
Family-friendly rentals near Old Town Kissimmee
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Top-rated family-friendly rentals near Old Town Kissimmee
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#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

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.

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.

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

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!

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!

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

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).

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!

*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!

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!

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
Family-friendly home rentals with a hot tub

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

Spacious Townhouse at Regal Oaks Resort – Old Town

Resort Style 12 min Disney, Jacuzzi, Sleeps 8

2 BR Harmony House at Regal Oaks Resort

AMAZING vacation house .Mins to Disney Regal oasks

#2662 Priv Jacuzzi Themed Villa Disney Universal

Waterfront Resort Condo near Disney &Universal

Lake View - 5 Miles to Disney!
Family- and pet-friendly home rentals

Pet friendly Orlando area near ESPN Center

Luxury 5BR free heat private pool Disney Universal

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

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

Modern 3 Bedroom Apartment Near the Theme Parks

Private Cottage. Only 5 miles from Disney.

Family friendly/Pet friendly Orlando paradise

Magical Family Escape | Disney | Epic Universe
Family-friendly home rentals with a pool

Great reviews! Tiny home in quiet & safe area

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

5 stars! waterpark! GameRm! Ariel Buzz StarWars

JRVacationHome@Regal Oak Resort-Old Town/Fun Spot

Bright & Cozy Cottage Near Disney

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

Magical Family Fun House Near Disney Luxury Villa

A Colorful Splash | Magical Disney Lakeside Resort
Family-friendly home rentals with wifi

Mickey's Hideaway Cottage - 5 miles from Disney!

Waterfront 2BR next to Disney, private hottub

TreeHouse in the Cloud, (Close toTheme Parks

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

EPIC Fortress

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

Regal Oaks Renovated 4 Bed Unit

4BR/3BA Townhouse w/ Private Pool in Storey Lake
Quick stats about family-friendly rentals near Old Town Kissimmee

Total holiday rentals
Explore 390 holiday rentals in Old Town Kissimmee

Nightly prices starting at
Old Town Kissimmee holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 31,860 verified reviews to help you choose

Pet-friendly holiday rentals
Find 100 rentals that welcome pets

Holiday rentals with a pool
350 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wifi availability
380 of Old Town Kissimmee holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Old Town Kissimmee rentals

4.7 Average rating
Old Town Kissimmee stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Rentals with an EV charger Old Town Kissimmee
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- Family-friendly rentals Kissimmee
- Family-friendly rentals Osceola County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Walt Disney World Resort Golf
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure
- Ventura Country Club
- Kissimmee Lakefront Park
- Bok Tower Gardens
- Shingle Creek Golf Club




