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Holiday houses in Kissimmee

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Top-rated holiday rentals in Kissimmee

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, 143 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
The open living area features a contemporary design with a curved sofa in neutral tones, two blue accent chairs, and a glass coffee table. A textured area rug complements the decor. Large windows allow natural light to illuminate the space, enhancing the connection to the outdoors.
Townhouse in Kissimmee
4.88 out of 5 average rating, 214 reviews

Adorable 2 bdr lakefront w/jacuzzi 5 min *Disney*

This townhouse provides an open main living space that allows you to connect the dining and a fully equipped kitchen. The house can accommodate up to 6 guests, divided into one luxe king en-suite, and a design theme two full en-suite. After a long day at the parks with a beautiful lakefront view, relax in your private spa. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant, and only 5 min from Disney and golfing area Free Parking Close to lakes, camping, beach, vineyards, farms

Top Guest favourite
A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.
Home in Kissimmee
4.95 out of 5 average rating, 79 reviews

Paradise Suite

Relax with the whole family at this peaceful place to stay. The spacious living area features windows that flood the space with natural light, while the kitchen is equipped with stainless steel appliances and granite countertops. The master bedroom offers a peaceful oasis with a spa-like master bath and walk-in closet. Property is located in a gated Golf community with a 3 mile walking trail that offers beautiful lake views. close to major intersections and shopping mall less than 2 miles

Top Guest favourite
Villa in Kissimmee
4.99 out of 5 average rating, 104 reviews

Minutes to Disney 6BR Immaculate Vacation Villa

This stunning Storey Lake Resort Villa is the perfect getaway to relax and enjoy your time in Orlando, Florida. Just minutes to Disney World & within easy reach of attractions, shopping and dining. This immaculate & exceptional villa has a heated pool and spa (no additional charge) to relax in after a busy day at the parks. Family friendly featuring Super Mario & Frozen bedrooms, as well as three king size bedrooms, along with a Harry Potter themed movie loft & Spider-Man themed game room!

Top Guest favourite
The vibrant Mickey-themed bedroom features a spacious bed adorned with yellow and white bedding, accented by playful green pillows. Wall murals showcase iconic Mickey Mouse imagery, while a colorful area rug adds warmth to the hardwood floor. Two nightstands with lamps provide illumination.
Home in Championsgate Village
5 out of 5 average rating, 26 reviews

Disney 6 bedroom Luxury Villa Arcade Pool Heat bbq

Discover the enchantment of our Disney Fantasy 6 bedroom LUXURY Villa, nestled in the vibrant Champions Gate Resort. A stone's throw from the Oasis clubhouse and a mere 12 miles from Magic Kingdom, this is your ideal Disney getaway. Boasting 6 lavish themed bedrooms, 6 bathrooms, a private arcade, heated pool, BBQ, and essential modern amenities like high speed internet, air conditioning, and a fully equipped kitchen, your stay promises comfort and fun. Perfect for families

Top Guest favourite
A modern apartment features a spacious bedroom with themed decor, showcasing vibrant wall art and a cozy sleeping area. An open kitchen adorned with sleek cabinetry and a dining space with four chairs is highlighted. A decorative living space includes a friendly mural, adding a playful touch.
Condo in Kissimmee
4.94 out of 5 average rating, 173 reviews

302_10 Pixie Dust Paradise - 10 min from Disney

A Magical Stay for the Whole Family! Welcome to your family's happy place near Disney! Our 3-bedroom apartment is cozy, kid-friendly, and fully stocked with everything you need to feel right at home. Whether you're starting your day with excitement or coming back from the parks with tired little feet, this is the perfect place to relax and recharge. And guess what? The waterpark is FREE and super fun—a splash-tastic way to end your day with big laughs and happy memories!

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, 241 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.

Top Guest favourite
A modern kitchen features white cabinetry and dark appliances, complemented by a large central island with a light countertop. Pendant lighting hangs above, illuminating the space. A dining area is visible with sleek white chairs positioned around a table, creating an inviting atmosphere for meals.
Apartment in Kissimmee
5 out of 5 average rating, 36 reviews

2 Bedrooms Apartment in Storey Lake

Experience the perfect Orlando getaway in this comfortable and convenient 2-bedroom, 2-bathroom apartment, ideal for families or groups of up to 6 guests. Located in Storey Lake Resort, just 10 minutes from Disney and 25 minutes from Universal Studios. This property offers access to incredible amenities, including pools. Our resort-style community offers: pools, bar, gym, mini golf, tennis, volleyball and basketball court, arcade room, BBQ area, etc.

Top Guest favourite
The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.
Home in Four Corners
5 out of 5 average rating, 101 reviews

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Stylish Design, Luxurious Comfort & Endless Entertainment, with a sprawling 2200 ft2 southwest facing pool deck & outdoor kitchen, no rear neighbors on a beautiful forest in the stunning 3.5 square mile Reunion Resort. You will have your own private pool with overflow spa, movie room, billiards - game room, 4 theme rooms: OUTER SPACE, MARVEL SUPERHEROES with a TUBE SLIDE, FROZEN II, HARRY POTTER CUPBOARD, PS5, within minutes to Disney.

Superhost
Condo in Kissimmee
5 out of 5 average rating, 3 reviews

Moana Adventure Suite Near Disney

Answer the call of the ocean in this beautifully designed Moana-themed studio just minutes from Disney. While the outside may look simple and unassuming, opening the door begins a speakeasy-like adventure with Moana and her friends. With acrylic water-effect flooring, 3D character art, and family touches like a crib, this joyful island-inspired space is perfect for young explorers and Moana fans alike.

Top Guest favourite
Home in Kissimmee
4.97 out of 5 average rating, 121 reviews

3BD/3BA Themed House Near Disney

Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Guest favourite
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, 141 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.

Popular amenities for Kissimmee holiday rentals

When is the best time to visit Kissimmee?

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Avg. price$211 AUD$217 AUD$226 AUD$220 AUD$195 AUD$207 AUD$219 AUD$192 AUD$177 AUD$189 AUD$202 AUD$238 AUD
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Frequently Asked Questions

  • What are the best places to stay in Kissimmee?

    Kissimmee has accommodations in resort areas near theme parks, private homes around Reunion and Storey Lake, and family-friendly neighborhoods with easy access to local attractions. Many spaces feature pools, spacious layouts, and outdoor amenities for group stays.

  • What are the best things to do in Kissimmee with kids?

    Families can explore fun attractions like Gatorland, ride thrilling coasters at Old Town, or enjoy large playgrounds and splash pads in city parks. Themed entertainment and interactive experiences are frequently suggested for younger visitors.

  • What are some of the best things to do in Kissimmee?

    Discover live shows and rides at Old Town, visit Gatorland for wildlife encounters, or explore regional history at the Osceola County Historical Society. The area is also known for airboat tours and vibrant outdoor markets.

  • How is the weather in Kissimmee?

    Kissimmee has mild winters around 49–72°F (10–22°C) and hot, humid summers reaching 74–92°F (23–33°C) with frequent rainfall from May through September. Lightweight clothing, sunscreen, and a rain jacket are recommended.

  • What are the best places to visit in Kissimmee?

    Popular places include Old Town for entertainment and shops, Gatorland for reptile encounters, and the Kissimmee Lakefront Park with walking trails and playgrounds. Museum enthusiasts will often find exhibits at local historical centers.

  • What are some hiking trails in Kissimmee?

    Stroll boardwalks and shaded paths at Shingle Creek Regional Park, walk lakeside trails at Kissimmee Lakefront Park, or explore nature preserves nearby. Trails often highlight local wildlife and peaceful scenery.

  • What are some family activities we can do in Kissimmee?

    Explore Gatorland’s exhibits, ride classic attractions at Old Town, or play in the splash pads at Kissimmee Lakefront Park. Family-friendly dining spots and arcades are also popular choices for shared outings.

  • What are some of the best day trip ideas from Kissimmee?

    Explore Orlando’s theme parks, stroll nature reserves around Lake Tohopekaliga, or enjoy coastal beaches for a change of scenery. You can also visit nearby state parks or experience local wildlife tours.

  • Are there any pet friendly accommodations available in Kissimmee?

    Many Kissimmee neighborhoods, including those near Central Kissimmee and the resort communities, have pet-friendly vacation rentals. Parks and outdoor spaces throughout the area make traveling with pets convenient.

  • What are some local tips for visiting Kissimmee?

    Hydrate frequently in warm months, and bring insect repellent for outdoor activities near lakes. Book popular attractions in advance and explore local eateries for regional flavors beyond the main tourist areas.

  • What is Kissimmee known for?

    Kissimmee is known for its proximity to major theme parks, distinctive wildlife experiences like Gatorland, and vibrant entertainment districts such as Old Town. Airboat rides and access to lakes add an outdoor adventure element.

  • What are the best hidden gems to explore in Kissimmee?

    Visit Shingle Creek Regional Park for quiet paddling and wildlife spotting, shop local at farmers markets, or discover history at the Osceola County Historical Society museum. Neighborhood spots often have authentic flavors and art.

  • What are the best foods to try in Kissimmee?

    Enjoy Southern-style barbecue, fresh seafood, and Latin flavors like Cuban sandwiches or empanadas at locally rooted eateries. Homemade ice cream and citrus-inspired desserts are frequently suggested, especially in summer.

  • What should I bring for a trip to Kissimmee?

    Pack lightweight clothing, sunscreen, and a hat for sun protection. A rain jacket, comfortable walking shoes, and insect repellent are useful for exploring parks and outdoor attractions.

  • What is the nightlife in Kissimmee like?

    Kissimmee has lively spots for live music, themed bars, and outdoor events in areas like Old Town. Nighttime entertainment often includes family-friendly shows and locally owned restaurants with late-night menus.

  • What are the most popular events or festivals in Kissimmee?

    Kissimmee hosts car shows, holiday parades, and cultural festivals around Old Town, with seasonal fairs and outdoor concerts often taking place in parks. Late spring and holiday weekends feature many community gatherings.

  • Are there family friendly vacation rentals in Kissimmee?

    Family-friendly vacation rentals are available throughout Kissimmee, particularly in resort-style neighborhoods and private home communities. Many have amenities like pools, recreation rooms, and easy access to parks and attractions.

  • When is the best time to visit Kissimmee?

    Late autumn and early spring are often recommended, with milder temperatures and smaller crowds. Summer brings lively local events and frequent afternoon rain, while winter stays mild and sunny.

Quick stats about holiday rentals in Kissimmee

  • Total holiday rentals

    Explore 7,290 holiday rentals in Kissimmee

  • Verified guest reviews

    Over 257,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    6,160 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 1,150 rentals that welcome pets

  • Holiday rentals with a pool

    6,590 properties feature pools

  • Rentals with dedicated workspaces

    4,000 properties have a dedicated workspace

  • Wi-Fi availability

    7,110 of Kissimmee holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Gym across Kissimmee rentals

  • 4.7 Average rating

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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee