Best Vacation rentals and Airbnb offers in Winter Park, FL
9.8 16 reviews
Winter Park, FL
06/28 – 07/18
$98/nighttotal: $1960 (20 )
Yania's Cozy Getaway
1 1
apartment , Azalea Park
This Azalea Park apartment rental is minutes from Waterford Lakes Town Center and major highways, offering easy access to Orlando's theme parks, including Universal Studios' Wizarding World of Harry Potter. The one-bedroom, one-bathroom unit sleeps two guests and features a private patio, internet, air conditioning, parking, and a kitchen with a fridge and microwave; nearby attractions include the Florida Mall and Central Florida Fairgrounds.
Winter Park, FL
06/28 – 07/18
$108/nighttotal: $2160 (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.
9.8 1328 reviews
Winter Park, FL
01/08 – 01/29
$90/nighttotal: $1890 (21 )
Downtown (Ivanhoe Village) Loft Apartment
1 2
apartment , Orlando
This studio apartment is located in Orlando's Ivanhoe Village, known for its lively atmosphere and within walking distance to popular attractions and amenities, including the Science Center, Museum of Art, and Lake Ivanhoe. With excellent user, location, and cleanliness ratings, this studio offers a comfortable stay for two guests. The loft-style studio features modern appliances and furnishings, keyless entry for convenient self-check-in, and a spacious layout with high ceilings and exposed beams. Guests can enjoy amenities such as a fully equipped kitchen with a fridge and microwave, air conditioning, parking, and proximity to entertainment options, outdoor recreation, and cultural attractions.
9.7 123 reviews
Winter Park, FL
07/10 – 07/18
$203/nighttotal: $1624 (8 )
213 Winter Park/downtown Villa+studio Pri Entrance
1 4
apartment , Fern Park
This Fern Park studio, located in Kissimmee, offers convenient access to I-4, placing Universal Studios, Disney World, and SeaWorld within a short driving distance, and is also near Winter Park and Wekiwa Springs State Park. The 5-bedroom, 3-bathroom house includes a fully equipped studio apartment with a kitchenette, high-speed internet (300 Mbps), a Jacuzzi, a private fenced backyard with a play structure, and parking for multiple vehicles, accommodating up to 14 guests.
9.6 119 reviews
Winter Park, FL
06/28 – 07/18
$85/nighttotal: $1700 (20 )
1bd Apt In Downtown W/ King Bed |Office, Free Prkg
1 1
apartment , Orlando
This downtown Orlando rental is three blocks from bustling thoroughfares, near Lake Eola Park, and a short drive from Universal Studios and Walt Disney World. The one-bedroom apartment sleeps two, features a king-size bed, smart TV, fully equipped kitchen with washer/dryer, private parking, and a dedicated workspace, all within a high Walk Score neighborhood.
9.9 164 reviews
Winter Park, FL
09/03 – 09/08
$119/nighttotal: $595 (5 )
Cozy Cottage In College Park.
1 2
bungalow , Orlando
This cozy Orlando cottage, located near Winter Park and a short drive from major attractions like Universal Studios and Walt Disney World, offers easy access to the Dr. Phillips Center for the Performing Arts and Dubsdread Golf Course. The 300-square-foot guesthouse features a queen bed, a sofa bed, an adult-accessible sleeping loft, a kitchenette with a convection oven and double hotplate, a full bathroom, and access to a neighborhood pool and bikes; it comfortably sleeps three guests.
9.6 19 reviews
Winter Park, FL
07/28 – 08/01
$104/nighttotal: $416 (4 )
Tiny Unit In Cottage In The Middle Of Downtown
1 2
apartment , Orlando
This downtown Orlando apartment rental boasts an exceptional location, steps from Lake Eola Park, Amway Center, and the Dr. Philips Center for the Performing Arts, with Universal Studios and Disney World within a short drive. This 100-square-foot studio features a private entrance, bedroom, bathroom, and outdoor porch space, accommodating two guests and offering amenities such as a mini-refrigerator, coffee maker, and streaming services; free parking is included.
