Holiday rentals in Kissimmee

4.84 out of 5 average rating, 90 reviews

Private Backyard/Top Rated Resort/3 mi to Disney

Looking for privacy on your vacation? This 3-bedroom townhouse in Regal Oaks offers a king bed with ensuite bath in the primary bedroom, a queen bed in the second, and twin beds in the third. There’s a second full bath and half bath on the main level. The open-concept main floor features a fully equipped kitchen, breakfast bar, and living area with a fold-out sofa, accommodating up to 8 guests. Enjoy a private lanai with a hot tub, dining area, loungers, and fiber-optic WiFi for all your needs.

4.99 out of 5 average rating, 193 reviews

A themed kitchenette features a bamboo bar with high seating and colorful pendant lighting. The walls are adorned with tribal art and shelves hold various artifacts. Kitchen appliances, including a refrigerator and counter space, reflect a blend of modern convenience and cultural decor.

Cottage in Kissimmee

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

4.89 out of 5 average rating, 18 reviews

An outdoor area showcases a private pool surrounded by sun loungers, with views of a golf course in the background. The pool's rippling water reflects the clear sky, complementing the serene atmosphere.

Villa in Four Corners

Amazing New Villa! Well Maintained! Fun for all!

My name is Mike and I’m the proud owner of Castle Pines Cove. This 6 bedroom Villa was completed and furnished in the spring of 2022. I love this house. I spend a lot of time here with my family. I have a 5 and 8 year-old and this is their favorite place to visit. It’s extremely important to me to ensure not only the house is clean but also maintained to the highest standard. Just like with my family, I want everyone who stays here to feel the exact same love for the house that we do.

5 out of 5 average rating, 59 reviews

An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.

Home in Four Corners

Gorgeous 5BR @ Encore Next to Disney - 305

Modern 3,000sf luxury home, with 5 bedrooms, at world's renowned Encore Resort at Reunion. Featuring 5 bedrooms, 5 1/2 bathrooms, a game room, a beautiful backyard, a 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*

Superhost

5 out of 5 average rating, 9 reviews

Themed 6BR | Game Room | Private Pool & Spa w/View

Stay at Time-Out Corner, Too @ Windsor Hills for an incredible vacation filled! Enjoy a game room, themed bedrooms, a private pool and spa w/gorgeous sunset view, and more. Plus, free access to the resort’s clubhouse and water park. Just 5 mins from Disney! 🎮Toy Story Game Room. Play Air Hockey, Skee-Ball, Arcades, Xbox, PlayStation, and more. 🏊 Private West-Facing Heated Pool/Spa. 🛏️ 6 BR & 4 BA. 3 Themed Bedrooms (UP, Alice in Wonderland, and Orange Bird). Sleeps 14.

The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.

4.99 out of 5 average rating, 143 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

4.9 out of 5 average rating, 29 reviews

Think Pink 2BR • Pool, Free Park, Priv Patio, Gym

Escape to this modern 2BR/2BA vacation rental just minutes from Disney, Universal, and Old Town Kissimmee! Families, couples, and friends will love the bright open layout, fully equipped kitchen, smart TV, and free Wi-Fi. Enjoy the resort pool, private balcony, and in-unit laundry, perfect for short or extended stays. With stylish décor and a prime location near theme parks, dining, and shopping, this home is your ideal Florida getaway.

Superhost

4.87 out of 5 average rating, 159 reviews

Fantasy World Enchanted Harry Potter Wizard Villa

Dive into magic at our villa in Fantasy World Villas, near Disney, Universal & Sea World. Be spellbound by the Hogwarts-themed double bedroom, king-size master, modern kitchen, and private patio. Resort: pools, slides, lazy river, kids' activities, gym, sports courts & more. Walk to shops & restaurants. Free WiFi, parking & resort access. Immerse yourself in enchantment and excitement, steps from theme parks & resort fun! Book now!

4.94 out of 5 average rating, 16 reviews

Best Location! Disney-Universal-Kid gear-Lakeview

Enjoy your stay and make family memories! ✦Prime Location-Minutes to Disney & Orlando attractions ✦Private heated splash pool looks on the lake ✦Open and spacious floor plan for the whole family ✦Sought-after resort community of Storey Lake ✦FUN themed Mickey and Marvel bedrooms ✦Highchair, booster and pack-n-play available ✦Lake view- no rear neighbors Many nearby golf courses- Please ask us any of your golf course questions!

A spacious living area features a modern sectional sofa and two blue lounge chairs. A large flat-screen television displays a fireplace design, creating a cozy focal point. Natural light fills the room through window coverings, and a potted plant adds a touch of greenery.

4.91 out of 5 average rating, 247 reviews

Cozy House with Private Pool. Kissimmee/Orlando

Travelers will love staying at this home for its perfect mix of comfort and fun. Enjoy a private pool to relax after a long day, plus a gas BBQ included for easy outdoor meals with family or friends. The spacious and cozy layout is ideal for unwinding, while the peaceful setting makes it feel like a true getaway. Whether you’re here to relax or explore, this home offers everything you need for an unforgettable stay.

A private, enclosed swimming pool is highlighted, surrounded by a spacious patio area. Comfortable seating is arranged for relaxation and a dining umbrella offers shade. Lush greenery can be seen in the background, contributing to a serene ambiance.

4.97 out of 5 average rating, 29 reviews

* Water View * Heated Pool * near Disney

Brand new fully renovated and updated! Spend some time at your private Florida vacation home & unwind in a spacious & contemporary interior with all the amenities you need to stay in. Right by US 192, next to Old Town, & just 15-20 minutes drive to Disney, you will have access to your private enclosed pool with a peaceful view of Florida's protected wilderness with no neighbors to the back!

4.87 out of 5 average rating, 62 reviews

3BR Pool Townhome Near Disney

Enjoy your dream stay in this charming 3bedroom, 2.5bathroom townhome located in the beautiful Bella Vida Resort, just 15–20 minutes from Disney. With a private pool, modern comforts, and access to excellent resort amenities, this home is ideal for families and groups looking for convenience, comfort, and a touch of Orlando magic.

Popular amenities for Kissimmee holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

What Airbnb hosts recommend seeing in Kissimmee

Find unforgettable activities and unique points of interest near you. Our hosts share their favourite things to do and must-visit places to see in Kissimmee.

Old Town

Retro-themed district with shops, restaurants, live music, and classic car shows

Summarised by AI

At Old Town, ride the iconic hand-built Ferris wheel, try the Hurricane coaster, play classic Skee-Ball and arcade games at Happy Days, and test your courage at Mortem Manor’s haunted attraction. Browse more than 70–80 unique shops and specialty stores, from retro memorabilia and woodcrafts to Disney souvenirs, then grab pizza, gator bites, snacks, or a cocktail. Catch free live entertainment, magic shows, karaoke, and street performers most evenings. On weekends, don’t miss the famous classic, muscle, and import car shows and cruises with live music.

Mentioned by 2,371 local hosts

Island H2O Water Park

Interactive water park featuring thrilling slides, a lazy river, and live entertainment

Summarised by AI

Spend the day on high-speed slides like Follow Me Falls and Profile Plunge, then slow down on the Chat Creek lazy river or in the Live! Lagoon wave pool. Kids can splash in Pelican’s Paradise and Candy Stripe Cove, while teens and adults enjoy the tech-savvy side: customizable music on rides, interactive games, and live social media feeds. Rent a private cabana, refuel with on-site dining, and stick around for glow foam parties, DJ sets, and nighttime movie or light-show events.

Mentioned by 470 local hosts

Kissimmee Lakefront Park

Scenic park with walking trails, playgrounds, and fishing piers along Lake Tohopekaliga

Summarised by AI

Spend time right at the lakefront with paved walking and bike paths, a scenic boardwalk, and wide green lawns for a relaxed stroll or jog. Kids can enjoy shaded playgrounds and a splash pad, while adults use picnic tables, grills, and rentable pavilions for easy cookouts. Fish from the pier, watch boats at Big Toho Marina, or look for birds and the occasional alligator along Lake Tohopekaliga. Explore the lighthouse, Monument of States, Veterans Memorial, and Bataan-Corregidor Memorial, and check out concerts, festivals, or movie nights in the park.

Mentioned by 332 local hosts

Fun Spot America Theme Parks - Kissimmee

Family-friendly amusement park with thrilling rides, go-karts, and a giant skycoaster

Summarised by AI

Ride Florida’s only wooden coaster with a 360-degree inversion on Mine Blower, drop 80 feet, and soar 300 feet on the world’s tallest SkyCoaster if you’re up for major thrills. Race friends on multi-level go-kart tracks like Vortex, let kids loose on kiddie coasters, bumper cars, carousels, and the Fun Slide, then cool off in the arcade and splash pad. Enjoy free admission and parking, with pay-per-ride or all-day pass options. On Friday and Saturday evenings, stick around for live bands and classic cars, or wander into neighboring Old Town Kissimmee for a relaxed walk and something to eat.

Mentioned by 1,001 local hosts

Medieval Times Dinner & Tournament

Immersive dinner show featuring jousting knights, swordplay, and a medieval feast

Summarised by AI

Inside Medieval Times Dinner & Tournament, you’ll walk over the moat into an 11th‑century-style castle filled with coats of arms, weaponry, and a medieval village that shows daily traditions, arts, and crafts. Sit at the regal banquet and dig into a four‑course, utensil‑free feast with tomato bisque, roasted chicken, sweet buttered corn, potatoes, dessert, and drinks, with vegetarian and gluten‑free options available. During dinner, cheer loudly for your knight as Andalusian horses, falcons, and armored champions deliver jousting, sword fights, and medieval games in a two‑hour tournament. Expect interactive fun for all ages, with knights engaging the crowd and everyone choosing a favorite champion to defend the throne.

Mentioned by 432 local hosts

The Loop Kissimmee

Open-air shopping center with diverse stores, dining options, and a movie theater

Summarised by AI

At The Loop Kissimmee, you can spend the day shopping over 40 stores across Loop East and West, from Nike Clearance, Kohl’s, Old Navy, Ross, JCPenney, TJ Maxx, Best Buy, Target, and Books-A-Million to specialty shops for clothes, shoes, jewelry, wine, bakery items, and books. Grab casual meals or sit-down dinners at places like BJ’s, Bonefish Grill, Macaroni Grill, Olive Garden, Abuelos, Chipotle, Panera, Chili’s, Wendy’s, and more, then finish with Ben & Jerry’s or frozen yogurt. Catch a film at Regal Cinemas with stadium seating, digital surround, and Real 3D, or let kids enjoy Chuck E. Cheese. The open-air layout has an outdoorsy, pet-friendly vibe, though individual shops may have their own pet policies.

Mentioned by 386 local hosts

Other great holiday rentals in Kissimmee

5 out of 5 average rating, 26 reviews

Gorgeous 4 bd Home w/private pool close to Disney

4.83 out of 5 average rating, 6 reviews

2773 BD - 5Bd Home with Private Pool 14 Guests

The living area features a modern sectional sofa with light-colored upholstery, complemented by bright throw pillows. A wall-mounted TV is positioned above a low media console, and large sliding doors open onto a patio overlooking the lake, creating an airy and spacious feel.

4.85 out of 5 average rating, 75 reviews

3141-103 Resort Lake View Disney Universal Orlando

4.95 out of 5 average rating, 98 reviews

Casita Disney! Cozy and Boho Townhouse near Disney

A playground area is featured, equipped with a slide, climbing structure, and monkey bars. Paved pathways surround the play equipment, and a bench is positioned nearby for seating. Lush greenery provides a backdrop, enhancing the space's appeal for families and children.

4.74 out of 5 average rating, 120 reviews

Lucaya! 4 bdr for 10. 15’ to Disney Parks/Outlets

5 out of 5 average rating, 7 reviews

Epic Home-FREE Water Park/Disney/South Facing Pool

Superhost

5 out of 5 average rating, 3 reviews

S3910 | Near Disney Home w/ Pool & Games

A modern living room is depicted with a full sofa, coffee table, and a smart TV. Natural light enters through the sliding glass door leading to the balcony. Three framed botanical prints decorate the wall, while a floor lamp adds soft illumination.