Private suite holiday rentals in Winter Park

Sprawling Studio + BEST local eats & by Downtown

Orlando Bound? ⚠️Look. No. Further.⚠️ 🫵 YOU'LL ENJOY🫵 Orlando as a local in our gorgeous, modern, near-perfectly located space. 🏡 YOUR HOUSE 🏡 Sprawl out in a newly renovated duplex—1 studio-style bedroom, 1 bath, a FULL stovetop + toaster oven, and laundry (washer dryer combo). 💤 MEMORY FOAM 💤 Cooling bedding, hypoallergenic crisp white sheets and duvet, 4 pillows (2 firm and 2 plush to choose AND have an extra for the knees), and liquid-proof protectors for peace of mind. 🚸WALKING DISTANCE🚸 Convenience stores (Wawa/Circle K), a full grocery store, amazing restaurants, and an iconic local dessert shop, Charlie's Bakery. And that's just the beginning! ⚡MINUTES FROM⚡ Foodie paradise! Indulge in historic icons like Stasio's Italian Deli, Beefy King, Gringos Locos Tacos (order the double D's!), and more. Don't miss the enormous Sunday Farmers Market in Downtown Orlando for souvenirs and local delights. ⏱️ONLY⏱️ 5️⃣min to major highways (408), SoDo District, Milk District, Hourglass District, and the Orlando Executive Airport 🔟min to Downtown, I-4, AMWAY Arena, Orlando City Soccer Stadium, Camping World Stadium, and Tinker Field (EDC Orlando Music Festival) 1️⃣5️⃣min to MCO International Airport (the most common airport) 2️⃣0️⃣min to Universal Studios, Citywalk, and International Drive (a dining, drinks and entertainment mecca with some of our favorite restaurants and the BEST escape games we've ever played) 3️⃣0️⃣min to Disney World, Disney Springs, and SFB Sanford Airport 1️⃣hr to Cocoa Beach 📖 LOCAL HANDBOOK 📖 Gives you the insider scoop. We're passionate food-obsessed travelers who've called Orlando home for over 7 years. Our recommendations are accessible online 📱 so they're always up-to-date because we live, eat, and experience Orlando with our friends and family Every. Single. Day. 🦸‍♀️ SUPERHOSTS 🦸🏼 For years, and worked with the same loyal, hard working, and well-paid cleaner for over 2 years and counting. 🎟️ BOOK WITH US 🎟️ Experience Orlando as a local.

A SUITE RETREAT with a Garden View in the City

A lovely remodeled in-law suite in a 1920s Mission Styled home in College Park suited for 2 people with a separate entrance, private bath & a little kitchenette.The Suite looks out into a garden to offer a relaxing view. Even though you are in the Downtown area, the suite was designed to offer solitude. We are walking distance to many restaurants & only an easy 5 minute drive to downtown Orlando. I am looking forward to hosting any and all who would like to visit. All are welcome. #STR-1009437

Thornton Park Loft Studio

Welcome to Thornton Park Lawsona Lake Historical District! You will be staying in unique place that matches the historical district vibe! This is small space, about 200 sq loft studio with a bed located above the bathroom, if you feel adventurous you can climb up and sleep there! If not that is ok, we have couch downstairs with a sleeper where you have comfortable rest! Lake Eola and Downtown is located within a 15 minute walk, 20 minutes from the airport, 25 minute drive to Disney and SeaWorld

Bonsai House

Welcome to Bonsai Home, a unique blend of modern comfort and nature's embrace. Our charming abode, nestled between Orlando and Winter Park, offers a harmonious fusion of stylish interior design and a soothing ambiance. As you settle into your cozy living space, indulge in our thoughtful amenities and captivating details inspired by the tranquility of bonsai. Rest assured that we are at your service whenever you need assistance or have any inquiries. We extend our warmest welcome to Bonsai Home!

Guesthouse in Mills 50 with yard walking to bars

If you are looking for a private space close to the heart of downtown, you found it! This cute mid-century modern guesthouse has everything you need. Enjoy the full kitchen, shower, and outdoor space. You will have an outdoor seating area where you can enjoy a meal or just the relaxing sounds of the fountain. This property is within walking distance of some of Orlando's best bars and restaurants and a short uber to all the other hot spots in Orlando and Winter Park. Doorbell camera on front.

St. Augustine suite

Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

The Secret Sanctuary in Sanford, 5min from Airport

Welcome to your quiet, spacious, and private sanctuary. Enjoy all new appliances in the full size kitchen, a 50” flat screen TV, and a shaded outdoor area surrounded by greenery. It is located only minutes from the Orlando Sanford International Airport, Historic Downtown Sanford’s restaurants and shops, Lake Monroe’s scenic waterfront, and is centrally located between Florida’s beaches and the amusement parks. **Space is cleaned with EPA approved cleaners, including high touch surfaces**

The Paradise Bird Cottage

" This cozy Home it’s private with own access located at beautiful Baldwin Park, not far from downtown Orlando and Winter Park. Great and convenient location,few miles from Orlando International Airport easy access to restaurants, shops along with Baldwin Park Lake, beautiful park for your enjoyment, walk, run or biking. This apartment has big tv screen, washer and dryer. It is clean, private newly renovated with a wildlife theme that provides a peaceful atmosphere to relax and enjoy

Orlando Oasis in the heart of Thornton Park

The perfect Oasis located in the beautiful Historic Thornton Park, one of the safest and quietest neighborhoods in Downtown Orlando, this brand new studio apt is perfect for couples, business travelers, and families of 3. Enjoy custom cozy decor, a super-comfy queen bed, full kitchen amenities, and a private view of the pool & downtown skyline. Easily walk to great parks, restaurants, bars, shopping, and Lake Eola. 20 min to Universal. 25 min to Disney. *VIDEO TOUR* available on YouTube.

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

Luxurious Bath, Peaceful Stay: Private Guesthouse

This beautifully appointed guesthouse offers a serene retreat with a double sink, a large walk-in shower, and a luxurious bathroom. Enjoy complete privacy from the main house as you enter your secluded space through a private entrance and patio garden. Whether you're seeking a romantic getaway or a peaceful solo retreat, this guesthouse provides the perfect escape. ⁃ Orlando airport: 16 minutes ⁃ Downtown Orlando: 10 minutes ⁃ Disney parks: 25 minutes ⁃ Universal studio: 27 minutes

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort