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Family-friendly vacation rentals in Winter Garden

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Top-rated family-friendly rentals in Winter Garden

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Orlando
Your Home Away From Home
Stay in Orlando away from the hustle & bustle, but still close to everything, in a beautiful ranch style guesthouse on 2.5 acres. Approx. 800 sq ft w/10 ft ceilings! Our property is privately gated down a private drive. Cozy 2 bedroom 2 full bathrooms w/whirlpool bathtubs, full kitchen w/granite countertops, refrigerator, microwave, stove/oven, 2 large closets with plenty of storage for clothes, luggage and personal items, washer and dryer. Living Room has a flat screen with Spectrum cable.
Jul 12 – 19
$123 per night
Guest favorite
Townhouse in Winter Park
Beautiful Downtown Winter Park
WP requires rentals to be listed as 28 days. For alternate rentals please contact me with dates requested. A 1 bedroom New England style townhouse. Enjoy brick streets, old oaks and lake access all within a 5 minute walk to downtown Winter Park, home of nationally known art festivals and museums, Saturday farmers market, Rollins College and many fine dining establishments. Pick herbs from our garden to use in cooking. Lounge on your private deck to the relaxing waterfall sounds of our koi pond.
Nov 26 – Dec 3
$109 per night
Guest favorite
Townhouse in Clermont
Paradise Escape
Your paradise escape is finally here! In the Sunshine State, paradise is just one perfect cocktail away. Leave your worries away and relax - you are in a sunshine state of mind! My "paradise island" is conveniently located in the heart of Clermont. You will certainly enjoy the welcoming and colorful ambiance! Combination lock instructions will be sent after arrival time confirmation. I look forward to hosting all my guests and making sure that they have an unforgettable experience!
May 28 – Jun 4
$93 per night

Popular amenities for Winter Garden family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Guesthouse in Clermont
Discover Tranquility at Our Charming Guest House
Sep 14 – 21
$200 per night
Guest favorite
Guesthouse in Orlando
Garden House near Orlando's cultural hub
Apr 5 – 12
$92 per night
Guest favorite
Condo in Orlando
Lakefront Studio apt~ 5 min from Universal Studios
Jan 27 – Feb 3
$140 per night
Guest favorite
Apartment in Orlando
Beautiful View, Newly Renovated 1 Mile to Disney
Jan 18 – 25
$108 per night
Guest favorite
Condo in Kissimmee
Family Apartment Near to Disney Orlando Universal
May 3 – 10
$99 per night
Guest favorite
Condo in Kissimmee
Disney World Condo w/ Full Kitchen, Balcony & Pool
Nov 19 – 26
$126 per night
Guest favorite
Condo in Davenport
Disney Orlando Condo Bahama Bay Resort 3bed 2bath
Sep 20 – 27
$109 per night
Guest favorite
Townhouse in Kissimmee
Find a Little Magic in a Townhouse near Disney and Universal
Nov 9 – 16
$166 per night
Guest favorite
Home in Kissimmee
Luxury Disney Vacation Home on Reunion Golf Resort
Aug 10 – 17
$387 per night
Guest favorite
Home in Clermont
Caribe Villa Brisa- Disney is only 6 miles away!
Jan 10 – 17
$179 per night
Guest favorite
Villa in Kissimmee
7BD with Movie Theater Pool & Jacuzzi near Disney!
Jan 20 – 27
$290 per night
Guest favorite
Home in Kissimmee
RU Incredible Parents? Themed-7bed, 4mi. to Disney
Jan 10 – 17
$324 per night

Family- and pet-friendly home rentals

Guest favorite
Place to stay in Geneva
ManCave apartment
Sep 1 – 6
$146 per night
Guest favorite
Guest suite in Orlando
Charming Comfortable Cottage in College Park
Sep 17 – 24
$83 per night
Guest favorite
Home in Orlando
The Prince House w/Free Parking (Central Location)
Jun 30 – Jul 7
$130 per night
Superhost
Tiny home in Orlando
The Ritz- Lakefront Tiny House in Orlando
Feb 9 – 16
$126 per night
Guest favorite
Guesthouse in Maitland
Chez Bienvenu
Jan 3 – 10
$109 per night
Guest favorite
Guest suite in Orlando
The Coach House- 2 bedroom/3 bath Orlando getaway!
Jul 4 – 11
$124 per night
Guest favorite
Home in Altamonte Springs
Eclectic Home Where Luxury Meets Affordability
Jul 26 – Aug 2
$190 per night
Guest favorite
Home in Maitland
Orlando area pool home in Maitland
Sep 3 – 10
$179 per night
Guest favorite
Home in Orlando
Waterside Pet Friendly Lakefront
Jun 22 – 29
$149 per night
Guest favorite
Villa in Kissimmee
7Bed/4.5Bath, Disney Area, Pool/Spa and Game Room!
Oct 14 – 21
$269 per night
Guest favorite
Guest suite in Orlando
Private guest suite with enclosed porch
May 2 – 9
$79 per night
Guest favorite
Apartment in Orlando
Orlando Vacation Condo - 3bed/2bath
Sep 25 – Oct 2
$171 per night

Family-friendly home rentals with a pool

Superhost
Home in Davenport
Orlando Disney area home
Jun 23 – 30
$95 per night
Guest favorite
Home in Kissimmee
3 bedroom Villa in Kissimmee
Feb 7 – 14
$103 per night
Guest favorite
Home in Orlando
*HALF HOME* (read desc) Pool/Disney/Universal
Sep 16 – 23
$95 per night
Guest favorite
Guest suite in Kissimmee
Private Studio in POOL home
Aug 20 – 27
$65 per night
Guest favorite
Guest suite in Kissimmee
Private 2 bedroom w/bathrm in portion of POOL home
Aug 5 – 12
$64 per night
Guest favorite
Home in Davenport
Disney Area Luxury Villa with Private Pool
Sep 9 – 16
$126 per night
Guest favorite
Home in Clermont
Disney Pool Villa, Cranberry South,
Nov 2 – 9
$122 per night
Guest favorite
Condo in Kissimmee
Beautiful Beach Style Condo minutes from Disney
Aug 15 – 22
$101 per night
Guest favorite
Cottage in Kissimmee
Entire Cottage close to Disney, Universal, Airport
Oct 19 – 26
$77 per night
Guest favorite
Cottage in Kissimmee
Bright & Cozy Cottage Near Disney
Dec 25 – Jan 1
$112 per night
Guest favorite
Tiny home in Kissimmee
ZMZ Tiny House Living! Try it out while at Disney
Nov 15 – 22
$76 per night
Guest favorite
Apartment in Orlando
Adorable Orlando Studio Apartment!
Apr 13 – 20
$72 per night

Quick stats about vacation rentals that are family-friendly in Winter Garden

Total rentals

40 properties

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

10 properties allow pets

Total number of reviews

1.6K reviews

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