Kenwood, California

Wander Kenwood Retreat

8 bedrooms 14 beds 3 baths 19 guests 4.8 (15)

About the property

Escape to the Kenwood Family Estate, a luxurious Wine Country retreat perfect for families and groups. This stunning 8-bedroom estate boasts a private pool, hot tub, gym, and sports courts, offering endless entertainment. Located in the heart of Sonoma County, you'll be minutes from world-class wineries and restaurants. Enjoy the ultimate in comfort and convenience with resort-style amenities and breathtaking views. Book your unforgettable Wine Country getaway today! This home is proudly managed by LegacyRnR, your local Wine Country hospitality experts. We're here to make your stay effortless and unforgettable—from arrival to check-out. Need transportation for wine tasting or group outings? We offer two private, comfortable options: 11-Passenger Wine Tour Van – Perfect for group tastings, birthday trips, or bachelorette weekends. 6-Passenger Cadillac Escalade – Ride in style for intimate wine tours, airport pickups, or dinner reservations. Want to skip the grocery run? We also offer pre-arrival kitchen and pantry stocking, so you can start relaxing the moment you walk in. When you book with LegacyRnR, you’re not just booking a home—you’re booking your entire Wine Country experience, curated by locals who care. Welcome to the Family Estate with Pool, Gym & Sports Courts — your private Wine Country playground. Tucked into the hills of Kenwood, this expansive estate offers the perfect retreat for families, groups, and wine lovers looking to unwind in style and seclusion. With 8 bedrooms, resort-style amenities, and acres of oak-studded land, it’s your personal slice of Sonoma paradise. 🏡 The Property Surrounded by trees and golden light, the estate combines comfort and classic Wine Country charm. Floor-to-ceiling windows and vaulted ceilings fill the home with natural light. Lounge in the open living room with plush seating and a stone fireplace, or gather in the oversized dining room that opens to a massive deck for al fresco dining. 🛏️ Sleeping arrangements: 5 bedrooms with king beds 2 bedrooms with two twin beds each 1 bedroom with five twin beds, ideal for kids or singles 🛁 Multiple modern bathrooms, including double-vanity layouts and backlit mirrors, ensure space and privacy for all guests. 🍳 Chef’s kitchen with a gas range, Sub-Zero fridge, butcher block island, and all the essentials for group meals or a private chef experience. 🌿 Outdoor Amenities The grounds are where this estate truly shines: 75 foot pool (heating fee of $200/day May 1–Oct 1, $300/day otherwise) Hot tub with easy guest-controlled timer Full gym, tennis court, basketball court, pickleball, ping pong, bocce ball, putting green, zipline, and large grass play area Fire pits, outdoor dining areas, and extensive lounging decks surrounded by nature Beautiful string lights for magical evenings under the stars 🍷 Local Wineries & Dining Located in the heart of Sonoma County wine country, you’re minutes from world-class tasting rooms and restaurants: Mayo Family Winery, VJB Cellars, Ledson Winery, and Chateau St. Jean are all within a short drive Enjoy dinner at Glen Ellen Star (great for pickup too), Salt & Stone, or the charming Fig Café 🐾 Pet Policy We welcome well-behaved pets! Please note: The yard is not fenced A $300 per pet deep-clean fee applies to ensure the home is allergy-friendly for future guests 🚐 Add-on: Private Wine Tasting Transportation Let us drive you! Book our Cadillac Escalade (6 guests) or 11-passenger Transit Van for wine tasting or dinner outings. It’s the safest, most enjoyable way to explore Sonoma. 🕙 House Rules & Sonoma County Compliance Sonoma County Vacation Rental Information: Vacation Rental License #: LIC25-0491 Vacation Rental Permit #: TVR25-0030 Transient Occupancy Tax (TOT) Certificate #: 3033N Quiet Hours: 9:00 PM – 7:00 AM Parking: On-site parking only (no street parking) Events & Gatherings: Not permitted beyond the maximum overnight occupancy Trash: Place all refuse in provided bins; do not leave trash outside of containers Come stay where nature meets luxury, and create unforgettable memories in Wine Country. Getting around Kenwood is easy! While a car is recommended for exploring the area, we offer private transportation options (6-passenger Cadillac Escalade and 11-passenger Transit Van) for wine tours and airport pickups. The nearest major airport is Sonoma County Airport (STS), approximately a 30-minute drive. San Francisco International Airport (SFO) is about a 1.5-hour drive. Parking is free on the property. For public transit, options are limited in Kenwood, so rideshares or our private services are best for getting around. Important Details for a Relaxing Stay at Kenwood Family Estate: Check-in time is 4:00 PM, and check-out time is 10:00 AM. We offer complimentary parking on the premises. If you're traveling with furry friends, we're happy to welcome them for a deep-clean fee of $300 per pet. Please note our quiet hours are from 10:00 PM to 7:00 AM to ensure a peaceful environment for all. Pool heating is available for an additional fee. From May 1st to October 1st, the cost is $200 per day, and otherwise, it's $300 per day. Let us know in advance if you'd like to heat the pool. Please be aware that parties and events are not permitted. The maximum occupancy is 19 guests. For any assistance during your stay, contact us via the platform's messaging system. At Kenwood Family Estate, we're dedicated to making your stay seamless and enjoyable. Our team at LegacyRnR is available to assist you throughout your visit. We're generally available from 24/7 to answer any questions or address concerns. The best way to reach us is through the platform messaging system, where we aim to respond within one hour. For urgent matters, you can also contact us via the platform, and we'll do our best to assist you as quickly as possible. We're here to ensure you have a memorable Wine Country experience!

