
9.8 197 reviews
Winter Garden, FL
4 1
$222/nighttotal: $888 (4 )

Modern Studio On I-drive: Parking + Pool Included

studio - Orlando
This modern apartment is located in the Universal Orlando Resort Area district of Orlando, just 2 kilometres from the Wheel at ICON Park Orlando and 3 kilometres from Universal Studios Orlando. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
This self-catering apartment is 45 square metres and can accommodate up to four guests. Amenities include a private pool, hot tub, balcony, fully equipped kitchen, free Wi-Fi, and free parking.

Frequently Asked Questions about vacation rentals in Winter Garden, FL

  • What are the top family-friendly attractions in Winter Garden, FL?

    The Winter Garden Village is great for families, with the train depot and the Winter Garden Farmers Market. The nearby West Orange Trail is also a great option for a family bike ride.
  • What are the best Airbnb and vacation rentals in Winter Garden, FL?

    The Secret Garden Apartment, Paradise Nook Near Orlando's Theme Parks and Lakeview Garden Studio are the most popular Airbnb and vacation rentals in Winter Garden, FL among travelers.

  • When is the best time to book a vacation rental in Winter Garden, FL?

    It really depends on your preference. Winter Garden is a popular destination during the spring and autumn months, so booking in advance is recommended. If you prefer warmer weather, summer is a good option, but you might find it more crowded.
  • What are the most popular Airbnbs in Winter Garden, FL?

    Among the Airbnbs in Winter Garden, FL, The Secret Garden Apartment, Paradise Nook Near Orlando's Theme Parks and Lakeview Garden Studio are the most popular ones.

  • What events or festivals should visitors check out in and around Winter Garden, FL?

    The Winter Garden Farmers Market is held every Saturday morning, and there are many other events throughout the year, such as the Winter Garden Art Festival and the Winter Garden Wine & Food Festival.
  • What are the best vacation rentals with a pool in Winter Garden, FL?

  • What are the best budget-friendly activities in Winter Garden, FL?

    The West Orange Trail is a great option for a free walk or bike ride. You can also check out the Winter Garden Heritage Museum, which offers free admission on the first Saturday of each month.
  • What are the best rentals for families and kids in Winter Garden, FL?

  • What are the best restaurants with local dishes in Winter Garden, FL?

    There are many great restaurants in Winter Garden, but some local favourites include The Crooked Spoon, which serves up delicious Southern comfort food, and The Ravenous Pig, which offers a more upscale dining experience with a focus on fresh, local ingredients.
  • What are the best rentals or Airbnbs with a jacuzzi in Winter Garden, FL?

  • What are the best walking or cycling routes in Winter Garden, FL?

    The West Orange Trail is a popular choice for walking and cycling, and it runs for 21 miles through Winter Garden and other nearby towns. You can also explore the many parks and green spaces in Winter Garden, such as the Winter Garden Village Park and the Plant Street Market.
  • Are there pet-friendly attractions in Winter Garden, FL?

    Many of the parks and green spaces in Winter Garden are pet-friendly, including the Winter Garden Village Park and the Plant Street Market. You can also find pet-friendly restaurants and shops in the area.
  • What are the benefits of choosing a vacation rental in Winter Garden, FL?

    Vacation rentals offer more space and privacy than a hotel room, and they are often located in more residential areas. They can also be a more affordable option for families or groups.
  • What are the top sports attractions and facilities in Winter Garden, FL?

    Winter Garden is home to the National Training Center, which is used by professional athletes from all over the world. The city also has a number of other sports facilities, including the Winter Garden Recreation Complex and the West Orange Trail.

Popular destinations

Best Winter Garden, FL vacation rentals with a balcony

The Point Hotel & Suites - 503 Luxury - Pool View - Close To Universal - Winter Garden, FL
9.7 11 reviews
Winter Garden, FL
2 1
$179/nighttotal: $1074 (6 )

The Point Hotel & Suites - 503 Luxury - Pool View - Close To Universal

apartment - Orlando
This Orlando apartment is conveniently located approximately 1.9 kilometres from ICON Park and 2.4 kilometres from Universal Studios Florida, offering easy access to these popular attractions.
The 67-square-metre self-catering flat features one bedroom, one bathroom, sleeps five guests, and boasts a private balcony, hot tub, fully equipped kitchen, and access to a swimming pool, jacuzzi, fitness centre, and spa.
Charming Lakeview Retreat Iii - Winter Garden, FL
8.6 81 reviews
Winter Garden, FL
2 1
$187/nighttotal: $1122 (6 )

Charming Lakeview Retreat Iii

apartment - Doctor Phillips
This Doctor Phillips apartment, near SeaWorld (3.7-4.7 km) and ICON Park (5.6 km), offers a peaceful lake view and private parking.
The 102-square-metre self-catering flat features one bedroom, one bathroom, sleeps seven, and includes a fully equipped kitchen, terrace, garden, and free Wi-Fi.
Totally Remodeled Beauty Wow. Near All Parks. - Winter Garden, FL
10 170 reviews
Winter Garden, FL
4 2
$577/nighttotal: $2308 (4 )

