Best Vacation rentals and Airbnb offers in Winter Park, FL
8.8 74 reviews
Winter Park, FL
06/28 – 07/18
$129/nighttotal: $2580 (20 )
Suites By The Wellborn
1 1
apartment , Orlando
Accommodation with an excellent rating of 88% based on 74 reviews. You will be in Orlando. Services and facilities: a bar, a restaurant and a room service. This apartment in Orlando also has air conditioning!
Winter Park, FL
06/28 – 07/18
$120/nighttotal: $2400 (20 )
Beautiful Flat In Winter Park
1 1
apartment , Winter Park
This centrally located one-bedroom, one-bathroom condo in Winter Park provides easy access to Orlando's major attractions and hospitals, placing you within a few miles of Universal Orlando Resort and Walt Disney World. This apartment accommodates up to three guests and features a full kitchen, air conditioning, and access to a swimming pool, making it a convenient base for exploring the Orlando area.
9.6 117 reviews
Winter Park, FL
06/28 – 07/18
$101/nighttotal: $2020 (20 )
Renovated ✓Nature ✓Cozy ✓Walk To Mall Park Publix
1 1
studio , Altamonte Springs
This studio apartment is located in a peaceful area of Altamonte Springs, within walking distance of the mall, park, and Publix, and close to Orlando attractions and Uptown Altamonte Springs. It has consistently received excellent ratings for cleanliness, location, and user satisfaction. The studio comfortably accommodates up to three guests with a queen bed, rollaway bed, couch, and even a baby crib. You'll enjoy amenities like a private patio, laundry access, a fully equipped kitchen, and a fitness center.
9.6 79 reviews
Winter Park, FL
07/10 – 07/18
$137/nighttotal: $1096 (8 )
Walk To Bars, Coffee, Eateries-king Bed-workspace
1 4
apartment , Orlando
This two-bedroom Orlando vacation rental is located in the Colonial Town North neighborhood, a seven-minute drive from Downtown Orlando and attractions like the Amway Center. The unit sleeps six guests, offering two queen beds, Roku Smart TVs, a dedicated workspace, and family-friendly amenities including a stroller, pack 'n play, and high chair.
9.9 16 reviews
Winter Park, FL
07/28 – 08/01
$158/nighttotal: $632 (4 )
The Gojjo Retreat - Private Home Walkable Retreat
1 2
apartment , Orlando
This 2025-built luxury tiny home is located in a quiet neighborhood, a short walk from Orlando's top restaurants. This one-bedroom, one-bathroom dwelling accommodates up to four guests and features air conditioning, a full kitchen, and on-site parking, with an optional private chef service and a fire pit for guest enjoyment.
9.6 101 reviews
Winter Park, FL
06/28 – 07/18
$78/nighttotal: $1560 (20 )
Cozy Calm Blue One | Downtown Stay
1 1
apartment , Orlando
This one-bedroom, one-bathroom apartment rental in Orlando's Milk District offers easy access to numerous restaurants, breweries, and is within a 15-17 minute drive of Universal Studios and a 26-36 minute drive of Walt Disney World and Disney Springs. The 2-guest unit includes a private parking space, in-home office, fast Wi-Fi, and complimentary coffee, providing a comfortable and convenient stay near various Orlando attractions.
9.7 83 reviews
Winter Park, FL
07/10 – 07/18
$171/nighttotal: $1368 (8 )
Cozy Downtown Living Sleeps 8 W/ Free Parking
1 4
apartment , Orlando
This two-bedroom house is located in downtown Orlando, within walking distance of Lake Eola Park, offering easy access to restaurants and shops. The fully renovated home features a full kitchen with quartz countertops and stainless steel appliances, a bonus room with a pull-out sofa bed, in-unit laundry, two parking spaces, and sleeps up to eight guests.
9.9 61 reviews
Winter Park, FL
07/10 – 07/18
$209/nighttotal: $1672 (8 )
10 Min To Winter Park, Games, Gym, King Bd, Coffee
1 4
apartment , Casselberry
This Casselberry rental home is located 8 minutes from Winter Park and under 30 minutes from Walt Disney World and Universal Orlando Resort, offering convenient access to area attractions. This family-friendly residence accommodates up to 9 guests with 3 bedrooms and 2 bathrooms, featuring a chef's kitchen, a garage gym, a backyard play-park, and over 1,000 LEGO bricks for entertainment.