9.7 27 reviews
Winter Park, FL
06/28 – 07/18
$117/nighttotal: $2340 (20 )
The Emerald, Milk District Gem! Unit 2
1 1
apartment , Orlando
This Milk District rental is conveniently located one mile from Lake Eola and minutes from Downtown Orlando, offering easy access to Universal Studios (25-minute drive) and Disney World (30-40 minute drive). This one-bedroom, one-bathroom house sleeps three guests and features a kitchen with a fridge, freezer, and microwave, plus air conditioning, a garden, on-site parking, and free Wi-Fi; it's pet-friendly with self check-in and a 4/20 friendly policy (outdoor smoking/vaping only).
9.8 77 reviews
Winter Park, FL
07/10 – 07/18
$132/nighttotal: $1056 (8 )
College Park Home Next To Golf Course 5 Min To Wp
1 4
apartment , Orlando
This College Park duplex, minutes from Downtown Orlando, Lake Eola, and I-4, offers easy access to major theme parks (within 18 minutes). The two-bedroom, two-bathroom rental sleeps nine guests and features a fully equipped kitchen, Roku TV, dedicated parking for three vehicles, and a shared backyard with a gazebo and fire pit.
9.8 163 reviews
Winter Park, FL
06/28 – 07/18
$78/nighttotal: $1560 (20 )
Comfy Studio Guest Suite
1 1
house , Fairview Shores
This Fairview Shores studio apartment offers a private guest suite with separate entrance, located a 12-minute drive from Downtown Orlando and a 30-minute drive from Walt Disney World. The unit includes a queen-size bed, kitchenette with mini-fridge and microwave, and accommodates two guests, boasting convenient access to nearby shopping and dining.
9.9 99 reviews
Winter Park, FL
09/03 – 09/08
$134/nighttotal: $670 (5 )
Roy's Guest House
1 2
house , Orlando
Roy's guest house offers a private, quiet escape in Orlando, Florida, conveniently located 3.1 miles from Church Street Station, 3.7 miles from the Amway Center, and 4.7 miles from Camping World Stadium. This 420-square-foot house features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, free parking, Wi-Fi, and a garden patio; a nearby coffee shop adds extra convenience.
9.4 149 reviews
Winter Park, FL
01/08 – 01/29
$95/nighttotal: $1995 (21 )
Maria's Orlando Vacation Home
1 2
apartment , Azalea Park
This three-bedroom, two-bathroom house in Azalea Park offers convenient access to Orlando's attractions, being 10 minutes from Downtown Orlando, 20 minutes from various shopping malls, and 30 minutes from theme parks. The home comfortably sleeps six guests and includes a fully equipped kitchen with a refrigerator, freezer, and microwave, air conditioning, parking, and excellent guest ratings for cleanliness and location.
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.
9.2 17 reviews
Winter Park, FL
07/03 – 07/31
$128/nighttotal: $3584 (28 )
#1 Rated Neighborhood|.4 Mi. To Advent Hospital
1 2
apartment , Orlando
This College Park bungalow, a 2-bedroom, 1-bathroom house, is located 0.4 miles from AdventHealth Hospital and 0.7 miles from College Park's Main Street, offering easy access to local shops and restaurants. This Orlando vacation rental sleeps four, features a fenced backyard, a separate office, a full kitchen with dishwasher, and includes amenities such as a swimming pool, fitness center, and parking; a minimum 28-day stay is required.
9.6 15 reviews
Winter Park, FL
07/03 – 07/10
$363/nighttotal: $2541 (7 )
Cozy 4/2, King Beds, Pergola & Hot Tub, Local Pool!
