288 Vacation rentals and Airbnb in Winter Park, FL
9.7 28 reviews
Winter Park, FL
28/06 – 18/07
₹12481/nighttotal: ₹249620 (20 )
The Emerald, Milk District Gem! Unit 2
1 1
apartment , Orlando
This Milk District Airbnb in Orlando, Florida is conveniently located approximately 1.6km from Lake Eola and a short drive from Downtown Orlando, offering easy access to major attractions such as Universal Studios (25-minute drive) and Walt Disney World Resort (30-40 minute drive). The self-catering property features one bedroom, one bathroom, and sleeps three guests; amenities include a kitchen with fridge, freezer and microwave, air conditioning, a garden, parking, and excellent guest reviews, alongside pet-friendly and 4/20-friendly policies (outdoors only).
9.5 69 reviews
Winter Park, FL
28/06 – 18/07
₹10477/nighttotal: ₹209540 (20 )
Historic Home- Downtown Orlando
1 1
apartment , Orlando
This spacious two-bedroom apartment, situated near Lake Formosa in Orlando, Florida, is approximately 0.5 km from Interstate 4, offering easy access to both Walt Disney World and Daytona Beach, and is within walking distance of the Orlando Science Center and Mennello Museum of American Art. The self-contained flat, located in a historically significant 1927 Mediterranean Revival home, sleeps two guests and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, parking, and benefits from a peaceful setting adjacent to a jogging trail.
9.9 122 reviews
Winter Park, FL
28/06 – 18/07
₹13235/nighttotal: ₹264700 (20 )
The Emerald | Walk To Downtown Orlando & Lake Eola
2 1
apartment , Orlando
This charming apartment is located in Downtown Orlando, just 15 kilometres from Universal Studios and the airport. It has received excellent ratings for cleanliness, location, and user experience. The apartment, which can comfortably accommodate four guests, features a spacious living area and a well-equipped kitchen. It also offers amenities such as a private entrance, on-site parking, and a rainforest shower, making it a perfect choice for those looking for a comfortable and convenient stay in Orlando.
9.9 61 reviews
Winter Park, FL
10/07 – 18/07
₹19927/nighttotal: ₹159416 (8 )
10 Min To Winter Park, Games, Gym, King Bd, Coffee
1 4
apartment , Casselberry
This Casselberry apartment, less than 48km from Walt Disney World and Universal Studios and 13km from Winter Park, offers easy access to major Orlando attractions. The three-bedroom, two-bathroom property sleeps nine, boasting a chef's kitchen, dedicated home gym, children's play area with trampoline and slide, and amenities including fast Wi-Fi and a smart TV.
10 1 review
Winter Park, FL
14/08 – 21/08
₹26251/nighttotal: ₹183757 (7 )
237 M² Casa ∙ 5 Quartos ∙ 10 Hóspedes
5 2
house , Orlando
This luxury villa is situated in Reunion Resort, Kissimmee, Florida, a gated community approximately 24 kilometres from Walt Disney World and 48 kilometres from Orlando International Airport. This 237 square metre villa offers five bedrooms for up to ten guests, featuring a private pool and spa, a large gourmet kitchen with new appliances, and a covered lanai, all complemented by complimentary internet access.
9.9 99 reviews
Winter Park, FL
28/07 – 01/08
₹12078/nighttotal: ₹48312 (4 )
Roy's Guest House
1 2
house , Orlando
Roy's guest house offers a private, quiet retreat in Orlando, Florida, conveniently located 5km from Church Street Station, 6km from the Amway Center, and 7.6km from Camping World Stadium. This self-catering property boasts a 39 square metre floor area with one bedroom, one bathroom, sleeping up to three guests, and features a fully equipped kitchen, free Wi-Fi, and a private garden.
9.8 138 reviews
Winter Park, FL
10/07 – 18/07
₹22468/nighttotal: ₹179744 (8 )
Updated Home* 2 King Bed Suites * Downtown Orlando
1 4
apartment , Orlando
This charming two-bedroom apartment in Downtown Orlando is just a short distance from the Amway Center and Dr. Phillips Performing Arts Center, with Universal Studios and Disney World reachable within 30 minutes. With excellent ratings for cleanliness, location and user experience, this property offers a comfortable and convenient base for exploring the city. This spacious home sleeps up to six guests and features a well-equipped kitchen, a private garden and parking. Enjoy the convenience of being close to restaurants, bars and shops, as well as the option of preparing meals in the apartment.
