Luxury Vacation Rentals with a Private Pool in Pioneertown

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

Top-rated private pool vacation rentals in Pioneertown

Home in Pioneertown

1 bedroom•1 bath

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~$100 less than other sites

Luxury

Home in Pioneertown

3 bedrooms•2.5 baths

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~$40 less than other sites

Home in Pioneertown

2 bedrooms•2 baths

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~$30 less than other sites

Home in Pioneertown

2 bedrooms•3 baths

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~$45 less than other sites

Luxury

Home in Pioneertown

2 bedrooms•2 baths

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~$70 less than other sites

Home in Pioneertown

1 bedroom•1 bath

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~$90 less than other sites

Luxury

Home in Pioneertown

2 bedrooms•2 baths

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New

~$60 less than other sites

Home in Pioneertown

1 bedroom•1 bath

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New

~$75 less than other sites

Welcome to private poolside luxury in Pioneertown

Find your own desert horizon with Wander’s luxury private-pool vacation rentals in Pioneertown, California. Each stay balances boutique-hotel polish with the ease of a private home, framed by sweeping High Desert views and sun-soaked skies.

Expect resort-level privacy with a pool all to yourself, generous sun decks, spa hot tubs, and lounge-ready patios. Inside, enjoy hotel-grade bedding, pristine cleaning, designer kitchens, dedicated workstations with ultra fast WiFi, and fitness spaces for a quick sweat. With 24/7 concierge and consistently beautiful homes, Wander makes it effortless to arrive, unwind, and live poolside from sunrise to starlight.

Available soon in Pioneertown

Luxury

Home in Pioneertown

3 bedrooms•2.5 baths

•

~$40 less than other sites

Home in Pioneertown

2 bedrooms•2 baths

•

~$30 less than other sites

Home in Pioneertown

2 bedrooms•3 baths

•

~$45 less than other sites

Luxury

Home in Pioneertown

2 bedrooms•2 baths

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~$70 less than other sites

Luxury

Home in Pioneertown

2 bedrooms•2 baths

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New

~$60 less than other sites

Luxury

Home in Pioneertown

3 bedrooms•2 baths

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~$365 less than other sites

Luxury

Home in Pioneertown

3 bedrooms•3.5 baths

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~$70 less than other sites

Luxury

Home in Pioneertown

3 bedrooms•3 baths

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~$35 less than other sites

Featured private pool vacation rentals in Pioneertown

Luxury

Home in Pioneertown

3 bedrooms•2 baths

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~$365 less than other sites

Luxury

Home in Pioneertown

6 bedrooms•6 baths

Luxury

Home in Yucca Valley

2 bedrooms•2.5 baths

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New

~$200 less than other sites

Luxury

Home in Yucca Valley

2 bedrooms•2.5 baths

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~$220 less than other sites

Highlights in Pioneertown

Step back in time to the Old West in this historic movie-set town, offering desert scenery, unique shops, and legendary entertainment.

Mane Street

Pappy & Harriet's Pioneertown Palace

Pioneertown Film Museum

Red Dog Saloon

Pipes Canyon Preserve

Pioneertown General Store

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.

All homes in Pioneertown

Home in Pioneertown

1 bedroom•1 bath

•

~$100 less than other sites

Luxury

Home in Pioneertown

3 bedrooms•2.5 baths

•

~$40 less than other sites

Home in Pioneertown

2 bedrooms•2 baths

•

~$30 less than other sites

Home in Pioneertown

2 bedrooms•3 baths

•

~$45 less than other sites

Luxury

Home in Pioneertown

2 bedrooms•2 baths

•

~$70 less than other sites

Home in Pioneertown

1 bedroom•1 bath

•

~$90 less than other sites

Luxury

Home in Pioneertown

2 bedrooms•2 baths

•

New

~$60 less than other sites

Home in Pioneertown

1 bedroom•1 bath

•

New

~$75 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Pioneertown

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Other popular amenities & vacation types in Pioneertown

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Pet-friendly vacation rentals in Pioneertown

Hot tub vacation rentals in Pioneertown

Discover more beyond the pool in Pioneertown

Born as a live-in frontier set in the 1940s, Pioneertown blends Old West character with the quiet magnetism of the High Desert. Weathered facades along Mane Street, big-sky sunsets, and crystal-clear constellations create a sense of place that is cinematic yet unhurried.

Joshua Tree’s otherworldly boulder fields and yucca forests are close enough for sunrise outings and golden-hour photography. Add an acclaimed live music culture and a growing arts scene in nearby desert towns, and the area becomes a year-round draw for creatives and adventure seekers alike. This is why Wander’s luxury private-pool vacation rentals in Pioneertown are the perfect choice, whether you travel for work or leisure.

FAQs: Vacation Rentals in Pioneertown

Why should I book a Wander in Pioneertown 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 Pioneertown 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 Pioneertown?

Some of our most popular private pool vacation rentals in Pioneertown include Atomic Ranch, Wander Pioneertown Saloon, and Wander Pioneertown Desert. 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 Pioneertown?

Wander offers 28 private pool vacation rentals in Pioneertown, 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 Pioneertown?

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

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

Yes. Every Wander home in Pioneertown 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.