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Holiday houses in Osceola County

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Top-rated holiday rentals in Osceola County

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Guest favourite
Apartment in Kissimmee
4.88 out of 5 average rating, 48 reviews

Your Happy Place at Tuscana Resort

Tuscana Resort 2 bedroom 2 bath condo - New Listing - Special Rates Accommodates the needs of all types of travelers that want a cozy place to relax after a long day out and about. Close to Theme Parks, Golfing and many of Orlandos attractions. Sleeps 6 guests in this spacious open concept condo. 65" Smart flat screen TV in the living room. Both bedrooms have TV's Fully equipped kitchen for dining at home. Located on the first floor for easy access and a minute walk to the community pool.

Superhost
Townhouse in Kissimmee
4.64 out of 5 average rating, 11 reviews

Waterfront Escape/Private Hot Tub/3 miles 2 Disney

Discover the ultimate vacation experience in this freshly updated waterfront townhome, where comfort meets breathtaking views from your private lanai, hot tub and dining area. Wake up to serene water vistas from the spacious primary suite, featuring a plush king bed and a private ensuite bath. The guest bedroom offers two inviting double beds and 3-piece ensuite. The open-concept kitchen is a chef's dream, outfitted with modern appliances and flowing seamlessly into the dining and living areas.

Guest favourite
The outdoor area features a private pool accompanied by a spacious spa, inviting relaxation. Lounge chairs are arranged around the pool, and a shaded dining area is visible. The backdrop consists of a modern two-story home and lush greenery, creating an appealing outdoor retreat.
Home in Kissimmee
4.96 out of 5 average rating, 102 reviews

Gorgeous 5BR PetFriendly @Encore | Disney - 7693

Modern, stylish, and luxurious, 3000sf home, with 5 bedrooms, at the world's renowned Encore Resort at Reunion. It features a game room, a huge backyard, an oversized private pool, spa. A true dream vacation home. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE

Guest favourite
Home in Osceola County
5 out of 5 average rating, 27 reviews

The Magical 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 spacious living area features a light-colored sofa and a round coffee table at the center, surrounded by distinctive tile flooring. Large windows invite natural light, while plants and a ceiling fan add to the relaxed ambiance. The circular design enhances the open feel of the space.
Home in Lake Wales
4.92 out of 5 average rating, 92 reviews

La Casita Redonda (The little round house)

Enjoy a memorable visit when you stay in this unique and historical place in Lake Wales, FL. Constructed in 1936 this home is nestled within a quiet and friendly neighborhood just minutes from the downtown area and just a short walk to Lake Wailes itself. Although the current owner updated the home with practical renovations, the peculiar house still has the character and features from the time it was built, features that once granted it a place among the pages of Ripley’s Believe it or Not.

Top Guest favourite
A wooden dock extends into the calm waters of Lake Rosalie, featuring a small viewing platform at the end. Lush green grass surrounds the water's edge, complemented by reeds along the shore. Clear blue skies reflect off the tranquil lake surface.
Home in Lake Wales
4.98 out of 5 average rating, 52 reviews

Lake Rosalie Getaway

Escape the hustle and bustle of life and enjoy a relaxing vacation at our newly remodeled lakefront home in beautiful Lake Wales! Located on peaceful Lake Rosalie, our residence is the perfect isolated getaway, yet still close to popular attractions such as Bok Tower Gardens, Legoland, Lake Kissimmee Park, Westgate River Ranch Rodeo and more! Unique amenities: - Large, upper-story wooden deck - 2 kayaks - Outdoor games, fishing poles - Exercise bike - Office room with printer - New kitchen

Superhost
An open-concept living area features a light-colored sofa arranged around a circular coffee table. Two orange accent chairs provide additional seating. A flat-screen television is mounted on the wall, above a console table adorned with decorative items. Natural light fills the room, highlighting the space's welcoming design.
Home in Osceola County
4.91 out of 5 average rating, 11 reviews

Thematic 4 bdr house near Disney - 11-105LV

Welcome to your Disney getaway!! This fantastic 4-bedroom it's your ticket to a magical vacation experience. Nestled in a gated community, and just minutes from the excitement of Disney and Universal. The clubhouse pool and jacuzzi just a hop, skip, and a jump away! Whether you're looking to splash around with the kids or unwind under the stars, this is where memories are made. Book your stay now and get ready for the vacation of a lifetime memories at this unique and family-friendly place.

Top Guest favourite
Apartment in Kissimmee
5 out of 5 average rating, 15 reviews

8070-304 Luxury 2BR Apt Kissimmee Orlando Disney

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped Apartment Condo Hotel for up to 6 guests, located right behind Sunset Walk, MargaritaVille Resort & Island H2O Water Park in Kissimmee. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. Everything you need is steps away: Restaurants, Ice Cream, Shops, Studio Movie Theater, Water Park, Live Music, Slingshot, Supermarkets & more... EV Charger Available.

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, 1,097 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 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, 96 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
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, 66 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!

Guest favourite
Villa in Kissimmee
4.88 out of 5 average rating, 164 reviews

Premium 6BR | Theater, Games & Heated Pool

Welcome to your 3,400 sq ft luxury escape just minutes from Disney World! Perfect for families and friends, our villa sleeps 12 with ensuite bathrooms in every bedroom. Enjoy the home theater, game room, and a fully equipped kitchen—plenty of space to gather or relax. Close to shopping, dining, and all the Orlando magic. Book now for unforgettable memories in your private Disney-area villa.

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