Winter Park vacation rentals

We found 1,553 vacation rentals — enter your dates for availability

Discover a selection of 57 homes, 17 apartments, and other vacation rentals in Winter Park that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you expect for your stay, which might include a garden and WiFi. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Winter Park

Showing deals for:Jul 17 - Jul 24

Image gallery for Orlando 1 Acre 4 BD Home Central Near Universal

Exterior
9.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Orlando 1 Acre 4 BD Home Central Near Universal

Orlando

13% off
Price is $260
$1,817 for 7 nights
All fees included
Orlando 1 Acre 4 BD Home Central Near Universal

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Winter Park

Why visit Winter Park

  • Scenic Urban Parks: Winter Park boasts beautiful parks perfect for family outings and outdoor activities.
  • Picturesque Lakes: The area features stunning lakes ideal for leisurely walks, picnics, and water activities.
  • Vibrant Art Museums: Explore the local art scene through diverse museums and galleries showcasing unique collections.
  • Charming Neighborhoods: Wander through delightful neighborhoods filled with historic homes and local shops.
  • Diverse Accommodation Options: Choose from spacious vacation homes, villas, or cozy condos to suit your stay.

Popular types of accommodation in Winter Park

Winter Park offers an array of vacation rentals to suit every traveler's needs, including houses, villas, and condos. Whether you're seeking spacious house rentals for family gatherings or cozy condos for a romantic getaway, there's something for everyone. With convenient parking spaces and numerous options for a memorable stay, our Winter Park vacation rentals provide the perfect base to explore this stunning destination.

  • Houses: The top choice for travelers in Winter Park, these homes offer a spacious and comfortable stay for families and groups.
  • Villas: A close second, villas provide luxurious accommodations with stunning views and amenities for a relaxing getaway.
  • Condos: Ideal for shorter stays, condos offer modern conveniences and often come with access to shared facilities.
  • Apartments: A practical option, apartments give you the flexibility of home-cooked meals in a cozy setting.
  • Cottages: These charming retreats are perfect for a quaint and peaceful escape, surrounded by nature.**

Top attractions in and around Winter Park

Winter Park, Florida, offers a delightful vacation for families and entertainment seekers alike. Explore its urban parks, picturesque lakes, and vibrant art museums, perfect for outdoor adventures and cultural experiences. Whether you're traveling with family or friends, Winter Park promises a memorable getaway filled with local attractions and enriching activities to enjoy.

  • Orlando Science Center: Located 3 miles from Winter Park, this interactive science museum offers engaging exhibits and hands-on activities, perfect for families and curious minds alike.
  • Rollins College: Nestled in Winter Park, this modern college campus boasts beautiful architecture and vibrant city vibes, making it a great spot to explore the local culture.
  • Full Sail University: Also in Winter Park, this historic university is known for its creative programs and artistic community, offering a unique glimpse into the world of entertainment and media.

Things to do recommended for couples

For a romantic getaway in Winter Park, enjoy live music at The Social, or indulge in luxury at Rio Pinar Country Club. Don't miss the enchanting experience at Pirate's Dinner Adventure, where you can savor a delightful meal in a lively atmosphere perfect for couples.

Things to do recommended for families

Your family will love the excitement of Lil 500 Go-Karts, just 3 miles from Winter Park, and the refreshing Alfond Swimming Pool right in town. For sports enthusiasts, the Kia Center, located 5 miles away, offers a lively atmosphere perfect for a fun family outing.

Things to do recommended for groups

Group travelers in Winter Park can enjoy shopping and entertainment at Winter Park Village, experience a cultural night at The Plaza Theatre just 4 miles away, and play a round of golf at Dubsdread Golf Course located 3 miles from the city, perfect for outdoor enthusiasts.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winter Park

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, it's important to prioritize your needs when filtering your options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winter Park with a group: Think about how many bedrooms you'll require, as well as additional features like a full kitchen or outdoor area for group activities. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Park with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Winter Park: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, consider exploring Vrbo listings that are pet-friendly. Many of these properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winter Park: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the perfect spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Winter Park

Winter Park, Florida, offers a delightful blend of family-friendly attractions and vibrant urban experiences. Explore charming neighborhoods filled with picturesque homes, enjoy the scenic parks perfect for family outings, and indulge in local dining. Nearby cities also provide additional entertainment options, making it an ideal destination for a memorable vacation. Whether you're seeking a mountain getaway or a relaxing park visit, Winter Park is a fantastic choice for travelers of all ages.

