Vacation rentals in Winter Springs

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winter Springs

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Cottage in Kissimmee

4.81 out of 5 average rating, 21 reviews

Florida Retreat 3BR Resort Cottage near WDW

- Experience ultimate comfort at the Margaritaville Resort 3BR Cottage in Kissimmee. - Only minutes from Walt Disney World and a short drive to Universal Studios and other attractions in Central Florida. - Enjoy a spacious living area with a well-equipped kitchen, comfortable bedrooms, smart TVs and high-speed free Wi-Fi. - Relax on the outdoor patio or take advantage of free parking. This vacation home is perfect for creating unforgettable memories with easy access to all the area's highlights.

Guest favourite

Townhouse in Kissimmee

4.8 out of 5 average rating, 246 reviews

#5708 LakeFront, Two Master, Jacuzzi, Pool, Disney

Stunning LAKEFRONT view with SOUTH exposure for all day SUNLIGHT. MODERN furniture & HARDWOOD floors! Private JACCUZI! 5 SMART TVs & FREE WIFI. 4 BDS (2 with ensuite, one on each floor) & 3.5 BATH. SS appliances, water filter and quartz counter tops. 10 mins to Disney, 15 mins to Sea World, 20 mins to Universal. Walk to Old Town, Fun Spot, restaurants and stores. Uber/Lyft/Lynx bus to Disney. Resort heated pool, water slides, fitness, tennis, restaurant/bar, mini store and 24/7 gate with guard.

Guest favourite

Home in Kissimmee

5 out of 5 average rating, 17 reviews

My Disney Villa

Looking for the ultimate vacation spot near Disney Orlando and Epcot? Look no further! Our newly renovated large 5-bedroom Airbnb is just a genuine 12-minute drive away from these amazing parks, Our home features 2 amazing themed rooms, including a state-of-the-art Star Wars and Mickey Mouse rooms that will surely make your kids feel like they're in their own magical world. We also have 3 large adult rooms, each equipped with comfortable beds, a huge pool area with new furniture, 2 dining areas

Guest favourite

Condo in Kissimmee

4.91 out of 5 average rating, 46 reviews

Perfect Kissimmee Kondo with Jacuzzi!

Wonderfully Furnished Vacation Townhome with Private Hot Tub in gated Encantada Resort Community! The delightful open plan, just minutes from all parks, features ceramic tile flooring throughout downstairs & a modern gray/orange decor that'll provide a great place for you to relax while you're enjoying all that central Florida has to offer! Enjoy a beach entry pool, lap pool, hot tub, fitness center, playground, business center, and restaurant . Check out the tour: https://youtu.be/0QA3Z-MHKLM

Superhost

Home in Kissimmee

4.89 out of 5 average rating, 53 reviews

Baby Safe w *Indoor PlayGround*

*Free POOL HEAT*Close to Disney Parks! Home equipped for baby! Full nursery, double stroller, highchair, packnplay, outlet covers, baby gates, toys, books, bouncy, and more. Kids love the Toy Story indoor playground with ball-pit, trampoline & slide, the fun doesn't stop at Disney! 6 themed bedrooms (3 Kids & 3 Adult themes), 5 baths, appliance stocked kitchen, a movie/game loft w/ 2 queen sofa sleepers, in-ground pool and Jacuzzi with BABY GATE! Fully furnished high-end patio and pool area.

Superhost

Home in Kissimmee

4.69 out of 5 average rating, 16 reviews

Cozy VacationHome - Disney Parks

Have fun with the whole family at this comfortable and spacious townhome, take advantage of the full amenities that come with it. This space is great for both short and long stays and excellent for family visits. Close to Disney & more Orlando Areas *18 min or 11 miles to Disney Area *26 min or 17 miles to SeaWorld *30 min or 21 miles to Universal *40 min or 34 miles to MCO International Airport Orlando *50 min or 29 miles to Legoland *1h 15 min to Tampa Beach *1h 30 min to Melbourne Beach

Guest favourite

Home in Kissimmee

5 out of 5 average rating, 18 reviews

Disney Vacations Oasis

Experience the best of Disney's area with the comfort and luxury of our home. Whether you're here for adventure or relaxation, we provide everything you need for an unforgettable stay. We prioritize your health and safety. Our home undergoes a thorough professional cleaning and sanitization process prior to your arrival, ensuring every surface is spotless and ready for you to enjoy. Great amenities, including lazy river, restaurant, bar, gym and everything you may need during your stay.

Guest favourite

Villa in Kissimmee

4.81 out of 5 average rating, 63 reviews

Home w/ PVT Pool, Game Room & Resort access 2100

Our luxurious 5-bedroom, 5.5-bathroom home boasts a spacious living room with Smart TV, a fully-equipped kitchen and dining room, a cozy upstairs living area perfect for movie nights as well as an air-conditioned game room featuring a pool table and air hockey. Venture to the backyard to find even more amazing features such as a spacious private pool and SPA, sun loungers, a barbecue and a table with 6 seats where you and your guests will be able to enjoy some sun-filled al fresco dining.

Guest favourite

Home in Osceola County

4.8 out of 5 average rating, 5 reviews

Family vacation house near Disney! - 7105

Imagine this cozy getaway in a lush gated community, just a stone's throw away from the magic of Disney. This vacation home boasts four thematic bedrooms, perfect for hosting your family and friends. Step into the clubhouse, with an amazing bakery. It's the ideal spot for unwinding after a day of adventure in the nearby theme parks. With its welcoming atmosphere and convenient location, this retreat offers the perfect blend of relaxation and excitement for your dream vacation. Book now!

Guest favourite

Condo in Kissimmee

4.95 out of 5 average rating, 155 reviews

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

This modern 3-bedroom luxury condo (with an ELEVATOR right to the door) has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Superhost

Apartment in Kissimmee

4.86 out of 5 average rating, 224 reviews

Modern Great Villa near Disney & Parks

This place is 5 up to 20 minutes to all of orlando's amusement and water parks!. One of the best units in this resort, just book and see for yourself. An excellent unit with great reviews. There is an awsome pool and jacuzzi onsite (Please note, sometimes the jacuzzi breaks down and may not work during your stay). high speed wifi. easy smooth self checkin with a private keypad code that is being replaced between each new guest, walking distance to many shops and plazas, free parking.

Superhost

Home in Orlando

4.88 out of 5 average rating, 8 reviews

PuraVida Urban Lakehouse+Bungalow - Full Property

Welcome to our Pura Vida jungle-inspired urban lake house, nestled in the heart of Orlando! Combining tropical tranquility with modern luxury, this unique retreat offers the perfect escape for travelers seeking a serene atmosphere just minutes from the city's attractions. **NO PARTY OF ANY KIND OR EVENT ALLOWED** Circular driveway makes for free and easy parking. Located 15 min from the airport, 15 min to Universal, 30 min to Disney, and 50 min to Cocoa Beach.