Vacation rentals in Kissimmee

4.99 out of 5 average rating, 192 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!!

Home in Buenaventura Lakes

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

4.96 out of 5 average rating, 119 reviews

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

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.

5 out of 5 average rating, 59 reviews

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*

4.93 out of 5 average rating, 103 reviews

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

Villa in Citrus Ridge

Luxury Villa! /Game Room/ Pool Heater

Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

4.82 out of 5 average rating, 121 reviews

Renovated pond view home + pool & outdoor theatre!

Enjoy the elegance of this peaceful and centrally-located place just minutes away from Disney World, Sea World, Universal Studios & all other fun attractions of Florida. The house is tucked away in the tranquil zone next to a beautiful quiet pond that you can enjoy every evening after a busy day playing. Enjoy the pool with the sun all day and a private outdoor home theatre at night. We have a grill for your full enjoyment too. Just an hour away from sandy beaches.

A grand living area showcases a striking stone wall adorned with an extensive collection of framed artwork. Soft seating is arranged around a fireplace, providing a cozy yet elegant atmosphere. A staircase leads to the upper level, while rich drapery frames the large windows, allowing natural light to flow in.

4.96 out of 5 average rating, 200 reviews

Waterfront Wizarding Near Universal's Harry Potter

This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

4.92 out of 5 average rating, 143 reviews

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.

Condo in Kissimmee

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!

4.92 out of 5 average rating, 133 reviews

A private screened patio features a heated swimming pool and a Jacuzzi surrounded by a spacious deck. Outdoor seating is provided, with a dining table and lounge chairs positioned for relaxation. Sunlight glimmers on the water, creating a serene atmosphere.

Villa in Sunridge Woods

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi

Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

An open-concept living area features a large sectional sofa in soft gray, arranged around a circular coffee table. A contemporary fireplace is integrated into the wall, providing a focal point. Glass doors lead to the outdoor pool area, enhancing natural light throughout the space.

5 out of 5 average rating, 65 reviews

Luxury Home w/ Pool & 6 Beds near Disney

Welcome to your modern escape in Kissimmee! Just 15 minutes from Orlando International Airport, this beautifully renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and luxury. Every detail has been thoughtfully upgraded—from the brand-new kitchen and spa-like bathrooms to the pristine private pool area—ensuring a relaxing stay. With sleeping arrangements for up to 9 guests across six beds, there’s plenty of space to unwind.

The exterior of the pool house reveals a welcoming facade with a well-maintained lawn. A screened-in pool area showcases a spacious pool surrounded by tile flooring. The interior features a game room with a billiards table and air hockey, highlighted by modern entertainment options.

4.84 out of 5 average rating, 135 reviews

Pool House in Kissimmee

Quiet and spacious pool house in Kissimmee Florida, 20 minute away from Disney / Universal / Acquatica / SeaWorld theme parks. - 4 bedrooms - 2 bathrooms - Dining Room - Family Room - Kitchen - Double car garage - BBQ - Pool (heater optional) - Security Cameras Outside Only - WiFi 400 MBPS Pool Heater: If you want to use the heater please contact owner This will be your best vacation stay in Kissimmee / Orlando.

A spacious pool area is showcased under a protective screen. A large pool is bordered by a textured deck, with several lounge chairs arranged nearby. Lush greenery is visible in the background, and a covered patio area offers shaded seating.

4.94 out of 5 average rating, 288 reviews

Disney Orlando vacation home with private pool

Great location with private saltwater pool. 5 miles from Disney Parks and Disney Springs. 1.5 miles from Margaritaville Resort, which has the H2O water park, and 1.5 miles from Sunset Walk shopping mall, which there are variety of restaurants and entertainment, including the theater( Studio Movie Grill) and live music on the weekend.

4.96 out of 5 average rating, 55 reviews

Brand New 12br/33 ppl-Pool/Arcade/Theatre

🏰 Property Highlights 🏰 🌟 12-bedroom, 11.5-bathroom retreat (sleeps 33) 🌟 Batman Themed Movie Theatre 🌟 Spider Man Themed Arcade 🌟 Guardians of the Galaxy, Frozen, Minecraft, Harry Potter, and Tangled-themed kids rooms 🌟 Clubhouse Water Park, Resort Pools & Fitness Center 🌟 Private Pool & Spa 🌟 15 mins to Disney World

Popular amenities for Kissimmee vacation rentals

Self check-in

Beachfront

Gym

BBQ grill

Laptop-friendly workspace

What Airbnb hosts recommend seeing in Kissimmee

Find unforgettable activities and unique points of interest near you. Our hosts share their favorite 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

Summarized 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

Summarized 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

Summarized 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

Summarized 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

Summarized 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

Summarized 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

Private vacation rentals in Kissimmee

4.93 out of 5 average rating, 57 reviews

A galaxy-themed home theater is equipped with reclining leather chairs and plush bean bag seating. Colorful LED lighting creates an immersive ambiance, while a large screen displays a scene of a tropical beach. The walls are adorned with painted stars and planets.

Home in Davenport

7 BR Galactic Favorite Davenport

5 out of 5 average rating, 5 reviews

6BR 3.5BA Family Vacation Home

The exterior of the home showcases a two-story structure featuring a well-maintained façade with light-colored siding. Lush greenery surrounds the entrance, and a palm tree adds to the tropical ambiance. A spacious driveway accommodates multiple vehicles, with a garage door visible.

4.83 out of 5 average rating, 94 reviews

Welcome to the Oasis near Disney!

4.69 out of 5 average rating, 64 reviews

Fancy Lakefront 4BR Near Disney w/ themed bedrooms

4.95 out of 5 average rating, 37 reviews

A fenced heated pool area is visible, surrounded by lush greenery and palm trees. The villa entrance features a welcoming façade and a spacious driveway. Inside, a games room showcases vibrant Nemo-themed murals, along with seating and game tables for recreational enjoyment.

Home in Davenport

Adult Luxury - Magic for Families!

5 out of 5 average rating, 6 reviews

2.5 Aces Home with King bed & Jacuzzi! 2

A private pool area features a crystal-clear pool, complemented by a spa and surrounded by paving stones. Lush palm trees are visible on the sides, and views of the golf course stretch in the background, creating a serene atmosphere for relaxation.

4.88 out of 5 average rating, 81 reviews

Luxury 4 Bedroom Home - Resort Access! Disney!

4.85 out of 5 average rating, 33 reviews

Cabin in Kissimmee

Romantic getaway. Cabin w/ Indoor Soaking Tub

Kissimmee beach vacation rentals

A tranquil pool area is surrounded by lush greenery and palm trees. The water appears clear and inviting, with a rock formation creating a natural aesthetic. Lounge chairs are positioned around the pool, providing ample space for relaxation.

Apartment in Kissimmee

STar Island 1 Bedroom

4.96 out of 5 average rating, 121 reviews

The room features a spacious bed with a dark headboard and a blue accent pillow. A small table with two chairs is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through a window dressed with sheer curtains.

Home in St. Cloud

Comfy Studio w/ private Entrance

A bright living area features large windows that allow natural light to fill the space. A comfortable sectional sofa is paired with a wooden coffee table. A wall-mounted smart HDTV is visible, and greenery is positioned beside the windows, enhancing the inviting ambiance.

Villa in Clermont

4.82 out of 5 average rating, 104 reviews

Family Friendly w/ KING bed, Resort Pool Sleeps 5

4.79 out of 5 average rating, 24 reviews

A two-story building features a yellow exterior with white railings and a distinctive cupola. Palm trees and lounge chairs are situated near the swimming pool, creating a tropical ambiance. A large blue umbrella provides shade in the outdoor area, contributing to a relaxed setting.

Condo in Citrus Ridge

Perfect Disney\Golf Vacation

4.96 out of 5 average rating, 196 reviews

The expansive lake is showcased during sunset, reflecting vibrant colors in the sky. Surrounding greenery adds a natural touch, while a dock extends into the water, offering a serene view of the landscape. Soft light illuminates the pathway along the lake's edge.

Hotel room in Orlando

PentHouse Suite with 2X View

Condo in Orlando

Your Family's Disney HQ~Sleeps 8~No Extra Fees!

4.92 out of 5 average rating, 25 reviews

A mid-century home is framed by mature oak trees, providing shade to the grassy front yard. Large windows reflect the natural light, highlighting the clean lines of the exterior. The tranquil setting is complemented by the beauty of the surrounding landscape.

Home in Windermere

Water Front Haven

An expansive outdoor pool area features palm trees, sandy beach volleyball courts, and thatched umbrellas. Lounge chairs in blue and white are arranged around the pool, creating a vibrant atmosphere. The lush greenery of the surrounding landscape adds natural beauty to the setting.

4.75 out of 5 average rating, 12 reviews

Beach Resort with pool tiki bar near Disney World

Family friendly vacation rentals in Kissimmee

4.99 out of 5 average rating, 152 reviews

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

Villa in Citrus Ridge

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

4.75 out of 5 average rating, 136 reviews

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291

5 out of 5 average rating, 115 reviews

Themed Disney Villa | Pool | Arcade | Resort ºoº

4.86 out of 5 average rating, 437 reviews

A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.

Villa in Kissimmee

OMG! Disney Area, Movie Theater, Game Room & Pool!

4.91 out of 5 average rating, 154 reviews

Magical Pool Villa-close to Disney Game/movie Room

4.98 out of 5 average rating, 114 reviews

Dream Vacation | Sleeps 18 | Themed Arcade & Rooms

5 out of 5 average rating, 8 reviews

Condo in Kissimmee

Toy Story Magic Studio Close to Disney

A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.