Luxury Vacation Rentals with a Private Pool in Winchester

Luxury Vacation Rentals with a Private Pool in Winchester

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 3 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Winchester

Wine Country, Pool. Spa. Game Room. Fire Pit. BBQ property photo 1

Wine Country, Pool. Spa. Game Room. Fire Pit. BBQ

5 bedrooms•4 baths
1,789 US dollars for 3 nights•

~$140 less than other sites

Private Pool & Spa, Temecula Wine Country Close property photo 1

Private Pool & Spa, Temecula Wine Country Close

4 bedrooms•2 baths
1,353 US dollars for 3 nights•

~$105 less than other sites

Indian Knoll - Via De La Sky Ranch property photo 1
Luxury

Indian Knoll - Via De La Sky Ranch

6 bedrooms•4 baths
2,496 US dollars for 3 nights•

~$200 less than other sites

Welcome to private poolside luxury in Winchester

Welcome to private poolside luxury in Winchester

Swap the bustle for wide-open skies in Winchester, California, where our luxury private-pool vacation rentals put relaxation center stage. Each home pairs striking contemporary design with outdoor living that shines in Southern California light: sparkling pools, generous patios, and lounge-ready yards made for slow mornings and golden-hour swims.
Inside, expect hotel-grade comforts like crisp linens, ultra fast WiFi, and meticulous cleaning, supported by 24/7 concierge care. From smart kitchens to serene primary suites, every detail is dialed in so you can arrive and unwind. Choose a Wander in Winchester for a seamless blend of privacy, style, and resort-caliber pool time.

Available soon in Winchester

Wine Country, Pool. Spa. Game Room. Fire Pit. BBQ property photo 1

Wine Country, Pool. Spa. Game Room. Fire Pit. BBQ

5 bedrooms•4 baths
1,789 US dollars for 3 nights•

~$140 less than other sites

Private Pool & Spa, Temecula Wine Country Close property photo 1

Private Pool & Spa, Temecula Wine Country Close

4 bedrooms•2 baths
1,353 US dollars for 3 nights•

~$105 less than other sites

Indian Knoll - Via De La Sky Ranch property photo 1
Luxury

Indian Knoll - Via De La Sky Ranch

6 bedrooms•4 baths
2,496 US dollars for 3 nights•

~$200 less than other sites

All homes in Winchester

Wine Country, Pool. Spa. Game Room. Fire Pit. BBQ property photo 1

Wine Country, Pool. Spa. Game Room. Fire Pit. BBQ

5 bedrooms•4 baths
1,789 US dollars for 3 nights•

~$140 less than other sites

Private Pool & Spa, Temecula Wine Country Close property photo 1

Private Pool & Spa, Temecula Wine Country Close

4 bedrooms•2 baths
1,353 US dollars for 3 nights•

~$105 less than other sites

Indian Knoll - Via De La Sky Ranch property photo 1
Luxury

Indian Knoll - Via De La Sky Ranch

6 bedrooms•4 baths
2,496 US dollars for 3 nights•

~$200 less than other sites

View all homes

Highlights in Winchester

Discover Winchester's scenic charm, offering easy access to sparkling recreational lakes, renowned Southern California wineries, and fascinating prehistoric history.
Diamond Valley Lake
Western Science Center
Lake Skinner Recreation Area
Temecula Valley Wine Country
Old Town Temecula

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 Winchester

Jacuzzi (3)
Private chef (1)
Hot tub (3)
Outdoor pool (3)
Sound system (1)
Garden (3)
Bbq area (3)
Pool table (1)
Game console (1)
Mountain view (1)
Foosball table (1)
Ping pong table (1)
Fire place (1)
Dryer (3)
Washer (3)
Patio (1)

More popular private pool destinations near Winchester

Private pool vacation rentals in Palm Springs
Private pool vacation rentals in Cathedral City
Private pool vacation rentals in Big Bear Lake
Private pool vacation rentals in Rancho Santa Fe
Private pool vacation rentals in Rancho Mirage
Private pool vacation rentals in Dana Point
Private pool vacation rentals in Palm Desert
Private pool vacation rentals in Thousand Palms

Other popular amenities & vacation types in Winchester

Family vacation rentals in Winchester
Large group vacation rentals in Winchester
Discover more beyond the pool in Winchester

Discover more beyond the pool in Winchester

Framed by rolling hills and Temecula Valley’s vineyards, Winchester rewards travelers with wide horizons and golden light. Days are warm, evenings glow pink over the San Jacinto Mountains, and clear nights invite unforgettable stargazing. Nearby Lake Skinner and Diamond Valley Lake add serene shorelines, while the Santa Rosa Plateau paints the seasons with wildflowers and rustling oaks.
Positioned within easy reach of acclaimed tasting rooms and desert day trips, it offers a refined, low-key pace that makes every plan feel effortless. This is why Wander’s luxury private-pool vacation rentals in Winchester, California are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Winchester

Why should I book a Wander in Winchester 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 Winchester 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 Winchester?

Some of our most popular private pool vacation rentals in Winchester include Wine Country | Pool. Spa. Game Room. Fire Pit. BBQ, Private Pool & Spa | Temecula Wine Country Close, and Indian Knoll - Via De La Sky Ranch. 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 Winchester?

Wander offers 3 private pool vacation rentals in Winchester, 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 Winchester?

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

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

Yes. Every Wander home in Winchester 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.