Vacation rentals in Osceola County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Osceola County

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

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Guest favorite

Townhouse in Kissimmee

4.8 out of 5 average rating, 251 reviews

#5708 Lakefront Oasis,2 MBRs,Priv Spa,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.

Superhost

Home in Frostproof

5 out of 5 average rating, 3 reviews

Poshpadz at The Lakehouse Sebring Legoland Rodeo

Direct lakefront 5 bed home with hot tub, 2 kayaks, dock, foosball table, sleeps 10! Experience luxury like no other lakeside home in the area! This special 5-bedroom, 3.5-bathroom vacation rental has it all. Private hot tub - Private dock - Luxury and Kayaks with views to die for from every room! Whether it is relaxing on one of the covered decks or cruising around the freshwater lake, this lakeside sanctuary has something for everyone. National Bass fishing tournaments are held on Reedy Lake.

Guest favorite

Home in Kissimmee

4.87 out of 5 average rating, 23 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 favorite

A relaxing lazy river features colorful inner tubes floating along sparkling water. A thatched-roof cabana provides shaded seating among lush greenery, while palm trees frame the scene. A water slide is visible in the background, adding to the recreational atmosphere.

Home in Kissimmee

5 out of 5 average rating, 22 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 favorite

A meandering lazy river is surrounded by lush tropical landscaping, featuring palm trees and vibrant greenery. The clear water reflects the sky, creating a serene atmosphere. Sun loungers are situated along the riverbanks, inviting relaxation in the outdoor space.

Villa in Kissimmee

4.83 out of 5 average rating, 69 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.

Superhost

Home in Osceola County

4.57 out of 5 average rating, 7 reviews

Your 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 favorite

Condo in Kissimmee

4.95 out of 5 average rating, 161 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 favorite

A three-story cottage, painted in vibrant orange with white trim, features multiple balconies and large windows. Lush palm trees and manicured landscaping surround the entrance, contributing to a lively coastal ambiance.

Home in Kissimmee

5 out of 5 average rating, 16 reviews

Fireworks View - NEW 4BD Cottage In Margaritaville

RARE Fireworks View from 3rd Floor Balcony! Spacious 4 bedroom, island-inspired cottage in the heart of Margaritaville Orlando resort! Your perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, and within walking distance to a state-of-the art water park and newly opened 196k square foot shopping and dining district. memories at this unique and family-friendly place.

Guest favorite

A comfortable living area features a gray sofa with decorative throw pillows, a round mirror, and a colorful artwork on the wall. A flat-screen TV is positioned on a light-toned cabinet. Natural light streams in through large windows, enhancing the open ambiance.

Cottage in Kissimmee

4.86 out of 5 average rating, 29 reviews

Cottage Retreat 3BR w Free Parking near WDW

Welcome to the Margaritaville Resort 3BR Cottage in Kissimmee! - Spacious living area with a well-equipped kitchen and comfortable bedrooms. - Enjoy relaxing views in a tropical ambiance surrounded by palm-lined streets. - Short drive to Walt Disney World (10 min), Universal Studios (32 min), and SeaWorld Orlando (29 min). - Amenities include flat-screen TVs, high-speed Wi-Fi, outdoor patio, and free parking. - Perfect for creating unforgettable memories with family and friends.

Superhost

Home in Kissimmee

4.88 out of 5 average rating, 56 reviews

Baby Safe w *Indoor PlayGround*

**Property Requires refundable Security Deposit**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!

Top guest favorite

A staircase featuring light wooden steps leads to an upper level, surrounded by neutral-colored walls. A door is visible on the left side, while a cozy living area with a large sofa is partially shown in the background, enhancing the welcoming entryway.

Townhouse in Kissimmee

4.95 out of 5 average rating, 20 reviews

The Best New TownHome in Kissimmee.

Escape to sunny Kissimmee, Florida, and enjoy the ultimate vacation at our stunning Airbnb rental! Located just minutes from Walt Disney World, Universal Studios, SeaWorld, and other top attractions, this home is perfect for creating unforgettable memories. Perfect for families, couples, or groups, this rental combines convenience, comfort, and style in one incredible location. Your dream vacation in Kissimmee starts here—book now to secure your stay!

Top guest favorite

Home in Davenport

4.98 out of 5 average rating, 64 reviews

Elegant Large Private Home with Heated Pool!

This classy and stylish home is centrally located to all of the attractions. Peaceful gated community on the lake gives you privacy and feels like home. Take a stroll around the lake or enjoy the serenity of the beautiful heated pool. Plenty of room for the kids to play. Close to shopping and restaurants. You won't want to leave. Sleeps 8 with luxurious comfort. 10 year Superhost owner of Casa Claudio Vacations. "Relax... Your Home"