4 2
apartment , Casselberry
This 4-bedroom apartment is conveniently located in Casselberry, just a short drive from Winter Park, downtown Orlando, and major attractions like Disney. Guest reviews consistently rate this property as excellent, highlighting its comfortable and spacious accommodations. This 1550 square foot home comfortably sleeps 13 guests, providing ample space for families or groups. Enjoy modern amenities like high-speed Wi-Fi, a dedicated office space, a washer and dryer, and a mini-split air conditioning and heating system, along with a private patio with a hot tub and a spacious pool.
9.6 84 reviews
Winter Park, FL
07/10 – 07/18
$138/nighttotal: $1104 (8 )
"The Mouse" + The "Comforts Of Home"
2 4
apartment , Orlando
This 2-bedroom, 2-bathroom condo is located in the Ventura Country Club neighborhood of Orlando, just 6 miles from Orlando International Airport and within 20-30 minutes of Disney World, SeaWorld, and Universal Studios. It has an excellent user rating. The condo has a floor area of 850 square feet and can accommodate up to 6 guests. It features a fully equipped kitchen, three flat-screen TVs, a private screened patio, a washer and dryer, high-speed internet, and free local and long-distance telephone service in the US. Guests can also enjoy access to a swimming pool, Jacuzzi, terrace, balcony, garden, and parking.
Winter Park, FL
07/28 – 08/01
$147/nighttotal: $588 (4 )
93 M² Hus ∙ 2 Sovrum ∙ 6 Gäster
2 2
house , Orlando
This pet-friendly, family-friendly house in Orlando offers 2 bedrooms, 1 bathroom, and accommodates up to 6 guests with 1000 square feet of living space, featuring a full kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and internet access. Located in a district providing convenient access to Orlando's attractions, this residence has a primary front door entry with a separate key for a side door, and includes a shoe ottoman near the front entrance.
Best Winter Park, FL vacation rentals with parking
Winter Park, FL
06/28 – 07/18
$97/nighttotal: $1940 (20 )
Newly-built Beautiful \Nprivate Guest Studio In Orlando \Nfamily-friendly
1 1
studio , Azalea Park
This Azalea Park studio apartment offers convenient access to Universal Orlando Resort and Florida Mall, though precise distances to these Orlando attractions aren't provided. The unit features a private entrance, kitchen with fridge and microwave, air conditioning, a garden, parking, one bedroom, one bathroom, and sleeps up to three guests; nearby attractions include Universal CityWalk and the Kia Center.
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.
Winter Park, FL
06/28 – 07/18
$98/nighttotal: $1960 (20 )
Stylish Orlando Studio 2 Queens, Fast Wifi, Patio & Near Theme Parks
1 1
studio , Orlando
This modern studio apartment is situated in a quiet Orlando neighborhood, offering quick access to downtown and major theme parks, including Walt Disney World Resort and Universal Orlando Resort, just minutes away. This studio accommodates up to three guests with two queen beds and features a fully equipped kitchenette, a private fenced patio, a dedicated workspace with 300 Mbps Wi-Fi, a walk-in shower, air conditioning, and free parking.
9.4 6 reviews
Winter Park, FL
07/28 – 08/01
$132/nighttotal: $528 (4 )
Retro Lake Eola 1 Bedroom Condo Thornton Park
1 2
apartment , Orlando
This South Eola District condo offers stunning Lake Eola views, walking distance to Thornton Park's restaurants and the Dr. Philips Center for the Performing Arts, and easy access to Amway Center via various transportation options. The one-bedroom, one-bathroom apartment sleeps two guests and features a 55" flat-screen TV, queen-size bed, and a full kitchen with a refrigerator and microwave, plus one designated parking spot (additional parking available for a fee).
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
06/28 – 07/18
$394/nighttotal: $7880 (20 )
3 Bedroom Corner Suite
3 1
apartment , Orlando
This Orlando condo is located in the South Eola district, offering a 10-minute walk to the Dr. Phillips Center for the Performing Arts and a few minutes' walk to Lake Eola, with Church Street Station accessible in a 13-minute walk for public transport connections. This 2000 square foot apartment accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring a balcony, fitness center, barbecue area, and in-unit amenities including free Wi-Fi, air conditioning, and a washer/dryer, all supported by a concierge service.
