Family-friendly holiday rentals in Kissimmee

4.87 out of 5 average rating, 112 reviews

4m Disney, Pool Spa, Sundeck, Mini Golf• Games

Sun all day on our huge private sun deck, with shaded seating when you're ready to cool off! As the sun sets, enjoy the color-changing LED lighting around the pool and outdoor areas, creating the perfect atmosphere. Just 4 m from Disney, Mickey's Family Funhouse features a private pool, hot tub, brand-new mini golf, cornhole, game room with pool table, arcade, electronic pinball, darts, and a record player. Pet-friendly with a large fenced yard. Complimentary welcome snack basket included!

KitchenFamilyHospitality

5 out of 5 average rating, 137 reviews

Themed Disney Villa | Pool | Arcade | Resort ºoº

Stay in a luxury Disney-themed home just minutes from the parks. Perfect for large families and groups, this spacious retreat features a private heated pool and spa, outdoor kitchen with free propane, Mario Kart arcade game room, themed bedrooms, gourmet coffee, fast WiFi, smart TVs, and premium streaming. Enjoy full Windsor Island Resort access with a water park, lazy river, slides, and clubhouse. Loved by guests with over 100 5-star reviews. Let us give you a vacation within your vacation.

FamilyKitchenPool

4.9 out of 5 average rating, 173 reviews

Magical Pool Villa-close to Disney Game/movie Room

The magic starts the moment you walk through the door—and the memories will last a lifetime! ✨ Our themed vacation home features Mickey Mouse, Toy Story, Frozen, Star Wars and Minion rooms with motion-activated songs, UV artwork, and LED lighting. Enjoy a private pool with color-changing lights, BBQ area, sun loungers, and a fun-filled game room with air hockey and arcade games. Designed to delight kids and adults alike with immersive sights, sounds, and magical details throughout the home!

FamilyIndoor spacesHospitality

A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.

4.99 out of 5 average rating, 167 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

Spacious 4BR Home with a Private Heated Pool – 15 Minutes from Disney! Enjoy a large south-facing pool, Propane grill, Smart TVs with Disney+ in every room. Nintendo Switch in Living Room and an 85" screen with a PS5 in a temperature-controlled garage / game room. Fast WiFi, shuffleboard, pool table and plenty of board games. 🌴 Outdoor Fun Patio Seating for 14 + two lounge chairs. Propane Grill: $50 for length of stay Pool heat: $200 per stay (24-hour notice)

Indoor spacesKitchenAccuracy

A well-maintained exterior showcases a single-story house with a blue garage door and driveway, framed by a lush lawn and shaded trees. Inside, a bright living area is highlighted by modern decor and a large smart TV. A private screened pool is visible, surrounded by seating.

4.98 out of 5 average rating, 106 reviews

10 Min to Disney | Kings | Heated Pool | Games

✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!

Indoor spacesKitchenCheckout

A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.

4.99 out of 5 average rating, 254 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

FamilyKitchenOutdoor spaces

5 out of 5 average rating, 19 reviews

4BR Disney & Universal Themed Villa Reunion Resort

Welcome to our newly remodeled 4BR/4BA luxury villa in Reunion, designed for families and groups seeking comfort, style, and a magical Orlando escape. Enjoy brand-new furnishings, modern finishes, Toy Story and Mickey themed bedrooms, a spacious open living area with massage chair, and a fully equipped game room featuring air hockey, arcade basketball, and PlayStation. Relax in your private screened pool with optional heating after unforgettable park days.

Indoor spacesFamilyLocation

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

4.96 out of 5 average rating, 112 reviews

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

KitchenFamilyNearby

5 out of 5 average rating, 122 reviews

The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.

Home in Four Corners

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Stylish Design, Luxurious Comfort & Endless Entertainment, with a sprawling 2200 ft2 southwest facing pool deck & outdoor kitchen, no rear neighbors on a beautiful forest in the stunning 3.5 square mile Reunion Resort. You will have your own private pool with overflow spa, movie room, billiards - game room, 4 theme rooms: OUTER SPACE, MARVEL SUPERHEROES with a TUBE SLIDE, FROZEN II, HARRY POTTER CUPBOARD, PS5, within minutes to Disney.

FamilyKitchenAccuracy

5 out of 5 average rating, 12 reviews

Montego Bay Retreat | 15 Min to Disney

Enjoy a stylish stay in this newly renovated 3-bedroom, 2-bath home, perfect for families and groups of up to 9 guests. Located only 15 minutes (8 miles) from Disney and close to Orlando’s top attractions, restaurants, and shopping. Relax in modern, comfortable spaces after a fun day at the parks. Outdoor grill available for $30/day (gas included). The perfect mix of location, comfort, and convenience for your Florida vacation! ✨

