Family-friendly holiday rentals in Windsor

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Windsor

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

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Top Guest favourite

Guest suite in Windsor

4.97 out of 5 average rating, 450 reviews

Private Entrance Suite in Heart of Wine Country

Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.

Guest favourite

Guest suite in Santa Rosa

4.85 out of 5 average rating, 247 reviews

Cozy private quiet in-law with garden entrance

Our studio has a private entrance with SELF CHECK IN. Our city permit is SVR25-056. We are close to a lovely spot to run, walk or cycle at Paulin Creek Preserve. Grocery stores (including an organic one) and a variety of restaurants, coffee shops, and retail outlets are nearby. The views from your private covered deck are serene. You’ll love our place because of the outdoors space, light, comfy bed, and quiet neighborhood. It is good for couples, solo adventurers, and business travelers.

Top Guest favourite

Guesthouse in Santa Rosa

4.89 out of 5 average rating, 1,169 reviews

Clean Comfy Cottage Downtown

Our tree shaded studio cottage is one block from the heart of downtown. Stay just a two block walk from Russian River Brewing. This clean and quiet cottage has a full kitchen, a comfortable queen bed. I am happy to customize the space to your needs. I offer soft and firm mattresses. I use cotton blankets so that you can have any weight on your bed that you would like. You are welcome to stack seven or more blankets at a time. I will adjust my cleaning regimen to meet your preferences.

Top Guest favourite

Apartment in Windsor

4.97 out of 5 average rating, 109 reviews

Pool + 4 Hot Tubs! Gym, Luxury 2 bedroom villa.

Two Bedroom Twins: King in master, twins in second bedroom, queen Murphy bed in living area. Maximum occupancy 6. Full Kitchen: Unit includes refrigerator, sink, range and dishwasher. Resort has Pool, Children's Pool, Hot Tub, and much more. ❤ Free Parking. Free Internet ❤ ★ If reserving a FRIDAY OR SATURDAY there is a 2 night minimum unless request is made last minute (3 days before check in)★ ★24 hour reception★ ★Calendars updated daily★ ★Multiple Units/Room Sizes Available★

Guest favourite

Guest suite in Junior College

4.94 out of 5 average rating, 223 reviews

Cozy Private Guest Suite Centrally Located

This recently remodeled guest suite in Santa Rosa’s Junior College neighborhood offers a cozy retreat for 1-2 guests. It features a queen-size bed with a natural latex mattress, Smart TV, WiFi, mini fridge, microwave, Keurig coffee maker, and electric kettle. Relax in the shared garden courtyard with Adirondack chairs, a bistro table, and a propane grill. On-street parking is plentiful, and with a Walk Score of 85, you’re close to shops, dining, and the college.

Top Guest favourite

Farm stay in Healdsburg

4.97 out of 5 average rating, 617 reviews

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

Top Guest favourite

Home in Windsor

4.96 out of 5 average rating, 425 reviews

Winelight Vineyard Home With Spa

Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

Top Guest favourite

Apartment in Santa Rosa

4.99 out of 5 average rating, 301 reviews

Robin's Nest

Our home is a 10-minute drive to downtown Santa Rosa, where you will find Russian River Brewing Company, 45-minute drive to the coast, and a little over an hour to San Francisco. The apartment is above our 2-car garage. It's a quiet 1 bedroom, 1 bath, living room, full kitchen and dining area. A twin size daybed is in the living room. Local grocery stores are within a mile, and close to Sonoma County wineries, breweries and hiking trails. Permit #SVR23-170

Guest favourite

Home in Santa Rosa

4.92 out of 5 average rating, 238 reviews

The Explorer’s Wine Country Getaway

Discover the perfect mix of ease and comfort in this charming one-bedroom bungalow, nestled in the heart of wine country. Perfect for a relaxed escape, this cozy retreat features a queen-sized bedroom, a bathroom, and a full-size pullout sofa in the living room. Every detail is designed with your comfort in mind, ensuring a stay that’s both delightful and memorable. Experience the magic of wine country living and make your getaway one to remember!

Top Guest favourite

Guest suite in Santa Rosa

4.99 out of 5 average rating, 372 reviews

The Suite Life! Permit Number#SVR24-040

Our private Airbnb is an extremely comfortable guest suite of over 700 square feet with air conditioning and a gas fireplace. It's beautifully decorated with a large sofa and dining area. You'll have complete privacy with your own entrance and parking space plus free WiFi. Located in a beautiful area. World class wineries, and parks are minutes away. Please feel free to message Janette with any questions about the suite! Permit Number#SVR22-078

Superhost

Guest suite in Santa Rosa

4.78 out of 5 average rating, 427 reviews

Dedicated Patio, Roku & Self Check-In

Premium guest suite with private entrance, separate living room and dedicated outdoor patio area. Complete with complimentary popcorn, coffee, tea and water for your enjoyment. Located 2.4 miles to Down Town Santa Rosa & Russian River Brewing Company, half mile to groceries & restaurants, 7.4 miles to Sonoma County Airport and 2-5 miles to all major hospitals. Best for 2 guests due to size. Longer stays discounted. Permit Number: SVR21-197

Top Guest favourite

Cabin in Occidental

4.97 out of 5 average rating, 558 reviews

Rustic Yet Luxurious Cabin in the Redwoods

This rustic yet luxurious cabin is the perfect place to unplug. Walk through the woods, relax by a fire, and enjoy the food and wine of the Russian River Valley. 10 minutes from the beach. Minutes from Occidental, Graton, Forestville, and Guerneville. House has a full bathroom, bedroom downstairs with a Cal King bed and one upstairs with two twin beds. 5 acres in the redwoods, trampoline, fire pit area, high-speed Internet.