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Holiday houses 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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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, 160 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 favourite
Home in Lake Wales
5 out of 5 average rating, 6 reviews

Speck House: Lakefront, Fishing, Kayaks

Escape to lakefront serenity! A dream come true for fishermen! This cozy 2BR/2BA home features a full kitchen overlooking the water, stunning sunrises, and some of the best speck and bass fishing around. Enjoy a private boat ramp and dock (seasonal water levels may affect launching), 2 kayaks, bikes, cornhole, puzzles and games. Located on Lake Rosalie minutes from Camp Mack, local fishing tournaments, and nearby wedding venues-perfect for couples, family time, fishing, or a peaceful getaway.

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.
Condo 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)

Guest favourite
A modern digital door lock is mounted on a light-colored door, featuring a keypad for secure access. A blurred plant with lush green leaves is visible in the background, adding a touch of nature to the entryway.
Guest suite in Kissimmee
4.95 out of 5 average rating, 175 reviews

It's too much like a elegant mini-hotel (5)

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!

Top Guest favourite
A brightly painted tiny home is showcased against a serene backdrop. The exterior features red and yellow hues with a blue door and window. Two blue chairs are positioned beside a small table, creating an outdoor seating area surrounded by lush greenery.
Guesthouse in Kissimmee
4.96 out of 5 average rating, 104 reviews

Orlando Private Tiny Guest House

*Quiet, safe neighborhood Premium location *20 minutes to Orlando Airport *20 minutes to Disney parks & Disney Springs *25 minutes to Universal Studios & CityWalk *7 minutes to shopping plaza with top outlets and diverse dining *5 minutes to super Walmart *Local minimarkets. Inside your tiny home: *Queen-size bed *Coffee, fridge & microwave *Private entrance + patio *Modern shower *Air conditioning, Wi-Fi & Smart TV *Need transportation or special arrangements? Let us know

Guest favourite
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
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, 1,093 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 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, 65 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 favourite
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
4.94 out of 5 average rating, 77 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 favourite
A cozy bedroom features a spacious bed dressed in white linens, flanked by two nightstands. A decorative mirror is mounted above the bed, reflecting light. A small seating area includes a white wicker chair, while artwork adorns the adjacent wall, enhancing the calming design.
Apartment in Kissimmee
4.92 out of 5 average rating, 50 reviews

Relaxing Escape w/ Private Patio near MCO & Parks

Relájate en esta escapada única y tranquila, ubicado en Kissimmee , es un espacio acogedor y confortable para que pases unos días inolvidable, nuestro espacio tiene un amplio dormitorio y cuenta con baño , cocina y un amplio patio para que puedas compartir. Los huéspedes tienen acceso gratuito , además se encuentra cerca de los parques principales de Disney y otras atracciones de Orlando.

Guest favourite
The tranquil scene captures a lakeside view framed by trees at dusk. The horizon glows with soft orange and yellow hues, reflecting on the water. A hammock is visible, adding to the serene atmosphere of the wetlands beyond.
Guest suite in St. Cloud
4.93 out of 5 average rating, 407 reviews

LAKE FRONT Suite w FREE Kayaking/Canoe

Private Master Suite with it's own exclusive entry. It has a convenient kitchenette complete with mini refrigerator, microwave, toaster, toaster oven and an outside grill. Comfy Queen size bed with overhead ceiling fan. Private Bathroom and shower. Lake view from the front of property, unit is in the back overlooking wetlands. Plenty of parking, with enough room to bring a boat.

Popular amenities for Osceola County holiday rentals

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