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Family-friendly rentals near Old Town

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals near Old Town

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The master bedroom features a king-size bed adorned with plush pillows and a cozy blanket. Large sliding doors open to a private balcony with serene views. Stylish lamps illuminate the room, complemented by rich maroon and neutral tones on the walls.
Townhouse in Kissimmee
5 out of 5 average rating, 271 reviews

BOOK your Disney inspired Lakefront retreat NOW!

Begin and end your dream vacation in a place where modern comfort meets magical wonder! This one-of-a-kind retreat is sure to please the family looking for adventure in Orlando as well as couples in search of a relaxing, romantic getaway. Great location just minutes from Disney, Universal, SeaWorld, numerous restaurants, tourist attractions and easy access to major highways such as SR417 and I4. *FREE WIFI, Netflix & Disney+ included! *STROLLER, BABY GATE, HIGH CHAIR, PACKNPLAY, TODDLER BED

Top guest favourite
Townhouse in Kissimmee
4.96 out of 5 average rating, 130 reviews

3BR w/spa - Resort w/Pool, Waterslides - Disney

✨ Close to Disney, Universal, SeaWorld ✨ Fully stocked kitchen, Free parking, Free WiFi ✨ Access to all resort’s amenities: Heated Pool, Dual Water Slides, Clubhouse, Restaurant, Bar, Gym, Arcades, & more ✨ No Resort Fee ✨ Private hot tub ✨ Steps to Old Town for dining, shopping, live music, & entertainment, and to Fun Spot America Family Rides for rollercoasters, arcades & more! ✨ Perfect for you to relax after a day of magic at Disney or explore Orlando’s best attractions ✨ Gated community

Top guest favourite
Aerial view of the resort displaying a large, inviting swimming pool surrounded by palm trees and lounge chairs. Water slides are visible next to the pool area. The clubhouse is nearby, with additional greenery and a water feature enhancing the landscape.
Townhouse in Kissimmee
4.97 out of 5 average rating, 271 reviews

4M Disney! Private spa, Wi-Fi, Coffee/Tea

Welcome to our personal vacation home! Spacious townhouse located in Regal Oaks Resort! Coffee, Nespresso, tea, free Wi-Fi! It's close to the theme parks and everything that Orlando has to offer! Come relax in your own private spa after a long day at the parks, or enjoy the resort water slides, heated pool, pool side games and tiki bar with food and beverage, arcade games in the Clubhouse and more. If you're up for more fun, walk to Old Town next door! Our place is BABY and KID FRIENDLY!

Guest favourite
An aerial view of a uniquely shaped swimming pool is seen, surrounded by lush palm trees and blue umbrellas. The pool is designed with a gradual slope and steps, providing a relaxing environment for guests.
Townhouse in Kissimmee
4.85 out of 5 average rating, 325 reviews

*Private jacuzzi!* Spacious home! Next to parks!

Soak in a hot tub under the stars at this comfortable home! This home sits in the quiet and well located resort of Regal Oaks. The place offers all resort style amenities with the comfort of a home away from home to enjoy and relax. Enjoy your vacation at the outdoor private spa, have a nice homemade meal in the outdoor terrace, or let others take care of you in the resort restaurant in front of the pool, while kids enjoy the slides and resort activities. Disney parks are 10 min away!

Top guest favourite
A resort pool area is surrounded by palm trees and sunshine, featuring lounge chairs under white umbrellas. A paved deck encircles the pool, creating a relaxing atmosphere for guests. A blue slide can be seen in the background, enhancing the recreational space.
Townhouse in Kissimmee
4.88 out of 5 average rating, 144 reviews

Entire townhouse, Resort style, 5 miles to Disney!

Feel right at home in our outstanding location JUST 5 MILES FROM DISNEY! Exceptional 2 bed/2.5 bath townhome features premium one King bed, 2 twin beds and a queen size sofa bed with fully equipped kitchen, washing machine, smart TVs, a private patio, Jacuzzi and lake view. Contemporary furnishings, luxury feel. Located in gated resort with clubhouse, beautiful pool, water slide, gym, tennis court and more. Within 10 minutes drive to a variety of restaurants, shops, Fun Spot and more.

Guest favourite
The bedroom features two full beds, each with themed bedding showcasing Mickey and Minnie Mouse. A red nightstand is positioned between the beds, and playful accents include plush toys. Light filters in through the window, complemented by white walls with polka dot accents.
Townhouse in Kissimmee
4.93 out of 5 average rating, 115 reviews

1Private Heated HotTub Relaxing Resort near Disney

A cozy decorated and comfortable townhome with private jacuzzi. Minutes away from the magic, 15 mins to SeaWorld, 20 mins to Universal and walking distance to Old Town fun. This townhome was newly listed in February 2023, managed by an experienced co-host with 300+ nearly 5-star reviews. It is our top priority to make sure you have a smooth stay no matter one day, one week or one month. Our property is fully cleaned after each check out. You can book with us with confidence!

