Vacation rentals in Kissimmee

4.92 out of 5 average rating, 84 reviews

A vibrant game room is filled with Mario-themed arcade machines featuring colorful graphics and interactive screens. Brightly colored carpet adds a playful touch, while a basketball game and other activities occupy the space. The walls are adorned with mural artwork inspired by popular video games.

Home in Davenport

Dazzling 9 BR+Brand New MARIO KART @ Champion Gate

Bring the whole family to this great home with lots of room for fun. You will love our Peter Pan- themed bedroom; custom Mario-themed game room with commercial quality games, private pool and spa with a great outdoor dining area. Only a short walk to the resort pools, lazy river, restaurant, Tiki bar and much more. Located just 15 minutes from Disney World and 30 Minutes from Both Universal and Sea World, Close enough to the attractions to get there quickly, far enough away to enjoy family time.

A bright pool area is surrounded by a screened enclosure that offers protection from insects. A clear blue pool is visible, accompanied by six chaise lounge chairs positioned nearby. Warm yellow walls frame the space, enhancing the tropical feel of the private outdoor oasis.

4.93 out of 5 average rating, 341 reviews

*Disney Home* Heated Priv Pool/Spa 7beds, Arcade!

This gorgeous updated pool home is perfect for families and friends for a Florida vacation! Located just 5 mi from Disney! Close to Universal! Approx 2000 sq ft. No stairs! Chill in your own heated private pool and hot tub or enjoy the club house pool of Veranda Palms complete with a water park and splash pad! Work out in the fitness center or walk the gated neighborhood to the new community center, just steps away. Enjoy your private AIR CONDITIONED game room w/ arcade and air hockey table.

The image captures a view from the pool, showcasing the villa's large glass windows and covered outdoor seating area. Loungers are positioned around the pool, offering ample space for relaxation. The sparkling water reflects the modern architecture above, framed by a screened enclosure.

4.94 out of 5 average rating, 113 reviews

Private Pool & Free Heat - Close to Disney!

3 bed, 3 bath luxury villa in exclusive gated community 10 mins from Disney. Private pool & hot tub with free heat not overlooked by other homes. Main rooms open onto pool. Kitchen with granite counter tops. Outside bar, loungers, table & chairs. Master bedroom with double sink ensuite and twin with ensuite shower room. Queen is separate to main house providing additional privacy when travelling with friends/family. 32 inch tv's and comfortable beds with pillow top mattresses in all bedrooms

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.

Home in Buenaventura Lakes

The exterior of the house is displayed, featuring a well-maintained lawn with manicured shrubs and a palm tree. The light-colored structure is complemented by large windows, and decorative stones are arranged artistically in the landscape. A clear blue sky enhances the inviting appearance.

4.94 out of 5 average rating, 108 reviews

Your All in One Home, 17 mins from Disney World

Welcome to JeremyAnthonyHouse, a place that was created with so much love and care thinking of you. The house has everything you might need during your stay, it does not matter if it is for one night or an entire month; from bathroom amenities, free Netflix, Wifi, YouTube, in house laundry and dryer to kids' toys, security system. In addition, it has a private pool, easy access to expressways and theme parks. Very close to Disney springs and The Medieval Times Castle is a must see.

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.

The private pool area is surrounded by a screened enclosure, featuring a clear blue pool. A patio with dining furniture and a BBQ grill is visible, alongside lounging chairs. Two homes can be seen in the background, creating a spacious ambiance.

4.89 out of 5 average rating, 119 reviews

Retreat w/ Pvt Pool + Club Access | Disney 15min

Experience luxury in this spacious 5-bedroom, 5.5-bathroom home located just 15 minutes from Disney. Relax in elegant living areas with Smart TVs and an Xbox One, or step outside to your private pool with stylish patio furniture and BBQ grill. The open-concept kitchen and dining area are perfect for gathering, while the Windsor at Westside resort offers a lazy river, pools, fitness center, playgrounds, and sports courts, all just steps away.

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 :)

An outdoor space features a screened-in pool area with a clear blue pool and spa. Comfortable lounge chairs are positioned beside the pool, with a dining table set beside them. Lush greenery is visible beyond the fenced yard, creating a private and relaxing environment.

4.79 out of 5 average rating, 132 reviews

The Real Florida Whispering Oaks

The Oaktree home is a favorite among returning guests. Once you have stayed in this home you cannot wait to return. The spacious pool /spa and deck area, game room and provides all you could ask for to make your stay one to remember. Recently remodeled kitchen with updated appliances make this home shine! Partially fenced in yard with no rear neighbors offer you a quiet retreat. T.V. on pool deck! Complimentary Hot Tub Heat!

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.

5 out of 5 average rating, 7 reviews

9BR Retreat | Sleep 27 | Theater | Huge Pool & Spa

Welcome to your Storey Lake getaway! This spacious 9-bedroom home with a private pool, spa, and game room is designed for unforgettable family vacations—just minutes from Disney, dining, and top attractions. Relax, recharge, and make memories together.

4.89 out of 5 average rating, 273 reviews

The spacious living area features a comfortable gray couch adorned with vibrant cushions, complemented by two small tables. A large window provides natural light and a view of the outdoor area with a barbecue and pool, while a wall-mounted TV offers entertainment options.

Townhouse in Kissimmee

Luxurious Dream 4/3 Bedroom Home w/private Pool

Located a short 15 minute drive to Disney, this luxury design inspired 4 bedroom, 3.5 bath is perfect for a family, multi family or romantic weekend away with your favourite person.

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

5 out of 5 average rating, 9 reviews

The Disney House • Immersive Rooms • Gaming Lounge

4.8 out of 5 average rating, 70 reviews

The screened pool area features a spacious swimming pool, illuminated in calming blue tones. A jetted tub is integrated into the pool area, surrounded by brick paving. Lounge chairs are positioned nearby for relaxation under the protective screen.

Villa in Davenport

Best Value BnB Disney Villa W/ Private Pool & SPA

5 out of 5 average rating, 5 reviews

6BR 3.5BA Family Vacation Home

5 out of 5 average rating, 4 reviews

New! Epic Solara Playhouse | Custom Bunks + Slides

A private screened-in pool is surrounded by a clear enclosure, offering unobstructed views of a serene lake and lush greenery. Sunlight reflects off the water, enhancing the tranquil atmosphere. Comfortable lounge chairs are positioned nearby for relaxation.

4.92 out of 5 average rating, 61 reviews

Serene 4BR Pool Home Near Disney

4.61 out of 5 average rating, 18 reviews

Peaceful 5 BR Home w/Private Pool/Spa & Game Room!

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

Home in Buenaventura Lakes

5 out of 5 average rating, 35 reviews

Comfy Home with Hot Tub at Kissimmee/Orlando area

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, 119 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 4

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 Davenport

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

4.82 out of 5 average rating, 11 reviews

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.

Home in Davenport

Beach Resort with pool tiki bar near Disney World

Family friendly vacation rentals in Kissimmee

A collage of vibrant and themed recreational rooms showcases a game room with a Star Wars mural, a pool table, and unique lighting. The outdoor area features a large resort-style pool surrounded by palm trees and lounge chairs, complemented by a private spa.

5 out of 5 average rating, 36 reviews

Updated Vacation Home Solara by Disney w/Pool

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.

4.99 out of 5 average rating, 150 reviews

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

4.92 out of 5 average rating, 132 reviews

The image showcases various themed sleeping areas within the vacation home. A Superhero Room displays colorful walls with superhero motifs, while the Princess Room features castle imagery. A cozy nook with a bunk bed is visible, alongside arcade machines that add to the playful environment.

Townhouse in Kissimmee

Magical Hideaway - 15 min to Disney - Storey Lake

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.

4.86 out of 5 average rating, 436 reviews

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

5 out of 5 average rating, 8 reviews

Condo in Kissimmee

Toy Story Magic Studio Close to Disney

4.78 out of 5 average rating, 316 reviews

Townhouse in Kissimmee

Fantasy World 2br, Luxury on Wet n Wild #4

4.9 out of 5 average rating, 200 reviews

Modern home with heated pool 15 min. to Disney