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House holiday rentals in Kissimmee

Find and book unique houses on Airbnb

Top-rated house rentals in Kissimmee

Guests agree: These houses are highly rated for location, cleanliness and more.

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Top Guest favourite
A charming two-story cottage is featured, exhibiting a cheerful yellow exterior. A small balcony is visible above the entrance, flanked by white railings. Lush palm trees and landscaped foliage surround the property, enhancing the inviting open space in a sunny environment.
Home in Kissimmee
5 out of 5 average rating, 147 reviews

Margaritaville Cottage 10 Minutes to DisneyWorld!

Location location location! We are conveniently located at the Margaritaville Resort. We are just minutes away from DisneyWorld, Universal, and Seaworld, Sunset walk, and H20 Water Park. * THIS DOES NOT INCLUDE ACCESS TO THE RESORT AMENITIES/POOL, however many of our guests chose to purchase a membership at H20 water park with the money they’re saving in resort fees* • Sunset Walk - A brand new experience that provides a plethora of restaurants, shopping, live entertainment, and movie theatre. (Resort shuttle is available, or a 15 min walk). •H20 - A new water park located on the resort property that includes offerings for all ages. ADDITIONAL fees apply. • Formosa Garden Winery - a five minute walk to an abundance of wine and beer with incredible views. The winery is open Thursday-Sunday. We recommend a brunch reservation! Cottage Accommodations - • 2 spacious bedrooms • 2 full bathrooms • Couch that can be converted into queen bed • Free and easy parking • Free WiFi • TV’s with cable in living room and both bedrooms (Netflix & Disney plus available) • High ceilings • Back patio with lounge chairs • Balcony on second floor with two adirondack chairs • All kitchen supplies included • Security for entrances and 24 hour watch House Rules • NO parties under any circumstance per airbnb policy. • No smoking, a $200 fine will be imposed for guests who break this rule • No unregistered guests *if you’ll be bringing a pet, please let us know before your arrival, there is a $50 service fee, max 2 pets*

Top Guest favourite
A private pool area is surrounded by a screened enclosure, featuring a well-shaped pool and a jetted hot tub. Lounge chairs are positioned nearby, with a grassy area beyond. The evening sky displays hues of pink, creating a serene atmosphere, enhanced by string lights that illuminate the space.
Home in Kissimmee
4.94 out of 5 average rating, 178 reviews

*Luxe Disney Home* Priv Pool/Spa- 6BR Sleeps 15

JUST ADDED! (Check out our other reviews) New Construction!!! 3000ft2! Welcome to our luxury 6-BR private pool home near Disney World, Universal Studios, and Sea World! With 8 beds, it sleeps 15 people comfortably. Enjoy the private heated pool, hot tub, and game room with ping pong, cornhole, and arcade. Located in Veranda Palms community, you also have access to a large pool, clubhouse, gym, and splash pad. Perfect for large families or groups seeking a memorable Orlando stay. Book now!

Superhost
Home in Kissimmee
5 out of 5 average rating, 4 reviews

Reunion Resort Village Luxury Retreat moderna

Welcome to Reunion Luxury Retreat, experience the perfect blend of luxury comfort, and privacy in this elegant villa, located within the exclusive gate community of Reunion Village, just minutes from Orlando's world-famous theme parks. Our Home offers everything you need for an unforgattable stay. 4 spacious bedrooms , 5 different pools in our resort. Gate community with 24-7 security . Hi speed wifi , smart TV , fully equipped kitchen . Relax after a magical day al Disney or Universal.

Guest favourite
A resort area is depicted with a large swimming pool surrounded by palm trees. The two-story building features numerous windows and outdoor seating, creating an inviting space. Soft evening light reflects on the water's surface, enhancing the tranquil atmosphere.
Home in Kissimmee
4.87 out of 5 average rating, 129 reviews

Resort TH 2b/2.5b With Private Hot Tub near Disney

Visit Regal Oaks Resort, with an onsite waterpark and private hot tub. We're close to everything in Orlando and a 10 min drive to Disney! Our Resort-Style Villa Includes: ❤Onsite Waterpark and Heated Pools ❤Walkable to Old Town Restaurants and Shops ✔No Hidden Fees ✔Onsite Fitness Center ❤24/7 Security ✔Onsite Concierge, Restaurant and Bars Our Home Offers: ❤Private Hot Tub ✔Comfy King and 2 Full-Size Beds ❤Fast WiFi ✔Cable TVs ✔Private Patio ✔Washer/Dryer ✔Stocked Kitchen

Guest favourite
The exterior of the home is shown, featuring a tiled roof and lush landscaping. Tropical plants and vibrant flowers surround the property, while Spanish moss hangs from a nearby tree. Clear blue skies create a bright atmosphere, highlighting the welcoming entrance.
Home in Kissimmee
4.89 out of 5 average rating, 178 reviews

VerandaPalms/HeatedPool/Carpet free/NearDisney

This beautiful 4 bedroom home is 10 minutes from the Disney parks !!! Walking distance from Shingle Creek Reg. Park, just in the corner of Veranda Palms main entrance. This home has 2 suites, a private heated pool and is located near Sams Club and restaurants. Complimentary XBOX and Nespresso Coffee machine. ROKU in all bedrooms. Non smoking policy. Clubhouse with large swimming pool and gym. Well-maintained home, with new appliances. Superhost awarded 34 times in a row !!!

