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.

4.92 out of 5 average rating, 106 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 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, 211 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, 367 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

4.86 out of 5 average rating, 306 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

Cozy cottage located only 4 MILES TO DISNEY WORLD!!! The cottage is so close to everything yet surrounded by lush trees, established landscaping and an ever so peaceful setting. 10 minute walk to ALDI, Dunkin Donuts, Chilis, Longhorn, Krispy Kreme, Dollar Tree, Waffle House, IHOP, Cracker Barrel, CVS and much more! 2 miles to Wal-Mart. 7 miles to Sea World. 8 miles to Orange County Convention Center. 13 miles to Universal Studios. 14 miles to Premium Outlet.

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!

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, 218 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.

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, 311 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!

4.88 out of 5 average rating, 113 reviews

Kid-Approved Stay – Pool, Parks & Themed Rooms!

Give your family a stay they’ll never forget! Kids can rule their own Frozen kingdom or battle in a galaxy far, far away, while adults unwind after action-packed park days. ✔ Themed kids’ rooms – Frozen castle & intergalactic escape ✔ Private splash pool for a refreshing break ✔ Spacious & modern layout for families & groups ✔ Prime location near Disney, dining & top attractions Don’t miss out—book Let It Go Galaxy before it’s gone!

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, 500 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.

The image displays a resort landscape featuring various pastel-colored buildings surrounding a large pool area. A view of the tranquil lake is visible, with numerous palm trees and lounge chairs positioned near the water. The highlighted apartment is located on the second floor of one building.

4.97 out of 5 average rating, 397 reviews

Gorgeous❤️ Pool & Lake View Condo near Disney Parks

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!

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.

4.97 out of 5 average rating, 231 reviews

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

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

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

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

A clear blue swimming pool features gentle curves and shimmering water, surrounded by lounge chairs and palm trees. A waterslide is visible in the background, offering a fun attraction for guests. The inviting pool area is framed by a modern building with large windows.

4.84 out of 5 average rating, 317 reviews

Resort Living 4 Bed 3.5 Bath Townhome

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, 255 reviews

BOOK your Disney inspired Lakefront retreat NOW!

A renovated living space is shown with a cozy sofa and a dining area featuring a dark wood table. The kitchenette is equipped with modern appliances, and a large screen TV is mounted on the wall. Natural light enters through large windows, illuminating the inviting atmosphere.

4.8 out of 5 average rating, 169 reviews

Renovated First Floor Disney Family Condo

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, 130 reviews

Lake View - 5 Miles to Disney!

A comfortable living room features a sofa with plush cushions, alongside a pair of accent chairs. A wooden coffee table rests on a patterned area rug, while two large framed artworks are displayed on the wall. Natural light enters through glass doors, complemented by soft drapes.

4.93 out of 5 average rating, 309 reviews

Comfy 2 Bedroom Townhouse w/ hot tub - Disney Area

Aerial view of the resort’s expansive pool area features a lazy river, multiple waterslides, and designated lounge spaces among lush landscaping. Vibrant blue poolside chairs are arranged around the large pool, while various amenities and activities are visible in the surrounding area.

4.8 out of 5 average rating, 241 reviews

*Water park!*Resort Villa! close to parks!

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, 190 reviews

Townhouse - 5 miles to Disney!

Family- and pet-friendly home rentals

A living room is furnished with a light grey sofa and a matching armchair, offering ample seating. Two coffee tables are positioned centrally on a patterned area rug. Artistic wall decor and warm lighting create a relaxed ambiance, with a dining area visible in the background.

4.7 out of 5 average rating, 175 reviews

Cozy Townhouse in Kissimmee, near Orlando!

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, 270 reviews

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

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, 292 reviews

Private Cottage. Only 5 miles from Disney.

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.

4.9 out of 5 average rating, 150 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

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.

4.96 out of 5 average rating, 201 reviews

Magical Family Escape | Disney | Epic Universe

A Disney-themed double bedroom features two yellow beds adorned with black-and-white polka dot pillows and playful Mickey Mouse accents. A luminous mural of Mickey and Minnie Mouse is highlighted against a castle backdrop. Additional images showcase the master bedroom, resort pool, and a modern living area.

4.74 out of 5 average rating, 123 reviews

New Listing! Free Waterpark 2br/2ba, Fantasy World

4.98 out of 5 average rating, 215 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 and Universal

4.9 out of 5 average rating, 243 reviews

Bohemian Bungalow! <5 Miles from Parks! 2 Masters!

Family-friendly home rentals with a pool

Townhouse in Four Corners

4.96 out of 5 average rating, 169 reviews

Near Disney/Kid-Friendly/Disney-Themed/Water Park

4.96 out of 5 average rating, 106 reviews

Cottage of Charms

4.98 out of 5 average rating, 86 reviews

A large, inviting pool area is surrounded by palm trees and lounge chairs, offering a relaxed atmosphere. A two-story building with a terracotta roof is visible in the background, featuring several windows that reflect the bright blue sky.

Home in Kissimmee

Resort themed home near Disney with spa

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, 135 reviews

Regal Oaks Resort Lake View 2BR near Disney Parks

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, 63 reviews

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

A modern living space showcases a kitchen with white cabinetry and stainless steel appliances. The open layout includes a dining area with a red and white checkered table, comfortable seating, and a vibrant accent wall. Natural light enters through large windows, illuminating the cozy atmosphere.

4.83 out of 5 average rating, 427 reviews

Mickey Mouse Themed Getaway next to Disney 1

A modern kitchen features crisp white cabinetry and sleek stainless-steel appliances. A spacious island is complemented by contemporary stools, with an organized countertop housing kitchen essentials. Gray tile backsplash adds a subtle texture, while natural light brightens the open layout.

4.94 out of 5 average rating, 154 reviews

BRAND NEW 2BR Apt, 5mi to Disney - Storey Lake 401

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.

4.97 out of 5 average rating, 37 reviews

6min to Disney - Retro Studio - Resort Pool

Family-friendly home rentals with Wifi

4.88 out of 5 average rating, 16 reviews

10 Min from Disney • Great Location & Comfort

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

4.91 out of 5 average rating, 67 reviews

A private patio area features a hot tub next to two comfortable lounge chairs, all surrounded by a screened enclosure. Beyond the enclosure, a serene view of green landscaping and a lake is visible under a partly cloudy sky.

Home in Kissimmee

Magic Pond View TH 2b/2.5b Private Spa by Disney!

A colorful children's bedroom is adorned with Minions-themed decor. Two spacious beds are dressed in white bedding with Minions patterns. The walls feature cheerful Minion illustrations, and a playful garland hangs overhead, adding to the vibrant atmosphere.

4.98 out of 5 average rating, 45 reviews

Waterfront 2BR in Family Resort next to Disney

4.96 out of 5 average rating, 1,056 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, 99 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

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, 34 reviews

Regal Oaks Renovated 4 Bed Unit

An aerial view showcases the expansive resort featuring a meandering pool with water slides and lounging areas surrounded by lush green lawns. The modern interior is highlighted by a spacious family room with comfortable seating and large windows allowing natural light to flow in.