Luxury Vacation Rentals with a Private Pool in Windsor

Luxury Vacation Rentals with a Private Pool in Windsor

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 4 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Windsor

Station House property photo 1

Station House

4 bedrooms•3.5 baths
2,468 US dollars for 3 nights•
New

~$190 less than other sites

Boho Betty property photo 1

Boho Betty

4 bedrooms•2.5 baths
13,987 US dollars for 31 nights•
New

~$1,240 less than other sites

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting property photo 1
Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths
3,633 US dollars for 3 nights•

~$280 less than other sites

Spacious Santa Rosa Retreat - Outdoor Kitchen, Pool, Spa property photo 1

Spacious Santa Rosa Retreat - Outdoor Kitchen, Pool, Spa

4 bedrooms•3 baths
3,818 US dollars for 3 nights•

~$295 less than other sites

Welcome to private poolside luxury in Windsor

Welcome to private poolside luxury in Windsor

Find your own resort-style retreat with Wander’s luxury private-pool vacation rentals in Windsor, California. Each residence combines five-star consistency with the comfort of a private home, so the pool and terrace are always yours.
Swim unhurried laps in crystal-clear water, lounge on sunlit decks, and gather for golden hour dinners beside the pool. Inside, expect chef-ready kitchens, plush suites, dedicated workspaces, and ultra fast WiFi. Every stay includes inspiring views, pristine cleaning, and 24/7 concierge support for a truly effortless escape.

Available soon in Windsor

Station House property photo 1

Station House

4 bedrooms•3.5 baths
2,468 US dollars for 3 nights•
New

~$190 less than other sites

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting property photo 1
Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths
3,633 US dollars for 3 nights•

~$280 less than other sites

Spacious Santa Rosa Retreat - Outdoor Kitchen, Pool, Spa property photo 1

Spacious Santa Rosa Retreat - Outdoor Kitchen, Pool, Spa

4 bedrooms•3 baths
3,818 US dollars for 3 nights•

~$295 less than other sites

All homes in Windsor

Station House property photo 1

Station House

4 bedrooms•3.5 baths
2,468 US dollars for 3 nights•
New

~$190 less than other sites

Boho Betty property photo 1

Boho Betty

4 bedrooms•2.5 baths
13,987 US dollars for 31 nights•
New

~$1,240 less than other sites

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting property photo 1
Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths
3,633 US dollars for 3 nights•

~$280 less than other sites

Spacious Santa Rosa Retreat - Outdoor Kitchen, Pool, Spa property photo 1

Spacious Santa Rosa Retreat - Outdoor Kitchen, Pool, Spa

4 bedrooms•3 baths
3,818 US dollars for 3 nights•

~$295 less than other sites

View all homes

Highlights in Windsor

Discover a charming Sonoma County getaway filled with world-class wineries, scenic regional parks, and a vibrant, family-friendly town center.
Windsor Town Green
Foothill Regional Park
Riverfront Regional Park
Kendall-Jackson Wine Estate & Gardens
Notre Vue Estate Winery & Vineyards
Windsor Golf Club

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for private pool vacation rentals in Windsor

Outdoor pool (4)
Ev charger (2)
Jacuzzi (3)
Hot tub (3)
Sound system (1)
Garden (4)
Bbq area (2)
Patio (2)
Dryer (4)
Fire pit (1)
Hammock (1)
Washer (4)
Oven (4)
Kitchen (4)
Tv (4)
Dishwasher (4)

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Discover more beyond the pool in Windsor

Discover more beyond the pool in Windsor

Set within northern Sonoma County, Windsor offers an elegant slice of wine country with relaxed rhythm and beautiful light. The Town Green anchors the community with leafy promenades and seasonal events, while nearby vineyard hills and the Russian River create a cinematic backdrop that shifts from bright afternoons to pastel sunsets.
Mild weather invites outdoor moments throughout the year, from leisurely bike rides to scenic drives through valley floors and foothills. Excellent tasting rooms, farm stands, and arts events round out days that move at your pace. This blend of scenery and sophistication is why Wander’s luxury private-pool vacation rentals in Windsor are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Windsor

Why should I book a Wander in Windsor over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.
Every home in Windsor delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Windsor?

Some of our most popular private pool vacation rentals in Windsor include Station House, Boho Betty, and Healdsburg Haven - 3 BD plus Den, Pool, Spa & Wine Tasting. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Windsor?

Wander offers 4 private pool vacation rentals in Windsor, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Windsor?

You can check-in to Wander private pool vacation rentals in Windsor after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Windsor have WiFi access?

Yes. Every Wander home in Windsor has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.