8.7 6 reviews
Winter Park, FL
28/06 – 18/07
₹7809/nighttotal: ₹156180 (20 )
Botanical Tranquility
1 1
apartment , Casselberry
This Casselberry apartment is conveniently located approximately 17-24 km from various Orlando attractions including Orlando Sanford International Airport, Addition Financial Arena, and the Florida Mall. The self-catering flat offers one bedroom, one bathroom, sleeps three guests, and boasts a private pool, free Wi-Fi, and parking; nearby activities include visiting the Amway Center and Camping World Stadium.
10 3 reviews
Winter Park, FL
28/06 – 18/07
₹10214/nighttotal: ₹204280 (20 )
Cute & Quaint Private Guesthouse With 1 Bed/1 Bath
1 1
house , Winter Park
This guesthouse is situated in a central Winter Park location, just minutes from Advent Health and the dining and shopping on Park Avenue, with easy access to the I-4 for broader Orlando exploration. This one-bedroom guesthouse for two guests offers a fully equipped kitchen, a comfortable living area with a large television, a king-sized bed, and a shared courtyard, all within a quiet neighbourhood setting.
9.9 85 reviews
Winter Park, FL
10/07 – 18/07
₹26633/nighttotal: ₹213064 (8 )
Winter Park Townhouse - Near Downtown & Parks
1 4
house , Fairview Shores
This Winter Park townhouse, offering easy access to I-4, is ideally located for exploring nearby attractions such as Winter Park, College Park, and Park Avenue, all within a short driving distance. The three-bedroom, three-bathroom property sleeps six guests and boasts a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, plus a garden, parking, and air conditioning.
9.9 774 reviews
Winter Park, FL
28/07 – 01/08
₹9641/nighttotal: ₹38564 (4 )
Tiny House Shed In Downtown
1 2
cabin , Orlando
The Shed is a private guest house located in a quiet neighbourhood just 5 kilometres from the Amway Center and the Soccer Stadium, with easy access to the Sun Rail and a hospital. The accommodation has received excellent ratings for its location, cleanliness, and overall experience. The self-catering unit has one bedroom and one bathroom, accommodating up to two guests. Amenities include a kitchen with a microwave, mini-fridge, and a shared backyard with a deck and fire pit.
10 7 reviews
Winter Park, FL
10/07 – 18/07
₹12696/nighttotal: ₹101568 (8 )
Sunny Oasis: Downtown Orlando With Suburban Feel
1 4
apartment , Orlando
This Orlando flat offers a prime location, a short walk from the Milk District and its amenities, with immediate access to the Cady Way and Orlando Urban trails, and is situated 4.8 kilometres from Lake Eola and a 10-minute drive from Orlando Regional Medical Center. This two-bedroom, two-bathroom apartment accommodates up to four guests, featuring air conditioning, a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher, and a private driveway for parking.
Best family friendly Winter Park, FL vacation rentals
Among the 288 accommodations in Winter Park, FL, here are the 4 best family friendly rentals
9.8 13 reviews
Winter Park, FL
14/08 – 21/08
₹13245/nighttotal: ₹92715 (7 )
Entire Condo At Ventura - Comfy, Quiet Oasis In The Heart Of Orlando
2 2
apartment , Orlando
This two-bedroom apartment is situated in Ventura, a quiet neighbourhood in Orlando, just 10 kilometres from Orlando International Airport and 20 kilometres from the Disney Parks. It has received excellent reviews from previous guests. The apartment is ideal for families or groups of up to six people. It features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, and parking. You can also enjoy on-site amenities such as tennis and pickleball courts, and an 18-hole golf course.
9.7 151 reviews
Winter Park, FL
28/07 – 01/08
₹31310/nighttotal: ₹125240 (4 )
Bonheur Ala Maison
3 2
apartment , Casselberry
This Casselberry apartment, conveniently located near numerous shops and parks, offers a fantastic base for exploring the area. Sleeping up to six guests, this three-bedroom, two-bathroom property boasts a fully equipped modern kitchen, marble bathrooms, a private backyard with a swimming pool, hot tub, and BBQ grill, plus smart TVs and high-speed Wi-Fi throughout.
9.6 135 reviews
Winter Park, FL
10/07 – 18/07
₹20953/nighttotal: ₹167624 (8 )
Charming Heated Pool Home In Altamonte Springs
3 4
apartment , Altamonte Springs
This house is located in Altamonte Springs, just 5 kilometres from Altamonte Mall, Maitland Art Center, and Cranes Roost Park, making it easy to explore the area. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience. The property is a 3-bedroom, 2-bathroom house with a floor area of 153 square metres, comfortably accommodating up to 6 guests. This family-friendly home offers a range of amenities including a swimming pool, terrace, garden, and parking, as well as a fully equipped kitchen and air conditioning for a comfortable stay.
