Winter Park holiday rentals

We found 1,609 holiday rentals — enter your dates for availability
Discover a selection of 51 homes, 17 apartments and other holiday rentals in Winter Park that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include parking and a pool. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Winter Park

Showing deals for:20 Nov - 27 Nov

Image gallery for Key West Themed Lakefront Oasis with Liveaboard Sailboat!

Dock on Lake Hiawassee is a great spot to fish, have coffee, or catch a sunset!
10 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)

Key West Themed Lakefront Oasis with Liveaboard Sailboat!

Orlando

15% off
Price is AU$4,560
for 7 nights, 1 home
AU$651 per night
includes taxes & fees
Key West Themed Lakefront Oasis with Liveaboard Sailboat!

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    Enjoy full kitchens, laundry, pools, gardens and more

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The lively area of Winter Park awaits your stay

Enjoy the live music and other features of Winter Park. Renowned for its university setting, shopping and gardens, this city welcomes all visitors. Universal Studios Florida and Universal Orlando Resort are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Winter Park

Are you searching for attractions to visit in the area? Venture out of your holiday home and experience everything that makes Winter Park a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Universal Studios Florida (11.6 mi / 18.7 km)
  • Universal Orlando Resort (11.7 mi / 18.9 km)
  • Universal’s Volcano Bay (12.5 mi / 20.2 km)
  • Walt Disney World® Resort (19.4 mi / 31.3 km)
  • The Wizarding World of Harry Potter™ (11.5 mi / 18.5 km)
  • Universal CityWalk (11.6 mi / 18.7 km)

Exploring the natural landscape of Winter Park

Whether you're an active traveller or just want to take in the scenery, Winter Park is a great place to spend some time outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Harry P. Leu Gardens (2.3 mi / 3.8 km)
  • Festival Park (3.7 mi / 5.9 km)
  • Lake Eola (4.4 mi / 7 km)
  • Lake Eola Park (4.4 mi / 7.1 km)
  • Cranes Roost Park (5.3 mi / 8.5 km)
  • Tinker Field (5.8 mi / 9.3 km)

Travelling to and around Winter Park

The nearest airport is in Orlando International Airport (MCO), located 11.8 mi (19 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Orlando, FL (SFB-Orlando Sanford Intl.), which is 13.4 mi (21.6 km) away.

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

Frequently asked questions

What is the best area to stay in Winter Park when booking a holiday rental?
When considering the best area to stay in Winter Park, Florida for a holiday rental, the charming neighbourhood of Park Avenue stands out. This picturesque street is lined with a delightful array of boutique shops, cafes, and restaurants, making it a vibrant hub for both locals and visitors alike. Just a short stroll away, you'll find the beautiful Central Park, which offers lovely walking paths, gardens, and a serene lake, superb for a leisurely afternoon.

Another fantastic option is the area around the Winter Park Chain of Lakes. This scenic area is not only visually stunning but also provides opportunities for various water activities such as kayaking and paddle boarding. Additionally, the nearby Mead Botanical Garden is a great spot for nature lovers, featuring lush greenery and beautiful landscapes that are ideal for a peaceful escape.

In terms of holiday rentals, Winter Park offers a diverse selection of properties, ranging from quaint bungalows to modern villas.
Where are the best Winter Park ski resort rentals?
For renting ski accommodations in Winter Park, Florida, travellers should focus on the area surrounding the Winter Park Resort, which offers a variety of rental options close to the slopes. Many properties here include ski-in/ski-out access, allowing guests to hit the slopes directly from their doorstep. These rentals often feature modern amenities such as fully equipped kitchens, spacious living areas, and private balconies with stunning mountain views.

In the nearby town of Winter Park, visitors can find a range of charming cabins and lodges that provide a more rustic experience, often equipped with fireplaces and outdoor hot tubs for relaxing after a day of skiing. Properties in this area typically offer easy access to dining and shopping options, adding convenience for those looking to explore local cuisine and shops.

For a more family-friendly option, consider accommodations near the nearby Fraser River, where you can find spacious condos with multiple bedrooms, great for larger groups. Many of these rentals come with communal amenities like swimming pools and fitness centres, making them ideal for families or groups seeking both comfort and entertainment.

Moreover, Winter Park is known for its stunning mountain scenery and outdoor activities beyond skiing, including snowshoeing and snowmobiling.
What is the most popular type of holiday rental accomodation in Winter Park?
In Winter Park, holiday houses are the most popular type of holiday rental, with around 248 available throughout the area. These houses typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy the natural surroundings. Additionally, there are approximately 80 apartments, which offer a more compact and often more affordable option, complete with kitchen facilities and living areas. Condos, while fewer in number at about 16, also provide convenient amenities and are often located close to local attractions.
Are there any family house rentals in Winter Park?
In Winter Park, Florida, there are numerous family-friendly holiday rentals available, with around 53 options to choose from. This charming area is known for its inviting atmosphere and proximity to outdoor activities, making it a superb spot for families. Many homes feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces ideal for children to play.

In addition, some properties may offer amenities such as private pools, game rooms for entertainment, and laundry facilities for added convenience. Visitors can enjoy nearby attractions like scenic parks and trails, superb for hiking and cycling, as well as local shops and dining options that capture the spirit of the town.
Can I rent a holiday home with a pool or hot tub in Winter Park?
In Winter Park, Florida, there are several holiday homes available for rent that come with pools and hot tubs, with around 27 options to choose from. This charming area offers a mix of quaint neighbourhoods, such as the picturesque downtown with its local shops and eateries, and the more residential areas which provide a tranquil setting for relaxation.

Travellers can expect a variety of amenities in these rentals, including private pools, inviting hot tubs, and spacious outdoor areas great for entertaining or enjoying the warm Florida evenings. Many properties also feature fully equipped kitchens, comfortable living spaces, and sometimes additional perks like barbecue grills and access to community facilities. Find your rental in Winter Park with a pool or a hot tub.
Are there pet-friendly house rentals in Winter Park?
In Winter Park, there are numerous pet-friendly house rentals available for those looking to enjoy a getaway with their furry friends. With around 60 options, travellers can find properties that cater to various group sizes and preferences. Many of these rentals come equipped with amenities such as fully outfitted kitchens, spacious living areas, and outdoor spaces like patios or gardens, ideal for pets to roam and play.

The area is also home to several parks and outdoor spaces that are welcoming to pets. The nearby Winter Park Village features walking paths and green areas where pets can enjoy some fresh air. Additionally, the scenic surroundings provide a great backdrop for outdoor activities such as hiking or biking, making it a fantastic destination for pet owners looking to explore the natural beauty of the region.
Are there any remote work holiday rentals in Winter Park?
In Winter Park, Florida, there are numerous options for remote work holiday rentals, with around 336 available to suit various needs. This charming destination combines the beauty of nature with convenient amenities for those looking to work while enjoying a holiday. Many properties come equipped with reliable internet access, including Wi-Fi in-room and additional third-party services to ensure a seamless working experience.

Travellers can expect a range of amenities such as comfortable desks or workspaces, spacious living areas, and fully equipped kitchens, allowing for both productivity and relaxation. The area also boasts access to beautiful parks and recreational activities, making it a great choice for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winter Park?
In Winter Park, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy the convenience of home cooking. Many properties also offer onsite parking, which is particularly beneficial for those travelling with a vehicle. Outdoor spaces such as decks or patios are common, providing a lovely area to relax and take in the surrounding scenery. For those travelling with pets, a number of rentals permit pets, making it easier for families to bring their furry friends along. Additionally, many accommodations feature coffee and tea makers, ensuring that guests can enjoy a hot beverage at their leisure.
When is the best time to visit Winter Park for a holiday rental?
February is the most popular time to visit Winter Park, Florida, as it falls within the peak season from January to March. During this vibrant period, visitors flock to the area to enjoy pleasant temperatures and a variety of outdoor activities, making it the great time for those seeking a holiday rental. With daily highs averaging around 24 degrees Celsius, the comfortable climate invites exploration of the beautiful parks and charming downtown area.

For those who appreciate a more tranquil atmosphere, May presents a fantastic alternative for a visit. While this month is considered low season, it offers a unique opportunity to enjoy the blooming gardens and lush landscapes without the crowds. Plus, you'll likely find more competitive rates on holiday rentals, allowing you to experience Winter Park's charm at great value.
What are the top attractions in Winter Park?
In Winter Park, Florida, visitors can enjoy a variety of attractions that showcase the area's charm and natural beauty. The picturesque Park Avenue serves as the heart of the town, lined with boutique shops, galleries, and delightful dining options. The nearby Central Park features beautiful gardens, a playground, and seasonal events, making it a lovely spot for relaxation and enjoyment.

For those interested in art and culture, the Charles Hosmer Morse Museum of American Art is a must-visit, housing an extensive collection of works by Louis Comfort Tiffany. Additionally, the scenic Winter Park Chain of Lakes offers opportunities for canoeing and paddleboarding, allowing visitors to appreciate the area's stunning landscapes from the water.

The scenic Lake Baldwin Park is another highlight, great for walking, jogging, or picnicking while enjoying views of the water and the local wildlife.
Are all fees included in the Winter Park holiday homes prices shown on Stayz?
Stayz 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.
Are there any Winter Park holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winter Park with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Winter Park holiday homes?
You can find great discounts on holiday homes in Winter Park on Stayz, 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.
Can I change or cancel my Winter Park holiday home booking on Stayz?
To find Winter Park holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winter Park?
A long-stay holiday home in Winter Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Winter Park holiday home?
Book your Winter Park holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winter Park?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winter Park to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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