Family-friendly rentals near Old Town Kissimmee

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.

4.93 out of 5 average rating, 102 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

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.

4.94 out of 5 average rating, 160 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.

4.92 out of 5 average rating, 172 reviews

Luxury Townhouse 2 Bedroom/ Hot Tub

Welcome to your storybook stay at Regal Oaks Resort. Relax on your private screened patio with a nice tree-lined views of the Regal Oaks natural reserve. This 2BR, 2.5BA townhouse delights guests of all ages with a Toy Story kids’ room, Beauty & the Beast dining, and Cinderella-inspired living. Family-friendly amenities include a baby chair, pack & play, Roku TV, backyard cornhole, and “Hey Disney” magic. The kitchen is ready for cozy meals with a coffee maker, kettle, and Mickey sandwich maker.

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.

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

An expansive pool area is surrounded by palm trees and lounge chairs, with colorful umbrellas providing shade. A large water slide is visible in the background, complemented by vibrant buildings under a clear blue sky.

4.81 out of 5 average rating, 144 reviews

Perfect FantasyWorldClub NrDisney Amzing Amenities

Dazzling Newly Renovated condo with superb amenities, a host of on-site amenities and activities, only 4 miles from Disney and 12 miles to Universal. This unit has been completely renovated as of December 2021 with brand new furniture, TVs and linens. Nicest unit at Fantasy World at the most affordable prices. This stunning Kissimmee Townhouse is located in a lovely gated resort. You'll get to enjoy the resort's Swimming pool, Golfing, tennis, Ping-Pong, batting Cage etc! Never a slow day here!

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.

4.98 out of 5 average rating, 185 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!

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.

4.88 out of 5 average rating, 210 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

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.

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).

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.

4.95 out of 5 average rating, 310 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!

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.

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!

4.95 out of 5 average rating, 296 reviews

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

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!

4.84 out of 5 average rating, 268 reviews

A comfortable living area features a soft blue sofa adorned with patterned pillows. Natural light enters through window treatments, brightening the space. Nearby, a dining area accommodates four with a wooden table, while a well-equipped kitchen is visible in the background.

Tiny home in Kissimmee

Jubilee Cottage 12 miles from Epic Universe

Quaint cottage with high-end appliances, perfect for business travelers or small families. Fully equipped kitchen. Lovely porch. Comfortable loving room with 2 recliners. A/C and 5 fans keep the unit cool! Full use of facilities: pools, gym, reception area, game room, miniature golf. 5 minutes from Disney, walking distance to Old Town. Why stay in a hotel when you can stay in Jubilee Cottage??

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

4.91 out of 5 average rating, 173 reviews

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.

Apartment in Kissimmee

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

The resort features a large swimming pool surrounded by palm trees and deck chairs. A two-story clubhouse is visible in the background, along with water slides and a separate pool area. Lush greenery and blue skies create a vibrant atmosphere.

4.8 out of 5 average rating, 190 reviews

Spacious Townhouse at Regal Oaks Resort – Old Town

A private patio features a bubbling hot tub alongside a dining area with a table and chairs, shaded by a vibrant orange umbrella. The space is enclosed by screens, offering a bright atmosphere with clear blue skies in the background.

4.85 out of 5 average rating, 248 reviews

Resort Style 12 min Disney, Jacuzzi, Sleeps 8

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.

4.94 out of 5 average rating, 216 reviews

2 BR Harmony House at Regal Oaks Resort

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.

4.9 out of 5 average rating, 205 reviews

AMAZING vacation house .Mins to Disney Regal oasks

Superhost

4.82 out of 5 average rating, 164 reviews

#2662 Priv Jacuzzi Themed Villa Disney Universal

4.97 out of 5 average rating, 400 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Apartment in Orlando

Waterfront Resort Condo near Disney &Universal

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.

4.99 out of 5 average rating, 128 reviews

Lake View - 5 Miles to Disney!

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 118 reviews

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.

Apartment in Kissimmee

Pet friendly Orlando area near ESPN Center

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.

