Vacation rentals in Kissimmee

A private pool area features a crystal clear pool with a built-in spa, surrounded by a screened enclosure. A spacious patio is equipped with lounge chairs, a dining set, and a barbecue grill, offering a relaxed outdoor environment.

4.95 out of 5 average rating, 141 reviews

Vacation Home 3 bedroom/2 full bath/private pool

Bring the whole family to this great place with lots of room for fun. This house is perfect for you, your family, and friends! Spacious 3 bedrooms and 2 full baths that can accommodate up to 9 people. The house is fully air conditioned and has a pool. Indoor entertainment such as board games, ping pong table and TV cable. 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**

A spacious living area features a comfortable dark gray sofa and a stylish coffee table, surrounded by neutral decor. A large flat-screen TV is positioned on a modern console against a bright wall, while natural light fills the space through multiple windows.

4.97 out of 5 average rating, 175 reviews

Cozy Disney Oasis Pool Home 10 Mins from Parks!

Our charming, pet-friendly home is located in the prime area of Kissimmee, Florida. Your family will be close to Disney parks, restaurants, Old Town, and Downtown Disney. Just bring your bag—we have everything you need! Settle into our fully equipped home, thoughtfully designed to create lasting memories with family and friends. Enjoy the Florida weather by cooling off in our open-air pool or grilling by the poolside lounges. Relax in our airy bedrooms, including Mickey and Minnie themed rooms!

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!

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.

4.89 out of 5 average rating, 61 reviews

The Denmark

The Denmark House it is the perfect home away from home. This lovely home features a lake view, a peaceful private pool area including a hot tub, a game room, and smart TVs. We are Ideally located in Kissimmee just 15-30 minutes from Disney World, Sea World, Universal Orlando, and shopping areas. Pool heating is available upon request (Price varies). Late checkout is available for a $40 fee. BBQ rental available for a $100 fee. All Requests must be submitted at least 24 hours in advance.

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*

4.82 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.

A game room is presented with a red and neutral color scheme, featuring a billiard table with a set of colorful pool balls arranged on it. A television is mounted on the wall, and a dartboard is visible. The space is accented with vibrant wall art and seating areas.

4.9 out of 5 average rating, 135 reviews

No Airbnb Fee | Newly Renovated 4BR w/ Pool!

**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

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!

A spacious living area features a modern sectional sofa and two blue lounge chairs. A large flat-screen television displays a fireplace design, creating a cozy focal point. Natural light fills the room through window coverings, and a potted plant adds a touch of greenery.

4.91 out of 5 average rating, 247 reviews

Cozy House with Private Pool. Kissimmee/Orlando

Travelers will love staying at this home for its perfect mix of comfort and fun. Enjoy a private pool to relax after a long day, plus a gas BBQ included for easy outdoor meals with family or friends. The spacious and cozy layout is ideal for unwinding, while the peaceful setting makes it feel like a true getaway. Whether you’re here to relax or explore, this home offers everything you need for an unforgettable stay.

4.91 out of 5 average rating, 47 reviews

A bright living area is featured, with large windows allowing natural light to fill the space. A comfortable sofa and loveseat are positioned around a center coffee table. Decorative artwork adorns the walls, and a flat-screen TV is mounted above a wooden console. A patterned area rug anchors the room.

Apartment in Kissimmee

Spacious 3BR/2BA Retreat • Near Disney

Welcome! My husband Dande and I created this cozy 3-bedroom, 2-bath condo as a relaxing retreat for families visiting Disney and beyond. Centrally located in Kissimmee, you’re just minutes from Disney World, Universal Studios, SeaWorld, Gatorland, and more! Enjoy comfort, space, and style in a peaceful, family-friendly setting — the perfect home base for your Florida adventure.

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

4.67 out of 5 average rating, 24 reviews

Villa in Kissimmee

Exquisite Villa, Private Pool/Spa, Game Room

An outdoor space features a private screened-in pool surrounded by landscaped areas. A hammock is seen in the foreground, offering a place for relaxation. Sun loungers are positioned nearby, and tropical plants add a touch of greenery to the serene setting.

4.85 out of 5 average rating, 46 reviews

PrivatePool*NearDisney*EpicGameRoomTropicalGetaway

4.94 out of 5 average rating, 80 reviews

The well-lit bedroom features a spacious bed with white linens. A small armchair with a geometric pattern sits in one corner. Light curtains frame the window, allowing natural light to brighten the room. A small nightstand with lamps is positioned beside the bed.

Townhouse in Kissimmee

Summer Studio at Kissimmee

An outdoor space features a stylish fire pit with colorful flames, surrounded by comfortable seating. A hanging chair is visible nearby, along with shaded areas illuminated by string lights. In the background, the private pool area and a putting green can be seen, enhancing the outdoor experience.

4.71 out of 5 average rating, 225 reviews

Theater House / Outdoor Game Area / Pool / Disney!

4.98 out of 5 average rating, 54 reviews

A modern living room is depicted with a full sofa, coffee table, and a smart TV. Natural light enters through the sliding glass door leading to the balcony. Three framed botanical prints decorate the wall, while a floor lamp adds soft illumination.

Apartment in Kissimmee

Modern Condo: 10 Min to Disney + Fireworks Views!

4.95 out of 5 average rating, 37 reviews

Sunny Fun Disney – Pool, Style & Serenity

Townhouse in Citrus Ridge

4.82 out of 5 average rating, 22 reviews

Disney 10 Min • Universal 20 Min • Pool Home

4.88 out of 5 average rating, 26 reviews

Home in Davenport

VillaLumine•PrvtPool•Heater•Aesthetic•NearDisney

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 4

5 out of 5 average rating, 43 reviews

Home in Clermont

Lakefront home - country - check for seasonal rate

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

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

4.97 out of 5 average rating, 104 reviews

Magical Moments Luxury Disney Villa, Pool & Arcade

4.91 out of 5 average rating, 154 reviews

Magical Pool Villa-close to Disney Game/movie Room

4.9 out of 5 average rating, 31 reviews

10BR Theater Pool Little Mermaid Alice 16295

4.98 out of 5 average rating, 114 reviews

Dream Vacation | Sleeps 18 | Themed Arcade & Rooms

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.

4.86 out of 5 average rating, 140 reviews

Resort Home 3.5 miles to Disney with home theater

A vibrant hallway showcases colorful murals featuring beloved characters, including Mickey Mouse and his friends, amidst playful scenes of amusement and adventure. The walls are painted with a blend of whimsical colors that add charm to the spacious area, complemented by a clean marble floor.