Family-friendly holiday rentals in Maitland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Maitland

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

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Guest favourite

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.

24–31 Jul

€ 239 per night

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

€ 132 per night

Guest favourite

Guest house 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)

5–12 Jun

€ 116 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

13–20 Jul

€ 111 per night

Guest favourite

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.

21–28 Mar

€ 242 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!

31 Mar – 7 Apr

€ 136 per night

Guest favourite

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.

3–10 Apr

€ 181 per night

Guest favourite

Guest suite in Altamonte Springs

4.92 out of 5 average rating, 316 reviews

The Bungalow

Welcome to your home away from home! Enter through a private driveway and enjoy the ease of keyless entry. Located across the street, Sanlando Park offers walking trails, basketball and popular tennis courts. Whether your interests are peace and quiet or adventure, you are only 30 minutes or less away from our beautiful natural springs, beaches and all major attractions. Wake up with the sunshine, put on a pot of coffee and welcome to Florida!

26 Sep – 3 Oct

€ 114 per night

Guest favourite

Guest house 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

31 Mar – 7 Apr

€ 127 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.:)

18–25 Apr

€ 108 per night

Guest favourite

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.

17–24 Aug

€ 161 per night

Guest favourite

Guest house 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.)

13–20 Aug

€ 112 per night