Family-friendly holiday rentals in Kissimmee

4.97 out of 5 average rating, 153 reviews

The living area features a modern sectional sofa adorned with decorative pillows. A sleek coffee table is positioned on a patterned rug, while large sliding doors lead to a balcony, enhancing natural light. An adjacent dining area with stylish chairs is visible in the background.

Flat in Kissimmee

3121-402 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Townhouse in Four Corners

4.96 out of 5 average rating, 162 reviews

Near Disney/Baby Friendly/Water Park/Mini-Golf/Gym

Welcome to your stylish, themed vacation home in one of the most popular resort communities in the Four Corners/Championsgate area just 15 minutes away from Disney World and close to other local theme parks. The home is crafted with love for your enjoyment & comfort. This beautiful townhome has 3 bedrooms, 2.5 bathrooms, all new furniture, and super fast 1 Gbps internet speed. You will have free access to a large beach-entry pool, kids water park, beach volleyball, mini-golf, arcade, and gym.

An aerial view of the community water park features vibrant water slides and a children's water play area. Lounge chairs are arranged around the expansive pool, surrounded by lush greenery. Additional seating is provided near the water slides, creating an inviting space for relaxation and fun.

4.85 out of 5 average rating, 194 reviews

Heated Waterpark 10 mins to Disney in Windsor Hill

Welcome to Windsor Hills' Gated Vacation Community! Perfect for an adventurous family vacation or a relaxing getaway in the sun. I am excited to host your stay. Your unit is located on the 3rd floor. Get a quick exercise and hike up (39 stairs) to the front door or catch a break and use the elevator located on the ground level. Once inside, enjoy the newly remodeled 2Bdr, 2Bth condo, fully equipped to accommodate your stay. We are a PET and SMOKE-FREE property. Additional cleaning fee applied.

Home in Championsgate Village

The game room features a vibrant blacklight theme with neon accents. There are various arcade games, including a basketball game and air hockey table. The floor is decorated with playful, glowing images. This space is designed for family entertainment.

4.97 out of 5 average rating, 105 reviews

Magical Family Fun House Near Disney Luxury Villa

Experience the Magic of Disney in our Luxury Villa! BBQ Included! Tesla / EV Charging Station! Free Pool Heat! Our private 8 bedroom, 5 bathroom one of a kind pool home is meticulously clean & newly renovated. Newly remodeled kitchen and themed rooms, and richly-appointed spaces include large gathering areas, a bright, professional-grade kitchen, spectacular dining room, 2 walk-out master suites, a home theater & Tesla / EV Charging Station! Sparkling pool and spa. Only 15 miles from Disney

The outdoor living space features a cozy seating area surrounding a fire pit and a large dining table. A private swimming pool is illuminated in blue, with sun loungers lining the edge. The backyard is framed by palm trees, creating a tropical ambiance at dusk.

5 out of 5 average rating, 110 reviews

8 BR Villa, Private Pool, Theater, Min to Disney!

Big and Beautiful Themed Vacation Villa in premium gated Encore Resort. Spacious main floor for entertaining large groups - bring the family and friends! Enjoy the included resort amenities a minute's walk from the front door. Or, relax around your private pool and custom summer kitchen. Enjoy big-screen movies and sound in the theater in premium loungers, and play classic arcade games! 10-15 min from Disney, one of the closest villa resorts. Tons of shopping and dining nearby!

4.98 out of 5 average rating, 119 reviews

The image showcases a vibrant collage of the villa's features. The top left displays a colorful Encanto-themed bedroom with a playful bed. The top right features the modern living area with large windows and comfortable seating. The bottom left presents a private pool area, and the bottom right highlights a Mario-themed game room with arcade games.

Villa in Davenport

5BR Family Vacation Villa w/Free Pool Heat

Professional Hosts & Guest Favorite Home! Immaculate and well equipped Stargazer Villas vacation home at Windsor Island Resort now featuring Pickleball Court! This central Florida villa has heated pool included for your family to relax in after a busy day at the parks. Family friendly, featuring Star Wars, Harry Potter, & Encanto themed bedrooms, and a new Mario World game room! Stargazer Villas provides the perfect place to create unforgettable memories with your family.

A private pool area is enclosed by a screened patio, featuring a hot tub and space for lounging. The vibrant colors of the themed rooms are visible, showcasing unique decor and playful designs that appeal to families. Soft lighting highlights the inviting atmosphere throughout the home.

