Holiday rentals in Osceola County

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Top-rated holiday rentals in Osceola County

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Top guest favourite
A compact kitchen features white cabinetry and modern stainless steel appliances. An electric stovetop is positioned beside a microwave, with a coffee maker and various kitchen utensils visible. A small refrigerator stands nearby, complemented by decorative items on the open shelves.
Home in Kissimmee
4.99 out of 5 average rating, 143 reviews

Private Suite with Independent Entrance

Private Suite with Independent Entrance Kissimmee, Fl Enjoy a modern and fully equipped private suite, perfect for couples or travelers looking for comfort, privacy, and a relaxing stay just minutes away from Orlando’s top attractions. 📍Perfect Location Conveniently located in Kissimmee, just minutes from: 🎢 Disney World 🎬 Universal Studios 🌊 SeaWorld and Aquatica You’ll also find restaurants, supermarkets, outlets, and gas stations nearby an excellent location for your Orlando vacation!

Guest favourite
Home in Osceola County
4.88 out of 5 average rating, 17 reviews

The Villa Retreat / near Disney

Welcome to a newly built 5bedroom/4bath, 2 Story townhouse dream vacation. Located in a prime area, just 20 mins away from Disney World,Disney springs,SeaWorld, Orlando Outlets, restaurants, shops & more. Just 5 mins off of I-4. (Resort is still under construction during the weekdays but nearing the end phase . Come enjoy a peaceful , family oriented stay at the Azur Resort before things get into full effect. Each unit is fully furnished and equipped for your family stay. Must be 21 to rent.

Guest favourite
The open living area features a contemporary design with a curved sofa in neutral tones, two blue accent chairs, and a glass coffee table. A textured area rug complements the decor. Large windows allow natural light to illuminate the space, enhancing the connection to the outdoors.
Townhouse in Kissimmee
4.88 out of 5 average rating, 214 reviews

Adorable 2 bdr lakefront w/jacuzzi 5 min *Disney*

This townhouse provides an open main living space that allows you to connect the dining and a fully equipped kitchen. The house can accommodate up to 6 guests, divided into one luxe king en-suite, and a design theme two full en-suite. After a long day at the parks with a beautiful lakefront view, relax in your private spa. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant, and only 5 min from Disney and golfing area Free Parking Close to lakes, camping, beach, vineyards, farms

Top guest favourite
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.
Flat in Kissimmee
5 out of 5 average rating, 63 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 favourite
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, 134 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 favourite
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
4.95 out of 5 average rating, 79 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 favourite
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, 77 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 favourite
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
4.97 out of 5 average rating, 1,068 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.

Top guest favourite
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, 57 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 favourite
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.
Apartment in Osceola County
4.93 out of 5 average rating, 72 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 favourite
Home in Kissimmee
4.97 out of 5 average rating, 121 reviews

3BD/3BA Themed House Near Disney

Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Guest favourite
A keyless entry system is prominently displayed on the door, providing convenient access. In the blurred background, a bed with a blue and white coverlet can be seen, suggesting a cozy sleeping area. Soft lighting enhances the inviting interior ambiance.
Guest suite in Kissimmee
4.94 out of 5 average rating, 141 reviews

It's too much like a elegant mini-hotel (4)

It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

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