Vacation rentals in Osceola County

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Top-rated vacation rentals in Osceola County

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Superhost

Townhouse in Kissimmee

4.83 out of 5 average rating, 168 reviews

Disney 15 Minute Away, Gated Resort & Private Pool

Modern house 15 minutes to Disney. With 5 bedrooms, a private heated pool, and space for 12 people to sleep comfortably. Located at the Solara Resort, this house is less than 2-minute walk to the clubhouse and all amenities. This is a resort idealized for vacation and enjoyment, with amazing amenities like a large community pool, artificial surf, kids splash pad, tiki bar, restaurant, mini-market, gym, sports courts, and much more. Universal Studios and Sea World are only 20-25 minutes away.

Top guest favorite

The living area features a spacious gray sectional sofa arranged around a white coffee table, with decorative items adding style. A large window provides natural light, complemented by modern shelving and a lamp. The open kitchen is visible in the background, emphasizing a comfortable layout.

Apartment in Kissimmee

5 out of 5 average rating, 49 reviews

Modern Luxury Kissimmee Retreat

Welcome to our stunning Kissimmee apartment, where modern luxury meets ultimate comfort! This renovated 2-bedroom, 2-bathroom retreat offers high-end finishes, a fully equipped kitchen, large screen TVs, PlayStation 5, and high-speed Wi-Fi. Enjoy blackout curtains and white noise machines for restful nights. Complex amenities include a pool, gym, sauna, and tennis court. Located near Walt Disney World, Universal Studios, and top shopping, our apartment is the perfect base for your adventures.

Top guest favorite

A private pool features a spacious deck and a whimsical swan float. Adjacent is a covered dining area with views of landscaped grounds. Inside, a kids’ tube slide and superhero-themed decor are seen, along with a game area featuring a billiards table and arcade console.

Villa in Osceola County

4.99 out of 5 average rating, 127 reviews

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

Top guest favorite

A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.

Home in Kissimmee

4.94 out of 5 average rating, 66 reviews

Paradise Suite

Relax with the whole family at this peaceful place to stay. The spacious living area features windows that flood the space with natural light, while the kitchen is equipped with stainless steel appliances and granite countertops. The master bedroom offers a peaceful oasis with a spa-like master bath and walk-in closet. Property is located in a gated Golf community with a 3 mile walking trail that offers beautiful lake views. close to major intersections and shopping mall less than 2 miles

Top guest favorite

The exterior of a large, two-story home is displayed, featuring a light-colored facade and a covered front porch. Lush landscaping surrounds the driveway, which is paved with stone. A garage door is positioned on the right side, complemented by decorative lanterns and palm trees.

Home in Osceola County

4.97 out of 5 average rating, 68 reviews

Large Private Home on Golf course by Disney

Bring the whole family to this great place with lots of room for fun. With fantastic views of the 4th hole on the Tom Watson golf course and your own private pool and hot tub everyone will enjoy this stylish and modern vacation home. Located in premier Reunion Resort and only 10 minutes to Disney you can have it all! This home boats over 4000sq feet, two very large masters suites, 2 additional bedrooms and plenty of space throughout the home. There are 6 tvs! Pets are welcome too!

Top guest favorite

A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.

Treehouse in St. Cloud

4.96 out of 5 average rating, 1,020 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Guest favorite

A serene landscape captures two shipping container structures amidst lush greenery. Soft colors of the sunset blend with a gentle rainbow, enhancing the natural surroundings. The garden features various plants and mulch, creating a peaceful retreat atmosphere.

Shipping container in Osceola County

4.96 out of 5 average rating, 50 reviews

Beautiful off-grid tiny home cottage #3

Retreat to the food covered grounds of this off-grid oasis in Central Florida, reconnect to the beauty and vibrancy of nature, and experience the magnitude of freedom and abundance it has to offer on your sustainable getaway. Your shipping container has a full kitchen, mini-split cooler and spacious shower with an on-demand water heater fed by pristine well water... you would never know you're off-grid!

Top guest favorite

Townhouse in Kissimmee

4.95 out of 5 average rating, 102 reviews

Mickey Safari near Disney 2 Master rooms 4708

Welcome to Our Stunning 4-Bedroom Townhouse – Perfect for Families & Groups! Experience comfort and top-tier hospitality. Spacious bedrooms designed to accommodate up to 13 guests. Fully equipped kitchen. Just minutes from Disney's theme parks. Book a stay of 7 days or more and receive an exclusive 5% discount! For extended stays of a month or longer, enjoy a 10% discount. (Some restrictions apply.)

Guest favorite

A private patio features two modern sun loungers positioned beside a small side table. The area is surrounded by manicured greenery and offers views of the expansive golf course, showcasing the resort's tranquil atmosphere.

Condo in Osceola County

4.93 out of 5 average rating, 67 reviews

Casa Ida

Keep it simple at this peaceful and centrally-located Luxury condo. Only 9 miles away from Disney World. . . 27 minutes away from Universal Studios. Access to 5 Pools, The Pavillion, and all restaurants on the property. Relax and enjoy beautiful views of the Signature Golf Course all from the patio of this beautiful home. This condo boasts a fully equipped kitchen for those who like to cook.

Top guest favorite

A spacious resort-style pool is enveloped by tropical palm trees and vibrant pink flowers. Comfortable lounge chairs line the pool area, with yellow umbrellas providing shade. The surrounding pavement pathway leads to a central pavilion, enhancing the inviting atmosphere for relaxation and socializing.

Apartment in Kissimmee

4.93 out of 5 average rating, 40 reviews

Spacious King Bed, Pet-Friendly, 15 Min from Parks

Welcome to our Cozy 1-Bedroom, 1-Bathroom Apartment in Kissimmee, FL! This modern and charming apartment offers the perfect vacation retreat with resort-style amenities and a prime location just minutes from Disney and other Central Florida attractions. We’re also pet-friendly, so your furry friends are welcome too! Please reach out for any potential additional multi-day discounts available

Guest favorite

The entrance features a spacious, modern foyer with a wooden double door framed by vertical light fixtures. The neutral-colored walls provide a clean backdrop, while a wooden bench and planters enhance the welcoming atmosphere. Lush greenery and a well-maintained lawn are visible in the foreground.

Home in Kissimmee

4.92 out of 5 average rating, 26 reviews

Florida HappyNest Secluded Luxury Guesthouse

Escape to Florida Happy-Nest, a stunning, brand-new guesthouse designed for luxury and relaxation. Nestled behind a main home, this 2024-built retreat offers high-end finishes, a fully equipped kitchen, serene outdoor living, and proximity to a tranquil fishing lake. Whether you’re seeking a romantic getaway or a quiet escape, this home promises an unforgettable experience.

Guest favorite

The exterior features a light blue structure complemented by a covered carport. A well-maintained lawn with decorative stones and shrubs adds to the inviting atmosphere. Large windows provide natural light into the living spaces.

Home in Kissimmee

4.94 out of 5 average rating, 134 reviews

Summer Villa by the Lakes

Relax with your whole family at this peaceful haven which boasts a backyard view to golf course and pond and easy access to local boat docks and fishing. You can also get to Disney, Universal Studios and other Kissimmee attractions in minutes. The community offers a gated pool and quiet neighbors that make you feel welcomed.