House vacation rentals in Winter Park

An outdoor seating area is shown, featuring several tables adorned with colorful tablecloths. Bright flowers enhance the vibrant atmosphere, while a view of parked cars and lush trees creates a lively streetscape in the background.

4.93 out of 5 average rating, 122 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, 116 reviews

A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.

Home in Orlando

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

A spacious living area features a large, deep-seated sectional couch adorned with decorative pillows. A wooden tray rests on the couch. A dining table with chairs is positioned near bright windows, enhancing the natural lighting in the room.

4.99 out of 5 average rating, 126 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)

4.93 out of 5 average rating, 180 reviews

The living area features a leather sofa and a stone fireplace as a focal point, complemented by a ceiling fan and natural light. A decorative mirror hangs on the wall above a console table, and the space connects to an updated kitchen visible through an open doorway.

Home in Orlando

The Orlando Retreat.

When you visit the Orlando retreat, you will find every amenity that you, your family and fur babies will need to make this stay the best one yet! Unwind at its stunning pool and outdoor area equipped with a BBQ, lounging chairs, and outdoor dinning. In addition, this house features a beautiful fire place, home office, laundry room, and an updated kitchen with everything you will need. Finally, to top it off, free Wi-Fi and parking! * Within 30 min to Disney World, shopping centers, and MCO*

4.93 out of 5 average rating, 105 reviews

A refreshing pool is captured, with sunlight sparkling on the water's surface. The stone-accented summer kitchen with a wooden pergola is visible in the background, along with plants and seating, creating a relaxed outdoor setting.

Home in Casselberry

Villa with Guest House & Pool-Patio

Welcome to this Amazing House Pool-Patio with 4 Bedrooms + 2 Bathrooms and optional guest house. Luxury and true gem with covered summer kitchen, covered pergola, garage for two cars and a large driveway. 30 Minutes distance to Universal, Sea World, Volcano Bay and others. UCF in 15 minutes and Daytona beach/Cape Canaveral in 50’. Great restaurants and shops. The house is conveniently located and accessible for all attractions in Central Orlando. Airport is 25 minutes. SAFE NEIGHBORHOOD

4.86 out of 5 average rating, 122 reviews

A spacious living area features a modern sectional sofa arranged facing a stone fireplace. Large glass doors provide natural light and views of the outdoor space. Decorative plants and a wall-mounted mirror add elegance to the cozy atmosphere.

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!

4.95 out of 5 average rating, 165 reviews

A private pool area is surrounded by lush tropical landscaping, featuring tall palm trees and vibrant greenery. The sparkling blue water of the pool reflects the sky, while a paved pathway leads to the entrance. A serene atmosphere is created by the nearby plants and outdoor decor.

Home in Maitland

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.

Superhost

The living area features a modern design with a gray sectional sofa adorned with decorative pillows. A wooden coffee table sits atop a textured area rug, accompanied by a floor lamp and potted plant. A wall-mounted TV and large windows allow natural light to fill the space.

4.88 out of 5 average rating, 113 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

4.9 out of 5 average rating, 132 reviews

An outdoor space features a heated pool and a hot tub, surrounded by stone masonry. A custom bar, crafted from wood, is visible alongside tropical plants. Two built-in TVs are fitted above the bar area, enhancing the outdoor living experience.

Home in Orlando

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.

4.95 out of 5 average rating, 114 reviews

A modern living area is highlighted by a neon 'Orlando' sign on the wall. Three dark gray sofas, accented with patterned cushions, surround a light wooden coffee table. Two round natural fiber poufs add texture, with a large TV displaying a city skyline in the background.

Home in College Park

Trendy Downtown Orlando Oasis

Updated three-bedroom home, only minutes from I-4, which means easy access to your favorite spots in and around Orlando. - Winter Park Village: 5 minutes - Downtown Orlando: 10 minutes - Amway Center and Camping World Stadium: 10 minutes - Disney World, Universal Studios, and I-Drive: 20 minutes Perfect for groups or families. Plenty of free parking in driveway and curb side. No parties or events please. Orlando Permit #: STR – 1094537.

4.98 out of 5 average rating, 101 reviews

A spacious dining area is illuminated by overhead lighting, featuring a large wooden table surrounded by upholstered chairs. A contemporary kitchen is visible in the background, equipped with modern appliances and a breakfast bar with additional seating.

Home in Casselberry

Spacious 3 BR Home Perfect for Orlando Getaway

Relax with friends or family at this peaceful parkside home, while enjoying everything that makes Central Florida so special. From Disney and Universal Studios to Downtown Orlando. Entertainment is just minutes away in either direction with an abundance of shopping and dining options to choose from. Our family absolutely loves this area! We have a recommendation for just about anything and are excited to share this home with you!

Superhost

The living area features a navy blue sofa and chaise lounge, complemented by a gold-accented coffee table. A textured area rug connects the space, while a mirrored wall decor adds depth. The bar top with stylish stools creates a casual dining option, illuminated by soft lighting.