Family-friendly rentals near Old Town Kissimmee

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Top-rated family-friendly rentals near Old Town Kissimmee

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Guest favourite

The resort-style pool is surrounded by palm trees and lounge chairs with blue umbrellas. A spacious deck features seating areas overlooking the water. The expansive pool area is designed with different sections for relaxation and recreation, enhancing the appeal of the outdoor environment.

Townhouse in Kissimmee

4.94 out of 5 average rating, 158 reviews

Resort Style Vacation Townhouse, 10 Mins to Disney

Located only 10 minutes from DISNEY, this RESORT STYLE townhouse provides the perfect home for your vacation! Luxury 2 bedroom, 2.5 bathroom with 1 King-sized bed, and 2 double beds. Charming conservation view with screened patio featuring private Jacuzzi. Regal Oaks at Old Town community has world class Clubhouse: large pool, water slide, indoor gym, tennis court, restaurant, bar, convenience store, and 24HR security with gates. Walking distance to Old Town and Fun Spot, restaurants and stores.

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, 254 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

Guest favourite

The open living area features a contemporary design with a curved sofa in neutral tones, two blue accent chairs, and a glass coffee table. A textured area rug complements the decor. Large windows allow natural light to illuminate the space, enhancing the connection to the outdoors.

Townhouse in Kissimmee

4.88 out of 5 average rating, 208 reviews

Adorable 2 bdr lakefront w/jacuzzi 5 min *Disney*

This townhouse provides an open main living space that allows you to connect the dining and a fully equipped kitchen. The house can accommodate up to 6 guests, divided into one luxe king en-suite, and a design theme two full en-suite. After a long day at the parks with a beautiful lakefront view, relax in your private spa. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant, and only 5 min from Disney and golfing area Free Parking Close to lakes, camping, beach, vineyards, farms

Guest favourite

A private screened patio features a jacuzzi with colorful lights, creating a calm ambiance. Two outdoor chairs are positioned nearby, providing a comfortable spot to relax. Soft lighting illuminates the area against a backdrop of lush greenery and a clear evening sky.

Townhouse in Kissimmee

4.9 out of 5 average rating, 201 reviews

AMAZING vacation house .Mins to Disney Regal oasks

Beautiful luxury Resort style Vacation house! Big screened patio with private jacuzzi . Excellent Location! 3miles from Disney resort, just 10 minutes form Disney, universal, sea world , 0.1 mile walking distance to Old Town fun. numerous restaurants ,tourist attractions and easy access to major highways such as SR 417 and 14 .Uber /Lyft stop ,lynx bus to Disney . Guests also have full access to all resort amenities and activities ! *FREE- WiFi and 3 Cable TV for each rooms 52” living room

Superhost

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

4.84 out of 5 average rating, 290 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!

Superhost

The dining area features a large wooden table set for dinner, with stylish chairs surrounding it. A cozy seating space is visible in the background, accompanied by a large window allowing natural light to enhance the warm tones of the decor.

Townhouse in Kissimmee

4.89 out of 5 average rating, 266 reviews

RUSTY'S DEN House with Hot Tub 3 miles from Disney

This spacious and recently updated townhouse is located in a beautiful private and gated resort, which offers guests their own private hot tub, a shared pool with pool bar, gym, and a convenience store. No resort or parking fees! Guests have a private hot tub and enjoy neutral colors in the interior design that lend a gentle aesthetic, while modern industrial accents add a charm and character. Located just 3 miles from Disney & 11 miles to Universal Studios!

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

4.84 out of 5 average rating, 129 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!

Superhost

A modern dining area features a long white table set for meals, accompanied by comfortable gray chairs. The open kitchen area showcases sleek appliances and cabinetry. Natural light floods the space, highlighting the contemporary design elements and decorative wall accents.

Townhouse in Kissimmee

4.76 out of 5 average rating, 163 reviews

#2647 Resort 3/3 Modern Home Priv Spa Pool Disney

LUXURIOUS and MODERN VILLA! NO RESORT FEE! HARDWOOD FLOOR! PRIVATE JACUZZI! FREE WiFi! FREE COFFEE! TVs IN ALL BEDROOMS & LIVING ROOM! 3 miles from Disney Entrance! Walk to famous Old Town/Fun Spot/Stores, Uber/Lyft stop, Lynx bus to Disney; 15 mins to SeaWorld, 20 mins to Universal. 3 BD 2.5 BA, wood cabinets, granite counter, Bosch stainless appliances; Pool, water slides, fitness, tennis, restaurant, bar, mini store, and 24-hour security guard

Guest favourite

The image showcases the vibrant swimming pool area of the resort, featuring a water slide and surrounded by palm trees. The kitchen area displays modern appliances, including a stove and granite countertops. A dining table is set for six, and a comfortable living space is visible with seating for relaxation.

Townhouse in Kissimmee

4.94 out of 5 average rating, 308 reviews

Disney/Universal Home Away from Home!

At the Regal Oaks Resort you will find a fantastic pool, water slides, games room, gym, sauna, onsite dining at the clubhouse and much more! We DO NOT have any additional resort fees, the price you pay is final, it includes everything and all free amenities at our resort! Nature's little get away. Our home is located in a very private section of the resort backing onto a large conservation area. Nothing but green life and palm trees!

Top guest favourite

An aerial view of the resort reveals a scenic layout surrounding a sparkling blue pool and vibrant water slides. Palm trees line the poolside area, where lounge chairs are arranged around the water's edge. The lush greenery and nearby lake add a natural touch to the inviting ambiance.

Townhouse in Kissimmee

4.96 out of 5 average rating, 249 reviews

*LAKEVIEW* Resort 4m Disney! Private Spa Wi-Fi

Beautiful LAKEVIEW property 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 food and beverage stand. If you're up for more fun, walk to Old Town next door! Our place is BABY and KID FRIENDLY! Welcome to our Old Town Oasis!

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, 495 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.

Top guest favourite

A charming view of the colorful condominiums reflects on a serene pond, framed by lush greenery and palm trees. The buildings are adorned with pastel hues of pink and blue, creating an inviting scene highlighted by a whimsical representation of Mickey Mouse.

Apartment in Kissimmee

4.95 out of 5 average rating, 291 reviews

Lovely ❤️ Beach style Apt near Disney & Universal

Welcome to Runaway Beach Club — your peaceful escape just minutes from the magic! With airy high ceilings and Key West-style decor, you’ll feel at home the moment you walk in. Whether you’re visiting theme parks or just want to relax, this cozy retreat is tucked away from the chaos but close to everything. Perfect for couples, small families, or business travelers. Book your stay and unwind in your own private slice of paradise!