This Mills50 holiday home in Orlando is conveniently located 2.2 km from downtown Orlando, 3.4 km from Church Street Station, and 4.2 km from the Amway Center, offering easy access to major attractions. The 91 square metre property features one bedroom, one bathroom, sleeps ten guests, and includes a fully equipped kitchen, private patio, garden, free Wi-Fi, and a washing machine.
Best Winter Park, FL holiday rentals with parking
9.2 7 reviews
Winter Park, FL
10/07 – 18/07
₹17044/nighttotal: ₹136352 (8 )
Cozy 2bd 2bth House Walk To Local Gems
2 4
house , Orlando
This Orlando house, situated 2.6km from the city centre and within 8km of Church Street Station, Camping World Stadium, and the Kia Center, offers convenient access to major attractions. This two-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen with dishwasher, a terrace, garden, free Wi-Fi, and free private parking; enjoy al fresco dining and proximity to local amenities.
Winter Park, FL
28/06 – 18/07
₹13982/nighttotal: ₹279640 (20 )
Romantic Lakefront Getaway With Balcony Near Downtown Orlando
1 1
cottage , Conway
This non-smoking cottage, situated by the water in Orlando, is a 13-minute drive from the Kia Centre and a 8-minute drive from Florida Mall. This one-bedroom, one-bathroom lodge accommodates two guests and features a garden, balcony, Wi-Fi, air conditioning, and a full kitchen, with lake activities and on-site parking readily available.
9.6 19 reviews
Winter Park, FL
28/06 – 18/07
₹129708/nighttotal: ₹2594160 (20 )
Renovated Luxury 6000 Sqft Mansion In Downtown Orlando Sleep 14 Near Theme Parks
6 1
apartment , Orlando
This six-bedroom Orlando holiday home is centrally located, within a 2.4km walk of Lake Eola and the Dr Phillips Center for the Performing Arts, and under 5km from Camping World Stadium and the Kia Forum. The 557 square metre property boasts a private water park, on-site arcade, and sleeps up to 14 guests, offering a fully equipped kitchen, swimming pool, spa, and a relaxing garden with a living plant wall.
9.4 11 reviews
Winter Park, FL
28/07 – 01/08
₹10429/nighttotal: ₹41716 (4 )
Traveler's Dream: Refresh & Recharge Poolside
1 2
apartment , Casselberry
This Casselberry flat is conveniently located approximately 3.5 km from Secret Lake Park and 4.5 km from Red Bug Lake Park, offering easy access to outdoor recreation. The one-bedroom, one-bathroom apartment sleeps two guests and features a private pool, free Wi-Fi, a fully equipped kitchen with fridge and microwave, a smart TV, and access to a community pool; Winter Park Village and Altamonte Mall are within a 10 km radius.
Frequently asked questions about holiday rentals in Winter Park, FL
What are the top family-friendly attractions in Winter Park, FL?
The Central Florida Zoo & Botanical Gardens is great for kids of all ages. You can also take a boat ride on the Winter Park Scenic Boat Tour, which is a fun way to see the area.
What are the best Airbnb and vacation rentals in Winter Park, FL?
When is the best time to book a vacation rental in Winter Park, FL?
If you're looking for warmer weather, book your vacation rental during the spring or autumn. If you want to escape the crowds, consider visiting during the off-season, but be aware that some attractions may have limited hours.
What are the most popular Airbnbs in Winter Park, FL?
What are the best budget-friendly activities in Winter Park, FL?
Take a walk or bike ride along the scenic Winter Park Chain of Lakes. It's a great way to enjoy the outdoors without spending any money. You can also visit the free museums, like the Albin Polasek Museum & Sculpture Gardens.
What are the best vacation rentals with a pool in Winter Park, FL?
What are the best walking or cycling routes in Winter Park, FL?
The Winter Park Chain of Lakes Trail is a great option for both walking and cycling. It's a scenic 14km loop that takes you past beautiful parks and lakes.
What are the best rentals or Airbnbs with a jacuzzi in Winter Park, FL?
Are there pet-friendly attractions in Winter Park, FL?
Yes, many of the parks and trails in Winter Park are pet-friendly. You can also find dog-friendly restaurants and cafes. The Winter Park Farmers Market is a great place to bring your furry friend on a Saturday morning.
What are the benefits of choosing a vacation rental in Winter Park, FL?
Vacation rentals often offer more space and privacy than hotels. They can also be more affordable, especially for families or groups. You can often find rentals with unique features like private pools or hot tubs.
What are the top sports attractions and facilities in Winter Park, FL?
Winter Park is home to the Winter Park Racquet Club, which offers a variety of tennis courts and programs. The Winter Park Golf Course is also a popular destination for golfers.
