Family-friendly holiday rentals in Kissimmee

Private Backyard/Top Rated Resort/3 mi to Disney

Looking for privacy on your vacation? This 3-bedroom townhouse in Regal Oaks offers a king bed with ensuite bath in the primary bedroom, a queen bed in the second, and twin beds in the third. There’s a second full bath and half bath on the main level. The open-concept main floor features a fully equipped kitchen, breakfast bar, and living area with a fold-out sofa, accommodating up to 8 guests. Enjoy a private lanai with a hot tub, dining area, loungers, and fiber-optic WiFi for all your needs.

Magical Adv 5 Star Villa Movie Room Arcade Pool an

Experience enchantment at Magical Adventure Villa, a top-rated 6-bedroom and 4-bath home for 12 guests. Conveniently located in Windsor Hills Resort, just 2 miles from Disney World®. Experience the highly acclaimed getaway that has garnered rave reviews. Enjoy a private pool, home theater, and a thrilling arcade. Unleash your inner Jedi at the state-of-the-art Star Wars gaming center with a movie theater, Xbox One, Nintendo Switch, and immersive 3D designs. *Work vehicles are not permitted to b

Encanto at Emerald Island-Pool House by Disney

POOL HEATER OPTION!! Make some memories at this unique and family-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles aways from Disney's exit & parks!

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.

Mickey's Mansion Luxury Themed Pool Home, Arcade, Theater

Welcome to Mickey's Mansion, your magical vacation rental in the heart of Champions Gate! 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! Pool heat & the 1st tank of propane for the BBQ is included. Booking with us includes full access to the Champions Gate Clubhouse & Oasis Resort

Amazing New Villa! Well Maintained! Fun for all!

My name is Mike and I’m the proud owner of Castle Pines Cove. This 6 bedroom Villa was completed and furnished in the spring of 2022. I love this house. I spend a lot of time here with my family. I have a 5 and 8 year-old and this is their favorite place to visit. It’s extremely important to me to ensure not only the house is clean but also maintained to the highest standard. Just like with my family, I want everyone who stays here to feel the exact same love for the house that we do.

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*

DisneyTheme Storey Lake Resort Pool/Spa/BBQ6Br/5b

Brand New Home! Wonderful house, located in the best spot of STOREY LAKE RESORT! Fully Furnished! Swimming pool and Spa! Free Access to Clubhouse (Gated Community) DISNEY/STAR WARS/FROZEN/POKEMON THEMED! Modern Floorplan! 1 bedroom Downstairs 5 Bedroom plus game room Upstairs Community: Storey Lake Resort (THE BEST LOCATION IN TOWN). -6 Bedroom/5 Bathroom/Sleeps 13 -Target/ Sam's Club ( 3 miles ) -Disney (5 miles) Sea World (7 miles) Universal (10 miles) -Convention Center (9 miles)

Themed 6BR | Game Room | Private Pool & Spa w/View

Stay at Time-Out Corner, Too @ Windsor Hills for an incredible vacation filled! Enjoy a game room, themed bedrooms, a private pool and spa w/gorgeous sunset view, and more. Plus, free access to the resort’s clubhouse and water park. Just 5 mins from Disney! 🎮Toy Story Game Room. Play Air Hockey, Skee-Ball, Arcades, Xbox, PlayStation, and more. 🏊 Private West-Facing Heated Pool/Spa. 🛏️ 6 BR & 4 BA. 3 Themed Bedrooms (UP, Alice in Wonderland, and Orange Bird). Sleeps 14.

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.

Best Location! Disney-Universal-Kid gear-Lakeview

Enjoy your stay and make family memories! ✦Prime Location-Minutes to Disney & Orlando attractions ✦Private heated splash pool looks on the lake ✦Open and spacious floor plan for the whole family ✦Sought-after resort community of Storey Lake ✦FUN themed Mickey and Marvel bedrooms ✦Highchair, booster and pack-n-play available ✦Lake view- no rear neighbors Many nearby golf courses- Please ask us any of your golf course questions!

Disney Villa w/ Priv Pool & Lake View-12 Mi Parks

We’re a husband & wife duo thrilled to welcome you! ✨ Our home features Moana, Mickey & Harry Potter–themed rooms, a private pool, and hidden Disney surprises throughout. Minutes from parks, dining & shops. Ask about free early check-in & late check-out—make magical memories