8.3 4 reviews
Winter Park, FL
06/28 – 07/18
$2132/nighttotal: $42640 (20 )
Luxury 6000 Sqft Mansion In Downtown Orlando Sleeps 12
6 1
house , Orlando
This luxurious 6,000-square-foot mansion is centrally located in Downtown Orlando, a short distance from Church Street Station (1.1 miles), Amway Center (1.4 miles), and Camping World Stadium (2.6 miles). The six-bedroom, five-bathroom villa offers ample space for up to 23 guests, boasting three living rooms, a fully equipped kitchen, a private pool table, free Wi-Fi, and an indoor play area, ensuring a comfortable stay near Orlando's major attractions.
8.0 8 reviews
Winter Park, FL
06/28 – 07/18
$120/nighttotal: $2400 (20 )
Modern Oasis Near Lake Eola
1 1
apartment , Orlando
This Lake Eola Heights apartment rental is conveniently located less than a mile from Lake Eola Park, and within three miles of the Kia Center and Camping World Stadium. This one-bedroom, one-bathroom unit sleeps three guests and features a fully equipped kitchen, in-unit laundry, a balcony, and access to community amenities including a garden and grills; enjoy nearby attractions and public transportation via the Lynx Central Station, a 21-minute walk away.
8.0 4 reviews
Winter Park, FL
07/10 – 07/18
$525/nighttotal: $4200 (8 )
Modern 3 Bedroom Condo In Downtown W Free Parking
3 4
apartment , Orlando
This three-bedroom, two-bathroom Orlando apartment rental is located in Thornton Park, four blocks from Lake Eola and within walking distance of restaurants and bars like Bynx Coffee and The Stubborn Mule. The 2,000-square-foot unit features an open-concept living area, a terrace, and accommodates up to six guests, with amenities including a fridge, microwave, dishwasher, in-building parking, and concierge service; a nearby 24-hour gym and 9th-floor amenity area are also available.
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.
9.4 17 reviews
Winter Park, FL
07/03 – 07/31
$147/nighttotal: $4116 (28 )
Charming Winter Park 3 Bedroom Villa With Pool
4 2
house , Goldenrod
This Goldenrod villa, near Full Sail University (1.6 miles) and Winter Park Village (2.5 miles), offers convenient access to Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens (both within 6 miles). This spacious 4-bedroom, 2-bathroom home boasts 11,630 square feet, comfortably accommodating 7 guests with a private pool, terrace, and fully equipped kitchen including a dishwasher; free WiFi is also provided.
9.6 25 reviews
Winter Park, FL
06/28 – 07/18
$290/nighttotal: $5800 (20 )
Amazing Five-star Luxury Thornton Park Two Bedroom Apt - Close To Kia Center.
2 1
apartment , Orlando
This two-bedroom apartment is located in Thornton Park, a lively neighborhood just a short walk from Lake Eola and a quick drive to the Kia Center and Camping World Stadium. Guests rave about the apartment's excellent location and amenities. The apartment comfortably sleeps four guests and is equipped with a full kitchen, in-unit laundry, and a private patio. Enjoy the on-site swimming pool, spa, and water park, or take advantage of the free Wi-Fi and relax in the garden.
9.9 148 reviews
Winter Park, FL
07/10 – 07/18
$190/nighttotal: $1520 (8 )
Spacious 3 Br Home Perfect For Orlando Getaway
1 4
apartment , Casselberry
This Casselberry house, near Dew Drop Park, offers easy access to major Orlando attractions like Disney World and Universal Studios, all within a short drive. The three-bedroom, two-bathroom home sleeps six, features a fenced backyard, attached garage with washer/dryer, free Wi-Fi, and a dedicated workspace; nearby, enjoy Dew Drop Park's lake, playground, and pavilion.
9.6 135 reviews
Winter Park, FL
06/28 – 07/18
$233/nighttotal: $4660 (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.