  • Orlando: As a bustling metropolis, Orlando is a premier destination for family-friendly entertainment and outdoor experiences. Located just a short drive from Winter Park, visitors can explore world-renowned theme parks, such as Walt Disney World and Universal Studios, which offer thrilling rides and immersive attractions. The city is also home to vibrant shopping areas and arts centers, making it a great spot for leisure activities. Don't miss the beautiful Lake Eola Park, perfect for a leisurely stroll or a paddleboat ride, and be sure to check out the local dining scene for a taste of Orlando’s diverse culinary offerings.
  • Baldwin Park: Nestled around Winter Park, Baldwin Park is a charming neighborhood known for its family-oriented atmosphere and city vibes. This planned community features scenic lakes and parks, providing a peaceful escape for outdoor enthusiasts. Enjoy shopping at boutique stores or indulge in a meal at one of the many restaurants lining the streets. Baldwin Park is also close to educational institutions and film studios, making it an exciting area to explore for both leisure and learning. The community hosts various events throughout the year, adding to its lively charm.
  • Goldenrod: Located near Winter Park, Goldenrod is a vibrant neighborhood that offers a blend of family, city, and business experiences. The area is known for its convenient shopping centers and educational facilities, catering to both residents and visitors. Explore local shops or unwind at the parks in the area, which are perfect for family outings. Goldenrod’s proximity to modern and historic colleges adds a unique cultural aspect, while its closeness to theme parks ensures there's always something exciting to do. Whether you're here for business or leisure, Goldenrod has something for everyone.

Best time to go to Winter Park

If you're planning a trip to Winter Park, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like May, August and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
February64.0°F (17.8°C)Light RainMostly SunnySlightly HighSlightly Low
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
April72.5°F (22.5°C)Light RainMostly SunnyAverageSlightly High
May77.0°F (25.0°C)Light RainMostly SunnySlightly LowAverage
June81.0°F (27.2°C)Light RainMostly SunnyAverageAverage
July82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnySlightly LowAverage
September80.2°F (26.8°C)Light RainMostly SunnyAverageSlightly Low
October75.0°F (23.9°C)Light RainMostly SunnyAverageSlightly Low
November68.2°F (20.1°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December64.0°F (17.8°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can really help, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient space for you to plan new trips, keep your travel arrangements on track, or manage your existing bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Winter Park is warm enough to make your cares melt away

If the word "winter" conjures images of icy winds and smiling snowmen, think again. This city is where smart travelers flee the harshest winter climates for something a little more summery. Known for its chain of tree-lined lakes and colorful gardens, Winter Park has long been a retreat for families, older folks, and couples enjoying romantic honeymoons. These lucky visitors benefit from a surprisingly chic array of restaurants and classy boutiques, plus impressive art museums and historic homes. You can count on your Winter Park vacation rental being close to worldly attractions, but suffused with a get-away-from-it-all vibe.

A little city with big art, long history, and grand gardens

For a suburban city spread over a mere 10 square miles, Winter Park has an awfully swanky collection of cultural, historical, and natural attractions. Its Charles Hosmer Morse Museum of American Art is world-famous for its collection of Louis Comfort Tiffany pieces. The Hannibal Square Heritage Center is dedicated to the African Americans who lived and worked in the area in the 19th century. Plus, no matter where your Winter Park vacation rental lies, it'll be close to a botanical garden. The Mead Botanical Garden on Lake Sue and the Kraft Azalea Gardens on Lake Maitland are standouts.

Enjoy the sunny scene on foot, on wheels, or on the water

The easiest way to enjoy Winter Park is simply to step outside and start walking toward Park Avenue, a prime destination for excellent restaurants, upscale shopping, and cocktail bars with outdoor seating. Tired of walking? Keep the sightseeing going with a scenic boat tour through the lakes, or take a bike tour of historic homes and buildings. Of course, you can always head 30 minutes south to Walt Disney World if that's what the family is clamoring for, but Winter Park has a way of making anything other than its quaint southern charm seem unnecessary.

