Family-friendly holiday rentals in Kissimmee

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

Unable to book this house? Don't worry! Feel free to check my profile for similar homes that might suit your needs WE HAVE 24/7 CUSTOMER SERVICE Disney is just a short 8-mile drive away Tired of visiting the parks every day? Step inside this beautiful thematic 2,169 sqft house with a private pool, spa, BBQ, Star Wars themed movie theater, and a Mario Kart game room complete with arcades, pool table and foosball table all designed for family enjoyment! Make your vacation truly unforgettable!

Private Pool Luxurious Modern Lake Home Disney

This astounding townhouse is brand new and furnished to a high standard. It’s the ideal retreat for an exquisite & up-scale family stay, located close to a wide variety of go-to attractions. This gated property at Paradise Palms can host up to 10 people. We believe it’s the ultimate location to experience the area and to start discovering what adventure awaits in Kissimmee. Get ready to get inspired! Very close to some fabulous sites. All in all, guaranteed enjoyment and relaxation.All day long

Stunning Disney Home w/Pool & Free Resort Access

Our property was featured in Travel Guide USA - 2025 Orlando Edition!! Welcome to our beautiful spacious home, featuring 3 king-sized bedrooms, 2 themed bedrooms, an entertainment loft and 4.5 bathrooms, which will comfortably accommodate three families. We are located in the upscale gated resort of Windsor at Westside with a 10,000 sq. ft. of state-of-the-art club house with a large pool, lazy river, water park, hot tub, gym, beach volleyball and basketball courts, restaurant & bar, arcade.

Disney Retreat | Huge Pool with Spa | 2 King beds

Don’t leave that Disney Magic at the parks - experience it by coming home to your spacious 5 BR with 2 King suites, 3.5 baths, and newly renovated design. The high ceilings and open floor plan make it perfect for family time, while the private backyard oasis, complete with a pool and spa (heating optional) and Tiki Bar, offers a great space for relaxation. The themed bedrooms, including Star Wars, Frozen, and Mickey & Minnie, add a fun and whimsical touch that’s perfect for guests of all ages.

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

"Guest favorite" - This home is in the top 5% of eligible listings based on ratings, reviews, and reliability. Comfort and Space in an Elegant home with a lot of amenities, 4Bed/3Bath. Private Movie Theater, Game Room, Pool and Themed Rooms. A well equipped Kitchen, Laundry, 3 parking spaces, WiFi, Smart TVs. Located at Crystal Cove Resort, a gated community, close to Disney. Few minutes to Walmart, Target, Sams Club, Publix, Outlets, Restaurants, Disney, Sea World, OCCC, EPIC and Universal.

Free Waterpark|Game Room|Near Dis!

Welcome to Playcation Paradise by Cosmic Vacations. This is your dream getaway in Windsor Hills Resort—just 3 miles from Disney World, 15 miles from Universal, and only 0.4 miles to Windsor Hills’ incredible amenities! Enjoy your private pool and spa, or have a blast in the custom game room with commercial-grade arcade games set to free play. Plus, you’ll have free access to Windsor Hills’ top-tier amenities, including a lagoon-style pool, water slides, and sports courts.

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!

Disney Themes Villa | Pool+Gameroom | Near Parks

Escape to Magical Magnolia Manor, a family oasis 10-15 mins from Disney! This unique home features incredible themed rooms (Harry Potter, Star Wars, Lion King) while adults unwind in two luxurious king en suites plus a private, heated pool with no rear neighbors. With 2 king suites and fun beds, for kids, it comfortably sleeps large families up to 8. Enjoy a game room, chef's kitchen, and a serene lanai. Perfect for creating unforgettable memories!

The Disney House • Immersive Rooms • Gaming Lounge

Welcome to our magical 3-bedroom getaway, newly decorated and thoughtfully designed to create an immersive Disney experience for the whole family! Step into beautifully themed bedrooms featuring Toy Story, Star Wars, & Beauty and the Beast, making every stay unforgettable. Also enjoy a Mario arcade room and Mickey decorations at the home. Perfect for families and Disney lovers! The Grill has an additional cost to rent for the reservation of $75.

3-103 Legacy Dunes, Heated Pool, Free Wifi/Parking

Two Bedrooms 1 Queen Sized Bed 2 Twin Sized Beds 1 Queen Sized Sofa Sleeper bed Sleeps up to 6 Guests Two Full Bathrooms Ground Floor, No Stairs to Climb Fully Equipped Kitchen Close to Shopping and Restaurants Screened Patio with Seating Washer and Dryer Heated Outdoor Swimming Pool Close to Disney Free Wi-Fi and Free Parking Game Room Playground Tennis, Pickleball, Basketball, Volleyball Gated Community

Epic Disney Villa • Hidden Arcade & Playroom!

Welcome to Your Magical Vacation Retreat! Step into a world of comfort, fun, and enchantment at our family-friendly, baby-friendly, pet-friendly, and magic-friendly six-bedroom villa—just 12 minutes from Walt Disney World! Whether you're here for the parks, relaxation, or making unforgettable memories, our spacious and newly renovated home offers something for everyone.

Perfect Disney Relaxation! Water Park, Lazy River!

Welcome to Perfect Disney Relaxation at the highly-rated Solterra Resort, with one of the best water parks in the area featuring a Water Slide, a Lazy River, Zero entry pools, and spas. This fully equipped and upgraded private pool home offers everything for a perfect vacation, including poolside dining.