
Pet-friendly vacation rentals in Windsor
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Windsor

Total vacation rentals
Explore 30 vacation rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at R 809 ZAR per night before taxes and fees

Verified guest reviews
Over 1,310 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 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!
Top-rated pet-friendly home rentals in Windsor
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Gourmet Kitchen in Wine Country w/Hot Tub + Office
There is no better way to enjoy your stay in wine country than sipping on a glass of wine in this this stunning home! The 14ft bifold door invites out to the beautiful spacious yard where you can relax at any of the 4 sitting areas nestled under a beautiful display of lights. Featuring a chef kitchen, an office, large yard for children & pets, spacious bedrooms, stunning master bath, hot tub, fire table, games & more. Just minutes from elite award winning wineries, craft breweries & restaurants
WalkabilityPetsLaundry

Stunning Sauna Cottage Retreat on Private Vineyard
Welcome to our private, renovated, personal spa in the woods. Including a large wood-burning Finnish sauna, it features a picturesque deck with hot/cold plunge over breathtaking untouched forest with fire pit vineyard-side. This all-cedar cottage is nested below Halleck Vineyard, one of Sonoma County’s prestigious wineries. A perfect retreat, you are centrally located for the best Sonoma has to offer Sonoma County Wine Tastings (0-20 mins) Bodega Bay (20 mins) Armstrong Giant Redwoods (30 mins)
Outdoor spacesWalkabilityAccuracy

Healdsburg House - Chiquita Road
Relax with the whole family at this peaceful and private home mins to the Healdsburg Square, Montage Resort, and Dry Creek/Alexander Valley Wineries. The updated home features an open concept kitchen, two family rooms, and a sparkling hot tub on 1.5 private acres surrounded by vineyards and oak trees. Cruise your bike to town or head directly out Chiquita Road to some of the world's greatest cycling. 2.4 miles to the Montage Resort. 2.5 miles to the Healdsburg Square. Welcome to Wine Country!
PetsWalkabilityParking

Spacious 3BD/2BA, ideal for families!
Located in a quiet residential neighborhood in Santa Rosa, this spacious single level house is in the heart of California's Wine Country. With 3 bedrooms, 2 bathrooms, an open-plan living room and fully equipped kitchen there is plenty of room to cater for friends and family. The property has parking for two cars and outdoor seating to enjoy the great California weather on the new patio. Enjoy a local wine tour, explore a Giant Redwood forest or explore the stunning coastline at your feet.
PetsWalkabilityGetting around

Botany House Designer Home with Hot Tub
Property is managed by Inspired in Sonoma 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 and look forward to hosting you.
Outdoor spacesWalkabilitySleep quality

Wine Country Villa Heated Pool Hot Tub Upper Level
Welcome to Brush Creek, 20-minutes from Sonoma, Napa, Russian River, Alexander, and Knight's Valleys. Our cozy villa offers 2 unique bedrooms, including a regal King Master suite and a second King bedroom. Complimentary EV charging. Healdsburg, Calistoga, and the trendy Barlow are easily accessible. Brush Creek: where comfort, luxury, and character converge for an unforgettable wine country retreat. Heated Pool (fees may apply). No one else in the property during your stay. SVR26-101
PetsOutdoor spacesWifi

Elegant & Spacious Luxury Wine Country Estate
The perfect place for your group to stay in Wine Country! Featuring two large entertaining areas and an additional dining room, this is a great place for fun and relaxation! Play ping pong, pool or poker in our game room, or dine on our spacious patio under the pergola! Relax and soak in our hot tub and enjoy the zen gardens and tranquil water feature, or sip on a glass of wine by the outdoor fire pit. Close to the Sonoma County Airport, wineries, and world-class dining. Welcome home!
Outdoor spacesWalkabilityAmenities

Eagle's Nest Treehouse Farm Stay
Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.
WalkabilityPetsHeating

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
WalkabilityPetsKitchen

Wine Country Retreat | Pool, Hot Tub + Vibes
Summer-ready backyard + hot tub | Close to wineries Welcome to Happy House, a comfortable, clean, and welcoming home—perfect for a Sonoma County getaway any time of year. Ideal for wine tasting, visiting local breweries, hiking, mountain biking, plus weekend escapes, or remote work. 🌿 Private Backyard Large yard with pool, hot tub, and easy parking. 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal note: Outdoor cushions/umbrellas stored late Oct–mid May. Permit # SVR25-160
Outdoor spacesPetsAccuracy

