Holiday rentals in Osceola County

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Top-rated holiday rentals in Osceola County

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Top guest favourite

Cottage in Lake Wales

4.97 out of 5 average rating, 143 reviews

Charming, renovated 1917 Cottage

Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!

Top guest favourite

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 favourite

Home in Kissimmee

4.97 out of 5 average rating, 108 reviews

Modern House with Private Pool Getaway Kissimmee

This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.

Top guest favourite

Home in Kissimmee

4.94 out of 5 average rating, 67 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

Guest favourite

Flat in Kissimmee

4.97 out of 5 average rating, 60 reviews

Small Studio Apartment

The apartment is attatched to the main house, but has its own entrance. The studio will provide guest with complete privacy The kitchen is equipped with a fully furnished setup; including pots, pan oven, fridge and more. Full size bed is provided. Bathroom will have towels, soap, shampoo, conditioner, and hair dryer Othe amenities include a TV with Netflix, wifi, Alexa, window AC unit, parking right in front, and a quiet neighborhood. Any questions or concerns you can contact me.

Top guest favourite

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 favourite

Treehouse in St. Cloud

4.96 out of 5 average rating, 1,021 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

Flat in Osceola County

5 out of 5 average rating, 20 reviews

VIP Luxury ZONE & Disney 15 mns

🌟 Luxury Retreat at Reunion Resort – Your Ultimate Getaway! 🌟 ✨ Fully remodeled 3-bedroom villa with high-end decor, modern kitchen, and spacious living areas. Enjoy a 5-star resort experience just 6 miles from Disney! 🏡 Located in Reunion Resort, a 2,300-acre exclusive community with world-class amenities: restaurants, gym, and more—just minutes from Margaritaville & Celebration Town. 🔑 Book now and experience luxury near Orlando’s top attractions! 🌴🔥

Top guest favourite

Flat in Kissimmee

4.89 out of 5 average rating, 84 reviews

Relax in Cozy Apt 1/1 near to Disney

Your family will be close to everything when you stay at this centrally located accommodation. It is a beautiful completely renovated property, new on Airbnb, it is located on the third floor, accessed by stairs, there are no elevators, please evaluate this information carefully before booking, it is fully equipped for you to enjoy of your stay You will be very close to the main theme parks of the city such as Disney World and Universal Studios.

Top guest favourite

Townhouse in Osceola County

4.99 out of 5 average rating, 87 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!

Top guest favourite

Home in Kissimmee

4.99 out of 5 average rating, 120 reviews

Guest Suite

A totally independent suite * 1 Queen bed. * 1 single sofa bed * Equipped kitchen * Private bathroom * Free parking. * Wi-Fi * Terrace The location is perfect for enjoying all the theme parks Orlando has to offer: Disney Universal Studios Aquatica and Sea World. (they're just minutes away). It is conveniently close to restaurants, supermarkets, outlets, gas stations, excellent location for your vacation

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!