Totally Remodeled Beauty Wow. Near All Parks.

apartment - Williamsburg
This two-bedroom apartment is situated just 0.9 kilometres from Shingle Creek Golf Course and within 5 kilometres of the Orange County Convention Center and Aquatica, offering a convenient base for exploring Orlando. The property has received excellent ratings for location, cleanliness and user experience.
The apartment spans 113 square metres and comfortably accommodates up to 6 guests. Amenities include a fully equipped kitchen, a balcony, a swimming pool, a fitness centre, and a concierge service, providing everything you need for a relaxing and enjoyable stay.
Westgate Palace Hotel - Universal - I-drive - Winter Garden, FL
9.3 3403 reviews
Winter Garden, FL
2 1
$298/nighttotal: $596 (2 )

Westgate Palace Hotel - Universal - I-drive

resort - Orlando
The Signature Two-bedroom Deluxe Villa is located in the Florida Center district, a short walk from Pirate's Dinner Adventure and CoCo Key Water Resort and within a mile of Universal Orlando Resort and ICON Park, offering a quieter alternative to the main tourist areas. It has very good user ratings and excellent location and cleanliness ratings.
This smoke-free apartment building has two bedrooms and bathrooms, providing ample space and comfort. Guests can enjoy an outdoor pool, a Jacuzzi, a terrace, a garden, a spa, a concierge, a restaurant, a bar, a fitness centre, room service, a tennis court, and parking.

Best pet friendly Winter Garden, FL vacation rentals

Among the 134 accommodations in Winter Garden, FL, here are the 4 best pet friendly rentals

Gorgeous Vista Cay Town Home, Vista Cay - 4002 - Winter Garden, FL
9.7 2 reviews
Winter Garden, FL
1 3
$219/nighttotal: $4380 (20 )

Gorgeous Vista Cay Town Home, Vista Cay - 4002

house - Williamsburg
This Vista Cay townhouse in Orlando is located 2.4 kilometres from Universal Epic Universe and 8 kilometres from The Wizarding World of Harry Potter, with a 17-minute walk to the Orange County Convention Centre and 13 kilometres to Orlando International Airport.
This spacious three-bedroom, four-bathroom property offers 167 square metres of living space, featuring a fully equipped kitchen, free Wi-Fi, air conditioning, a swimming pool, hot tub, and an on-site games room.
2bdrm Home Near Orl Fairgrd, Downtwn, Wekiva Sprng - Winter Garden, FL
9.8 5 reviews
Winter Garden, FL
4 2
$366/nighttotal: $1464 (4 )

2bdrm Home Near Orl Fairgrd, Downtwn, Wekiva Sprng

house - Pine Hills
This holiday home is situated in Orlando, just 8 kilometres from the Orlando Fairgrounds and 9 kilometres from Downtown Orlando, offering easy access to both the city's attractions and the nearby Wekiva Springs. The property is also conveniently located near Camping World Stadium, Amway Center, and Church Street Station.
This two-bedroom, two-bathroom house offers 100 square metres of space and can accommodate up to six guests. The property features a fully equipped kitchen, air conditioning, free Wi-Fi, and private parking.
Waterfrontwntrgdnpoolhse Views Dock Wildl Nr Disn - Winter Garden, FL
9.9 143 reviews
Winter Garden, FL
2 4
$1285/nighttotal: $2570 (2 )

Waterfrontwntrgdnpoolhse Views Dock Wildl Nr Disn

apartment - Winter Garden
This four-bedroom holiday home is located in Winter Garden, Florida, just a short drive from Orlando's theme parks and the charming downtown area. It has received excellent ratings for its location, cleanliness, and overall user experience.
The property can accommodate up to eight guests and features a fully equipped kitchen, multiple Smart TVs, and comfortable seating areas. Guests can enjoy a screened-in porch, outdoor patios, a fire pit, and a fishing pier, as well as access to two bikes for exploring the nearby West Orange Trail.
Lake Lucy Waterfront Home With Bbq & Jon Boat - Winter Garden, FL
9.7 40 reviews
Winter Garden, FL
8 4
$599/nighttotal: $7787 (13 )

Lake Lucy Waterfront Home With Bbq & Jon Boat

apartment - Pine Hills
This waterfront property is located in Pine Hills, just six miles from Orlando Health - Health Central Hospital, Central Florida Fairgrounds, and Westgate Square Shopping Center, offering easy access to local attractions and amenities. The property enjoys excellent ratings for user experience, location, and cleanliness.
This four-bedroom, three-bathroom house spans 192 square metres and comfortably accommodates up to 10 guests. The property offers a range of amenities, including a private water park, a spa tub, a garden, barbecue grills, a fireplace, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.
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