Destinations nearby
Best Winter Park, FL holiday rentals with a balcony
9.9 9 reviews
Winter Park, FL
10/07 – 18/07
₹29986/nighttotal: ₹239888 (8 )
2 Bdrm Penthouse With Billiards
1 4
apartment , Orlando
This Orlando penthouse apartment is situated in the city centre, less than 0.6km from various attractions and 14km from Orlando International Airport. The 150 square metre dwelling boasts two bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry, a billiards table, free Wi-Fi, and accommodates up to seven guests.
9.4 225 reviews
Winter Park, FL
14/08 – 21/08
₹13297/nighttotal: ₹93079 (7 )
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
3 2
apartment , Goldenrod
This Goldenrod holiday home is located just 2.2 kilometres from Full Sail University, and within a 10-kilometre radius of the University of Central Florida, Albin Polasek Museum and Sculpture Gardens, Rollins College, and Kraft Azalea Gardens. The property has received excellent ratings for location, cleanliness and user experience. The house has three bedrooms and two bathrooms, accommodating up to six guests. Amenities include a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, a garden, parking, and internet access.
8.4 16 reviews
Winter Park, FL
28/07 – 01/08
₹15138/nighttotal: ₹60552 (4 )
Spring Lake King Balcony Suite
1 2
apartment , Conway
This pet-friendly Conway apartment, near Spring Lake, is situated approximately 3.5 kilometres from Conway's city centre and within 7-8 kilometres of the Amway Center, Camping World Stadium, and Orlando International Airport. The 33-square-metre self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a private balcony, garden, parking, Wi-Fi, and a kitchen with a dishwasher, microwave, and fridge.
Winter Park, FL
10/07 – 18/07
₹14307/nighttotal: ₹114456 (8 )
Apartment ∙ 2 Bedrooms ∙ 4 Guests
2 4
apartment , Orlando
This Orlando flat is located within a secure resort community, 16 kilometres from the main theme parks and 8 kilometres from Orlando International Airport. This two-bedroom, two-bathroom apartment sleeps four and offers resort-style amenities including a swimming pool, fitness centre, tennis, pickleball, and basketball courts, alongside a furnished patio and a fully equipped kitchen.
Best pet friendly Winter Park, FL vacation rentals
Among the 288 accommodations in Winter Park, FL, here are the 4 best pet friendly rentals
Winter Park, FL
28/07 – 01/08
₹14295/nighttotal: ₹57180 (4 )
Cozy Apt With Pool, Hot Tub, Golf, Near Downtown
2 2
house , Orlando
This Orlando dwelling is situated 8.05 kilometres from Church Street Station and 8.19 kilometres from the Kia Centre, with Orlando International Airport a mere 8.05 kilometres away. This 76 square metre holiday home accommodates up to seven guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, hot tub, balcony, garden, fitness centre, and tennis courts, with free Wi-Fi provided.
9.3 40 reviews
Winter Park, FL
10/07 – 18/07
₹22691/nighttotal: ₹181528 (8 )
Drayton Place Staycation - Private Lk/pk Front Ste
2 4
apartment , Orlando
This waterfront holiday home is located just 1.6 kilometres from the Kia Center, within a 10-minute walk of Camping World Stadium and Tinker Field. It has excellent user, location and cleanliness ratings. The property offers two bedrooms and a bathroom, covering 42 square metres and accommodating up to four guests. It has a range of amenities including a swimming pool, spa, garden, terrace, and a fully equipped kitchen.
Winter Park, FL
14/08 – 21/08
₹10678/nighttotal: ₹74746 (7 )
Cozy Golf Condo With 3 Pools, Gym And Just 15 Minutes To Airport
1 2
house , Orlando
This golf condo is situated approximately 8 kilometres from Orlando International Airport and within 12.4 kilometres of downtown Orlando attractions, including Church Street Station and the Kia Centre. This property offers accommodation for up to seven guests, featuring a fully equipped kitchen with a dishwasher and oven, air conditioning, complimentary WiFi, access to three swimming pools, a fitness centre, a hot tub, and a garden, with a floor area of 63 square metres and one bathroom.
9.0 22 reviews
Winter Park, FL
28/06 – 18/07
₹20640/nighttotal: ₹412800 (20 )
3bdrm Fruit Tree Home Near Downtown Orlando
3 1
apartment , Orlando
This Orlando home is located just 1.1 km from Grand Avenue Park and within 5 km of Kia Center and Camping World Stadium, making it a convenient base for exploring the city's attractions. It has received excellent user ratings, so you can be sure of a comfortable stay. The property has 3 bedrooms and can accommodate up to 8 guests, making it suitable for families or groups of friends. The house offers a range of amenities, including a swimming pool, jacuzzi, garden, and free Wi-Fi, ensuring a relaxing and enjoyable stay.