House holiday rentals in Winter Park

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

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)

SoDo 3 BR Oasis w/Outdoor Spaces * Sleeps 8*

* No Cleaning Fee * Pet-Friendly * Sleeps 8 * Club Osceola is located in the SoDo district, one of the most central & desirable neighborhoods in Orlando. Offering 3 bedrooms, 1.5 baths, large patio/backyard & all the household essentials, you’ll feel right at home during your stay. Surrounding Club Osceola are tons of great restaurants, shopping & the conveniences of city living. Whether you’re traveling for business or pleasure, you’ll have everything you need for an amazing, memorable stay!

Yale House in College Park 2 mi from Downtown

Yale House is a charming, historic 1927 home. This happy place is a stylish mix of nostalgia and modern life. The home is only steps away from shops & restaurants. The full kitchen and laundry have everything one needs for longer stays and includes a dedicated workspace with ethernet. There is wifi & 4 streaming TV’s with a huge comfy couch. Two bedroom choices provide for a peaceful rest. Driveway parking, outdoor spaces and a top of the line home gym make this unique for long term comfort.

The Boho Jungalow - Private | HotTub | Downtown

This relaxing 1 bed 1 bath space in Downtown Orlando boasts a lush fenced-in private yard, hot tub, and fully equipped kitchen. We pride our studio on comfort, wellness, and delicate attention to detail to experience the magic of a trendy space in the heart of Orlando. Enjoy brand-new remodeling, furnishings, and appliances. This is the back unit of a 2-unit property. We include: ✅50" TV ✅Luxury mattress ✅Fiber optic Wi-Fi ✅Decaf Coffee & Tea ✅Disney Plus, Hulu, Max, Netflix ✅ Free Parking

Bonheur Ala Maison

Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

Downtown Orlando Modern Zen Studio Private Hot Tub

I built my dream vacation home in Downtown Orlando and am thrilled to share it. It’s modern, Zen-inspired, and meticulously clean—a true reflection of my personality. This private studio offers a serene, modern retreat. Featuring a cozy queen-size bed, a sleek white kitchen fully stocked with essentials, and a tub-shower combo for relaxation. Enjoy the convenience of an in-unit washer and dryer. Thoughtfully designed with a clean, modern aesthetic, get ready for a great stay

Hot Tub, Fire Pit, Private Backyard, King Bed

Welcome to our home centrally located between Downtown Orlando, UCF, Orlando Airport, and near to the parks. Our 2 bed 1.5 bath home with an additional sleeper sofa is a great vacation spot for your next visit to Central Florida. Beaches, Disney, the Amway Center, Dr. Phillips Center, UCF and so much more. Our home is a quiet place to rest your head at night or enjoy a relaxing beverage in our custom hot tub after a long day enjoying all Orlando has to offer.

Sleeps 3, Winter Park & Downtown

Welcome to gorgeous Winter Park! Enjoy this stylish centrally-located 1/1 home with newly renovated bedroom and fully remodeled bathroom. Just a few minutes from the beautiful cobblestone Park Avenue with the best restaurants, shops and Rollins College, always happening downtown Orlando (Kia Center, Camping World Stadium, Orlando City Stadium etc) and vibrant College Park neighborhood. Take a 25 min drive to south and you'll reach all major theme parks.

Priv. Modern Cozy CP 1B/1Ba Suite near DT Orl & WP

Private & Comfortable 1 bd/ba suite in a 2021 townhome with front view windows, queen size bed, walk-in shower& private entrance. Equipped w/ ceiling and portable fans, Roku smart TV, mini fridge/freezer, microwave, and Keurig. Located in a safe, quiet, walkable neighborhood. 5 minutes of College Park shops, 10 minutes from downtown Orlando, 25 minutes to Universal Studios, 30 minutes to Orlando International Airport, & 40 minutes to Disney.

Stunning Orlando Getaway w/Spa & Heated Pool

The whole group will enjoy easy access to everything from this centrally located Orlando location. This 1950s beautifully designed space has all modern amenities with an amazing outdoor living space. Located in College Park situated close to many amenities Orlando has to offer. Only 9 Minutes to downtown Orlando or 15 Minutes to Universal. The Acre & The Cottage Wedding venues are both within Walking Distance. Dubsdread is only 4 Minutes Away.

The Little Tree House at Country Club of Orlando

Urban cool meets childhood fancy in this upper separate downtown boutique bungalow in the Country Club of Orlando. The Little Treehouse is the perfect Central Florida romantic getaway for two in this 260 sq. ft. 2nd floor renovated 1926 carriage house. Conveniently located 5 minutes from Downtown, Amway Arena, Camping World Stadium and just 15 minutes to Universal Studio and 25 minutes from Disney!