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Family-Friendly rentals near Old Town Kissimmee

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Top-rated family-friendly rentals near Old Town Kissimmee

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Top guest favorite
A resort-style swimming pool is framed by palm trees and lounge chairs. The image shows a screened patio with a private jacuzzi and outdoor dining space, along with a colorful water slide visible nearby. The themed bedroom features bright decor and ample bedding, appealing to families.
Townhouse in Kissimmee
4.93 out of 5 average rating, 101 reviews

#2609 Resort Home near Disney Themed Jacuzzi Pool

Relax in this LARGE FULLY RENOVATED LUXURY DESIGNER HOME in the famous REGAL OAKS RESORT w/ THEMED BR near DISNEY WORLD in ORLANDO FLORIDA! Enjoy the STUNNING LAKE FRONT VIEW, PRIVATE JACUZZI, NEW STYLISH FURNITURE, HEATED POOL, Waterslides, Poolside Bar, GAME ROOM, BILLIARD TABLES, Ping Pong, Restaurant, GYM, Tennis Court, and 24/7 Security Guard! - Walk 5 min to Old Town Amusement Park and World Food Trucks. - Drive 8 min to DISNEY, 20 min UNIVERSAL STUDIO, 15 min SEAWORLD and DISNEY SPRINGS

Guest favorite
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, 159 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 favorite
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

Top guest favorite
An outdoor patio area is enclosed with a protective screen, featuring a dining table with an umbrella. Comfortable seating is arranged nearby. A hot tub is positioned to the side, surrounded by lush greenery and a wall for privacy.
Townhouse in Kissimmee
4.98 out of 5 average rating, 187 reviews

Townhouse - 5 miles to Disney!

Dip in the heated community pool, enjoy the many amenities at this amazing resort, unwind in this vacation rental’s private hot tub with Bluetooth and night lights when you book in this exciting stay in Kissimmee! Going out? Gather family and friends & experience the magic of Disney World, Harry Potter rides at Universal Studios, Sea World, etc. At less than a mile to Old Town where you can go on rides, shop, and dine! Return to the 3-bd, 2.5-bths townhome and lounge in the sunny lanai & ENJOY!

Top guest favorite
A collage showcasing the townhome's features. The Mickey-themed guest room displays a bright mural, while the master suite is elegantly arranged. The kitchen is equipped with stainless steel appliances, and the living area offers a serene pond view through large sliding glass doors. A resort-style pool area is depicted from above.
Townhouse in Kissimmee
4.98 out of 5 average rating, 134 reviews

Regal Oaks Resort Lake View 2BR near Disney Parks

Our gorgeous 2 bed 2.5 bath DELUXE townhome is located in the pristine Regal Oaks Resort located just behind Old Town theme park and minutes from Disney, shopping, restaurants & more. Inside our home you will find a living/dining room combo and a kitchen boasting stainless steel appliances and granite countertops. Upstairs an in suite beautiful Mickey decor guest room and one master suite with private balcony overlooking a beautiful pound view and huge conservation area (all rooms no carpet).

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 in Kissimmee
4.84 out of 5 average rating, 291 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, 268 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 favorite
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
4.85 out of 5 average rating, 131 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 favorite
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, 309 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 favorite
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, 251 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!

Top guest favorite
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, 498 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 favorite
A bright dining area with a large table set for meals overlooks a modern kitchen with amenities, including stainless steel appliances. A cozy bedroom features a bed adorned with black and red accents. An aerial view displays a vibrant resort pool area with water slides and lounging spaces.
Townhouse in Kissimmee
4.92 out of 5 average rating, 361 reviews

Waterpark, Mini Golf, Batting Cage | Near Disney!

Stay at our Mouse Townhouse #2 just minutes from Disney World & steps from restaurants & stores. Your reservation will give you access to the resort’s amenities for up to 6 people without an additional charge! ✪AMENITIES✪ FantasyWorld amenities include: -Lazy river -Water slides -Heated pools -Pool bar -Splash pad -Jacuzzi -Gym -Picnic & BBQ areas -Playground -Arcade -Batting cages -Sports courts -Mini golf & more

Popular amenities for family-friendly rentals near Old Town Kissimmee

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
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
4.94 out of 5 average rating, 216 reviews

2 BR Harmony House at Regal Oaks Resort

Superhost
Townhouse in Kissimmee
4.82 out of 5 average rating, 164 reviews

#2662 Priv Jacuzzi Themed Villa Disney Universal

Guest favorite
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, 204 reviews

AMAZING vacation house .Mins to Disney Regal oasks

Top guest favorite
A luxurious cabana overlooks a sparkling pool, surrounded by palm trees and lounge chairs. A tray with drinks and snacks rests on a soft seating area, while the vibrant clubhouse is visible in the background, creating an inviting atmosphere for relaxation.
Townhouse in Kissimmee
4.89 out of 5 average rating, 142 reviews

Orlando Disney Premium Home in Resort & Lake View!

