Holiday houses in Osceola County

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Top-rated holiday rentals in Osceola County

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Guest favourite

Villa in Kissimmee

4.87 out of 5 average rating, 521 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. Asegú

Guest favourite

Townhouse in Kissimmee

4.88 out of 5 average rating, 152 reviews

Luxury 4BD All-suites w/BBQ - minutes from Disney!

Welcome to our captivating 8 guest haven! Experience the seamless fusion of opulence and coziness at this spacious retreat! Our unbeatable location situates you just minutes from the magic of Disney World, the excitement of Universal Studios, an array of exclusive dining options, outlet shopping, and much more! Enjoy your private grill area, creating cherished family moments. This perfect property provides everything you need to relax! *Themed Breakfast service is optional at an additional fee.

Top Guest favourite

Villa in Kissimmee

5 out of 5 average rating, 113 reviews

Villa Sol Peaceful Pool/Hot tub Home

Close to all major attractions, and airport sits this private villa. It has a little something for all ages! Your family can play in the pool or relax in the hot tub. Enjoy fun game nights with the cabinet full of games, or play a little game of basketball right outside the pool. Enjoy the tennis courts and playground. Stay in shape while you travel just steps away from the clubhouse gym. There is everything for the beach trips or the ball games. All of your baby's needs are covered as well.

Top Guest favourite

Villa in Osceola County

4.99 out of 5 average rating, 123 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.

Superhost

Home in Osceola County

4.93 out of 5 average rating, 120 reviews

Pirate & Princess: Themed/Disney/Resort

Wishes come true at The Pirate & Princess 5BR/6BA immersive vacation home, 6 miles from Disney. Seeking enchanted adventure? Sprinkle pixie dust, second star to the right, to… Reunion Resort! Gated golf resort; pools/dining/gym. Treasure Island, Peter Pan, Tinker Bell, Captain’s Lounge, Little Mermaid & Moana; Disney-inspired rooms, professionally designed! Private Pool/Spa/BBQ/Chef’s Kitchen/Office/Laundry/WiFi/In-Law Apt./Sunset Lake Views. Family-friendly gem to delight kids! Sleeps 15.

Top Guest favourite

Home in Osceola County

4.97 out of 5 average rating, 63 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!

Guest favourite

Home in Kissimmee

4.91 out of 5 average rating, 166 reviews

Arcade Garage | King Bed | 15 Min to MCO & Disney

Sit back and relax in this stylish home with all the amenities you need for a fun family getaway. This home has a spacious layout with 3 bedrooms and 2 baths. Send me a message to find out if we’re offering any additional seasonal discounts! -25 mins to Disney Parks -15 mins to Orlando International Airport - 12 mins to Silver Spurs Arena/Osceola Heritage Park -15 mins to Lake Nona -15 mins to USTA National Campus -1 hour from Cocoa Beach - 3 mins to Walmart & Plaza.

Top Guest favourite

Treehouse in St. Cloud

4.96 out of 5 average rating, 1,002 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

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 favourite

Home in Osceola County

4.97 out of 5 average rating, 29 reviews

The Modern Retreat by Disney

The Azur Resort, a luxurious and family-friendly community, is ideally situated close to Disney World, offering the perfect balance of comfort and convenience for your vacation home needs.This stunning three-bedroom townhome at The Azur Resort exemplifies modern elegance and thoughtful design, ensuring a memorable stay for all.

Guest favourite

Home in Kissimmee

4.94 out of 5 average rating, 127 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.

Superhost

Home in Kissimmee

4.83 out of 5 average rating, 12 reviews

Luxury Themed House 7BR, Private Cinema & More

We know that this may be a lot to read, but we suggest that you read everything and ask any questions you may have to see if it really is the right place for you and your group! :) Transparency and communication is very important to us! We want to make it clear, that we are here available, for any questions or suggestions.