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Holiday rentals in Osceola County

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Top-rated holiday rentals in Osceola County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A shaded lounging area features comfortable seating and a glass-top table, set with refreshments. In the background, a large pool glistens under the sun, surrounded by palm trees and various seating options, including cabanas and sun loungers.
Townhouse in Kissimmee
4.84 out of 5 average rating, 214 reviews

Orlando Disney ºoº 3BD in Resort | Kissimmee

Modern Townhouse in Resort w/ preserve area and Amazing Clubhouse. (NO resort fees!) | 1 min | Old Town Kissimmee | 3 min | Publix®, McDonald's®, Wendy's®, Miller's Ale House® and more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | DISNEY® AREA (All Theme Parks) | 9 min | Premium Outlet® | 11 min | Disney Springs | 11 min | ESPN® Sports | 13 min | Convention Center | 15 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 70 min | Bush Garden's® | 95 min | Sarasota & Clearwater

Top guest favourite
Cottage in Lake Wales
4.97 out of 5 average rating, 151 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
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, 159 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!

Guest favourite
Apartment in Kissimmee
4.86 out of 5 average rating, 133 reviews

Stylish Condo 20 mins to Disney/King Bed

Escape to our lovely vacation villa, nestled in the vibrant heart of Orlando's premier golfing destination. Just a 7-mile drive from Disney attractions and 30 minutes from Orlando International Airport. Discover the awe-inspiring Reunion Resort, offering an array of delights. Indulge in delectable dining experiences, take a dip in sparkling pools, savor refreshing drinks at poolside bars and grill. Embark on an extraordinary getaway that exceeds all expectations. Book your stay with us today!

Top guest favourite
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, 47 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 favourite
A bright living room features a spacious gray sofa oriented toward a large flat-screen TV, with large windows allowing natural light to fill the space. A contemporary ceiling fan adds to the modern ambiance, while minimalist decor completes the inviting setting.
Flat in Kissimmee
5 out of 5 average rating, 72 reviews

Modern Luxury Kissimmee Retreat

Welcome to our stunning Kissimmee apartment, where modern luxury meets ultimate comfort! This renovated 2-bedroom, 2-bathroom retreat offers high-end finishes, a fully equipped kitchen, large screen TVs, PlayStation 5, and high-speed Wi-Fi. Enjoy blackout curtains and white noise machines for restful nights. Complex amenities include a pool, gym, sauna, and tennis court. Located near Walt Disney World, Universal Studios, and top shopping, our apartment is the perfect base for your adventures.

Top guest favourite
Tiny home in Kissimmee
5 out of 5 average rating, 34 reviews

Casa Bonita

Experience a unique and romantic retreat in our charming tiny home—ideal for couples or solo travelers seeking peace and tranquility. Nestled in a serene neighborhood, it features a cozy full-size bed, a fully equipped compact kitchen, and a peaceful outdoor space. Enjoy morning coffee on the patio, stargaze at night, and embrace tiny living with modern comforts. Plus, you’re just minutes away from top attractions like Disney, Epic Universe, SeaWorld, Volcano Bay, and the Convention Center.”

Guest favourite
An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.
Apartment in Osceola County
4.89 out of 5 average rating, 119 reviews

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

Top guest favourite
The entrance to the studio is shown, featuring a solid grey door with a simple handle. A small welcome mat is placed at the door. A wooden fence provides privacy, while a small porch area is seen beside the entrance.
Flat in Kissimmee
4.98 out of 5 average rating, 97 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
A keyless entry system can be seen installed on the door, featuring a numeric keypad for access. In the background, soft, colorful curtains frame a window, while a glimpse of a bed with decorative bedding is slightly blurred, suggesting a cozy sleeping area.
Guest suite in Kissimmee
4.92 out of 5 average rating, 166 reviews

It's too much like a elegant mini-hotel (2)

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. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

Guest favourite
Guest house in Kissimmee
4.93 out of 5 average rating, 29 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 sofabed 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 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, 1,088 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.

Popular amenities for Osceola County holiday rentals

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