Enjoy the winter of your content in Winter Park

What's in a name? In this case, plenty. Maybe it's called Winter Park because you should park yourself here all winter. Temperatures range from the high 50s to the 70s on most days from November through February, and although prices are at a premium, the sunny skies might be worth it. Spring and fall are also special, especially if you're looking for a bargain on a Winter Park vacation rental. Just remember that rainy weather (and occasional hurricanes) can hit from June to November. Bring your rain gear and listen to local meteorologists.

Tropical trees and feathered friends abound in Winter Park

Winter Park's warm, watery climate is perfect for the oaks and moss-draped camphor trees that make you feel like you're on the edge of a wetland wilderness, even while strolling through the middle of town. Paddle a kayak, or take a boat tour through the city's many lakes and admire the banana trees as you keep an eye out for black anhingas and purple martins. This is an ideal destination for bird watchers. The Mead Botanical Garden has reported sightings of barred owls, Cooper's hawk, and the rare red-headed woodpecker.

Traveling to and around Winter Park

The nearest airport is in Orlando Intl. Airport (MCO), located 11.8 mi (19 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Orlando Sanford Intl. Airport (SFB), which is 13.4 mi (21.6 km) away.

If you prefer train travel, the main station is Winter Park Station.

Frequently asked questions

What is the best area to stay in Winter Park, Florida, United States of America when booking a vacation rental?
When considering the best area to stay in Winter Park, Florida, the charming downtown area stands out as a top choice for vacation rentals. This vibrant neighborhood is known for its picturesque streets lined with oak trees and an array of boutiques, cafes, and art galleries. One of the highlights of this area is the beautiful Central Park, which hosts various events throughout the year and offers lovely spots for relaxation and picnicking. Additionally, the nearby Charles Hosmer Morse Museum of American Art showcases an impressive collection of Tiffany glass, making it a must-visit for art enthusiasts.

Another excellent option is the area around Park Avenue, where you can find a delightful mix of dining and shopping experiences. The combination of historic charm and modern amenities makes it ideal for those looking to immerse themselves in the local culture. This neighborhood typically has a wide selection of vacation rental properties, accommodating various preferences and group sizes.
How much does it cost to rent a vacation home in Winter Park?
Prices for vacation rentals in Winter Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winter Park to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winter Park vacation house rentals?
You can find great discounts on house rentals in Winter Park on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Winter Park ski resort rentals?
For skiing in Winter Park, travelers should focus on the area around the Winter Park Resort, which offers a variety of rental options close to the slopes. Properties in the vicinity of the resort typically include cozy condos and spacious townhomes, many of which feature amenities such as ski-in/ski-out access, hot tubs, and fireplaces, ensuring a comfortable stay after a day on the mountain.

The neighborhoods surrounding the resort, such as Fraser and downtown Winter Park, offer additional lodging choices. In Fraser, visitors can find rustic cabins and lodges that provide a more secluded experience, often with amenities like full kitchens, outdoor grills, and access to community recreational facilities. Some properties even feature scenic mountain views, which enhance the relaxing atmosphere.

In downtown Winter Park, guests can enjoy the convenience of being close to local restaurants, shops, and nightlife. Rentals here frequently come with modern amenities such as Wi-Fi, laundry facilities, and parking. Additionally, the area offers easy access to outdoor activities beyond skiing, including snowshoeing and winter hiking, making it a well-rounded destination for winter sports enthusiasts.
What is the most popular type of vacation rental accomodation in Winter Park?
In Winter Park, vacation houses are the most popular type of rental accommodation, with about 62 available throughout the area. These properties often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor areas that are superb for enjoying the pleasant Florida weather. Many of these homes are situated in family-friendly neighborhoods, making them ideal for groups or families looking to experience the local attractions.

Apartments are also a popular choice, with around 20 units available. Typically, these apartments come with modern amenities such as cozy living areas and kitchens, providing a more compact yet comfortable lodging option for travelers. Additionally, several condos, villas, and cottages are scattered throughout Winter Park, offering diverse options for those seeking a unique stay.
Are there any family house rentals in Winter Park?
In Winter Park, Florida, there are numerous family-friendly house rentals available, with about 53 options to choose from. This charming area is known for its outdoor recreation and vibrant community atmosphere, making it an excellent choice for families. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and comfortable accommodations that can host larger groups.

Visitors can expect amenities such as private backyards where children can play, game rooms for entertainment, and proximity to local parks and attractions. The nearby Winter Park Village features shopping, dining, and entertainment options, ensuring there are plenty of activities for everyone. See all family-friendly rentals in Winter Park.
Can I rent a vacation home with a pool or hot tub in Winter Park?
In Winter Park, there are several vacation homes available for rent that come equipped with pools or hot tubs, with around 27 options to choose from. This charming city offers a variety of neighborhoods where these properties can be found, including the scenic areas near Lake Bessie and the more residential zones close to downtown, which provide easy access to local amenities and attractions.

Travelers can expect a range of amenities in these rentals, including private pools, soothing hot tubs, spacious outdoor areas for relaxing, and fully equipped kitchens for home-cooked meals. Many properties may also feature additional comforts such as game rooms, outdoor grills, and proximity to beautiful parks and nature trails, making them ideal for both relaxation and family gatherings.
Can I find long-stay vacation rentals in Winter Park?
A long-stay vacation rental in Winter Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winter Park?
In Winter Park, travelers can find a variety of pet-friendly house rentals, with around 60 options available. Many of these properties come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces that are superb for enjoying the beautiful Florida weather. Some rentals even feature private pools or hot tubs, providing a relaxing retreat after a day of exploring the area.

The neighborhood offers easy access to parks and outdoor activities, making it an ideal spot for pet owners. Nearby, the scenic Winter Park Chain of Lakes provides opportunities for boating and fishing, while the extensive park system features walking trails and open spaces for pets to roam. Additionally, pet-friendly cafes and shops are scattered throughout the area, enhancing the overall experience for travelers with furry companions.
Are there any remote work vacation rentals in Winter Park?
In Winter Park, Florida, there are numerous vacation rentals well-suited for remote work, with about 84 options available. Travelers can expect a variety of properties equipped with essential amenities for a productive stay, including high-speed internet, dedicated workspaces with desks and chairs, and comfortable living areas. Many of these rentals also offer free Wi-Fi, ensuring seamless connectivity for virtual meetings or online tasks.

The area is known for its charming atmosphere and is close to local attractions, including parks and nature trails, which provide great opportunities for outdoor activities during breaks from work. In addition, the nearby downtown area offers cafes and restaurants where you can unwind after a day of remote working. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winter Park with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winter Park?
In Winter Park, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many vacation rentals also offer onsite parking for convenience. Travelers can expect outdoor spaces like decks or patios, great for enjoying the pleasant Florida weather. Additionally, some rentals are pet-friendly, accommodating those who wish to bring their furry companions along. Coffee and tea makers are commonly found in these properties, ensuring guests can enjoy a warm beverage anytime during their stay.
When is the best time to visit Winter Park for a vacation rental?
The best time to visit Winter Park for a vacation rental is during the peak season from January to March, with February being especially popular. This vibrant period attracts travelers eager to enjoy the pleasant Florida climate, which typically ranges from the mid-50s to low 80s Fahrenheit. Visitors can take advantage of the beautiful weather to explore outdoor activities like hiking, biking, and engaging with the local arts scene.

During these months, Winter Park comes alive with cultural events, including the Winter Park Sidewalk Art Festival, where art enthusiasts can admire the work of talented artists while enjoying the charming downtown area. The inviting atmosphere makes it a great time for families and friends to gather and experience the unique offerings of this delightful destination.

If you're looking to save a bit while still enjoying the area's attractions, consider visiting in May. Although it's outside the peak tourist season, May offers warm weather and fewer crowds, creating a more relaxed environment to explore the picturesque parks and gardens that Winter Park is known for.
How early should I book a Winter Park vacation rental?
Book your Winter Park vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winter Park, Florida, United States of America?
In Winter Park, Florida, visitors can enjoy a variety of attractions. The historic Park Avenue is lined with charming boutiques, cafes, and art galleries, making it a delightful area to explore. The scenic Central Park, located right in the heart of the city, features beautiful gardens, a playground, and often hosts local events and festivals throughout the year.

For those interested in art and culture, the Charles Hosmer Morse Museum of American Art showcases an impressive collection of Tiffany glass and other artworks. Just a short distance away, the Winter Park Scenic Boat Tour offers a picturesque journey through the city's lovely chain of lakes, allowing guests to appreciate the area's natural beauty and wildlife.

Additionally, the nearby Mead Botanical Garden provides a serene retreat with walking trails, a butterfly garden, and a variety of plant species, great for nature lovers.
Can I change or cancel my Winter Park home rental booking on Vrbo?
To find Winter Park vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winter Park vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas