Family-friendly holiday rentals in Winter Garden

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winter Garden

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

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Guest favourite

Guest suite in Winter Park

4.96 out of 5 average rating, 245 reviews

Atmospheric Studio in the Garden

Enjoy a little piece of Florida's lush paradise. Full studio suite lives elegantly & comfortably for longer-term stays. We've taken such pride in the opportunity to allow old Florida to intersect with compelling modern design and styling. Relax in this fully furnished studio apartment with kitchenette nestled among a verdant garden. Home boasts modern kitchen, comfy memory foam bed, separate shower and bath & spacious living and entertaining areas. Available for stays of one month or longer.

15–22 Jun

$138 SGD per night

Guest favourite

Flat in Orlando

4.95 out of 5 average rating, 619 reviews

Quiet Shed in Downtown

Nestled behind my 1920s bungalow in one of Orlando’s best neighborhoods, The Shed is a local experience and retreat. Located in the city center, just a 5 min Uber to Amway, Soccer Stadium, and walking distance to the Sun Rail and hospital, you’ll love The Shed, because of its chill vibe and privacy. Perfect for couples, traveling professionals, and those new to Airbnb. Note: I rent my main house so you may see those guests in the backyard. No smoking/vaping allowed. Early check-in @ $20/hr

11–18 Jul

$143 SGD per night

Guest favourite

Home in Orlando

4.95 out of 5 average rating, 313 reviews

*HALF HOME* (read desc) Pool/Disney/Universal

We LOVE hosting! Think of us as friends you’re staying with, but haven’t met yet. We are happy to interact, but also happy to remain out of sight to ensure your privacy. We live in the master (on OTHER SIDE w/own bath) when not traveling and we DO use kitchen. Everything else is exclusive to you! You get plenty of space & PRIVACY. Photos represent YOUR space (we use kitchen too, but rest is exclusive) If you’re not comfortable with on-site host w/kitchen usage, we aren’t right choice.

12–19 Jun

$149 SGD per night

Guest favourite

Townhouse in Clermont

4.93 out of 5 average rating, 193 reviews

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!

22–29 Mar

$146 SGD per night

Guest favourite

Home in Clermont

4.99 out of 5 average rating, 157 reviews

Clermont Cottage Near the Lake

Enjoy your stay in beautiful sunny FL in our fully renovated 2 bed/2 bath home. We've added ENHANCED CLEANING AND DISINFECTING after every guest's stay. This home is located in a quiet neighborhood less than a mile from Clermont's WATERFRONT PARK and the WEST ORANGE TRAIL. It's a great location for Triathlons and activities at Victory Point. If you are visiting to enjoy Universal Studios and Disney, they are only 28 miles away! Come stay at our home with everything you'll need!

16–23 Oct

$164 SGD per night

Guest favourite

Home in Clermont

4.93 out of 5 average rating, 188 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow full disinfecting of the house.

10–17 Jul

$234 SGD per night

Guest favourite

Home in Clermont

4.86 out of 5 average rating, 117 reviews

Cozy Family Home near Disney

Escape to our charming 3BR, 2BA house in a peaceful Disney-adjacent neighborhood. Meticulously maintained, it radiates warmth and comfort. Enjoy streaming on Roku-equipped TVs with fast 300 Mbps WiFi. Fenced yard for play, short walk to heated saltwater pool. Community offers pickleball, tennis, ping pong, pavilion, playground. Please read all details & rules. Experience the perfect blend of comfort, convenience, and Disney magic. Book now and create unforgettable memories!

19–26 Oct

$188 SGD per night

Guest favourite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 790 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. For a video tour type the following link into your browser: https://tinyurl.com/a72vevp5 There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; meemaws-country -cottage which sleeps six.

21–28 Apr

$229 SGD per night

Guest favourite

Guest house in Windermere

4.94 out of 5 average rating, 240 reviews

Small Guesthouse near Orlando's Theme Parks

A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

26 Oct – 2 Nov

$183 SGD per night

Guest favourite

Townhouse in Kissimmee

4.92 out of 5 average rating, 227 reviews

Beautiful Farm House Decor near Disney, Sleeps 6

Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

18–23 Sep

$142 SGD per night

Guest favourite

Cottage in Kissimmee

4.96 out of 5 average rating, 421 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.

17–24 Sep

$135 SGD per night

Guest favourite

Guest suite in Orlando

4.93 out of 5 average rating, 562 reviews

Charming Comfortable Cottage in College Park

Welcome to the 1942 Cottage. This quaint cottage boasts an outdoor table, screened front porch, living room , bathroom, and a comfortable oversized bedroom that has a microwave, refrigerator/ freezer, and Keurig coffee maker all for your private use. PLEASE note, I live in the actual back of the cottage, like a bnb. It’s an older home with a few quirks but it’s comfortable and clean.:)

2–9 Aug

$159 SGD per night