9.5 122 reviews
Winter Park, FL
06/28 – 07/18
$98/nighttotal: $1960 (20 )
1 Bed Apt Dt |Walk To Concerts | Private Workspace
1 1
apartment , Orlando
This Downtown Orlando apartment rental is situated in the Lake Eola Heights district, three blocks from major thoroughfares and a short walk from Lake Eola Park, the Amway Center, and the Dr. Phillips Center. The one-bedroom unit, sleeping two guests, features a fully equipped kitchen, in-unit washer/dryer, private parking, and keyless access, with easy walking access to numerous restaurants and bars, and short driving distances to Universal Studios and Walt Disney World.
9.9 774 reviews
Winter Park, FL
08/14 – 08/21
$88/nighttotal: $616 (7 )
Tiny House Shed In Downtown
1 2
cabin , Orlando
"The Shed" is located in a quiet Orlando neighborhood, just a short Uber ride from Amway Center and the Soccer Stadium. This rental has received excellent ratings for location, cleanliness, and overall user experience. The one-bedroom apartment can accommodate up to two guests and features a kitchenette, a private bathroom, and a shared backyard with a deck and fire pit. Amenities include a Keurig coffee maker, a smart TV, and a steamer.
9.5 8 reviews
Winter Park, FL
07/28 – 08/01
$160/nighttotal: $640 (4 )
Paradise Apartment
2 2
apartment , Winter Park
Paradise Apartment, located in Orlando, is approximately 8 miles from downtown attractions including Church Street Station and Spectrum Stadium, and 7.9 miles from Addition Financial Arena. This 80 square foot rental unit features 1 bedroom, 2 bathrooms, a full kitchen, air conditioning, Wi-Fi, a swimming pool, garden, and parking, with a guest capacity of 11.
8.8 19 reviews
Winter Park, FL
06/28 – 07/18
$95/nighttotal: $1900 (20 )
Sunshine Escape Guesthouse
1 1
apartment , Maitland
This Eatonville vacation rental is conveniently located near the RDV Sportsplex (1.7 miles) and Enzian Theater (2 miles), with easy access to Lee Road Shopping Center and the Casa Feliz Historic Home Museum within a 6-mile radius. This one-bedroom, one-bathroom house comfortably sleeps two guests and features a kitchenette with a refrigerator and microwave, in-unit laundry, free WiFi, and a Smart TV, making it ideal for a Maitland getaway.
Our Favorite Family-Friendly Vacation Rentals in Winter Park, FL
Booking a family-oriented vacation rental in Winter Park, FL keeps you close to top city attractions for a stress-free getaway.
10 21 reviews
Winter Park, FL
07/28 – 08/01
$189/nighttotal: $756 (4 )
Modern 2br Near Park Ave Perfect For Groups
1 2
apartment , Goldenrod
This family-friendly apartment is located in a quiet residential neighborhood in Goldenrod, offering easy access to Park Avenue's dining and shopping, and is less than 2 miles from Rollins College and Full Sail University. This 2-bedroom, 2-bathroom rental accommodates up to 6 guests and features a full kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, parking for 4 cars, and an in-unit washer and dryer.
9.9 379 reviews
Winter Park, FL
08/14 – 08/21
$103/nighttotal: $721 (7 )
Oasis Garden Cottage -Cozy, Chic, Near Everything!
1 2
house , Fairview Shores
This cozy cottage is conveniently located within minutes of Winter Park, College Park, Disney, and Universal in the heart of Orlando. It has excellent user, location, and cleanliness ratings. The cottage has 1 bedroom and 1 bathroom and can accommodate up to 5 guests. It features a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a garden, and parking. Guests can also enjoy the homey atmosphere with a fireplace, board games, and a claw foot tub, as well as a tranquil porch and thoughtful amenities like complimentary snacks, beverages, books, bath salts, and bath bombs.
