Holiday houses in Osceola County

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Top-rated holiday rentals in Osceola County

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Guest favourite
A serene view of a dock extending into a calm lake at sunrise. The sun rises above the horizon, casting warm hues across the sky and reflecting on the water's surface. Reeds frame the scene, enhancing the natural surroundings.
Home in Lake Wales
4.87 out of 5 average rating, 31 reviews

Lakefront 2br w/pier & dock 4,500-ac Lake Rosalie

Peaceful getaway on Lake Rosalie w/ 4,530 ac of beautiful water w/ bass, catfish and crappie fishing. Birds routinely viewed from the dock include eagles, osprey, sandhill cranes, herons and more! Often making an appearance are a pair of otters and the Florida alligator! Morning sunrise over the lake from the sunroom or the dock is one of our favorite times! Add a cup of coffee is the best! Rowboat, golf cart, large patio w/grill and pier & dock to view the wildlife and enjoy time at the lake!

Top Guest favourite
Townhouse in Osceola County
4.94 out of 5 average rating, 32 reviews

The Sun-Kissed Retreat / near Disney

Welcome to your Orlando retreat! This spacious 5-bedroom, 4.5-bathroom townhome at the exclusive Azur Resort offers everything you need for an unforgettable vacation. Designed with comfort and style in mind, this home is ideal for families, groups, and anyone looking to explore the magic of Orlando. Located just mins from Orlando's top attractions- Disney World, Universal, and world-class shopping and dining. You’re at the center of it all! Book now and start making memories at the Azur Resort!

Top Guest favourite
A serene lakeside scene featuring colorful Adirondack chairs arranged on a grassy area. A calm lake reflects soft evening light, with a palm tree visible in the distance. The sky is adorned with clouds, hinting at a gentle sunset.
Home in Babson Park
5 out of 5 average rating, 10 reviews

Midcentury Lakefront Home on Crooked Lake

Located in Babson Park on Crooked Lake in Central Florida, our 3/2, 1500 sq feet midcentury modern home, sits at the end of a private drive on a family-owned peninsula, surrounded by water, with 100 feet of private beachfront. Minutes from several theme parks and family restaurants. Secure your boat in the canal in the back of the a house. There 2 kayaks, outdoor seating, a 2-car carport, gas BBQ grill, with views from every room. Your family can enjoy fishing and water sports all day long!

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, 140 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.

Guest favourite
Home in Lake Wales
4.94 out of 5 average rating, 119 reviews

Fishing Lakefront Paradise w/ Boat Slip & Parking!

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

Top Guest favourite
A large wooden dining table is surrounded by eight wooden chairs, set against a backdrop of stone-like walls with arched windows. A metal chandelier hangs overhead, while a decorative knight statue stands in the corner, adding character to the atmospheric space.
Villa in Kissimmee
4.87 out of 5 average rating, 568 reviews

Magical 5-Bedroom Villa Near Universal's Wizarding

Ensure an enchanted holiday in Orlando. Inspired by everyone’s favorite castle, this magical home provides an immersive experience with 5 bedrooms, common room with large screen TV with Netflix & Nintendo Switch, dining hall, fully equipped kitchen, swimming pool, patio with grill and laundry room. Located in a quiet residential community, 10 miles to the Wizarding World of Harry Potter, 6 miles to Disney, 5 miles from Celebration, 4 miles from Old Town and 18 miles from downtown Orlando.

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
4.98 out of 5 average rating, 81 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, 1,096 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 favourite
Townhouse in Kissimmee
4.86 out of 5 average rating, 101 reviews

Disney Area| Private Pool| Resort Waterpark 2956

Minutes from Disney, this spacious 4-bedroom townhome is located in the sought-after Storey Lake Resort. Relax in your private screened pool after a day at the parks and enjoy access to amazing resort amenities including water slides, lazy river, clubhouse, fitness center and kayak rentals. Comfortably sleeps up to 12 guests with a full kitchen, fast WiFi and free parking. Perfect for families visiting Disney and Orlando attractions.

Guest favourite
An outdoor space features a screened-in pool area with a clear blue pool and spa. Comfortable lounge chairs are positioned beside the pool, with a dining table set beside them. Lush greenery is visible beyond the fenced yard, creating a private and relaxing environment.
Home in Kissimmee
4.79 out of 5 average rating, 132 reviews

The Real Florida Whispering Oaks

The Oaktree home is a favorite among returning guests. Once you have stayed in this home you cannot wait to return. The spacious pool /spa and deck area, game room and provides all you could ask for to make your stay one to remember. Recently remodeled kitchen with updated appliances make this home shine! Partially fenced in yard with no rear neighbors offer you a quiet retreat. T.V. on pool deck! Complimentary Hot Tub Heat!

Guest favourite
Home in Kissimmee
5 out of 5 average rating, 10 reviews

Boho Luxe Retreat • Near Disney Parks

Welcome to Boho Luxe retreat ✨ a beautifully designed house created for comfort, rest, and unforgettable moments. This spacious home blends modern elegance with a cozy boho touch, perfect for families and groups. Enjoy stylish bedrooms, inviting living spaces, and a relaxing atmosphere after a day at the parks. Conveniently located near Disney, dining, and attractions, this home is your ideal Florida getaway. ☀️🎢

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
4.97 out of 5 average rating, 65 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!

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