Top Guest favourite
A charming two-story cottage is framed by lush palm trees and vibrant landscaping. The pastel-colored exterior features a welcoming front porch with seating. A private hot tub is visible in the courtyard, surrounded by patio space suitable for relaxation.
Home in Kissimmee
4.97 out of 5 average rating, 30 reviews

2BD Cottage w/Spa in Margaritaville

Welcome to your own island-inspired oasis. Our charming 2Bd spa cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. Relax with the whole family at this peaceful place to stay.

Superhost
A serene outdoor area features a private pool with a gentle waterfall and a spa, surrounded by chaise chairs and a lush green landscape. Hammocks are visible in the background, and bright sunlight reflects off the water. A basketball hoop adds to the recreational amenities.
Home in Four Corners
4.83 out of 5 average rating, 223 reviews

Gorgeous 8BR at Encore Resort next to Disney - 281

Modern luxury home built in 2020, located at world renowned Encore at Reunion. Almost 4,000sf of a/c area, featuring 8 bedrooms, 6 full baths, game room, private pool and spa. 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 HOUSE RULES*

Top Guest favourite
A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.
Home in Kissimmee
5 out of 5 average rating, 244 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

Superhost
A spacious living area features a light-colored sofa with decorative pillows and a sleek coffee table. A large television hangs on a textured black feature wall. Natural light fills the space, highlighting the contemporary decor and the open layout leading to a dining area in the background.
Home in Kissimmee
4.82 out of 5 average rating, 22 reviews

Modern Escape in Kissimmee

Relax with the whole family at this peaceful,modern and clean place to stay. 20-25 mts away from Disney, Big yard to relax and have outdoor activities, quiet community, sunset view and much more to do. ALSO 35 MTS APPROXIMATELY FROM THE SOON TO BE OPEN UNIVERSAL EPIC UNIVERSE Which will be Open on MAY 22,2025 Universal’s largest park to date . house includes Netflix,wifi and Garage beeper Any booking over 30 days, the cleaning fee is $200

Guest favourite
A modern kitchen features stainless steel appliances, including a refrigerator and a gas stove. Dark cabinetry is complemented by a honeycomb-patterned backsplash. Counter space is provided with rich wood accents, and small kitchen essentials are neatly arranged, creating a functional cooking environment.
Home in Kissimmee
4.82 out of 5 average rating, 151 reviews

8052 Heated Pool Grill House Kissimmee by Disney

Relax with the whole family at this peaceful HEATED POOL & GRILL house in Kissimmee, just minutes from Disney Parks and Margarita Ville Water Park. Master Suite has a great view to screened Pool & Lanai. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 4 Smart TV's and strong Wi-Fi all around the house. Enjoy our Games Room with a Foosball table and a Pool table located in the garage!

Top Guest favourite
A private swimming pool is surrounded by a screened enclosure, featuring a poolside theatre with a large projector screen. Lush greenery is visible beyond the pool area, creating a serene environment. Lounge chairs are positioned nearby for relaxation.
Home in Kissimmee
4.9 out of 5 average rating, 118 reviews

8 mins. to Disney W/Poolside Theater & Game Room

Are you looking for a vacation home with an incredible game room, a very private south facing saltwater complimentary heated pool with children's wading pool, hot tub and poolside theatre featuring a 120" screen with 4K UHD, and a new modern kitchen, in Formosa Gardens Estates (the gated community known for its large estate lots), and is very close to Disney World? This is it . . .

Guest favourite
A sprawling resort-style pool area is seen, featuring lazy rivers, waterslides, and mini-golf. Lush palm trees and landscaped greenery surround the pools, creating a relaxed atmosphere. A clubhouse with a tan roof is visible in the background, alongside a tranquil water view.
Home in Kissimmee
5 out of 5 average rating, 10 reviews

Heated pool~Lazy River~Mini Golf~Near DisneyResort

Welcome to Lazy Lagoon, your ultimate vacation retreat in the heart of Kissimmee, FL! Our inviting 4-bedroom, 3-bathroom home offers the perfect blend of comfort and adventure, making it ideal for families, friends, or any group getaway. With space to accommodate up to 10 guests, you'll find everything you need for an unforgettable stay just minutes from Orlando's top attractions.

Popular amenities for Kissimmee house rentals

When is the best time to visit Kissimmee?

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Avg. price$275 NZD$280 NZD$302 NZD$299 NZD$261 NZD$284 NZD$301 NZD$261 NZD$234 NZD$248 NZD$273 NZD$318 NZD
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Quick stats about house rentals in Kissimmee

  • Total holiday rentals

    Explore 3,600 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 99,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    3,090 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 630 rentals that welcome pets

  • Holiday rentals with a pool

    3,260 properties feature pools

  • Rentals with dedicated workspaces

    1,880 properties have a dedicated workspace

  • Wi-Fi availability

    3,570 of Kissimmee holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kissimmee rentals

  • 4.7 Average rating

    Kissimmee stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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