Vacation rentals with a patio in Winter Park

Stylish newly updated home in Winter Park

Sleeps 8 people comfortably but can fit 10. This home has VERY CONVENIENT ACCESS TO I-4 making it easy to get to Orlando's most sought after attractions, including Park Avenue, Downtown Orlando, Rollins College, Leu Gardens, Mills Ave, Baldwin Park, College Park, Camping World Stadium, Amway Arena, SunRail, and many hospitals. SHORT WALK to 3 notable restaurants Also nearby: Universal Studios (20 min) Outlet Mall (20 min) International Drive (25 min) Orlando Airport (30 min) Disney (~30-40 min)

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!

King/Queen Bungalow w/ porch | central vibey area

Our 1920's historic home is nestled in a quiet neighborhood just a few blocks from everything. The ColonialTown North district of Orlando (also called Mills/50) is a vibrant, central area with exceptional walkability to grocery stores, a trendy bar scene, LOTS of coffee and boba options, foodie restaurants and casual late night eats. When you're ready, retreat to our porch swing and watch the sunset reflect off the trees. We lived in this space for four years and left it just as we crafted it.

Cozy Cottage in College Park.

Whether you're coming to Orlando for adventure at one of the theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden with a stock tank pool in College Park, in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

Comfy Tiny Home @WP. Large Private Deck+Queen bed

This memorable place is anything but ordinary. Welcome to our charming TINY house in the heart of Orlando! Nestled in a quiet neighborhood, this cozy retreat offers the perfect blend of comfort, privacy, and convenience. Whether you're here for business or leisure, our centrally located TINY house is an ideal home base for exploring all that Orlando and Winter Park have to offer. ✅️Private Patio ✅️Free Parking ✅️Deck with outdoor seating 🎢10-15 min from Universal ✈️20-22 min to airport

Lake View From Bed | Romantic Cabin

Romantic lakefront cabin with Costa Rica vibes in Orlando. Wake to sunrise views from your heated king bed. Sip Cuban espresso in the garden, walk or bike to Baldwin, Winter Park & Downtown or explore The Cady Way Trail. Enjoy a couple’s rain shower, grill, fire pit, and hammock. Guests love the peaceful setting, artful touches, and location minutes from the airport, arena & trails. Perfect for anniversaries, solo stays, and creative escapes. ⚠️Sorry - there is no lake DOCK access.

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

Adorable, private studio in College Park

Currently opening up this space for long term rentals (20-60 days). Perfect for travel nurses- about 10 min drive to Orlando Advent Health Hospital. This spot is perfect for 1 or 2 people looking for a private, welcoming place to stay! It is completely separate but does share a wall with the owners unit, so you could potentially hear some noises through there. The fenced in back yard is shared as well, both back doors open up to the yard. Its about 10 mins from downtown Orlando

𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜| ᴏʀʟᴀɴᴅᴏ

Enjoy this private 2/1 home with stylish decor. The property is very well located! Just a short car ride away from gorgeous Park Avenue and the best restaurants, Rollins College, College Park, downtown (Kia Center, Camping World Stadium, Dr. Phillips Center) and 30 minutes from all major theme parks. ✔ Comfortable 3 x Queen beds + pull out sofa ✔ Full Kitchen ✔ Parking on driveway and free street parking ✔ Smart TV ✔ Washer/Dryer "FREE" ✔ Dining table ✔ High-Speed Wi-Fi

Jefferson St. Cottage

This cottage is a unique free-standing detached dwelling in the heart of Lawsona Park in the Historic District in downtown Orlando. It sits behind the owner's main house in the back of the lot; privacy is not an issue. The cottage is loaded with all the amenities needed to enjoy your stay. We are close to highways to visit Universal, Disney World, Sea World any more attractions in central Florida. In addition, Uber is a very good option for transportation.

Luxury Container Home w/ {repaired} Hot Tub Oasis

Step into this unique experience: a shipping container transformed into a luxury 1 bedroom 1 bathroom suite. The space is perfect for couples, business travelers, tourists, and families. After a busy day in the parks or shopping, come back to a cozy outdoor paradise with lights strung up under a covered pergola. Lounge on the couch and enjoy a gas fireplace table, grill a meal on the Weber Spirit 2 gas grill, and soak your tired feet in the hot tub.