Holiday rentals in Kissimmee

A bright living room showcases a high ceiling and large windows allowing natural light. Two brown sofas and a light grey armchair surround a circular coffee table on a decorative rug. A large flat-screen TV is mounted on the wall, complementing the serene outdoor view visible through glass doors.

4.93 out of 5 average rating, 108 reviews

Neverland Found-Minutes from Disney Free Waterpark

Welcome to Neverland Found! This unique property inspires us to never grow up with themed rooms of Peter Pan, The Lost Boys, and Tinkerbell. Our home has 2 Master Suites, a fully equipped kitchen, 5 bedrooms, 5 baths, pool and spa, Pirates of the Caribbean game room, and loft area. Our home is located in the resort community of Storey Lake with access to multiple clubhouses and pools and all of it's amenities. Located within minutes of the theme parks & attractions that Orlando has to offer.

5 out of 5 average rating, 5 reviews

15 minutes from Disney Luxury Retreat at Reunion

Relax after a magical day at Disney or Universal. 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 unforgettable stay. 4 spacious bedrooms, 5 different pools in our resort. Gate community with 24-7 security. Fast wifi , smart TV, fully equipped kitchen.

4.95 out of 5 average rating, 149 reviews

A living room is presented with green accent walls and hardwood flooring. A comfortable sofa with orange throw pillows faces two small coffee tables. Wall decorations include woven art pieces. A ceiling fan hangs above, and a door leads to a balcony, allowing natural light into the space.

Flat in Kissimmee

Cozy 2Bed Boho Hideaway 10 Min to Parks Allows Pet

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 8 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.

4.92 out of 5 average rating, 143 reviews

Modern Condo with Lake View Near Disney 3151

STOREY LAKE RESORT A premier vacation community just 8 miles from Disney and minutes from Universal & SeaWorld, this community is surrounded by restaurants, shops, and top malls. Only 30 minutes from Orlando Airport, it offers easy access to everything you need. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Stay 30+ nights and save 10% (Discount will apply on selected stays) Reserve now! we would love to be your host!

4.98 out of 5 average rating, 126 reviews

The cottage features a charming exterior with bright yellow siding and a classic gabled roof. Lush palm trees and manicured hedges frame the entrance, which includes a welcoming porch with yellow chairs. Large windows allow natural light to enhance the inviting facade.

Cottage in Kissimmee

1BD Cottage "Limoncello" in Margaritaville

Welcome to your own island-inspired oasis. Our charming 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. All Pets Must Be Preapproved :)

4.97 out of 5 average rating, 30 reviews

5BR Golf View Penthouse • Near Disney • Luxe Stay!

✨ Spacious 5BR Loft Condo near Disney! ✨ Located in a gated resort, this stylish family-friendly getaway features a full kitchen, washer/dryer, and access to a resort pool, fitness center, and game room. Just minutes from Walt Disney World, Universal, and shopping outlets. Sleeps 12—perfect for large families or group trips. Enjoy comfort, space, and unbeatable location for your Orlando vacation! Book your dream stay now! 🏰🌴💫

4.83 out of 5 average rating, 234 reviews

Home 6 BDR at Solara Resort/Private Pool LED

The Space * Accommodates: 16 * Bedrooms: 6 * Bathrooms: 4.5 * Property type: Luxury Villa * Location: Solara Resort * ONLY 0.2 miles away from The Clubhouse! * 12 miles from Magic Kingdom * 8 miles from Animal Kingdom * 16 miles from SeaWorld * 21 miles from Universal Studios * Property and resort close to the US 27 highway where some restaurants, market, gas station, pharmacies are located.

5 out of 5 average rating, 5 reviews

Sunset Lakeview Retreat – Heated Pool Near Disney!

Escape to this 5BR, 3.5BA villa in gated Sunset Lakes, Kissimmee. Enjoy a private pool with lake views, outdoor dining, and a game room with 85” TV, pool table, and air hockey. Kids love the Disney-themed bedrooms, adults love the quiet location steps from the playground. 10 mins to Disney, 20 to Universal, 5 to Publix/Target — perfect for families near Orlando’s top attractions.

A family room features a neutral-toned sofa and armchair, accompanied by a mounted flat-screen TV. A children's bedroom displays two twin beds, adorned with playful wall murals. A primary bedroom includes a king bed, with bedside lamps enhancing the calm ambiance. A resort pool area showcases a large pool surrounded by lounge seating and loungers in a vibrant outdoor setting.

4.96 out of 5 average rating, 165 reviews

202_Magical and Cozy 2BR minutes from Disney

The ultimate choice for your Orlando getaway! Our cozy apartment is thoughtfully designed to make you feel right at home, with all the comforts and amenities you need. Plus, enjoy complimentary access to the waterpark – the perfect way to relax and have fun after a day of exploring the parks or shopping in Orlando!

4.82 out of 5 average rating, 33 reviews

Resort Water Park Home with Private Pool

Step into an elegant 7-bedroom retreat at the exclusive Solara Resort, perfectly designed for large families and groups of up to 15. This luxurious home combines the magic of Orlando with the comfort of a private oasis, complete with your own pool, spa, and incredible entertainment spaces.

A modern living space features a neutral color palette, with plush seating arranged around a wooden dining table. Natural light streams through large windows, highlighting the open layout and tasteful decor elements. An inviting ambiance is created by soft furnishings and well-placed lighting.

4.82 out of 5 average rating, 215 reviews

2BD/2BA condo at Storey Lake, close to Disney #70

A beautiful themed vacation condo for you to relax and spend time with your family and friends! With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 2BD/2BA condo unit is designed for your best family vacation!

5 out of 5 average rating, 6 reviews

Townhouse in Kissimmee

4BR Retreat | Pool | Close to Disney

Home at Bella Vida. If you want a heated pool, you must notify us in advance and we charge $30 per day for pool heating and one time fee of $50 for the bbq. Starter amenities are provided for your arrival, intended for short stays or your first night convenience.

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

4.87 out of 5 average rating, 30 reviews

Chic & Spacious Best Vacation Home

4.62 out of 5 average rating, 117 reviews

4BD/3BA Private Pool @ Lake Berkley Resort

Townhouse in Kissimmee

5 out of 5 average rating, 5 reviews

Paradise Palms Resort 4 Bedroom Pool Townhome

Townhouse in Kissimmee

4.83 out of 5 average rating, 6 reviews

Perfect Family Getaway, 4BR & Themed Magic

5 out of 5 average rating, 3 reviews

5-Star stay near Theme Parks!

A large outdoor area features a private heated pool surrounded by lounge chairs and tropical palm trees. A hot tub is positioned next to the pool, with a barbecue grill nearby. Bright blue skies and soft clouds provide a scenic backdrop to this relaxing space.

5 out of 5 average rating, 22 reviews

ECR313 Resort Style Mansion + Pool/Spa/Theater/Gym

Villa in Kissimmee

5 out of 5 average rating, 3 reviews

6BR Home w/ Priv Pool Near Disney | Gated Resort

A modern kitchen and living area are showcased in an open plan layout. The kitchen features white cabinetry and stainless steel appliances, while a dining table accommodates six. A cozy couch with blue and yellow accents faces a large window, revealing distant views of the surrounding area.