Winter Park, FL
06/28 – 07/18
$195/nighttotal: $3900 (20 )
Sleek 2br Near Disney, Universal Stu & Downtown/ormc
2 1
apartment , Orlando
This 2-bedroom, 1-bathroom apartment in Orlando's Lancaster Park district is a 5-minute drive from the Kia Center and a 4-minute drive from the Dr. Phillips Center for the Performing Arts, offering 8610 square feet of living space. This family-friendly rental accommodates up to 6 guests and features a fully equipped kitchen, air conditioning, free Wi-Fi, on-site parking, and a garden, with a check-out time of 10:00 AM.
10 267 reviews
Winter Park, FL
08/14 – 08/21
$171/nighttotal: $1197 (7 )
King/queen Bungalow W/ Porch | Central Vibey Area
1 2
bungalow , Orlando
This charming 1920s bungalow is located in Orlando's ColonialTown North district, a lively area with easy walking access to shops, restaurants, and bars, just 10 minutes from Winter Park and 20 minutes from Universal Studios. Guests consistently rate this property excellent for cleanliness, location, and overall experience. This two-bedroom, two-bathroom home comfortably accommodates up to five guests. It features a well-equipped kitchenette, a private desk area with high-speed internet, a washer and dryer, and three smart TVs with streaming services.
Best Winter Park, FL vacation rentals with parking
9.1 22 reviews
Winter Park, FL
07/10 – 07/18
$183/nighttotal: $1464 (8 )
Necessary Retreat
3 4
house , Fairview Shores
Necessary Retreat, a spacious three-bedroom house in Orlando's Fairview Shores neighborhood, is conveniently located approximately 6.7 miles from Camping World Stadium and within 11-14 miles of attractions like the Holy Land Experience, Florida Mall, and Universal Studios' Islands of Adventure. This 10,760-square-foot vacation home features a fully equipped kitchen, two bathrooms, a private patio with garden views, free Wi-Fi, free parking, and outdoor amenities including a fireplace and barbecue.
8.8 11 reviews
Winter Park, FL
08/14 – 08/21
$77/nighttotal: $539 (7 )
Tiny House In Orlando
1 2
apartment , Lockhart
This Orlando apartment rental is conveniently located near Camping World Stadium and the Kia Forum, an 11-minute drive from each, offering easy access to major attractions. The one-bedroom, one-bathroom unit sleeps one guest and includes WiFi, air conditioning, and essential amenities like towels, linens, and toiletries.
10 2 reviews
Winter Park, FL
07/28 – 08/01
$63/nighttotal: $252 (4 )
Hogar Sobre Ruedas
1 2
apartment , Rio Pinar
This one-bedroom Rio Pinar apartment rental is conveniently located in Orlando, Florida, approximately 11 miles from Orlando International Airport and within a 7-13 mile radius of attractions like Church Street Station, Camping World Stadium, and the Addition Financial Arena. The 1-bathroom unit sleeps up to 3 guests and features free WiFi, private parking, a fully equipped kitchen, air conditioning, a terrace with garden views, and a flat-screen TV; nearby activities include exploring the Holy Land Experience.
8.5 85 reviews
Winter Park, FL
06/28 – 07/18
$129/nighttotal: $2580 (20 )
Suites By The Wellborn
1 1
studio , Orlando
This studio apartment is centrally located in Orlando, a 14-minute walk from Church Street Station and 0.9 miles from the Kia Center, offering convenient access to downtown attractions. This recently renovated apartment features complimentary WiFi, air conditioning, a garden, spa, restaurant, bar, room service, parking, and an outdoor fireplace area, with a check-out time between 1:00 AM and 11:00 AM.
Frequently Asked Questions about vacation rentals in Winter Park, FL
What should a first-time visitor not miss in Winter Park, FL?
You definitely want to check out the beautiful Park Avenue, with its charming shops and restaurants. Take a stroll through the scenic Rollins College campus, and don't miss the chance to explore the whimsical Morse Museum of American Art, showcasing the works of Louis Comfort Tiffany.
What are the best Airbnb and vacation rentals in Winter Park, FL?
Which neighborhood in Winter Park, FL should you consider for a vacation rental?
For a classic Winter Park experience, choose a vacation rental in the heart of the city, near Park Avenue. If you prefer a more residential feel, consider a rental in the charming neighborhoods of Hannibal Square or Winter Park Pines.
What are the most popular Airbnbs in Winter Park, FL?
What are the top family-friendly attractions in Winter Park, FL?
The Central Florida Zoo & Botanical Gardens is a must-visit for families, with its diverse animal exhibits and beautiful gardens. For a fun day out, head to the Winter Park Scenic Boat Tour, where you can enjoy a relaxing cruise on the waterways.
What are the best vacation rentals with a pool in Winter Park, FL?
When is the best time to book a vacation rental in Winter Park, FL?
To avoid the peak season crowds and higher prices, book your vacation rental in the shoulder seasons, like spring (March-May) or fall (September-November). You'll still enjoy pleasant weather and fewer crowds.
What are the best rentals for families and kids in Winter Park, FL?
What events or festivals should visitors check out in and around Winter Park, FL?
The Winter Park Sidewalk Art Festival is a popular event in the spring, showcasing a variety of art and crafts. In the fall, the Winter Park Autumn Art Festival is another great option for art lovers. The annual Winter Park Concours d'Elegance is a highlight for car enthusiasts.
What are the best rentals or Airbnbs with a jacuzzi in Winter Park, FL?
What are the best budget-friendly activities in Winter Park, FL?
Enjoy a picnic at the scenic Mead Garden, explore the free exhibits at the Albin Polasek Museum & Sculpture Gardens, or take a leisurely bike ride along the scenic Winter Park Chain of Lakes.
What are the best restaurants with local dishes in Winter Park, FL?
For authentic Southern comfort food, try Dixie Crossroads, known for its fried chicken and collard greens. If you're looking for fresh seafood, head to The Boathouse, located on the shores of Lake Maitland.
What are the best walking or cycling routes in Winter Park, FL?
The scenic Winter Park Chain of Lakes Trail offers a beautiful and easy walk or bike ride. For a longer route, try the West Orange Trail, which stretches for 22 miles and connects Winter Park to other nearby cities.
Are there pet-friendly attractions in Winter Park, FL?
Yes, many parks and trails in Winter Park are dog-friendly. You can enjoy a walk with your furry friend at Mead Garden, the Winter Park Chain of Lakes Trail, or the Kraft Azalea Garden.
What are the benefits of choosing a vacation rental in Winter Park, FL?
Vacation rentals offer more space and privacy compared to hotels, and often come with amenities like a kitchen and laundry facilities. They can also be a more budget-friendly option, especially for families or groups.
What are the top sports attractions and facilities in Winter Park, FL?
Winter Park is home to the Winter Park Racquet Club, offering tennis courts and other amenities. The city also has several golf courses, including the Winter Park Golf Course and the Alaqua Lakes Golf Course.
Destinations nearby
Find the Best Vacation Rentals with Balconies in Winter Park, FL
Wake up to breathtaking views at these Winter Park, FL vacation rentals with balconies, perfect for your morning coffee.
8.0 1 review
Winter Park, FL
08/14 – 08/21
$160/nighttotal: $1120 (7 )
Great Central Location
2 2
house , Orlando
This centrally located Orlando vacation home is 1.6 miles from the city center, offering convenient access to the Kia Center (3.4 miles) and Camping World Stadium (4.6 miles). This 650 sq ft rental accommodates up to 7 guests with 1 bedroom, a fully equipped kitchen, air conditioning, complimentary WiFi, parking, and a terrace.
8.0 13 reviews
Winter Park, FL
07/10 – 07/18
$214/nighttotal: $1712 (8 )
Upstay - Home W Garden, Bbq And Games At Golf Club
4 4
apartment , Orlando
This four-bedroom, three-bathroom home is located in the Ventura gated community in southeast Orlando, just six miles north of Orlando International Airport. This 1,920-square-foot vacation rental comfortably sleeps eight guests and features a private patio, a garden, a BBQ grill, a game room with a table tennis table, and access to a clubhouse with a swimming pool, tennis courts, and a fitness center.