Top guest favorite
The collage showcases various areas of the lakeside home. Highlights include a private patio dining set, a resort-style pool, a comfortable living space with a dining table, and vibrant bedrooms featuring bunk beds and colorful decor. The picturesque lake view complements the outdoor spaces.
Townhouse in Kissimmee
4.99 out of 5 average rating, 126 reviews

Lake View - 5 Miles to Disney!

Guest favorite
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, 209 reviews

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

Guest favorite
A modern living area is presented with a dining table and four chairs positioned beside a kitchenette. A green sofa adds a pop of color, while large windows provide ample natural light. The space opens to a bedroom area, creating an inviting atmosphere.
Condo in Kissimmee
4.89 out of 5 average rating, 402 reviews

Family Apartment Near to Disney Orlando Universal

Guest favorite
A vibrant pool area is showcased, featuring bright water play structures including a pink water umbrella and colorful fountains. Sun loungers and umbrellas in various colors surround the pool, with palm trees lining the background under a clear blue sky filled with fluffy clouds.
Condo in Kissimmee
4.86 out of 5 average rating, 403 reviews

Gated community, 5 miles from Disney

Family- and pet-friendly home rentals

Guest favorite
A bright bedroom contains two spacious beds dressed in light blue bedding. Floral accent pillows add color, while a large mural of a castle and lush greenery serves as a captivating backdrop. Natural light filters through pink curtains, enhancing the cheerful ambiance.
Townhouse in Kissimmee
4.88 out of 5 average rating, 109 reviews

Pets Welcome, Close to Parks, Stocked Kitchen

Guest favorite
The image captures a vibrant pool area surrounded by lush palm trees and comfortable lounge chairs. An inviting infinity pool is centrally located, accompanied by cabanas and umbrellas. Multiple water slides are visible in one corner, enhancing the family-friendly atmosphere of the space.
Condo in Kissimmee
4.92 out of 5 average rating, 118 reviews

Pet friendly Orlando area near ESPN Center

Top guest favorite
A lush outdoor water complex showcases a winding lazy river surrounded by palm trees and landscaped greenery. Lounge chairs are positioned alongside the water, providing ample space for relaxation. In the background, a clubhouse and scenic waterfront can be seen under a bright blue sky.
Townhouse in Kissimmee
4.97 out of 5 average rating, 122 reviews

Luxury 5BR free heat private pool Disney Universal

Top guest favorite
A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.
Villa in Kissimmee
4.86 out of 5 average rating, 424 reviews

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

Guest favorite
A colorful bunk bed structure is featured, decorated in vibrant shades of yellow, blue, and orange. The mural backdrop depicts a jungle scene with a leopard and tropical plants, enhancing the playful atmosphere of the room. Spiral staircases offer access to the upper sleeping area.
Townhouse in Davenport
4.95 out of 5 average rating, 105 reviews

Themed Home + Near Disney + Arcade + King Bed + Water Park + Spa

Guest favorite
A bright, airy living area is showcased with large windows covered by sheer curtains. A cozy sectional couch is paired with a circular table, accented by a patterned rug. Decorative plants and vibrant yellow textiles add warmth to the space, creating a comfortable atmosphere.
Cottage in Kissimmee
4.83 out of 5 average rating, 289 reviews

Private Cottage. Only 5 miles from Disney.

Top guest favorite
Home in Kissimmee
4.89 out of 5 average rating, 161 reviews

Flexible Early Check ins / Late Check outs*

Top guest favorite
A balcony view captures a vibrant sunset over Lake Bryan, with hues of pink and orange reflected on the water. Outdoor seating includes two chairs and a small round table, inviting relaxation while enjoying the scenic surroundings.
Condo in Orlando
4.98 out of 5 average rating, 212 reviews

Lakefront Resort Condo near Disney & Universal

Family-friendly home rentals with a pool

Top guest favorite
A picturesque view of the resort-style pool area is presented, featuring several palm trees and lounge chairs around the sparkling water. Colorful slides and a splash park are visible, with pathways leading to different activities amidst landscaped greenery.
Condo in Kissimmee
4.91 out of 5 average rating, 172 reviews

P-Gated Resort-5 miles to Disney-2 FREE Water Park

Top guest favorite
A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.
Condo in Kissimmee
4.97 out of 5 average rating, 195 reviews

303_To Infinity & the Ocean Breeze Apartment

Top guest favorite
A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.
Condo in Orlando
4.94 out of 5 average rating, 142 reviews

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Top guest favorite
A refreshing swimming pool features a large water slide in vibrant green and blue. Palm trees provide shade around the area. Several lounge chairs are positioned beside the pool, inviting relaxation while enjoying the sunny landscape.
Condo in Kissimmee
4.96 out of 5 average rating, 150 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

Guest favorite
A screened patio features a hot tub surrounded by lounge chairs and a dining area. An umbrella provides shade over the table, and potted yellow flowers add a touch of color. The backdrop includes the exterior of the house and a glimpse of the landscape.
Townhouse in Kissimmee
5 out of 5 average rating, 10 reviews

Waterfront Views/Private hot tub/3 miles to Disney

Guest favorite
A cozy studio is shown, featuring a king-sized bed with an accent wall in warm colors. A seating area with a couch and smart TV is visible. The kitchen area includes a table for two. The outdoor pool reflects sunlight, surrounded by loungers and palm trees.
Apartment in Kissimmee
4.97 out of 5 average rating, 34 reviews

6min to Disney - Retro Studio - Resort Pool

Guest favorite
An outdoor patio area features a hot tub, accompanied by colorful chairs and a small table. The scene is set against a scenic lakeside view, framed by a protective screen enclosure, with gentle evening light illuminating the space.
Home in Kissimmee
4.94 out of 5 average rating, 51 reviews

Once Upon A DreamStay: *Luxury *Lakeview *Disney

Top guest favorite
A spacious outdoor pool area is surrounded by lounge chairs and palm trees, with a large building in the background. A waterslide can be seen to the left, and the setting sun casts a warm glow over the entire scene.
Townhouse in Kissimmee
4.96 out of 5 average rating, 236 reviews

Resort-style home close to Disney with jacuzzi

Family-friendly home rentals with Wifi

Top guest favorite
A cozy living area features a light-colored sofa with coordinating cushions, positioned beside large windows that allow natural light to flood in. A colorful area rug depicting Mickey Mouse adds playfulness, while a glass coffee table sits in front. An open kitchen area is visible in the background.
Cottage in Kissimmee
5 out of 5 average rating, 11 reviews

Mickey's Hideaway Cottage - 5 miles from Disney!

Top guest favorite
An inviting bedroom features a Mickey-themed design with two spacious beds, ideal for children. The cozy living area showcases a comfortable sectional sofa, a flat-screen TV, and modern lighting. A stylish dining space with a table and six chairs is also visible, enhancing communal dining.
Condo in Kissimmee
5 out of 5 average rating, 18 reviews

4731-103 Stay Magical • 2BR with Mickey Room & Mor

Top guest favorite
The exterior of the townhouse features a welcoming entrance with a decorative wreath on the door. Light-colored siding complements the lush greenery surrounding the front yard. Windows with white shutters allow natural light to enter the interior spaces, while a parking area is visible in the foreground.
Townhouse in Kissimmee
4.99 out of 5 average rating, 86 reviews

JRVacationHome@Regal Oak Resort-Old Town/Fun Spot

Top guest favorite
A private hot tub is situated on an outdoor patio, enclosed by a screened area. Surrounding greenery and a tranquil water view are visible beyond the patio, providing a serene setting for relaxation.
Townhouse in Kissimmee
4.98 out of 5 average rating, 43 reviews

Waterfront 2BR next to Disney, private hottub

Guest favorite
Home in Kissimmee
5 out of 5 average rating, 6 reviews

Entire house 15min to Disney with Hot Tub

Guest favorite
An aerial view highlights a vibrant pool area featuring a multi-loop waterslide. Surrounding the pools are shaded lounge chairs and umbrellas, with palm trees adding a tropical touch. The layout showcases a spacious lazy river and areas for relaxation.
Townhouse in Kissimmee
4.82 out of 5 average rating, 85 reviews

Free Waterpark, Fantasy World, The Mickey House

Top guest favorite
A vibrant dining area is shown, featuring a large table set for six. Below, a private hot tub is visible on a patio, surrounded by lush greenery. A spacious bedroom with elegant decor is highlighted, showcasing a comfy bed and large windows letting in natural light.
Townhouse in Kissimmee
4.98 out of 5 average rating, 61 reviews

Disney Getaway, Hot Tub, 10 min to Parks, 6 people

Top guest favorite
Tiny home in Kissimmee
5 out of 5 average rating, 11 reviews

EPIC Fortress

Quick stats about family-friendly rentals near Old Town Kissimmee

  • Total rentals

    390 properties

  • Nightly prices starting at

    G$8,365 GYD before taxes and fees

  • Total number of reviews

    32K reviews

  • Pet-friendly rentals

    100 properties allow pets

  • Rentals with a pool

    350 properties have a pool

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

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