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Discover Your Perfect Winter Park Rentals by Owner

Winter Park Rentals by Owner

More Top-Rated Rentals by Owner in Winter Park Area

Why Choose Rent By Owner for your Winter Park vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Winter Park Rentals by Owner

Where are the best neighborhoods to stay in Winter Park?

When planning your stay in Winter Park, Florida, choosing the right neighborhood can greatly enhance your experience. Residential areas close to downtown Winter Park offer charming streets and easy access to local shops and dining options, making them ideal for exploring the vibrant community. If you prefer a more tranquil setting, neighborhoods near scenic parks provide serene environments and picturesque views, perfect for relaxation. Whether you're seeking convenience or peace and quiet, selecting a neighborhood in Winter Park ensures you enjoy a comfortable and memorable visit, with seamless booking options through Rent By Owner to find the ideal vacation rental tailored to your preferences.

Goldenrod

Located nearby, this neighborhood offers a peaceful setting for your stay with easy access to local amenities and outdoor spaces, making it an ideal choice for those seeking comfort and convenience.

View 127+ Rentals in Goldenrod

College Park

Nestled within the region, College Park provides a vibrant atmosphere paired with charming streets and diverse dining options, perfect for travelers looking to explore local culture during their visit.

View 53+ Rentals in College Park

Baldwin Park

This stylish neighborhood boasts scenic parks and walkable neighborhoods, offering a relaxed environment where you can enjoy the beauty of the area while staying conveniently close to key attractions.

View 151+ Rentals in Baldwin Park

Orwin Manor

Here, you'll find a residential area characterized by historic charm and tranquility, providing a cozy backdrop for your winter getaway or extended stay.

View 775+ Rentals in Orwin Manor

Northeast Orlando

Known for its suburban appeal, this part of the region offers spacious accommodations and easy access to local shopping and services, ideal for families or longer visits.

View 1557+ Rentals in Northeast Orlando

North Orange

This area combines accessibility with a quiet community vibe, making it a practical choice for visitors who prioritize both comfort and convenience during their time here.

View 796+ Rentals in North Orange

Best Times to Visit Winter Park

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation here allows you to experience the region's unique charm while enjoying a seamless booking process through Rent By Owner for your Winter Park, Florida rental by owner.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you can enjoy the region's mild climate and attract visitors seeking a warm escape from colder areas. This is a popular time for tourists to visit, leading to increased demand for rental properties here.

Average Temperature Daytime: Mid-70s°F - Nighttime: Mid-50s°F
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Spring Break (March to April)

Spring break attracts families and travelers looking for a pleasant getaway, making this period one of the busiest times in the area. Booking your rental early ensures access to the best properties during this lively season.

Average Temperature Daytime: Low to mid-80s°F - Nighttime: Mid-60s°F

Off-Season Highlights

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Summer (June to August)

While summer sees higher temperatures and humidity, it remains a quieter period for visitors. If you prefer less crowded accommodations and more relaxed surroundings, this season could be ideal for your stay.

Average Temperature Daytime: Upper 80s to low 90s°F - Nighttime: Mid-70s°F
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Fall (September to November)

The fall months bring cooler weather and fewer tourists, providing an excellent opportunity for a tranquil retreat. Booking earlier or later in the season often offers better rates on vacation rentals here.

Average Temperature Daytime: Mid-70s°F - Nighttime: Mid-50s°F

Weekly Weather Forecast for Winter Park

How to Book Your Winter Park vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Winter Park

More Top-Rated Rentals by Owner in Winter Park Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor grilling with access to a private or shared barbecue area.
  • Relax by the swimming pool surrounded by lush landscaping.
  • Take advantage of scenic patios or decks for outdoor dining and lounging.
  • Make use of well-maintained walking or biking trails nearby.
  • Benefit from dedicated outdoor parking spaces for convenience.
  • Experience peace and privacy with fenced yards or garden areas.
  • Utilize outdoor recreational facilities such as tennis courts or playgrounds, if available.

Top Attractions Around Winter Park

What attractions are nearby?

Within this charming destination, you can enjoy a variety of outdoor activities, cultural experiences, and scenic parks that showcase the best of the region, all conveniently accessible from your Rent By Owner rental in Winter Park.

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Family Activities

  • Winter Park Scenic Boat Tour: Explore the picturesque waters of the region on a guided boat tour, offering stunning views and family-friendly adventure in the area's beautiful lakes.
  • Central Park in Winter Park: Enjoy a relaxing day outdoors with picnic areas, playgrounds, and scenic walkways that make it perfect for family outings in this charming park.
  • Henry Flagler Museum: Discover the region's history and architecture at this historic estate, providing engaging exhibits and beautiful gardens for all ages to enjoy.
  • Winter Park Playhouse: Attend a family-focused theatrical performance or musical, offering entertainment that captures the essence of the area's vibrant arts scene.
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Adult Activities

  • Scenic Boat Tours: Experience the beauty of the region’s waterways by taking a guided boat tour that highlights the area's lush landscapes and wildlife.
  • Golfing at Premier Courses: Tee off at world-class golf courses nearby, offering a relaxing yet engaging activity amidst the picturesque surroundings.
  • Exploring Local Art Galleries: Discover vibrant art scenes in the area’s galleries, showcasing local talents and unique Florida-inspired pieces.
  • Dining at Gourmet Restaurants: Savor exceptional cuisine at renowned restaurants here, perfect for enjoying an elegant night out in this charming destination.

Other Places to Stay in Winter Park, FL

Mead Garden
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Hollie Anna Shopping Center
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Alfond Swimming Pool
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Lake Rose
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Lake Virginia
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Winter Park Playhouse
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Lee Road Shopping Center
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All Fired Up
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Cahall Sandspur Field
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Hannibal Square Heritage Center
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Virginia S. Nelson Rose Garden
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Goldenrod
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Winter Park Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the area's beautiful parks and waterways to enjoy a variety of outdoor adventures during your stay.
  • Choose accommodations with convenient amenities: Look for rentals that offer easy access to transportation, dining, and entertainment to maximize your experience here.
  • Plan your visit around seasonal events: Check the regional calendar for festivals or gatherings that highlight the area's unique culture and community spirit.
  • Connect with local guides or hosts: Engage with knowledgeable hosts or local guides through your rental to gain insider tips and personalized recommendations in this region.

Transportation Options

  • Rental Car Services: You can easily access rental car agencies in the area for flexible transportation during your stay, ideal for exploring Winter Park and nearby attractions.
  • Public Transit: The local bus systems provide an affordable and convenient way to navigate the region without the need for personal vehicles.
  • Taxi and Rideshare Options: Taxis and rideshare services are readily available here, offering quick and dependable transportation within the destination.
  • Bicycle Rentals: Biking is a popular choice for exploring this picturesque area at a leisurely pace, with numerous bike rental shops available for your convenience.

Local Customs Options

  • Southern Hospitality: You’ll notice a warm and welcoming attitude that reflects the region's friendly spirit when interacting with locals here.
  • Respect for Nature: It’s customary to appreciate and preserve the lush landscapes and outdoor spaces that are central to this area's charm.
  • Golfing Etiquette: When enjoying the many scenic courses in this destination, observing proper golf etiquette is highly valued by residents and visitors alike.
  • Local Art Appreciation: Supporting the vibrant arts scene by visiting galleries and local events is a common and appreciated custom in the region.

Frequently Asked Questions About Winter Park Rentals by Owner

1. What are the top vacation rentals in Winter Park?

There are a lot of options in Winter Park. If you plan on staying in the Winter Park area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winter Park:

2. How many Rentbyowner vacation rentals are available in Winter Park?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 147 in the Winter Park area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winter Park. 

3. What is the cancellation policy for a rental by owner in Winter Park, Florida?

Cancellation policies vary depending on the individual listing. You should review the specific cancellation terms outlined on the rental's page or contact the owner directly for detailed information before booking.

4. How do I communicate with the property owner when booking a rental in Winter Park?

You can typically reach out through the messaging system provided on the Rent By Owner platform. For any special requests or questions about the accommodation, contacting the owner directly ensures clear communication.

5. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees, such as cleaning fees or service charges, are often specified in the listing details. Make sure to review the entire listing and contact the owner if you have questions about extra costs.

6. Is there a minimum stay requirement for rentals here?

Minimum stay requirements depend on the individual property. Details are usually listed on the property's page, so be sure to check these before completing your reservation.

7. Can I find pet-friendly rentals in the region?

Pet policies vary among listings. To find suitable accommodations, filter your search for pet-friendly options or contact the owner directly to confirm their pet policy and any associated fees.

More Rentals You May Like Near Winter Park

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More Top-Rated Rentals by Owner in Winter Park Area