Vacation rentals in Kissimmee

4.93 out of 5 average rating, 159 reviews

Close 2 Disney, privatePool, Spa+pinball Game Room

Disney Playhouse – Your Dream Vacation Awaits! Indulge in elegance and comfort at this newly upgraded, pet-friendly retreat. Relax in your private pool & spa within a fully fenced backyard. Unwind in the plush master suite, enjoy Roku TVs in every room, and stay connected with blazing fast 1GB WiFi. The Diner Themed game room features a Marvel electronic pinball machine, pool table, and Wii. Pool heat is optional, hot tub always free! Pets welcome. King Master. Book your luxury getaway today!

4.97 out of 5 average rating, 103 reviews

A private pool area is enclosed with black mesh fencing, creating a secure environment. The pool features a smooth surface and is accompanied by loungers for relaxation. A vibrant mural is painted on one wall, adding a colorful touch to the outdoor space.

Townhouse in Kissimmee

Making memories on vacation!

Your family will be close to everything when you stay at this centrally-located home at Storey Lake Resort! The property less than five miles from Disney World. The gated community offers two clubhouses with water slides, pools, bars, and lazy rivers, and all restaurants, grocery stores, and everything you will need during vacation is within a short, few mile radius! In addition, the home offers a stroller, wagon, pack and play, and space saver high chair for families traveling with children.

A private pool area is enclosed with a screened patio. The pool features a built-in spa and a spacious deck, providing ample space for relaxation. Comfortable seating options are arranged nearby, overlooking the water. The area is designed for leisure and comfort.

4.9 out of 5 average rating, 112 reviews

Luxurious Pool Villa, Minutes From Disney World

Enjoy the big private pool after a long day at the themes park with family. Sun bath in a spacious pool deck all day or get a back massage by our spa. The villa had a gentle light system combined with the main cold color tone to create a feeling of comfort and relaxation. Your kids will love the Mickey twin beds and the game room very much. Our villa located within 5-15minutes of majors shopping center/outlets, restaurants, bars, water park, and themes park. We had everything, just missing you!

4.95 out of 5 average rating, 167 reviews

The image captures a beautiful aerial view of a community near a tranquil body of water at sunset. The surrounding landscape features lush greenery and well-maintained townhouses with a striking view of the water reflecting the colorful sky.

Townhouse in Kissimmee

Luxury 5BR free heat private pool Disney Universal

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

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 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

4.87 out of 5 average rating, 570 reviews

A large wooden dining table is surrounded by eight wooden chairs, set against a backdrop of stone-like walls with arched windows. A metal chandelier hangs overhead, while a decorative knight statue stands in the corner, adding character to the atmospheric space.

Villa in Kissimmee

Magical 5-Bedroom Villa Near Universal's Wizarding

Ensure an enchanted holiday in Orlando. Inspired by everyone’s favorite castle, this magical home provides an immersive experience with 5 bedrooms, common room with large screen TV with Netflix & Nintendo Switch, dining hall, fully equipped kitchen, swimming pool, patio with grill and laundry room. Located in a quiet residential community, 10 miles to the Wizarding World of Harry Potter, 6 miles to Disney, 5 miles from Celebration, 4 miles from Old Town and 18 miles from downtown Orlando.

Townhouse in Citrus Ridge

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, 135 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 private pool area is surrounded by a screened enclosure, featuring a jacuzzi spa and lounge chairs. The pool is inviting, with light blue water reflecting the sky's pink and purple hues. A serene lake is visible beyond the pool, adding to the tranquil setting.

4.91 out of 5 average rating, 255 reviews

House by the Mouse: Something for Everyone!

Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!

A private screened-in pool area features a spacious pool and spa, with a view of a serene lake at sunset. Comfortable lounge chairs are positioned around the pool, and a peaceful nature reserve is visible beyond the water.

4.99 out of 5 average rating, 131 reviews

Spectacular Lake View - Game Room- Close to Disney

Our home has all the features to comfortably provide your family with the amenities while on vacation! A kitchen ready for your cooking needs, a pool and spa(heating fee required), a Game/Media Room, and TVs throughout the house. The resort offers many amenities, including tennis courts, a sand volleyball court, walking trails, bike rentals, a huge pool, a poolside Tiki bar, a fitness center, a mini-golf, and so much more! Just a short walk away.

4.92 out of 5 average rating, 142 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!

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.

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, 5 reviews

6BR 3.5BA Family Vacation Home

4.57 out of 5 average rating, 67 reviews

5 Bd/5Ba Game Room! Paradise Palms (2954 BP)

5 out of 5 average rating, 4 reviews

New! Epic Solara Playhouse | Custom Bunks + Slides

4.89 out of 5 average rating, 47 reviews

4 BR/2Master Private Pool & Spa

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

4.61 out of 5 average rating, 18 reviews

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

4.83 out of 5 average rating, 18 reviews

Epic 12BR Disney-Theme Lakefront Villa | Sleeps 30

5 out of 5 average rating, 3 reviews

4bd house | Resort | private pool | sleeps 12

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 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.

4.82 out of 5 average rating, 11 reviews

Beach Resort with pool tiki bar near Disney World

Family friendly vacation rentals in Kissimmee

5 out of 5 average rating, 4 reviews

Game Room|Movie Room|Free Pool Heat&BBQ|Sleeps 23

5 out of 5 average rating, 8 reviews

The Disney House • Immersive Rooms • Gaming Lounge

A children's bedroom features a vibrant underwater theme, with blue walls and colorful murals depicting marine life. Bedding includes a twin-over-twin boat bunk bed and a separate twin bed. Decorative elements like shells and a net create a playful atmosphere, while curtain-filtered light adds a soft glow.

5 out of 5 average rating, 139 reviews

All 5 star stay with Waterpark, GameRm, Ariel Buzz

4.91 out of 5 average rating, 154 reviews

Magical Pool Villa-close to Disney Game/movie Room

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.

4.92 out of 5 average rating, 84 reviews

Dazzling 9 BR+Brand New MARIO KART @ Champion Gate

An inviting pool area features a screened enclosure that allows natural light while providing a sense of privacy. To the right, a cinema room showcases comfortable seating and a large screen, surrounded by colorful Mario-themed decor, creating a playful ambiance perfect for family entertainment.

4.89 out of 5 average rating, 65 reviews

2362 SW 6BD - Amazing Sunny Pool - Near 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.

4.86 out of 5 average rating, 139 reviews

Resort Home 3.5 miles to Disney with home theater