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

Villa in Kissimmee

4.89 out of 5 average rating, 56 reviews

SuperHost! Entire New Home! Pool, Near Dis! LOW $!

As Airbnb Superhosts for 7 consecutive years, we'll give you the most perfect home and experience! Believe your eyes! We just gave this beautiful home a total makeover, brand new decor, etc. Gorgeous from top to bottom! Granite kitchen with new cabinets, spectacular dining room -- this home has everything you could ever ask for plus 3 BR's/2 Baths, and slps 7. Your private patio/balcony overlooks a nature preserve. Heated pool, BBQ area, spa, tennis, fitness center, and just 7 min's from Dis!

Guest favourite

Home in Kissimmee

4.94 out of 5 average rating, 16 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

Superhost

Tiny homes in Kissimmee

5 out of 5 average rating, 9 reviews

2766 Disney Universal Sea World 1 Bedroom

Located at "MILL CREEK SUN RESORT" voted best Disney area resort by "Tewks & Tani" Just a short drive to the entrance to "Walt Disney World" and around the corner from "THE LOOP" shopping area Great place in clean, safe resort Outside deck with table and chairs Private driveway Kitchen with utensils, dinnerware, cookware ect. Queen bed in separate bedroom Pullout couch in the living room Dining area with table and chairs Towels and linens included Modern Gym Swimming Pool Playground Dog Park

Superhost

Home in Kissimmee

4.9 out of 5 average rating, 52 reviews

Free Pool Heat! 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.

Guest favourite

Home in Kissimmee

5 out of 5 average rating, 16 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

4.8 out of 5 average rating, 60 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

Amazing vacation spot 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!

Superhost

Townhouse in Davenport

4.83 out of 5 average rating, 36 reviews

Vacation Townhome Davenport ChampionsGate

This rental is gorgeous Townhome located in Davenport Champion Gate, and it sits in the perfect spot for family vacation, meeting friends, or a couple’s getaway. You will be close to everything when you stay at this centrally-located place. You have plenty of choices from Disney parks, Water parks, Universal Studios, Canoeing, Obstacles Park, Paddleboard to Shopping, and Nights on the Oldtown. There’s something for everyone in your group. Recreation area with FREE mini golf, and pool

Guest favourite

Condo in Kissimmee

4.95 out of 5 average rating, 152 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.

Guest favourite

Apartment in Kissimmee

4.86 out of 5 average rating, 218 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 Davenport

4.85 out of 5 average rating, 20 reviews

Charming Vacation Cottage

Enjoy your own cottage in a resort atmosphere with lots of amenities and activities. Fully furnished, all bedding, kitchen needs and washer and dryer. Easy access to Disney Resorts, Lego Land, Bok Tower Gardens, Sea World, Universal, Disney Springs and other Central Florida attractions. On-site heated pool, miniature golf, pickle ball, shuffle board, horseshoes, fitness center, library and billiards. Some pet friendly units. Book your next vacation with us.

Superhost

Apartment in Davenport

5 out of 5 average rating, 3 reviews

Bahama Bay Resort * Disney Area

Bahama Bay is a Gated Resort just 10 miles from Disney! With 4 Pools * 6 Hot Tubs * A Splash Pad * Shuffleboard * Sandy Beach Area * Tiki Bar Restaurant * Walking Trails & More is a great place for a Vacation! * NO Resort FEE * Parking is FREE! Resort Villa * 2nd floor Villa * 4 Swimming Pools * 6 Hot tubs * White sandy Beach * On-site Restaurant Tiki & Bar * Beach Volleyball * Tennis * Pickle Ball * Basketball * Fishing * Nature Trails *