Top guest favourite
Townhouse in Kissimmee
4.98 out of 5 average rating, 106 reviews

Clean, stylish retreat • Resort pool • Near Disney

Welcome to Villa Marquesa (private mgmt), a revamped 4-bed, 3.5-bath townhome made for families. After a fun-filled day at the parks, come home to a clean, comfy space where everyone can relax—watch a movie, cook a meal, or unwind by the resort-style pool (no resort fee). Sleeps 6 adults & 4 kids, with lake views from the screened lanai. Just 3 miles to Disney, 20 mins to Universal, steps from Old Town. Includes WiFi, Disney+, Netflix. Your family retreat starts here!!

Top guest favourite
Townhouse in Kissimmee
4.95 out of 5 average rating, 119 reviews

4mi to Disney, Summer Oasis w/ Pool & Jacuzzi

Escape to our cozy Orlando townhouse where adventure meets nature! Relax in your private backyard jacuzzi with sunset views over lush greenery, sometimes even spotting deer. 🦌 Located in a resort-style gated community with a heated pool and water slides, it’s the perfect mix of fun and relaxation.🏖️ Minutes from theme parks, shopping, dining, and nightlife. In Regal Oaks Resort, a short walk to Old Town! – 10 min to Disney – 18 min to SeaWorld – 20 min to Universal

Guest favourite
The image presents a four-part collage, featuring a bright bedroom with two spacious beds adorned with decorative pillows, a private hot tub surrounded by nature, a resort pool with loungers and a water slide, and a clubhouse area with expansive outdoor seating and vibrant landscaping.
Townhouse in Kissimmee
4.83 out of 5 average rating, 157 reviews

♥Disney-3 Miles from ♥Private HotTub ♥to Top♥ Resort

Our gated-community townhouse offers a resort feeling with all the comforts of home, peaceful & quiet, yet central to Disney, Old Town, and all major attractions. After an exciting family day, relax in your private patio hot tub and enjoy the nature, or soak up some sun poolside at the resort. Fun for adults and kids of all ages! Also enjoy the resort tennis courts, pool table, gym, restaurant, and poolside snack bar! NO RESORT FEES! FREE PARKING!

Top guest favourite
A private screened hot tub is featured in the foreground, surrounded by an inviting outdoor seating area with a table and chairs. Lush tropical plants enhance the atmosphere, while a large mirror reflects the vibrant orange wall and soft natural light from the spacious windows.
Townhouse in Kissimmee
4.95 out of 5 average rating, 237 reviews

2 BR Harmony House at Regal Oaks Resort

Come get away to our modern, super-clean, self-contained garden oasis town house in the Regal Oaks Resort - close to grocery stores and take out food - minutes walk from Old Town Kissimmee and a short drive from Disney's ESPN - World of Sports and Town Center Celebration. We are 15 minutes drive from Epic - Universal and Disney parks. Our private screened in hot tub is the perfect place to relax in the Florida sun or under our sun shade.

Top guest favourite
A yellow cottage is featured, with a welcoming entrance that includes a set of wooden steps leading to a covered porch. White railings frame the porch, while a ceiling fan hangs above. Lush greenery and flowering plants are positioned near the entrance, enhancing the overall charm.
Cottage in Kissimmee
4.95 out of 5 average rating, 530 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.

Guest favourite
A sunlit community pool area showcases a large pool surrounded by palm trees and lounge chairs. The clubhouse, with expansive windows and a vibrant facade, stands in the background. Colorful slides and umbrellas add to the inviting recreational atmosphere.
Home in Kissimmee
4.95 out of 5 average rating, 102 reviews

A Colorful Splash | Magical Disney Lakeside Resort

Unwind in our 2-story, Colorful Retreat, Minutes from Disney's Magic! NEWLY Renovated, Covered Patio, and Woodland Seclusion. Your Dream Vacation Awaits - Modern Comforts, Magical Wonders. FREE WIFI, and Jacuzzi! Discover a 1500 sq ft Townhouse, a Gateway to Luxury and Adventure. Your Fairy-Tale Begins Here!

Popular amenities for family-friendly rentals near Old Town

Quick stats about family-friendly rentals near Old Town

  • Total holiday rentals

    Explore 270 holiday rentals in Old Town

  • Nightly prices starting at

    Old Town holiday rentals start at £53 per night before taxes and fees

  • Verified guest reviews

    Over 23,350 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    250 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wifi availability

    270 of Old Town holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Old Town rentals

  • 4.7 Average rating

    Old Town stays receive an average rating of 4.7 out of 5 from guests

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee
  6. Old Town
  7. Family-friendly rentals