4.96 out of 5 average rating, 123 reviews

Luxury 5BR free heat private pool Disney Universal

4.86 out of 5 average rating, 424 reviews

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

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

4.95 out of 5 average rating, 105 reviews

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

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

4.9 out of 5 average rating, 148 reviews

A bright living area features a light-colored couch with decorative cushions, a patterned armchair, and a wooden coffee table. Natural light enters through large windows adorned with blinds. A ceiling fan hovers above, and a potted plant adds a touch of greenery.

Flat in Kissimmee

Modern 3 Bedroom Apartment Near the Theme Parks

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.

4.83 out of 5 average rating, 291 reviews

Private Cottage. Only 5 miles from Disney.

A large swimming pool is set within a landscaped area, featuring a gentle curve and surrounded by lounge chairs and umbrellas. A clubhouse with a tiled roof is visible in the background, contributing to the inviting atmosphere of the gated community.

4.99 out of 5 average rating, 121 reviews

Family friendly/Pet friendly Orlando paradise

An aerial view of the pool area features two pools surrounded by lush greenery and palm trees. The shallow pool has a unique shape with lounging areas, while the larger pool offers numerous sunbed arrangements. Gazebos are visible near the water's edge.

4.95 out of 5 average rating, 198 reviews

Magical Family Escape | Disney | Epic Universe

Family-friendly home rentals with a pool

4.86 out of 5 average rating, 302 reviews

The exterior of the cottage is highlighted by a welcoming front porch featuring two teal chairs. A white railing surrounds the steps, leading to the entrance. Natural light pours in through large windows, illuminating the inviting facade.

Tiny home in Kissimmee

Great reviews! Tiny home in quiet & safe area

4.99 out of 5 average rating, 134 reviews

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

Villa in Kissimmee

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

5 out of 5 average rating, 129 reviews

A children's bedroom features a vibrant underwater theme, with blue walls and colorful murals depicting marine life. Bedding includes a twin-over-twin boat bunk bed and a separate twin bed. Decorative elements like shells and a net create a playful atmosphere, while curtain-filtered light adds a soft glow.

Home in Davenport

5 stars! waterpark! GameRm! Ariel Buzz StarWars

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.

4.99 out of 5 average rating, 86 reviews

JRVacationHome@Regal Oak Resort-Old Town/Fun Spot

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.

4.95 out of 5 average rating, 498 reviews

Bright & Cozy Cottage Near Disney

The image features a scenic view of a resort-style pool surrounded by palm trees, with clear blue skies overhead. On the right, a cozy lounge area is highlighted, showcasing a light-colored sofa and a playful mural of Mickey Mouse, complemented by a patterned area rug.

4.96 out of 5 average rating, 77 reviews

Disney Villa/Waterslides/Heated Pool/Hot Tub/Lanai

4.97 out of 5 average rating, 105 reviews

The game room features a vibrant blacklight theme with neon accents. There are various arcade games, including a basketball game and air hockey table. The floor is decorated with playful, glowing images. This space is designed for family entertainment.

Home in Davenport

Magical Family Fun House Near Disney Luxury Villa

4.94 out of 5 average rating, 82 reviews

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

A Colorful Splash | Magical Disney Lakeside Resort

Family-friendly home rentals with wifi

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.

5 out of 5 average rating, 11 reviews

Mickey's Hideaway Cottage - 5 miles from Disney!

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.

4.98 out of 5 average rating, 44 reviews

Waterfront 2BR next to Disney, private hottub

4.96 out of 5 average rating, 1,047 reviews

A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.

Treehouse in St. Cloud

TreeHouse in the Cloud, (Close toTheme Parks

4.98 out of 5 average rating, 98 reviews

The recreation area is designed with vibrant blue lighting and themed decor. It features a pool table, arcade games, and a commercial air hockey table. The walls are adorned with popular character themes, including Super Mario and Avengers, creating an engaging and playful atmosphere.

Home in Kissimmee

Dream Vacation w/Avengers, Star Wars, & Mario Kart

5 out of 5 average rating, 11 reviews

Tiny home in Kissimmee

EPIC Fortress

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.

4.98 out of 5 average rating, 62 reviews

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

A vibrant water slide structure features intertwining blue and green tubes, leading into a sparkling pool below. Lush potted plants surround the pool area, adding a touch of greenery to the fun atmosphere.

4.94 out of 5 average rating, 33 reviews

Regal Oaks Renovated 4 Bed Unit