Holiday rentals in Osceola County

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Top-rated holiday rentals in Osceola County

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Guest favourite
A modern living room is showcased, featuring a cozy seating arrangement with gray sofas positioned around a central table. A flat-screen TV is mounted on the wall, with plants and decor enhancing the space. Natural light floods in through the windows, brightening the room.
Home in Kissimmee
5 out of 5 average rating, 10 reviews

Haven Luxe

Welcome to Haven Luxe – A Cozy Retreat with a Touch of Elegance Escape to a sanctuary where comfort meets sophistication. Haven Luxe offers an inviting blend of warm ambiance and upscale design, perfect for travelers seeking both relaxation and style. Sink into plush velvet furnishings, Whether you're savoring morning coffee by the pool, or cozying up with a book inside. 5 min from brightline train station and (MCO) Airport. 20 minutes from Theme parks. 2 from Publix, Walmart, CVS, shoppes

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, 130 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 serene bedroom features a queen bed with light blue linens and an elegant headboard. A cozy wingback chair and a full-length mirror offer additional comfort. A woven rug complements the space, while windows allow natural light to brighten the room.
Guest house in Kissimmee
5 out of 5 average rating, 17 reviews

The Forrestry

The Forrestry is the ideal launching pad for visits to the parks. Perfectly priced so you can enjoy Disney, SeaWorld, Legoland & Universal's Epic Universe. The garden gate opens to a spacious patio. This cozy retreat is a great room concept. A coffee bar with snacks greets you on entry into the living room, with a comfortable sofa bed and a multi-use table for games and dining. A well-equipped kitchen and laundry room flank it. The bedroom suite has a spacious walk-in closet and bathroom.

Guest favourite
An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.
Apartment in Osceola County
4.89 out of 5 average rating, 107 reviews

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

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, 72 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
4.96 out of 5 average rating, 1,052 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
Guest house in Kissimmee
5 out of 5 average rating, 20 reviews

"Independent Golden Suite" Near the Disney Parks

✨"Golden Suite" in Kissimmee✨ Your perfect getaway near Disney's attractions! Welcome to a cozy modern family-friendly suite designed for up to 4 guests. Enjoy two full-size beds, a fully equipped kitchen and dining area, private entrance, and dedicated guest parking Just minutes away from Disney World, Universal Studios, Aquatica and more. After a fun-filled day, return home where you can relax with your loved ones. 🌟Book now and experience the magic of Kissimmee🌟

Top guest favourite
A dining area with a rectangular table set for six features simple decor and a centerpiece. A cozy living space is visible with a sofa, chairs, and a TV. Light streams in through large windows, accentuating the open layout and inviting atmosphere.
Townhouse in Osceola County
4.99 out of 5 average rating, 89 reviews

Amazing townhouse near Orlando theme parks

Welcome! This is your place to gather, relax and enjoy, near everything! Orlando theme parks are only between 6 to 20 miles away, and other attractions for all ages and preferences are also nearby. This spacious 4 beds and 2.5 baths home is fully equipped. It is also family friendly, so you will have the basic items for your children's stay. We are sure that you will experience a cozy ambience and that you will enjoy your stay here!

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, 52 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, 70 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.

Guest favourite
A modern keypad lock is installed on a door, featuring illuminated numbers for easy access. Blurred in the background, a vibrant green plant adds a touch of nature to the entryway, enhancing the welcoming ambiance of the space.
Guest suite in Kissimmee
4.93 out of 5 average rating, 173 reviews

It's too much like a elegant mini-hotel (7)

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.

Guest favourite
Townhouse in Kissimmee
5 out of 5 average rating, 5 reviews

Magic Village Resort | 5 Minutes to Disney

Only 5 minutes to Disney. High-end 3BR townhome with modern finishes and elegant design. Full kitchen, stylish living spaces, and private bedrooms. Located in a peaceful, nature-focused resort with tranquil Buda Park. Ideal for families and professionals seeking upscale comfort near Orlando’s top attractions.

Popular amenities for Osceola County holiday rentals

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