Holiday houses in Osceola County

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Top-rated holiday rentals in Osceola County

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Top Guest favourite
Home in St. Cloud
5 out of 5 average rating, 16 reviews

Home theater & pool table near Disney parks

Escape to your own private retreat just minutes from Walt Disney World. This well‑appointed four‑bedroom house offers a king suite, queen bedroom, single‑twin room and a triple‑twin room. Enjoy movie nights in a dedicated home theater, challenge friends at the billiard table, or cook in an open kitchen with dining area and outdoor grill and patio. You’ll have full use of washer/dryer, fast Wi‑Fi and smart TVs. Peaceful yet fun getaway close to the parks awaits—book now and start making memories.

Top Guest favourite
An inviting living area features a comfortable tufted chaise lounge and a cozy recliner. A flat-screen TV is mounted above a classic fireplace, surrounded by soft curtains that frame bright windows. The floor showcases warm wooden tones, contributing to a homely ambiance.
Cottage in Lake Wales
4.97 out of 5 average rating, 154 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
Townhouse in Osceola County
4.94 out of 5 average rating, 34 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!

Guest favourite
A bright and airy living space features a comfortable sofa and a coffee table atop a decorative rug. A ceiling fan and large glass doors lead to an outdoor area, while a sleek television adorns the wall opposite. Natural light enhances the neutral color palette.
Home in Lake Wales
5 out of 5 average rating, 28 reviews

Premium Lake Wales Getaway!

Beautiful townhouse, conveniently located in growing Lake Wales! Hotel-like feel with home-like comfort. Whether you're visiting for one night or planning an extended stay, this updated and stylish space lacks for nothing. We have you covered! Conveniently located near the infamous Bok Tower Gardens, Legoland, Peppa Pig Theme Park, with Disney World and world-famous, FL beaches within a couple hours away your options are endless. We hope you choose to stay with us for your special getaway!

Top Guest favourite
Villa in Osceola County
4.99 out of 5 average rating, 142 reviews

*Private Golf-Front Oasis with 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, 121 reviews

Sunshine on the Lake | Boat Slip+Lakefront Fishing

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

Guest favourite
A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.
Home in Kissimmee
4.94 out of 5 average rating, 123 reviews

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

Top Guest favourite
The modern home features a serene backyard with a private pool and spa, surrounded by lounge chairs. A shaded dining area provides ample seating for outdoor meals, alongside an outdoor kitchen space. The upper balcony offers additional seating with a view of the landscaped surroundings.
Home in Osceola County
5 out of 5 average rating, 27 reviews

Near Disney, free pool heat & resort membership

Newly built, modern home in desirable Reunion Resort with resort membership and pool/spa heat included. Enjoy knowing you will have no extra fees after booking. Free crib, grill, high chair and stroller included. I leave plenty of extra supplies in the unlocked black cabinet in the garage,like extra toilet paper, trash bags, olive oil packets, paper towels, condiments, laundry & dishwasher pods, toothbrushes, combs, bandaids, and many others. Let me know if you need any other supplies.

Top Guest favourite
A cozy living area features two leather sofas positioned around a wooden coffee table with a glass top. In the background, a well-equipped kitchen with wooden cabinetry is visible. Natural light fills the space, enhancing the warm tones of the decor.
Cottage in Lake Wales
4.9 out of 5 average rating, 132 reviews

The "Little ‘Toa" Ideal for short & long stays!

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

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, 83 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, 1,109 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, 99 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!

Popular amenities for Osceola County holiday rentals

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