House holiday rentals in Winter Park

Luxury Home by - SoDo + BEST local eats + 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—3 bedrooms, 2 baths, a FULL kitchen, and laundry. Plus, a game room with a solid wood Foosball table and tournament-grade Arachnid dartboard. Outside, a fully fenced backyard awaits with a FREE charcoal grill and cozy seating in the shade of a 9ft umbrella. 💤 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.

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)

Stylish New 1 Bed + Office ☼ In Downtown Orlando

Welcome to your comfy home & office away! This newly remodeled home is located in the prettiest part of Downtown Orlando. Closely surrounded by endless options of great food and city life, this is the perfect location for just about anything! Whether you're coming for fun, or traveling for work, this home has it all. A lot of love and detail was involved to make sure you feel at home and have all the essentials for a great stay! Airport 19 min Lake Eola 5 min Amway Center 7 min ORMC 10 min

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!

Walk Everywhere! Heart of Lake Eola Thornton Park

Located on a brick paved road in the heart of beautiful, historic Thornton Park in Downtown Orlando this cozy, private home is just steps from restaurants, coffee shops, bars, & Lake Eola! Walk to Kia Center, Dr. Phillips Center, Exploria Stadium, Central Business District, Publix, bars, restaurants, & lakes! Close to I-4 & freeways! 7 miles to Universal, International Drive, outlet malls, & springs! 16 miles to Disney Parks & Disney Springs! 50 miles to Daytona & Cocoa Beach!

Modern Tropical House Heated Salt Pool

☞Superhost 9 years ☞ Large Salt Pool (W/ heated option $ Oct-April) ☞3 Bedroom 3 Full Bath W/extra 4th queen daybed ☞ Easy access to the 417 East West express way (toll rd.) to get around Orlando ☞Easy smart lock self Check-in ☞ Driveway Parking ☞ Luxury bedding ☞65in Smart TV with Netflix in TV room ☞Dimmer mood lighting ☞Illuminated pool & landscape lighting ☞Full Kitchen ☞Dining & Picnic table seats 6 to 8 guests ☞Hi speed 231mb internet ☞Uber Eats Food Delivery

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.

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 & 3 streaming TV’s with a huge comfy couch. Driveway parking for two cars. Two bedroom choices provide for a peaceful rest.

The Blue Bungalow - Peaceful | Porch | HotTub

Escape to our delightful haven, thoughtfully designed with a colorful boho aesthetic. This front unit of a duplex offers its own private backyard and cozy porch, perfect for unwinding. Soak your cares away in the hot tub or enjoy culinary adventures in the fully equipped kitchen. A washer and dryer add convenience, while vibrant decor creates an inspiring retreat. Your ultimate getaway awaits in this charming oasis!