4.97 out of 5 average rating, 109 reviews

Magical 2 themed pool villa near “Disney”

Looking for stay away from the crowd but yet close to Disney ? This private pool themed home is perfect to complete your Dream Disney family vacation you always wanted. 15 miles /Magic kingdom -13 miles from Disney springs -15 miles from Epcot center -25 miles / 30 Universal Studios Make your stay Magical with our custom made themed rooms Star Wars play area and kitchen Romantic master Arabian night Avatar pandora Moana bedroom Just less than 2 miles from I4 hw

The collage showcases various areas of the lakeside home. Highlights include a private patio dining set, a resort-style pool, a comfortable living space with a dining table, and vibrant bedrooms featuring bunk beds and colorful decor. The picturesque lake view complements the outdoor spaces.

4.99 out of 5 average rating, 123 reviews

Lake View - 5 Miles to Disney!

This family friendly lakeside home is just five miles from your favorite theme parks and surrounded by a multitude of dining options, retail shopping, grocery stores and entertainment right outside the resort. This smart home offers high-speed internet/wifi and endless entertainment is just a voice command away. This home is located within the popular gated Encantada resort (staffed by security personnel 24 hours a day).

A themed bedroom designed with space motifs features a twin over twin bunk bed with a ladder for access. The walls are decorated with an illustrated planet scene, while a playful area rug adds color to the carpeted floor.

4.96 out of 5 average rating, 100 reviews

Virtual Reality | Simulators | Pool | Disney 20min

-20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charge on-site -Modern arcade: racing simulators, virtual reality, vintage games -3 king size suites with smart TVs; dedicated work space -2 pack-n-plays, highchair, strollers, wagon -Resort access: lazy river, splash pad, tiki bar, fitness center Arriving early in the day or leaving late? Ask about our half day add-on, if our calendar allows it.

A bright dining area with a large table set for meals overlooks a modern kitchen with amenities, including stainless steel appliances. A cozy bedroom features a bed adorned with black and red accents. An aerial view displays a vibrant resort pool area with water slides and lounging spaces.

4.92 out of 5 average rating, 360 reviews

Lazy River & Waterslides | Close to Disney | MT#2

Stay at our Mouse Townhouse #2 just minutes from Disney World & steps from restaurants & stores. Your reservation will give you access to the resort’s amenities for up to 6 people without an additional charge! ✪AMENITIES✪ FantasyWorld amenities include: -Lazy river -Water slides -Heated pools -Pool bar -Splash pad -Jacuzzi -Gym -Picnic & BBQ areas -Playground -Arcade -Batting cages -Sports courts & more

The image features a collage of vibrant themed bedrooms and a modern kitchen area. One room showcases a playful bunk bed against a backdrop reminiscent of a train station, while another has colorful Disney-themed décor. A spacious living area boasts light-colored furniture and a contemporary kitchen with stainless steel appliances.

4.97 out of 5 average rating, 103 reviews

3BD/3BA Themed House Near Disney

Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Villa in Championsgate Village

The image displays four distinct sections of Sky Lantern Manor. A vibrant kids' room with a whimsical design is featured. An indoor theater is shown with plush seating. An outdoor view reveals a private pool surrounded by a lanai. A game room is highlighted with colorful LED lighting.

4.96 out of 5 average rating, 105 reviews

Walk2Clubhouse|PickleBall|Pool Movies|GameRm|Theat

Sky Lantern Manor is your dream Disney escape! With 3 luxe Master Suites and 3 themed kids’ rooms (Rapunzel, Moana & Avengers), plus a Star Wars theater, outdoor movies, karaoke, and a game room with Xbox & arcades, the fun never stops! Splash at the Oasis Club’s lazy river & slides or dive into the Retreat Club’s new waterpark. Make every moment magical—your storybook adventure starts here!

Popular amenities for Kissimmee family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a 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, 120 reviews

Magical Hideaway - 15 min to Disney - Storey Lake

Superhost

A spacious living area is designed with light grey sofas and a glass coffee table, surrounded by greenery. Large windows with wooden blinds allow natural light to fill the room, while a ceiling fan enhances airflow. Soft, neutral tones create a relaxing atmosphere.

4.88 out of 5 average rating, 147 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

A charming view of the colorful condominiums reflects on a serene pond, framed by lush greenery and palm trees. The buildings are adorned with pastel hues of pink and blue, creating an inviting scene highlighted by a whimsical representation of Mickey Mouse.

4.95 out of 5 average rating, 292 reviews

Lovely ❤️ Beach style Apt near Disney & Universal

The spacious living area features comfortable seating arrangements, large windows, and a decorative area rug. The view leads to the private screened-in pool, providing a seamless indoor-outdoor experience. The room is illuminated by natural light and complemented by a modern ceiling fan.

4.99 out of 5 average rating, 137 reviews

Game & Theater Room, Castle Bunks, Pool & Spa

4.83 out of 5 average rating, 298 reviews

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!

4.94 out of 5 average rating, 150 reviews

A modern kitchen features crisp white cabinetry and sleek stainless-steel appliances. A spacious island is complemented by contemporary stools, with an organized countertop housing kitchen essentials. Gray tile backsplash adds a subtle texture, while natural light brightens the open layout.

