Holiday rentals in Kissimmee

An inviting pool area is framed by a screened enclosure, revealing beautiful water views at sunset. Soft lighting enhances the relaxing atmosphere, with lounge seating positioned nearby for comfort. The tranquil setting is ideal for unwinding and enjoying outdoor moments by the pool.

4.96 out of 5 average rating, 335 reviews

Game Room/HeatedPool/Piano Upscale Waterfront Home

Welcome to one-of-a-kind upscale contemporary waterfront oasis, where luxury meets comfort. This stunning house is nestled in a tranquil neighborhood, just moments away from the airport and all the attractions you desire. Step inside to find a beautifully renovated space: fully equipped open kitchen, game room, gym, pool table, grand piano etc Outside: private screened in heated pool($20/night heating fee)with breathtaking waterviews, patio equipped with grill, dining table, ping pong and more!

The cottage features a vibrant blue exterior with yellow accents on the balcony and windows. Tropical landscaping with palm trees frames the entrance, complemented by a covered porch. The structure is two stories high, showcasing a welcoming atmosphere in a gated community.

4.97 out of 5 average rating, 39 reviews

Margaritaville Cottage,Hot Tub,Arcade, near Disney

Kick back and relax in this cozy two-bedroom cottage inside the gated Margaritaville Resort, only 4 miles from Disney. While the kids have a blast playing over 1,000 games on the full-size arcade machine inside, you can chill out on the patio with a cold drink. Forget crowded resort pools- you’ve got your own private hot tub to unwind in after a long day at the parks. Sunset Walk and the new Island H2O water park are just a short walk away. And bring your furry friend too — we’re pet friendly!

4.76 out of 5 average rating, 87 reviews

Resort Access: 4BR Retreat w/ PVT Pool near Disney

Welcome to our 4BR townhouse in Solara Resort! - Enjoy themed bedrooms & an open-concept living space. - Private pool with a covered patio, outdoor dining, & a BBQ grill. - Full resort access includes a heated pool, hot tub, fitness center, & more. - Located just minutes of drive from Disney & other attractions, perfect home base for family fun. - Free Wi-Fi, smart TVs, & parking ensure a comfortable & connected stay for all guests. - Relax, recharge, & make memories in sunny Orlando!

A bright and playful Minnie-themed bedroom features pink striped walls and polka dot bedding. An inviting pool area is adorned with a large pink float, surrounded by well-maintained landscaping and palm trees. The exterior of the villa showcases a charming, pastel pink facade with window shutters.

4.99 out of 5 average rating, 82 reviews

5br/5ba/5mi Disney • Heated Pool/SPA • Free rides!

• SALE! 25% LOWER NIGHTLY RATE FOR ALL BOOKINGS TODAY • Coastal themed and pet friendly pink villa in the heart of Margaritaville • Only 5 miles away from Disney • 5br with private bathrooms, 2 of 5 bedrooms are downstairs • Cute Minnie's room • Hot tub and heated pool • No extra pool heating fee! • No resort fee, but no access to community pool • Free Uber rides to parks! (for stays under 7 nights ) • Discounted tix to H2O waterpark Click ♡ icon to wishlist

4.98 out of 5 average rating, 123 reviews

A spacious themed room is depicted, featuring an imaginative design with a dark, cosmic ceiling. The room includes a large blue slide and a staircase, adjacent to cozy bean bag chairs for seating. Colorful space-themed murals enhance the playful atmosphere.

Villa in Kissimmee

4mi to Disney | Games | Private Pool

Get ready to make memories of a lifetime just over 3 miles to Disney when you stay at this newly renovated Star Wars and Lego-themed private pool villa. Located in Formosa Gardens Estates, a prestigious gated community, our home is professionally furnished with multigenerational families in mind and can comfortably sleep up to 15 guests. After a trip to the parks, enjoy a refreshing dip in the private pool and rest those tired feet in the spa.

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!

4.84 out of 5 average rating, 153 reviews

The image showcases a resort swimming pool surrounded by lush greenery and palm trees. The clear blue water reflects the evening sky, while lounge chairs and colorful umbrellas are visible in the background, creating a serene and inviting outdoor environment.

Apartment in Kissimmee

1-104 Legacy Dunes, Pool View, Close to Disney

First floor, no stairs with a view of the resort swimming pool One bedroom Apartment 1 King Sized Bed 1 Queen Sized Sleeper Sofa Bed Sleeps up to 4 Guests Ground floor, No Stairs One Full Bathroom Roku TV's Living Room and Dining Room Area Screened Patio Area Fully Equipped Kitchen Free Washer and Dryer Heated Outdoor Swimming Pool Free Parking Free Wi-Fi Game Room Tennis Court Playground Gym Gated Community with Security

5 out of 5 average rating, 7 reviews

Villa in Kissimmee

4BR Jungle Cruise Villa w/Pool & Spa Near Disney

Welcome to your dream getaway just minutes from Disney! Luxury family retreat – Sleeps 8! Private pool, bubbling spa and jungle-themed theater. • 🛏️ 4 Disney-themed bedrooms with en-suite baths • 🏰 Under 5 miles to Disney parks, shops and dining • 🏝️ Adventureland décor • 👨‍🍳 Gourmet kitchen + washer/dryer & baby gear • 🅿️ Free parking • 📞 24/7 response Book now and let the adventure begin.

4.98 out of 5 average rating, 55 reviews

An inviting outdoor area is showcased with a clear swimming pool and hot tub, surrounded by a landscaped yard. The vibrant pastel-colored cottages create a cheerful atmosphere, with blue skies and scattered clouds visible above.

Cottage in Four Corners

"Peachy Keen" 3BD Pool & Spa Cottage Near Disney

All will be “Peachy Keen” in your sweet beach-bound getaway! You will love floating outdoors in your personal cottage pool and hot tub, based in a tropical setting, and relaxing in this upscale cottage decked out with charming décor. The cottage’s open concept, along with a generous covered lanai space by the pool, allows you to always be a part of the fun!

5 out of 5 average rating, 9 reviews

Family Villa w/ Pool + BBQ Grill | Disney 10 min

Experience the ultimate comfort in this stunning 6-bedroom, 5-bath home at Storey Lake Resort. Perfect for family vacations or business trips, it offers a spacious layout, stylish décor, and modern amenities. Highlights include a private pool with spa, BBQ grill, and beautifully integrated living and dining spaces designed to bring everyone together.

5 out of 5 average rating, 6 reviews

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.

The image captures the FlowRider® Surf Simulator surrounded by shaded seating areas and lounge chairs. Additional views include the exterior of the two-story home with a sunset backdrop, and the private screened-in pool area set within a fenced yard, featuring outdoor patio furniture.

4.73 out of 5 average rating, 167 reviews

5 Bd/5.5 Ba Sleeps 10! Solara Resort (9026 PCs)

• Community: Solara Resort • 5 Bedrooms/5.5 Bathrooms/Sleeps 10 • Disney (8 miles) Sea World (17 miles) Universal (20 miles) • Convention Center (18 miles) Legoland (29 miles) • Location: Pelican Cove Trace, Kissimmee FL 34747

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

The open living area showcases a comfortable sectional sofa arranged around a decorative coffee table. A dining space with modern chairs is visible, accompanied by a stylish chandelier overhead. Natural light brightens the space, complemented by palm-themed artwork on the walls.

4.89 out of 5 average rating, 9 reviews

Your Dream Vacation Starts Here

A two-story townhouse features a warm color palette, including yellow and light peach exteriors. Lush landscaping surrounds the entrance, with tropical plants and palm trees adding a touch of greenery. The driveway provides designated parking spaces, creating a welcoming atmosphere for guests.

4.96 out of 5 average rating, 28 reviews

ZOE Paradise Less Than 10 Miles to Theme Parks

4.76 out of 5 average rating, 71 reviews

* 5 Bedroom Villa with pool near Disney*

Townhouse in Four Corners

An open living and dining area features a comfortable sectional sofa, an accent chair, and a wooden dining table set for six. Decorative wall art complements the neutral tones, while natural light flows in through glass doors leading to a screened-in patio.

4.88 out of 5 average rating, 26 reviews

The Magical Townhouse

4.79 out of 5 average rating, 14 reviews

Incredible villa with themed bedrooms by Disney