Pet-friendly vacation rentals in Windsor

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Top-rated pet-friendly home rentals in Windsor

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

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Top guest favorite
A bright living area features a leather couch with orange cushions, complemented by a comfortable armchair. Natural light enters through large windows, illuminating a wooden coffee table stacked with magazines. A fan hangs from the ceiling, and a flat-screen TV is mounted on the wall.
Guesthouse in Sebastopol
4.93 out of 5 average rating, 812 reviews

Sun Drenched Flat

Put up the burnt-orange parasol and settle down with book on the patio while the barbecue heats up. Sitting above a garage in a serene, walkable neighborhood, this sunlit retreat's beachy cream painted paneling gives it a chilled, refined vibe. Check out all that Sebastopol has to offer at: visitsebastopolnow.come This second story house is a very desirable space, located close to town, still being set on a very beautiful street in an friendly established older neighborhood. It is nestled between other structures on the property. One being a "Tiny House" that is right next door, my home sits behind the flat. The house has a full kitchen with all the utensils and necessary cooking items, pots pans etc. Large toaster oven that will even fit your frozen pizza. There is a space in front with some Adirondack chairs and BBQ if you want to relax outside. The house has its own separate entrance off the driveway. My house is in back of the flat, I may or may not see you, but I am available for any questions at any time. You will more than likely be greeted by our white cat with orange tips (named White Boy). If he gets a chance, Charlie our very exuberant Golden Doodle will give you a warm excited welcome. Located just 1 mile from the heart of the sweet town of Sebastopol, this area is a handy stepping off point to explore nearby wineries, scenic beaches, and shopping and restaurants at redwoods. A very nice mile walk to town or a five minute drive. There is a flight of stairs that you climb to get to the Flat space, it does not have wheelchair access. There are cats on the property, but they do not go inside the flat. Our Goldendoodle is extremely friendly. The leather couch folds flat into a double bed for accommodating two more guests. Access to the bathroom is through the bedroom however. There is no dedicated parking, however the street parking directly across from the flat, just up from, but not in front of the three mailboxes is usually always open.

Top guest favorite
A modern studio space features a spacious layout with a queen bed and a desk area. Natural light streams in through skylights and a window, highlighting the warm wood tones of the cabinetry and furniture. A cozy seating area includes a round table and an ergonomic chair.
Apartment in Sebastopol
4.99 out of 5 average rating, 739 reviews

Amy's Local BNB - walk to town **and hot tub!**

Amy’s Local BNB is nestled among huge fir trees in a quiet neighborhood a short walk from downtown Sebastopol. This sunny contemporary gem focuses on our commitment to local and sustainably sourced food, wine, and crafts. With a full kitchen, you can enjoy the comforts of a meal cooked “at home” from the local farmer’s market, or walk to superb local eateries. We will share maps to our favorite swimming hole on the Russian River or to ocean beaches, or introduce you to excellent local vintners.

Top guest favorite
A bright and welcoming living space features a mix of modern and cozy elements. Wooden beams enhance the ceiling above various seating arrangements, including a plush sofa and a round dining table. Natural light filters through large windows, highlighting framed art on the walls.
Cottage in Sebastopol
4.99 out of 5 average rating, 243 reviews

Designer Wine Country Cottage in Perfect Location

Welcome to your wine country home, with every detail carefully designed to be the perfect luxury retreat. A 2 bed, 1 bath, 800 sq ft cottage on a private half acre garden. Walking distance to two tasting rooms, a sunny cafe, late-night gastropub, and nature trail. A ten minute drive to 18 more tasting rooms. 25 minutes to the coast. With a fully-stocked kitchen, outdoor barbecue, visiting chickens, and luxury linens and towels, this is the perfect base to explore the best of wine country.

Top guest favorite
A modern kitchen features a large island with four bar stools, blending navy cabinetry with marble countertops. Bright windows illuminate the space, revealing a glimpse of the outdoor area. An elegant gold sink contrasts with stainless steel appliances and minimalist decor.
Home in Santa Rosa
4.98 out of 5 average rating, 108 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 spacious private deck is seen with views overlooking the rolling hills and valleys. Comfortable green lounge chairs are positioned for relaxation. The deck features wooden railing and steps leading down, while a doorway connects to the guest suite.
Guest suite in Santa Rosa
4.96 out of 5 average rating, 361 reviews

Wikiup lookout retreat

We self-developed our rural property as a secluded retreat with dog-friendly gardens. To share our creation with you, we designed a private 2nd-floor guest suite (ok to bring your good dogs). Your suite includes secure parking, private entrance, deck, kitchen, dining, living, 3 beds (queen, double, twin), one bath & a fenced back yard. We are on a country road near Healdsburg, Windsor, Russian River, Sebastopol, Santa Rosa, Calistoga, Sonoma & Napa valleys, wineries & beaches.

Top guest favorite
A private backyard features a solar heated swimming pool surrounded by lounge seating and potted plants. A tiki bar is visible in the background, with palm trees providing shade in the sunlight. The space combines relaxation and outdoor living for a serene atmosphere.
Home in Graton
5 out of 5 average rating, 687 reviews

Eco Luxury Private Sanctuary / The Farmhouse Oasis

**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols

Guest favorite
Home in Santa Rosa
4.94 out of 5 average rating, 210 reviews

Downtown Santa Rosa Walk to Russian River Brewery

Stylishly remodeled 3-bed, 1-bath Santa Rosa home, ideal for families or friends seeking easy Wine Country adventures. Walk to downtown restaurants, bars, and cafés, or explore nearby wineries, vineyards, Armstrong Redwoods, and scenic coastlines. Enjoy a beautifully updated kitchen, comfortable bedrooms, and inviting living spaces. Book today and make this your gateway to Sonoma’s outdoor beauty and Wine Country lifestyle. NOTE- Fireplace is not - functioning. TOT tax ID 3577.

Guest favorite
A dining area features a simple wooden table surrounded by four matching chairs. Natural light filters through the window, enhancing the light-colored walls and warm wooden floor. A ceiling fan is positioned above, providing a cool breeze in the space.
Home in Santa Rosa
4.94 out of 5 average rating, 166 reviews

West End Neighborhood Cottage

ID Tax 3099 1 bedroom cottage with a victorian-style interior tucked away with a quiet, shared yard and picnic table. Enjoy staying walking distance from historic Downtown where you'll find numerous small shops, microbreweries, bars, restaurants, gardens, book stores, coffee and local events. Blocks from multiple modes of public transportation makes this location perfect if you want to venture farther and explore the diverse landscapes of Sonoma County. Quiet Hours 9PM to 7AM

Top guest favorite
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg
5 out of 5 average rating, 216 reviews

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

Top guest favorite
A bright living area features a spacious white sectional couch and a wooden coffee table. An expansive bookshelf holds various items, with a television and fireplace being focal points. Large glass doors open to a garden, bringing in natural light and outdoor views.
Guesthouse in Healdsburg
4.97 out of 5 average rating, 229 reviews

Healdsburg Contemporary Cottage With Lush Backyard Patio

Your private Healdsburg retreat—just a 4-minute walk to downtown wine tasting rooms, restaurants, shops, and the Farmers Market. This stylish guest cottage offers parking in front of a private entry, garden with al fresco dining, BBQ, lounge area, and a fully equipped Pilates studio. Designed with international contemporary art and thoughtful touches, it’s perfect for a weekend escape or a longer stay while house hunting.

Top guest favorite
A spacious living area is illuminated by natural light from large windows. Plush sofas are arranged around a coffee table, while a fireplace adds warmth. A wall-mounted TV is positioned for easy viewing. A sliding door leads to an outdoor space with seating.
Home in Santa Rosa
4.94 out of 5 average rating, 281 reviews

Russian River Valley Brew-cation Home

Welcome to the Russian River Brewhouse! Where modern comfort meets rustic charm, and the good beer vibes flow as freely as the wine. Enjoy up-to-date appliances and amenities paired with cozy wrought-iron framed beds wrapped in warm, inviting blankets. This home is your home, offering the ideal balance of relaxation and adventure. Step inside, unwind, and get ready to explore all the wonders wine country has to offer.

Guest favorite
A two-story home is presented with a light-colored exterior, complemented by large windows. A spacious driveway leads to the attached garage, while a covered porch area with seating is visible. The surrounding yard features low-maintenance landscaping and a wooden fence providing privacy.
Home in Santa Rosa
4.94 out of 5 average rating, 216 reviews

Centrally Located, Modern Wine Country Estate

Conveniently located in the heart of wine country! Just minutes away from famous wineries, breweries, world class-dining, family 'Epicenter', Sonoma County Airport and downtown Santa Rosa. This home features a gorgeous, new modern kitchen, outdoor dining area under the pergola with a BBQ and fire pit, pool table, washer and dryer, free wifi and parking. Welcome home! - Sincerely, Your Wine Country Concierge.

Popular amenities for Windsor pet-friendly home rentals

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR4,136 ZARR3,837 ZARR4,403 ZARR4,498 ZARR5,001 ZARR5,489 ZARR7,108 ZARR7,470 ZARR6,495 ZARR5,787 ZARR5,772 ZARR5,095 ZAR
Avg. temp10°C10°C11°C11°C12°C13°C14°C14°C15°C13°C12°C10°C

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

  • Total vacation rentals

    Explore 40 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at R786 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 1,400 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 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!

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