Vacation rentals in Kissimmee

4.97 out of 5 average rating, 110 reviews

"Castaway Oasis" 5 Bed Townhome, Heated Pool & BBQ

Welcome to“Castaway Oasis”,newly decorated luxury 5 bedroom 4.5 bath townhouse with private heated pool in the resort of Windsor at Westside. 3 KING Bedrooms,2 exciting Kids bedrooms, Lazy Boy Sleeper Couch in the Loft. The community is an upscale, gated resort with a 10,000 sqft Clubhouse, 2 Pools, Lazy River, Hot Tub, Kids Splash pool, Tiki Bar& Fireplace lounge, Fitness Center, Volleyball Court, Basketball Court, FREE Arcade. Complimentary access to all amenities is included for our guests.

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, 115 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.

The image displays a colorful two-story home with light green siding, accented by blue shutters. The pool area features a vibrant water slide and colorful play structures. The interior includes a children's sleeping area with themed decor and twin beds, creating a fun, inviting atmosphere.

4.92 out of 5 average rating, 134 reviews

Brand New Margaritaville Key Lime House by Disney

Close to Disney! Stunning *New 3 bedroom/ 3 bath home located inside the Luxury community of Margaritaville. This private oasis is centrally Located, few minutes away from the parks and restaurants. Sunset Walk is located next to the resort and it has more shopping, restaurants, Dine-in Lux Theater, & entertainment, including "Estefan Kitchen" by Gloria Estefan. While you unwind & relax, kids will love the new spectacular waterpark, Island H2O Live. Welcome to your island adventure!

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.

4.93 out of 5 average rating, 103 reviews

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.

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.

4.95 out of 5 average rating, 198 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.

4.89 out of 5 average rating, 120 reviews

Mi Casita Near Disney/Universal

Welcome to your own private oasis in Kissimmee! Our charming 3-bedroom home boasts a beautiful private pool. Unwind in the serene surroundings while still being just moments away from the excitement of world-class theme parks and entertainment. Enjoy a fully-equipped kitchen, comfortable living areas, and spacious bedrooms for a memorable stay that combines the comforts of home with a sun-soaked Florida experience. Book your escape today!

5 out of 5 average rating, 17 reviews

9BR Home at Storey Lake - Pool, Game Room, Spa

Make magical memories in this 9BR/5BA themed villa at Storey Lake Resort! Sleeps 27 with custom bedrooms (Harry Potter, Rapunzel, Smurfs & more). Enjoy a south-facing private pool & spa, game room with arcade, and fully equipped kitchen. Resort perks included—lazy river, water slide, mini golf, splash pad, fitness center & more. Just 15 mins to Disney, Universal & outlets. The perfect home base for your Orlando adventure!

5 out of 5 average rating, 5 reviews

6BR 3.5BA Family Vacation Home

Welcome to your perfect Florida getaway! This modern and spacious 6-bedroom, 3.5-bathroom home in Kissimmee is just minutes from Disney parks and top Orlando attractions. Designed for families and large groups, it comfortably accommodates up to 14 guests. Enjoy stylish living areas, a fun playroom, and thoughtfully designed bedrooms—everything you need for a relaxing, unforgettable vacation.

5 out of 5 average rating, 15 reviews

Casa Resort Storey Lake a minutos de Disney y Epic

Espectacular casa en Storey Lake Resort, con 4 habitaciones para 12 personas y piscina privada. Perfecta para familias que buscan comodidad y diversión. Acceso a río lento, piscinas, toboganes, mini-golf y gimnasio. A solo 10–15 min de Disney, 20–25 min de Universal y 15–20 min de SeaWorld. Ubicación ideal para unas vacaciones inolvidables.

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, 287 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

5 out of 5 average rating, 6 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.

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, 3 reviews

Apartment in Kissimmee

207 Storey Lake Brand new 7 Guests 2 BDR Lake view

4.98 out of 5 average rating, 52 reviews

Guesthouse in Kissimmee

Escape to the "Golden Suite" Private & Near Disney

An exterior view of a two-story home is presented, featuring a screened-in private pool and spa surrounded by a patio. Additional images showcase a game room with a pool table, vibrant wall art, and an inviting living space leading to the pool area.

4.93 out of 5 average rating, 84 reviews

* Top-Rated Villa - Sleeps 14 - Free Resort *

5 out of 5 average rating, 5 reviews

5BR Luxury Pool Home Near Disney

5 out of 5 average rating, 13 reviews

Home in Davenport

Modern 6BR Villa with Pool in ChampionsGate

5 out of 5 average rating, 10 reviews

NEW Modern Townhome w/ Themed Room | Near Disney

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, 80 reviews

Luxury 4 Bedroom Home - Resort Access! Disney!

5 out of 5 average rating, 12 reviews

Disney Magic | Game Room | Pool | 3 Kings | Slide

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 Sleep 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 sparkling private pool is surrounded by lounge chairs and tropical landscaping, providing a relaxing outdoor space. A gaming room features vibrant blue lighting, a pool table, and arcade games. A colorful playroom, equipped with a slide and play equipment, invites children to enjoy indoor activities. A movie theater room displays plush seating and a large screen for film viewing.

4.9 out of 5 average rating, 50 reviews

House Resort at Encore Reunion - Disney

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

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.

4.94 out of 5 average rating, 129 reviews

Magical Hideaway - 15 min to Disney - Storey Lake

4.75 out of 5 average rating, 134 reviews

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

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, 435 reviews

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

4.91 out of 5 average rating, 154 reviews

Home in Davenport

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