Some info has been automatically translated. Show original language

Family-friendly vacation 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.

%{current} / %{total}1 / 1
Top guest favorite
A warm living space features wooden paneling and natural light from large windows. A comfortable chair sits beside a small wooden table, and a piano is positioned nearby. Decorative plants hang from the ceiling, complemented by a cozy fireplace and a bookshelf in the background.
Home in Forestville
4.96 out of 5 average rating, 296 reviews

Forest Cozy Home

My house in Forestville is a walk to the river (Steelhead County Beach), near endless wineries, canoe rentals, gorgeous Sonoma coast beaches, Santa Rosa airport, a bicycle trail through West County with bike rentals in downtown Forestville offering immediate access to the trail, and a very well-stocked little grocery store a 5-minute walk down the hill. Lovely back roads take you to Healdsburg to the north or Sebastopol to the south. My dog & I stay in a basement studio when guests are here.

Top guest favorite
The inviting guest suite features a queen bed with soft linens, complemented by a cozy seating area with a light-colored sofa. Natural light flows through the plantation shutters, enhancing the neutral tones of the decor. A small table is set with a notepad and pen.
Guest suite in Windsor
4.97 out of 5 average rating, 462 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 favorite
A spacious sleeping area is highlighted by a large bed, adorned with a coral coverlet and decorative pillows. Two nightstands with lamps flank the bed, while colorful artwork decorates the walls, creating a bright and inviting atmosphere.
Guest suite in Santa Rosa
4.85 out of 5 average rating, 250 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 favorite
The studio cottage features a balanced layout with a queen bed highlighted by wooden furnishings. A small desk and an ergonomic chair are positioned near a wall-mounted television. Natural light illuminates the space through two windows, creating a comfortable environment.
Guesthouse in Santa Rosa
4.89 out of 5 average rating, 1,189 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 favorite
Home in Santa Rosa
4.98 out of 5 average rating, 103 reviews

Botany House Designer Home with Hot Tub

Discover your Wine Country sanctuary in this lush, design-forward Santa Rosa retreat. With a chef’s kitchen, a six-person hot tub, a fire pit, and Restoration Hardware furnishings, every detail is crafted for comfort and style. Perfectly located near wineries, Michelin-star dining, and redwood adventures, it’s ideal for families or friends seeking luxury and connection. Book your escape today. We are pet-friendly. Message us on Social Media at Inspired in Sonoma for Inspiration and Tips.

Top guest favorite
A cozy guest suite features a queen-size bed with a textured blanket and decorative pillows. A small desk with a chair and a mini fridge are positioned nearby. Soft lighting and wall art enhance the ambiance, while a ceiling fan provides comfort.
Guest suite in Junior College
4.94 out of 5 average rating, 231 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.

Guest favorite
A three-story building is seen with a colorful facade displaying verdant green, red, and yellow hues, surrounded by trees. The outdoor pool area features lounge chairs along the water's edge, illuminated against a night sky. The interior image shows a kitchen with wooden cabinets and dining space.
Apartment in Windsor
4.87 out of 5 average rating, 188 reviews

Windsor 2 Bed/2 Bath Condo ~ Pool ~ Hot Tub ~ Gym

***Condo: 1,023 square feet 2 bedroom/2 bath- King size bed in the master bedroom, two twin beds in the 2nd bedroom (can be put together to make a king), and one queen Murphy bed in the living room. Additional amenities include a full kitchen and dining area, gas fireplace, washer and dryer and a private terrace with gas barbecue. Maximum occupancy is six. *** twin beds in 2nd bedroom can be put together to make a king size bed. Please request in advance.

Top guest favorite
A spacious living area features a blue sofa adorned with a soft orange throw. A large area rug with intricate patterns anchors the space, while natural light floods in through large windows. A wooden coffee table rests centrally, complemented by decorative items.
Home in Windsor
4.96 out of 5 average rating, 432 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.

Guest favorite
A cozy living area features a light-colored sofa adorned with patterned cushions. A small wooden table sits in front, with a glass of water on it. A sliding glass door opens to the private patio, providing natural light and outdoor views.
Guest suite in Santa Rosa
4.77 out of 5 average rating, 441 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 favorite
A bright living area features a cozy twin size daybed with patterned pillows. Two upholstered chairs with a cow print design sit across from each other on a colorful area rug. Natural light streams through the windows adorned with shutters, creating a welcoming atmosphere.
Apartment in Santa Rosa
4.99 out of 5 average rating, 307 reviews

Robin's Nest

Your second home is above our 2-car garage, a 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, a 10-minute drive to downtown Santa Rosa, 45-minute drive to the coast and little over an hour to San Francisco. We are centrally located to explore Sonoma and Napa County wineries, breweries and hiking trails. Permit #SVR23-170

Guest favorite
A spacious studio apartment features a queen bed with neutral bedding, complemented by a small wooden table and two chairs positioned nearby. Natural light enters through a window adorned with a floral wall hanging, providing a cozy atmosphere.
Guest suite in Petaluma
4.88 out of 5 average rating, 171 reviews

Family Friendly Central Petaluma Studio

Our studio is only a few blocks from the heart of Petaluma. The Theatre District, Petaluma Market, and a myriad of local restaurants are all a 10 to 15 minute walk from your doorstep. We have two kids of our own (3 and 4) and we've set up the space to be comfortable for families traveling. There is ample space for everyone to spread out with a queen bed, 2 full size futons, and a crib included in the space.

Guest favorite
A private patio area is depicted, featuring wooden decking and surrounding foliage. A small metal chair is positioned on the patio, providing a peaceful spot to enjoy the outdoor scenery. In the background, a green landscape with distant hills is visible under a cloudy sky.
Guest suite in Santa Rosa
4.9 out of 5 average rating, 746 reviews

Wine Country guest house

This large private studio apartment is modern and cozy. You are next to beautiful country side while you are in the city. There is a large patio for you to relax and enjoy the beautiful wine country view. You can drive or ride your bike to Sonoma Wine Country at HWY 12 or to Russian River Brewery. The Listing excludes Tax. The unit has short term permit form Santa Rosa SVR24-056.

Popular amenities for Windsor family-friendly rentals

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$48,937 GYDG$47,055 GYDG$47,891 GYDG$46,428 GYDG$48,101 GYDG$50,401 GYDG$51,238 GYDG$49,565 GYDG$48,728 GYDG$49,774 GYDG$48,101 GYDG$50,401 GYD
Avg. temp10°C10°C11°C11°C12°C13°C14°C14°C15°C13°C12°C10°C

Quick stats about vacation rentals that are family-friendly in Windsor

  • Total vacation rentals

    Explore 250 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at G$10,457 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,790 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    200 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    240 of Windsor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor rentals

  • 4.9 Average rating

    Windsor stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore