Family-friendly vacation rentals in Winter Park

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winter Park

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

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Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 277 reviews

Eclectic Home Where Luxury Meets Affordability

Welcome to the Haven at Temper Wild - Your home away from home. We offer fully free amenities, luxury bedding and pillows, and quintessential design throughout the rooms and home. There are work spaces in every bedroom, ultra-fast wifi, games galore, and a beautiful outdoor space equipped with outdoor dining and lounging. Pet Fee's per pet: $100 (You must notify host if you are bringing a pet prior to booking) Read the rules of the property before booking, to ensure that you are OK with them.

Jul 7 – 14

R3,921 ZAR per night

Guest favorite

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.

Jun 15 – 22

R1,917 ZAR per night

Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 388 reviews

Garden House near Orlando's cultural hub

On a quiet cobblestone street, yet close to art and culture, more than 3 dozen restaurants in walking distance, Florida Hospital and family-friendly activities. You’ll love our place because of the location, the large bathroom with jacuzzi, the skylights, window seat, porch swing. It is nestled in our back yard surrounded by trees and has its own private entrance via a rustic walk way of pavers and stones. Couples, families, most anyone will find it charming. STR 1009942 (City registration)

May 23 – 30

R1,946 ZAR per night

Guest favorite

Tiny home 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

Apr 11 – 18

R2,294 ZAR per night

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 369 reviews

The Coach House- 2 bedroom/3 bath Orlando Getaway!

Pet-friendly 2 Bedroom/3 Bath House. Designed by renowned architect James Gamble Rogers II, the house is a 25-minute drive ($23 Uber) from the MCO Airport. Nestled in the heart of Orlando's College Park district, it is an oasis just moments away from Downtown Orlando: nightlife, museums, and funky art and music scene. Take a 25-minute drive into Disney, Universal, or The Outlets. Uber/Lyft/Walk to nearby trendy restaurants, museums, theaters, boutique shopping, and our craft beer scene.

Jul 11 – 18

R3,292 ZAR per night

Guest favorite

Home in Maitland

4.94 out of 5 average rating, 148 reviews

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Mar 19 – 26

R3,942 ZAR per night

Superhost

Farm stay in Orlando

4.9 out of 5 average rating, 159 reviews

Charming Guesthouse at Pine & Oak Place

Tucked away on a small farm, our Charming Guesthouse offers the comforts of home in a country setting. Whether you are looking for a family friendly getaway or are in town for a business trip, this property has the amenities you are looking for. Located in East Orlando, guests benefit from the privacy of a tucked away setting while remaining in close reach of World Class Theme Parks, Attractions, beaches, and the University of Central Florida. We look forward to hosting you!

Jun 5 – 12

R2,267 ZAR per night

Guest favorite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 793 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.

Apr 14 – 21

R3,171 ZAR per night

Guest favorite

Guesthouse in Maitland

4.87 out of 5 average rating, 381 reviews

Chez Bienvenu

Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space

Mar 30 – Apr 6

R2,191 ZAR per night

Guest favorite

Guest suite in Orlando

4.93 out of 5 average rating, 563 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.:)

Jun 30 – Jul 7

R2,259 ZAR per night

Guest favorite

Cottage in Tavares

4.97 out of 5 average rating, 204 reviews

Lakeside Cottage on Lake Dora

A charming 1200 sq ft, two bedroom, two bath cottage located on beautiful Lake Dora with white sand beach. A great place to relax and your home away from home. Just minutes from Tavares (known as the Seaplane City) and Mt. Dora (known as the City of Festivals.) You can bring your boat and tie it up to the dock. Large circular drive with plenty of parking for cars, trailers, etc.

Oct 18 – 25

R2,680 ZAR per night

Guest favorite

Guesthouse in Orlando

4.93 out of 5 average rating, 161 reviews

Private Backyard Cottage in Mills50

Airy one-bedroom garden cottage in Orlando's hippest historic neighborhood. Walk or bike to great restaurants, parks, and bars. Located 5 to 10 min to Downtown Orlando, Florida Hospital, and Winter Park; 20 to 30 min to Universal, Disney, and UCF. Recently upgraded with queen bed, stove, and access to brand-new washer/dryer. (City of Orlando Short-Term Rental registered.)

Oct 20 – 27

R1,947 ZAR per night