
Family-friendly vacation rentals in Kissimmee
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Kissimmee

Total vacation rentals
Explore 5,830 vacation rentals in Kissimmee

Nightly prices starting at
Kissimmee vacation rentals start at G$6,275 GYD per night before taxes and fees

Verified guest reviews
Over 251,460 verified reviews to help you choose

Pet-friendly vacation rentals
Find 1,020 rentals that welcome pets

Vacation rentals with a pool
5,450 properties feature pools

Rentals with dedicated workspaces
3,340 properties have a dedicated workspace

Wi-Fi availability
5,800 of Kissimmee vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kissimmee rentals

4.7 Average rating
Kissimmee stays receive an average rating of 4.7 out of 5 from guests
Top-rated family-friendly rentals in Kissimmee
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Pool Spa + Outdoor Entertainment | Golf Retreat
Escape to a one-of-a-kind golf retreat in Davenport, where resort-style outdoor living meets family-friendly entertainment. Spend your days relaxing by the private pool & spa, enjoying movies on the outdoor TV, and challenging the family in the Super Mario game room, all just minutes from Disney Whether you're planning a family vacation, golf getaway, or long weekend with friends, this beautifully renovated 4-bedroom home was designed for connection, comfort, and unforgettable Florida memories.
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Dazzling 9 BR+Brand New MARIO KART @ Champion Gate
Bring the whole family to this great home with lots of room for fun. You will love our Peter Pan- themed bedroom; custom Mario-themed game room with commercial quality games, private pool and spa with a great outdoor dining area. Only a short walk to the resort pools, lazy river, restaurant, Tiki bar and much more. Located just 15 minutes from Disney World and 30 Minutes from Both Universal and Sea World, Close enough to the attractions to get there quickly, far enough away to enjoy family time.
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New! Epic Dream House with Pool
Enjoy epic opening rates! Make some memories at this uniquefamily-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 away from Disney's exit & parks.
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Game Room|Movie Room|Free Pool Heat&BBQ|Sleeps 23
Step into this fully renovated ultimate Disney vacation home, designed to impress. All-new furniture and stylish finishes make it one of the most sought-after stays in the area. Featuring 6 king bedrooms plus 3 fun bunk-bed rooms, it’s perfect for large groups. Enjoy a fully immersive movie theater, a Hotel Transylvania–themed game room with arcade games and Xbox, PlayStation, Nintendo Switch, and Wii. Relax by the Lakeview pool with Pool Volleyball and Basketball Hoop. Free Pool Heat & BBQ.
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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.
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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!
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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!
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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.
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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.
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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!
KitchenIndoor spacesHospitality

Lux Disney Villa | Pool, Theater/games | Sleeps 22
Epic 10-bedroom themed luxury villa near Disney — sleeps 22 — with private pool & hot tub, movie theater with reclining seats, and a Marvel/LEGO arcade featuring racing simulators, air hockey, foosball & pinball. Includes elegant king suites and magical kids’ rooms (Toy Story, Star Wars, Minions, Beauty & the Beast). Perfect for multi-family getaways — just 20 minutes from Magic Kingdom.
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Disney Theme Rooms | Private Pool | Storey Lake
Welcome to your dream vacation at Storey Lake, one of the most loved resorts by travelers visiting Orlando. This beautifully designed 4-bedroom, 3-bath townhome was created to bring comfort, fun, and unforgettable memories all in one place, just minutes from Disney and the area’s top attractions.
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Popular amenities for Kissimmee family-friendly rentals
Family-friendly home rentals with a pool

Montego Bay Retreat | 15 Min to Disney
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Enchanted Windsor Estate by Vaya
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5BR Pool Villa • Themed Kids Rooms • 7 Mi Disney
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Brand New 12br/33 ppl-Pool/Arcade/Theatre
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Your Dream Vacation—Disney Magic Brought to You!
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Themed Villa:10 min to Disney: Pool, Gameroom, BBQ
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Brand New - 12br - Sleeps 34 - Theatre/Arcade/Pool
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Clubhouse Birdie: Resort Home near Disney
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Family-friendly home rentals with air conditioning

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

Luxury 7BR Orlando Villa | Pool, Spa & Game Room
FamilyIndoor spacesHospitality

Mario Arcade • Star Wars • Pool • 10 Mi Disney
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Orlando Dream Escape | Private Pool | Disney
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Star Wars & Wizard Themed XL Pool Home Near Disney
KitchenFamilyCondition

7839 6BD Beautiful Family Home in Reunion Resort
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6 miles from Disney ! Private pool ! 4 bedrooms
LocationHospitalityCleanliness

Mario Loft+Slide·Sleeps 26·Disney & Epic·Free Pool
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Family-friendly home rentals with Wifi

Family Paradise · 5BR/5BA Pool · Near Disney
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Themed 8BR retreat pool hot tub game room
FamilyIndoor spacesSleep quality

Magical Hideaway - 15 min to Disney - Storey Lake
FamilyKitchenNearby

Spacious 22-Guest Retreat in Four Corners
FamilyIndoor spacesPool

Magic House- Pool - Near Disney 14+
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Lakeview Villa w Spider~Star Wars Themed, Games!
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Magical Florida Stay | Pool & Harry Potter
FamilyIndoor spacesAccuracy

Ultra-themed family stay near Disney
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When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$33,047 GYD | G$34,720 GYD | G$36,812 GYD | G$37,648 GYD | G$32,419 GYD | G$33,465 GYD | G$33,047 GYD | G$29,073 GYD | G$26,145 GYD | G$27,400 GYD | G$30,746 GYD | G$36,812 GYD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
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- Family-friendly rentals Osceola County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- SeaWorld Orlando
- Disney Springs
- Universal Orlando Resort
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Universal's Volcano Bay
- Epcot
- Camping World Stadium
- Kia Center
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Tinker Field
- Old Town
- LEGOLAND Florida Resort
- ESPN Wide World of Sports
- Disney's Hollywood Studios
- ChampionsGate Golf Club
- ICON Park
- Aquatica







