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, 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

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, 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.

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 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, 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!

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, 209 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 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.

4.92 out of 5 average rating, 361 reviews

Waterpark, Mini Golf, Batting Cage | Near Disney!

**Waterpark closed for maintenance from January 5th to February 5th, 2026** (See photo 7 in album for details) Located just minutes from Disney World & steps from restaurants. 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 cage -Sports courts -Mini golf & more

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 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.

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!

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.

4.94 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!

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!

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

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.

A spacious Master Bedroom features a large bed dressed in white linens, complemented by neutral furnishings. A flat-screen TV is mounted on the wall opposite the bed, while soft natural light filters through the window adorned with light curtains.

4.91 out of 5 average rating, 324 reviews

Stylish Villa Near Disney | Hot Tub & Resort

Welcome to Casa del Sol! Experience the perfect blend of modern comfort and convenience in our 2-bedroom vacation home, just minutes from Disney World and top theme parks. Designed for families and groups, this home features contemporary décor, a fully equipped kitchen, and a private screened patio for ultimate relaxation. Take a refreshing dip in the resort pool or unwind with a cocktail at the Tiki Bar

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

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

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, 142 reviews

Perfect FantasyWorldClub NrDisney Amzing Amenities

4.82 out of 5 average rating, 164 reviews

#2662 Priv Jacuzzi Themed Villa Disney Universal

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, 204 reviews

AMAZING vacation house .Mins to Disney Regal oasks

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, 126 reviews

Lake View - 5 Miles to Disney!

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.

4.84 out of 5 average rating, 291 reviews

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

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.

4.89 out of 5 average rating, 268 reviews

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

4.94 out of 5 average rating, 161 reviews

An aerial view captures the expansive resort-style pool area, featuring tropical landscaping and winding water features. Sun loungers and cabanas line the poolside, while a lazy river and splash park invite guests to relax and enjoy. The serene water is bordered by a scenic lake.

Condo in Kissimmee

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

Family- and pet-friendly home rentals

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.

4.88 out of 5 average rating, 109 reviews

Pets Welcome, Close to Parks, Stocked Kitchen

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.

Condo in Kissimmee

Pet friendly Orlando area near ESPN Center

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

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, 289 reviews

Private Cottage. Only 5 miles from Disney.

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, 197 reviews

Magical Family Escape | Disney | Epic Universe

4.98 out of 5 average rating, 212 reviews

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

Lakefront Resort Condo near Disney & Universal

4.77 out of 5 average rating, 111 reviews

Apartment in Kissimmee

Cozy Vacation Condo next to Disney Universal

Family-friendly home rentals with a pool

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!

The image showcases various themed sleeping areas within the vacation home. A Superhero Room displays colorful walls with superhero motifs, while the Princess Room features castle imagery. A cozy nook with a bunk bed is visible, alongside arcade machines that add to the playful environment.

4.94 out of 5 average rating, 121 reviews

Magical Hideaway - 15 min to Disney - Storey Lake

4.97 out of 5 average rating, 195 reviews

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

303_To Infinity & the Ocean Breeze Apartment

4.94 out of 5 average rating, 142 reviews

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

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

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, 43 reviews

Waterfront 2BR next to Disney, private hottub

5 out of 5 average rating, 11 reviews

Tiny home in Kissimmee

EPIC Fortress

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

4.93 out of 5 average rating, 14 reviews

Apartment in Kissimmee

Stitch and Angel Studio

Family-friendly home rentals with Wifi

The resort pool area is surrounded by palm trees and features a large, curvy swimming pool with a separate children's slide. Lounge chairs and umbrellas are arranged neatly along the poolside, providing ample seating. The clubhouse is visible in the background, with warm lighting under a vibrant sunset sky.

4.93 out of 5 average rating, 55 reviews

Travel Theme Private Home@Disney

4.98 out of 5 average rating, 59 reviews

The themed bedroom features twin beds, designed to resemble spaceships, with bold, illuminated accents. A wall mural depicts a starry sky, while nearby, a gaming machine displays a classic arcade setup, creating an immersive atmosphere for guests.

Home in Davenport

Amazing Friends 5BR+Private Pool+Lazy River

4.74 out of 5 average rating, 68 reviews

Home in Kissimmee

RO2631 2BR Villa Near Disney + Resort Amenities

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 relaxing living area features a blend of neutral and blue walls, with a comfortable sofa and accent chairs arranged around a coffee table. Natural light brightens the space through large glass doors, leading to an outdoor patio area. Decorative pillows add a touch of color.

4.95 out of 5 average rating, 95 reviews

Cozy Disney Escape w/Heated Pool, Private Hot Tub

A poolside cabana is showcased with comfortable seating and a wooden tray displaying drinks and desserts. The refreshing pool is visible in the background, surrounded by lush palm trees and lounge areas. The warm colors of the resort buildings complement the inviting outdoor atmosphere.

4.89 out of 5 average rating, 95 reviews

Moana's New Home at Resort (w/no fees!) in Orlando

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, 61 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.