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)

Winter Park Guest Suite |near UCF/FullSail/Rollins

🏠Look no further than this newly constructed guest suite. It's located in a centrally located neighborhood in Winter Park just a short drive from UCF, Rollins College, Full Sail, and Park Avenue. The guest suite is attached to the main house; however, it has its own private entrance. Our guest suite was constructed with impeccable design and high-end finishes throughout. We hope you will get to enjoy! 📌Please note: There’s no stove; however, there is a cook-plate with two burners to cook on.

Charming Retreat In Winter Park

“Welcome to our renovated Winter Park home! This modern one-story property features 3 bedrooms plus a loft, comfortably sleeping 6 guests. Enjoy the large backyard with an extra-large pool and outdoor shower. Conveniently located near Orlando’s attractions, including Disney And Universal Studios as well as Rollins Collage and the Kia Center. Indulge in over 60 restaurants with in 10 min. Winter Park Village and Park Ave. Shopping. Experience comfort and style in this charming Florida retreat!”

King/Queen Quiet Vibey Bungalow

Our beautifully renovated 1950's 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. Families will love the playground just two streets away. When you're ready, retreat to our front deck and watch the sunset reflect off the trees!

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!

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Florida Poolside Paradise a Great Place to Unwind!

Welcome to our exquisite 4-bedroom vacation rental in the heart of Maitland, Florida – a true gem where luxury meets convenience. This upscale home boasts fine furnishings and a private pool, making it the ideal retreat for families or groups seeking both comfort and style during their Sunshine State getaway. The house is located in a residential neighborhood with plenty of restaurants and shopping within a 5 minute drive. Convenient location off Rt 436. and half hour to the airport.

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

Modern Tropical House Heated Salt Pool

☞Superhost 9 years ☞ Large Salt Pool (W/ heated option $ Sept-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 ☞Smart TV's with Netflix in each 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

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.