FamilyIndoor spacesLocation

Superhost

5 out of 5 average rating, 4 reviews

Mario Arcade • Star Wars • Pool • 10 Mi Disney

The Orlando vacation home your family will remember long after the parks ✨ Sleeps Up to 18 Guests 🚶 5-Minute Walk to the Clubhouse, Lazy River & Fitness Center 🎮 Mario Arcade & Interactive Kids Loft 🏰 Star Wars & Candy Kingdom Bedrooms 🏊 Private Heated Pool & Spa 🎢 10 Miles to Disney • 14 Miles to Universal 👑 3 King Bedrooms • 2 Main Floor 🔑 Easy Self Check-In

FamilyIndoor spacesValue

4.92 out of 5 average rating, 127 reviews

Magical Disney Family Escape with Pool & Game Room

OpenAGetaway Properties invites you to experience an immersive, family-friendly getaway at Mickey House. *Newly remodeled villa *Private villa pool *Superhero-themed arcade room *Desirable Windsor Resort Neighborhood *5 minute walk to the full-service resort & clubhouse

FamilyIndoor spacesBreakfast

Popular amenities for Kissimmee family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Pool Spa + Outdoor Entertainment | Golf Retreat

FamilyIndoor spacesCondition

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.

4.96 out of 5 average rating, 164 reviews

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

Indoor spacesFamilyDecor

Superhost

4.85 out of 5 average rating, 154 reviews

No Airbnb fees!Themed Home Pool/Spa/Gameroom 21811

KitchenFamilyCleanliness

New and Unique Disney Airbnb!

Indoor spacesFamilyAmenities

4.99 out of 5 average rating, 148 reviews

A vibrant hallway is adorned with deep blue walls, featuring golden stars and a playful Mickey Mouse theme. A picture of Mickey Mouse in a wizard hat is displayed on the wall, complementing the themed decor. A stylish side table is positioned against the wall.

Villa in Four Corners

Mickey Fantasia Family Friendly w/accessibility

Indoor spacesFamilyNearby

4.99 out of 5 average rating, 158 reviews

Game & Theater Room, Castle Bunks, Pool & Spa

FamilyIndoor spacesParks

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, 176 reviews

Spectacular! Disney/Universal Themed Home

Indoor spacesFamilyHospitality

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.

4.92 out of 5 average rating, 273 reviews

House by the Mouse: Something for Everyone!

Indoor spacesFamilyBackyard

Family- and pet-friendly home rentals

The fenced pool area features a vibrant pink flamingo float resting in an unheated pool. Nearby, patio furniture accommodates outdoor dining and relaxation, while a grill is available for barbecues. The spacious kitchen can be seen through an open layout, enhancing connectivity.

4.91 out of 5 average rating, 277 reviews

Cozy House with Pool. Kissimmee/Orlando

KitchenFamilyAmenities

Superhost

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.

Home in Buenaventura Lakes

4.9 out of 5 average rating, 167 reviews

Villa Resort Club

Indoor spacesFamilySleep quality

The themed bedroom features twin beds, designed to resemble spaceships, with bold, illuminated accents. A wall mural depicts a starry sky, while nearby, a gaming machine displays a classic arcade setup, creating an immersive atmosphere for guests.

4.95 out of 5 average rating, 106 reviews

Amazing Friends 5BR+Private Pool+Lazy River

KitchenIndoor spacesNearby

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.

4.87 out of 5 average rating, 455 reviews

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

FamilyKitchenQuiet

4.99 out of 5 average rating, 100 reviews

A hot tub is situated on a patio with a view of a lake at sunset. The vibrant sky features hues of orange, pink, and purple, while a railing surrounds the space, enhancing the scenic atmosphere. The tranquil water reflects the colors of the sky.

Cottage in Kissimmee

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

Indoor spacesKitchenLayout

4.98 out of 5 average rating, 122 reviews

Villa in Davenport

Amazing Villa near DisneyWorld FREE heated-pool

Indoor spacesKitchenGetting around

An outdoor dining area features a large custom-built farmhouse table surrounded by seating options. Flower arrangements are placed on the table, and a blue pool is visible in the background. The space is sheltered with a screen enclosure, allowing for a spacious view of the yard.

4.95 out of 5 average rating, 205 reviews

*Plumeria Place* Minutes to Disney+Free Resort!

KitchenIndoor spacesOutdoor spaces

A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.

4.94 out of 5 average rating, 162 reviews

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Indoor spacesKitchenQuiet

Family-friendly home rentals with a pool

5 out of 5 average rating, 9 reviews

7 Bd/ 7 Ba/ Solara Resort (2327 Sr)

KitchenFamilyLocation

Luxury Disney Villa | Game Room | Free Pool Heat

FamilyAccuracyHospitality

Star Wars & Wizard Themed XL Pool Home Near Disney

FamilyKitchenNearby

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, 93 reviews

Dazzling 9 BR+Brand New MARIO KART @ Champion Gate

KitchenFamilyCheckout

4.95 out of 5 average rating, 39 reviews

New! Epic Dream House with Pool

FamilyIndoor spacesComfort

4.89 out of 5 average rating, 28 reviews

Spacious 9BR Family Retreat at Solara 87SA

FamilyKitchenAccuracy

4.89 out of 5 average rating, 18 reviews

7839 6BD Beautiful Family Home in Reunion Resort

FamilyIndoor spacesLocation