10 1 review
Winter Park, FL
08/14 – 08/21
$275/nighttotal: $1925 (7 )
237 M² Casa ∙ 5 Quartos ∙ 10 Hóspedes
5 2
house , Orlando
This 5-bedroom luxury villa is located in Reunion Resort, Kissimmee, just 15 miles from Walt Disney World and 30 miles from Orlando International Airport. This spacious 2550 sq ft home accommodates up to 10 guests and features a private pool, spa, gourmet kitchen, and a covered lanai.
9.0 4 reviews
Winter Park, FL
07/10 – 07/18
$399/nighttotal: $3192 (8 )
Luxurious 2/2 Downtown Apartment
2 4
apartment , Orlando
This 1320 sq ft, 2-bedroom, 2-bathroom apartment in Orlando's South Eola district is a 4-minute walk from Bynx and The Stubborn Mule, and a 14-minute walk to the Dr. Phillips Center for the Performing Arts. This pet-friendly residence offers secure parking, concierge service, and a modern open-concept layout for up to 4 guests, with access to a 9th-floor lounge and future 24-hour gym.
Neighborhoods and points of interest in Winter Park, FL
Top Dog-Friendly Vacation Rentals in Winter Park, FL
Experience a pet-friendly stay in Winter Park, FL with vacation rentals located steps away from city dog parks and walking trails.
8.0 12 reviews
Winter Park, FL
07/10 – 07/18
$162/nighttotal: $1296 (8 )
2/1 With Private Backyard In The Heart Of Ivanhoe
2 4
apartment , Orlando
This 2-bedroom, 1-bathroom apartment in Orlando's Village Ivanhoe district is a 14-minute walk to AdventHealth Station and a short walk to Lake Ivanhoe, with the Orlando Science Center 12 minutes away. This pet-friendly rental accommodates up to 8 guests and features a fully equipped kitchen, complimentary Wi-Fi, on-site laundry, and is conveniently located near Universal Orlando Resort and the Kia Center.
10 1 review
Winter Park, FL
06/28 – 07/18
$170/nighttotal: $3400 (20 )
Enjoy Your Stay In Our Cozy 2 Bedroom 1 Bath Guest Suite.newly Renovated Space
2 1
apartment , Altamonte Springs
This 2-bedroom, 1-bathroom Altamonte Springs condo is centrally located, offering a 10-mile drive to downtown Orlando, a 20-mile drive to Universal Studios, and a 35-mile drive to the east coast beaches, with Winter Park's dining and boutiques nearby. This pet-friendly rental includes a swimming pool, jacuzzi, and parking, and is equipped with air conditioning, internet, and a kitchen featuring a fridge, microwave, and dishwasher, accommodating up to 4 guests with a 11:00 AM check-out.
9.6 135 reviews
Winter Park, FL
06/28 – 07/18
$232/nighttotal: $4640 (20 )
Charming Heated Pool Home In Altamonte Springs
3 1
apartment , Altamonte Springs
This vacation rental is conveniently located in Altamonte Springs, within a 5km radius of Altamonte Mall, Maitland Art Center, and Cranes Roost Park, offering easy access to shopping, art, and outdoor activities. Guests consistently rate the location, cleanliness, and overall experience as excellent. The 3-bedroom, 2-bathroom house comfortably accommodates up to 6 guests within its 1650 square feet of living space. The home features a fully equipped kitchen, a private garden with barbecue grills, a swimming pool, and a terrace/balcony for relaxing and enjoying the Florida sunshine.
10 1 review
Winter Park, FL
08/14 – 08/21
$102/nighttotal: $714 (7 )
Stylish 2br Home Near Disney And Universal Orlando
1 2
house , Orlando
This 2-bedroom house in Orlando is located approximately 5.3 miles from Church Street Station and 5.4 miles from Kia Center, offering convenient access to downtown attractions. This 850 square feet home accommodates up to 11 guests and features a well-equipped kitchen with a fridge and microwave, air conditioning, free Wi-Fi, and a garden, with a short drive to Disney and Universal Orlando.
