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Vacation rentals in Osceola County

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Top-rated vacation rentals in Osceola County

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Top guest favorite
Tiny home in Kissimmee
5 out of 5 average rating, 28 reviews

Pretty little house

You'll love this unique and romantic escape of our tiny home — perfect for couples or solo travelers seeking a peaceful retreat. Nestled in a quiet neighborhood, this space features everything you need: a comfy full size bed, a compact but fully equipped kitchen, and a relaxing outdoor area. Enjoy morning coffee on the back patio, stargazing at the stars and the simplicity of tiny living with modern comforts. Just minutes from local attractions, Disney, Epic universe, Sea World, Volcano Bay, etc

Top guest favorite
A compact kitchen features white cabinetry and modern stainless steel appliances. An electric stovetop is positioned beside a microwave, with a coffee maker and various kitchen utensils visible. A small refrigerator stands nearby, complemented by decorative items on the open shelves.
Home in Kissimmee
4.99 out of 5 average rating, 147 reviews

Private Suite with Independent Entrance

Private Suite with Independent Entrance Kissimmee, Fl Enjoy a modern and fully equipped private suite, perfect for couples or travelers looking for comfort, privacy, and a relaxing stay just minutes away from Orlando’s top attractions. 📍Perfect Location Conveniently located in Kissimmee, just minutes from: 🎢 Disney World 🎬 Universal Studios 🌊 SeaWorld and Aquatica You’ll also find restaurants, supermarkets, outlets, and gas stations nearby an excellent location for your Orlando vacation!

Top guest favorite
A serene lakeside view showcases a spacious home nestled among lush greenery. Relaxing lounge chairs are positioned on a sandy beach area, complemented by a wooden dock featuring seating options. The clear blue water reflects the calm sky, inviting guests to enjoy the natural surroundings.
Guest suite in Lake Wales
5 out of 5 average rating, 43 reviews

Lakefront Master Suite with Private Entrance

This peaceful master suite with deck overlooks Little Blue Lake and has relaxing outdoor spaces. The master bedroom has king-sized bed. The attached bathroom has a roomy shower with two shower heads and a soaking tub. The kitchenette area has a Keurig with coffee and tea. Also, a refrigerator/freezer, microwave, toaster oven, air-fryer, cups, dishes and utensils. 7 miles to Bok Tower Gardens. 5 miles to Webber and 3 miles to Warner. 6 miles to Lake Wales Skydiving and Paramotor training.

Top guest favorite
A serene bedroom features a queen bed with light blue linens and an elegant headboard. A cozy wingback chair and a full-length mirror offer additional comfort. A woven rug complements the space, while windows allow natural light to brighten the room.
Guesthouse in Kissimmee
5 out of 5 average rating, 25 reviews

The Forrestry

The Forrestry is the ideal launching pad for visits to the parks. Perfectly priced so you can enjoy Disney, SeaWorld, Legoland & Universal. The garden gate opens to a spacious patio. This cozy retreat is a great room concept. A coffee bar with snacks greets you on entry into the living room, with a comfortable sofa bed and a multi-use table for games and dining. A well-equipped kitchen and laundry room flank it. The bedroom suite has a spacious walk-in closet and bathroom.

Top guest favorite
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, 1,077 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 favorite
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, 59 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 favorite
A private patio features two modern sun loungers positioned beside a small side table. The area is surrounded by manicured greenery and offers views of the expansive golf course, showcasing the resort's tranquil atmosphere.
Condo in Osceola County
4.93 out of 5 average rating, 73 reviews

Casa Ida

Keep it simple at this peaceful and centrally-located Luxury condo. Only 9 miles away from Disney World. . . 27 minutes away from Universal Studios. Access to 5 Pools, The Pavillion, and all restaurants on the property. Relax and enjoy beautiful views of the Signature Golf Course all from the patio of this beautiful home. This condo boasts a fully equipped kitchen for those who like to cook.

Guest favorite
A keyless entry system is prominently displayed on the door, providing convenient access. In the blurred background, a bed with a blue and white coverlet can be seen, suggesting a cozy sleeping area. Soft lighting enhances the inviting interior ambiance.
Guest suite in Kissimmee
4.94 out of 5 average rating, 148 reviews

It's too much like a elegant mini-hotel (4)

It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

Top guest favorite
Home in Osceola County
4.97 out of 5 average rating, 39 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.

Top guest favorite
Guesthouse in Kissimmee
4.98 out of 5 average rating, 300 reviews

"Little Blue House" Getaway Near the Disney Parks

Your home away from home! Enjoy a comfortable and relaxing stay in our Casa Azul. Spacious and modern, it features a bedroom with a double bed, a private bathroom, a living room with a sofa bed, a dining room, and a fully equipped kitchen. Ideal for vacations with family or friends.

Top guest favorite
The room features a spacious bed with a dark headboard and a blue accent pillow. A small table with two chairs is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through a window dressed with sheer curtains.
Home in St. Cloud
4.96 out of 5 average rating, 110 reviews

Comfy Studio w/ private Entrance

Relax at this peaceful place to stay where you will feel at Home. This home and it’s located 14 miles away from Orlando International Airport, 30-50 min ( depending on the traffic)to Disney World, Sea World, Universal Studios, Outlets and other Orlando attractions.

Top guest favorite
The modern guesthouse is set against a spacious green lawn, with a paved walkway leading to the entrance. The structure features multiple glass windows, illuminated softly by exterior lights. A seating area with chairs is visible on the lawn, creating an inviting outdoor space.
Guest suite in Kissimmee
4.94 out of 5 average rating, 224 reviews

Stylish guesthouse close to Disney

Stylish guestroom just 6 miles from Disney and SeaWorld. Brandnew space with separate entrance. Queen size bed, down pillows and comforter, Nespresso coffee maker, mini fridge and microwave. Oversized rain shower.

Popular amenities for Osceola County vacation rentals

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