Welcome to Winter Park, Florida, a city known for its oak-lined avenues, shimmering lakes, and cultural vibrancy. Whether your plans include family time, a couple’s retreat, or an extended getaway, Wander’s luxury vacation rentals in Winter Park offer comfort, privacy, and a refined place to unwind. Choose peaceful lakeview homes or modern hideaways close to museums, dining, and green spaces. Each residence is designed with comfort and ease in mind.
Luxury Vacation Rentals in Winter Park, Florida
Book a Wander with inspiring views, hotel-grade amenities, modern workstations, top-tier cleaning and 24/7 concierge service. It’s a vacation home, but better.
Top-Rated Luxury Vacation Rentals in Winter Park, FL
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IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
A Guide to Luxury Travel in Winter Park, FL
Winter Park blends relaxed Florida living with a cultural edge. Spend your days exploring scenic canals, visiting galleries, strolling through gardens, or enjoying long meals outdoors.
A stay with Wander includes:
- Beautifully curated interiors in quiet neighborhoods
- High-speed Wi-Fi and work-friendly setups
- Private outdoor areas for dining or relaxing
- Round-the-clock guest support for planning and logistics
Everything is designed to create a smooth, restorative stay.
Best Places to Stay Around Winter Park
Park Avenue District
Stay close to boutiques, cafés, museums, and markets. Homes in this area are ideal for travelers who love walkable streets and cultural attractions.
Winter Park Chain of Lakes
Perfect for those who want calm mornings, water access, and scenic views. These homes are suited to families or couples who enjoy outdoor living.
Hannibal Square Community
A lively neighborhood known for its art spaces, modern restaurants, and local charm. A great fit if you enjoy character-rich surroundings.
Winter Park Weather: When Should You Visit?
Winter Park enjoys warm, bright days almost all year. Here is a quick look at typical conditions.
- January to April: Clear, comfortable days ideal for walking and culture
- May to August: Warm, sunny weather that suits lake activities
- September to December: Pleasant temperatures and festive evenings around town
No matter the season, Wander homes offer a calm retreat after a day of exploring.
Food and Drink in Winter Park
Winter Park’s dining scene shines with chef-driven restaurants, inventive menus, and plenty of outdoor seating. Expect global flavors, farm-fresh produce, great brunch options, and upscale spots for dinner.
Park Avenue offers fine dining and local favorites, while Hannibal Square has stylish Southern dishes and creative cocktails. For relaxed evenings, choose a lakeside restaurant with sunset views. Guests who prefer cooking can pick up fresh ingredients at the Winter Park Farmers Market.
Top Things to Do in Winter Park
- Join a Winter Park scenic boat tour for canal views and local history
- Visit the Charles Hosmer Morse Museum and its exceptional Tiffany glass collection
- Walk through Kraft Azalea Garden
- Shop, dine, and relax along Park Avenue
Winter Park delivers culture, nature, and serenity in equal measure.
Reserve Your Luxury Winter Park Vacation Rental with Wander
Wander’s luxury vacation properties in Winter Park, Florida, offer comfort, style, and thoughtful amenities that go beyond traditional hotel stays. Enjoy more space, a full kitchen, private outdoor areas, and work-friendly features crafted for both short visits and extended stays.
FAQs
Is Winter Park a Good Destination for Longer Stays or Remote Work?
Yes. Many Wander homes offer fast Wi-Fi, ergonomic workstations, peaceful neighborhoods, and well-equipped kitchens, which makes Winter Park ideal for extended stays.
What Amenities Are Included in Luxury Rentals in Winter Park?
Luxury vacation rentals in Winter Park often include spacious living areas, modern kitchens, high-quality furnishings, private outdoor spaces, comfortable bedrooms, and strong Wi-Fi. Some homes offer proximity to lakes or cultural attractions depending on the location.
Where Else Does Wander Have Luxury Vacation Rentals?
Beyond Winter Park, Wander offers exclusive vacation homes across the U.S., Canada, and Mexico, including:
- Marathon, Florida
- Fort Lauderdale, Florida
- Hudson Valley, New York
- Sedona, Arizona
- East Hampton, New York
- Lake Tahoe, California
- Telluride, Colorado
- Ponte Vedra Beach, Florida
- Bandon, Oregon
- Yucatán, Mexico
- Tulum, Mexico
Wherever you stay, Wander ensures elevated design, premium service, and spaces that feel like home, only better.