Three-Building Healdsburg Homestead with Wine Barn
Your Healdsburg Homestead for launching wine country adventure! Recently remodeled, 3 buildings on 1/2 acre, including a barn with a winetasting bar & game room! Great for families and groups. Perfectly located for cycling on the legendary Eastside/Westside loop. For wine lovers, we are across the street from Rodney Strong Vineyard and the amazing sparkling wines of the beautiful J Vineyard. Best of all, Healdsburg Plaza is just a short hop away!
WalkabilityOutdoor spacesWifi

Farmhouse Villa w/ Captivating Views & Hot Tub
Experience the ultimate Wine Country escape. The property sits on 11 private acres, offering complete privacy, peaceful surroundings, and stunning 360-degree views, including the iconic Mount Helena. Ideally located near Calistoga (15 minutes) and Healdsburg (20 minutes) and surrounded by top-rated wineries. Whether you’re here for wine tasting, relaxation, or a scenic getaway, this property delivers space, comfort, and unforgettable views.
Outdoor spacesPetsValue
Popular amenities for Windsor pet-friendly home rentals
Pet-friendly house rentals

Eco Luxury Private Sanctuary / The Farmhouse Oasis
WalkabilityOutdoor spacesBathroom

Wine Country Cottage Escape
PetsOutdoor spacesCheck-in

Healdsburg Garden House
Outdoor spacesPetsCheckout

Amazing Santa Rosa Wine Escape Home
Outdoor spacesWalkabilityComfort

Wine Country Backyard Escape
Outdoor spacesWalkabilityHot tub

Centrally Located Modern Wine Country Home
Outdoor spacesWalkabilityTV

Sonoma Wine Retreat | BBQ • 3 Ensuite Baths
WalkabilityPetsLaundry

Wood-Haven | In Redwoods Creekside Cabin / Hot Tub
Outdoor spacesWalkabilitySleep quality
Pet-friendly home rentals with a pool

Pacific Gardens Retreat
PetsOutdoor spacesLong stay

Wine Country Retreat- Privacy-Spa/Pool/Games
WalkabilityPetsKitchen

Sonoma Retreat w/Pool/Spa/Barn/OD Kitchen/Orchard
WalkabilityOutdoor spacesValue

2 Wine Country Gem 2 Bedroom Upstairs
PetsWalkabilityCheckout

Casa Chiquita - Coziest in town!
WalkabilityPetsTV

Vineyard Haven: Pool, Hot Tub & Wine Country Charm
PetsWalkabilityLocation

Family Fun in Glen Ellen: Pool, Hot Tub & Views!
Outdoor spacesWalkabilityHeating

Charming Home w Pool+Hot Tub. Walk to Shops & Wine
Outdoor spacesWalkabilityValue
Private, pet-friendly home rentals

Wikiup lookout retreat
Outdoor spacesWalkabilityHospitality

Luxe Guest Suite in Dry Creek 5 mins From Town!
Outdoor spacesWalkabilityLaundry

PEACE & QUIET Close 2 Wine Hot Tub Fenced Yard
WalkabilityOutdoor spacesGetting around

Pixel Place - A Private Arcade + Outdoor Sanctuary
WalkabilityOutdoor spacesBathroom

The Perch - Outdoor Clawfoot Tub
Outdoor spacesWalkabilityEV charging

Country Carriage House in Downtown Geyserville
Outdoor spacesWalkabilityHospitality

Stunning Sonoma | HOT TUB | Game Room | Sleeps 6
PetsWalkabilityQuiet

Casa de Gamay - Your Home Away From Home
WalkabilityOutdoor spacesLocation
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 3,723 ZAR | R 4,258 ZAR | R 3,383 ZAR | R 4,128 ZAR | R 4,128 ZAR | R 4,258 ZAR | R 7,317 ZAR | R 7,689 ZAR | R 6,686 ZAR | R 5,455 ZAR | R 5,342 ZAR | R 5,099 ZAR |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°C |
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