Flat in Kissimmee

BRAND NEW 2BR Apt, 5mi to Disney - Storey Lake 401

4.91 out of 5 average rating, 238 reviews

House by the Mouse: Something for Everyone!

A vibrant game room features arcade machines themed around racing and superheroes. Adjacent, an outdoor space showcases a heated pool and hot tub, complemented by a fully equipped kitchen. The playful bedrooms are designed for immersive adventures inspired by Toy Story and Marvel.

4.99 out of 5 average rating, 134 reviews

Spectacular! Disney/Universal Themed Home

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 119 reviews

Sleeps 17 | Pool + Game Room | Only 400' to Resort

Superhost

A living room is furnished with a light grey sofa and a matching armchair, offering ample seating. Two coffee tables are positioned centrally on a patterned area rug. Artistic wall decor and warm lighting create a relaxed ambiance, with a dining area visible in the background.

4.69 out of 5 average rating, 173 reviews

Cozy Townhouse in Kissimmee, near Orlando!

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, 422 reviews

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

A game room features striking themed decor, with large flat-screen TVs and seating. The private pool area showcases a serene swimming pool surrounded by a screen enclosure, highlighted by comfortable lounge furniture. A cozy outdoor seating area is visible, offering a relaxing view.

4.95 out of 5 average rating, 156 reviews

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

4.95 out of 5 average rating, 104 reviews

A colorful bunk bed structure is featured, decorated in vibrant shades of yellow, blue, and orange. The mural backdrop depicts a jungle scene with a leopard and tropical plants, enhancing the playful atmosphere of the room. Spiral staircases offer access to the upper sleeping area.

Townhouse in Davenport

Themed Home + Near Disney + Arcade + King Bed + Water Park + Spa

A private movie theater features a 150-inch screen displaying a Disney image. Black walls and hardwood flooring create a modern atmosphere. Comfortable reclining seats with cup holders are arranged for a cinematic experience, ensuring a cozy and immersive viewing environment.

4.82 out of 5 average rating, 266 reviews

150 Inch 4K Movie Theater Pool & Spa sleeps 16

The exterior of the home displays a welcoming front porch, accompanied by a bright red door. Lush greenery lines the pathway, with neat shrubs creating a private ambiance. The light beige facade is complemented by a well-maintained lawn leading up to the entrance.

4.81 out of 5 average rating, 222 reviews

Disney’s Home Away From Home (5 miles from Disney)

Two lounge chairs are positioned beside a heated pool, overlooking a serene lake. A pink flamingo pool float rests nearby. The outdoor area includes a large umbrella for shade, creating a peaceful space for relaxation.

4.89 out of 5 average rating, 100 reviews

Dreamy Waterside Villa | Heated Pool & Near Disney

Family-friendly home rentals with a pool

A spacious indoor pool area is featured, enclosed by a screened lanai. A large dining table is shown, accommodating multiple guests with modern lighting above. Various themed bedrooms are visible, showcasing decorative walls and sleeping arrangements that appeal to families.

4.95 out of 5 average rating, 62 reviews

Brand New Luxury 8BR Villa in Windsor Island

5 out of 5 average rating, 25 reviews

7BR Disney Villa Escape Room+ Pool +Cinema+Game Rm

A game room is showcased with a blue pool table at the center. Colorful wall murals feature animated scenes, including boats and castles. Comfortable seating is arranged nearby, and multiple screens display entertainment options. The space is designed for both relaxation and fun.

4.87 out of 5 average rating, 85 reviews

EPIC 8BR Theme Villa ~ Sleeps 19 ~ Close to Disney

A colorful mural of a train enhances the living room's ambiance, complemented by a large sectional couch. Adjacent, a vibrant LEGO-themed bunk bed room features bright wall colors, inviting playful interactions. An underwater mural decorates another space, showcasing immersive coral designs, enhancing the magical atmosphere.

5 out of 5 average rating, 88 reviews

Kids Dream Themed Home! Near Disney/Universal ºoº

A gaming room is equipped with two gaming chairs and an air hockey table, featuring blue walls adorned with thematic artwork. A private outdoor area contains a small pool surrounded by a paved space and protective screening. A well-lit bedroom showcases a spacious bed with organized linens, framed by wooden elements.

5 out of 5 average rating, 10 reviews

2025 NEW 04BDR/Solara Resort /Near Disney

A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.

4.94 out of 5 average rating, 71 reviews

Paradise Suite

An outdoor living space features a private splash pool surrounded by a screened enclosure. A comfortable seating area with bright cushions is complemented by a dining table. An outdoor grill is visible, alongside a wall-mounted television, with greenery and a clear sky in the background.

5 out of 5 average rating, 36 reviews

Magic Place | 15 Min Disney Park |Heated Pool |BBQ