House holiday rentals in Winter Park

4.92 out of 5 average rating, 126 reviews

A Rare Jewel in the heart of Winter park. Can walk

This lovely 3 bedrooms, 2 bath house is located in the most desirable area of Winter Park. Only few steps from Park Ave. You can walk to all the restaurants, Wine room, coffee shops, stores, art galleries, Museum, Park, Rollins College, Winter Park Community Center. Its only 25 minutes drive to the airport, 45 minutes to the beach, and close to family-friendly activities, nightlife, public transport. This house is great for families, couples, solo adventurers, business travelers, and big groups.

4.97 out of 5 average rating, 127 reviews

Home in Lake Formosa

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

4.97 out of 5 average rating, 151 reviews

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)

Superhost

4.86 out of 5 average rating, 110 reviews

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!”

4.91 out of 5 average rating, 158 reviews

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 ☞Pool Lounge Floats ☞Full Kitchen ☞Dining & Picnic table seats 6 to 8 guests ☞Hi speed 231mb internet ☞Uber Eats Food Delivery

4.95 out of 5 average rating, 112 reviews

Luxurious and modern cottage near UCF

This is peaceful and quiet place in a country seating yet in the middle of the city. It has been renovated and decorated in a luxurious and modern style by professionals. It’s better than the pictures. From here you can easily access the theme parks, beaches, downtown Orlando and all mayor attractions. Disney 24 miles. Universal studios 21 mi. Sea World 18 mi. Airport 12 mi. Beaches 50 mi. Downtown Orlando 15 mi. UCF 2.4 mi. And tons of restaurants! Come and experience Florida at its best

4.92 out of 5 average rating, 114 reviews

Charming 2BR Cottage, Downtown Orlando

Bright, cozy 1940’s cottage located in a quiet, safe, family-friendly Downtown Orlando neighborhood. 2 bedroom, 1 bath, onsite parking, full kitchen, washer and dryer, fenced-in back yard and patio area, working desk space in bedroom. Walking distance to the local gems and eateries of Audubon Park and the Mills 50 District! Central location minutes away from Winter Park and Downtown local attractions. 20-30 minutes from Universal, Disney and MCO. Great for a work trip or an Orlando getaway!

4.87 out of 5 average rating, 131 reviews

Home in Maitland

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!

Superhost

4.87 out of 5 average rating, 126 reviews

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

Home in Colonialtown South

4.95 out of 5 average rating, 167 reviews

Spacious 3BR/2B w/Workspace & Backyard Paradise

Bring the whole group to this great place with lots of room for fun and prime for a relaxing home base for your trip! With open concept common areas, full kitchen, laundry, and games to play, this makes for a super cute and spacious home! The backyard oasis has a hammock plus a patio with furniture, and partial sunshine. Located in a quiet neighborhood blocks from downtown Orlando and close to major attractions and highways. This home is loaded with everything you'll need!

4.91 out of 5 average rating, 142 reviews

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.