Escape to the Kenwood Family Estate, a luxurious Wine Country retreat perfect for families and groups. This stunning 8-bedroom estate boasts a private pool, hot tub, gym, and sports courts, offering endless entertainment. Located in the heart of Sonoma County, you'll be minutes from world-class wineries and restaurants. Enjoy the ultimate in comfort and convenience with resort-style amenities and breathtaking views. Book your unforgettable Wine Country getaway today! This home is proudly managed by LegacyRnR, your local Wine Country hospitality experts. We're here to make your stay effortless and unforgettable—from arrival to check-out. Need transportation for wine tasting or group outings? We offer two private, comfortable options: 11-Passenger Wine Tour Van – Perfect for group tastings, birthday trips, or bachelorette weekends. 6-Passenger Cadillac Escalade – Ride in style for intimate wine tours, airport pickups, or dinner reservations. Want to skip the grocery run? We also offer pre-arrival kitchen and pantry stocking, so you can start relaxing the moment you walk in. When you book with LegacyRnR, you’re not just booking a home—you’re booking your entire Wine Country experience, curated by locals who care. Welcome to the Family Estate with Pool, Gym & Sports Courts — your private Wine Country playground. Tucked into the hills of Kenwood, this expansive estate offers the perfect retreat for families, groups, and wine lovers looking to unwind in style and seclusion. With 8 bedrooms, resort-style amenities, and acres of oak-studded land, it’s your personal slice of Sonoma paradise. 🏡 The Property Surrounded by trees and golden light, the estate combines comfort and classic Wine Country charm. Floor-to-ceiling windows and vaulted ceilings fill the home with natural light. Lounge in the open living room with plush seating and a stone fireplace, or gather in the oversized dining room that opens to a massive deck for al fresco dining. 🛏️ Sleeping arrangements: 5 bedrooms with king beds 2 bedrooms with two twin beds each 1 bedroom with five twin beds, ideal for kids or singles 🛁 Multiple modern bathrooms, including double-vanity layouts and backlit mirrors, ensure space and privacy for all guests. 🍳 Chef’s kitchen with a gas range, Sub-Zero fridge, butcher block island, and all the essentials for group meals or a private chef experience. 🌿 Outdoor Amenities The grounds are where this estate truly shines: 75 foot pool (heating fee of $200/day May 1–Oct 1, $300/day otherwise) Hot tub with easy guest-controlled timer Full gym, tennis court, basketball court, pickleball, ping pong, bocce ball, putting green, zipline, and large grass play area Fire pits, outdoor dining areas, and extensive lounging decks surrounded by nature Beautiful string lights for magical evenings under the stars 🍷 Local Wineries & Dining Located in the heart of Sonoma County wine country, you’re minutes from world-class tasting rooms and restaurants: Mayo Family Winery, VJB Cellars, Ledson Winery, and Chateau St. Jean are all within a short drive Enjoy dinner at Glen Ellen Star (great for pickup too), Salt & Stone, or the charming Fig Café 🐾 Pet Policy We welcome well-behaved pets! Please note: The yard is not fenced A $300 per pet deep-clean fee applies to ensure the home is allergy-friendly for future guests 🚐 Add-on: Private Wine Tasting Transportation Let us drive you! Book our Cadillac Escalade (6 guests) or 11-passenger Transit Van for wine tasting or dinner outings. It’s the safest, most enjoyable way to explore Sonoma. 🕙 House Rules & Sonoma County Compliance Sonoma County Vacation Rental Information: Vacation Rental License #: LIC25-0491 Vacation Rental Permit #: TVR25-0030 Transient Occupancy Tax (TOT) Certificate #: 3033N Quiet Hours: 9:00 PM – 7:00 AM Parking: On-site parking only (no street parking) Events & Gatherings: Not permitted beyond the maximum overnight occupancy Trash: Place all refuse in provided bins; do not leave trash outside of containers Come stay where nature meets luxury, and create unforgettable memories in Wine Country. Getting around Kenwood is easy! While a car is recommended for exploring the area, we offer private transportation options (6-passenger Cadillac Escalade and 11-passenger Transit Van) for wine tours and airport pickups. The nearest major airport is Sonoma County Airport (STS), approximately a 30-minute drive. San Francisco International Airport (SFO) is about a 1.5-hour drive. Parking is free on the property. For public transit, options are limited in Kenwood, so rideshares or our private services are best for getting around. Important Details for a Relaxing Stay at Kenwood Family Estate: Check-in time is 4:00 PM, and check-out time is 10:00 AM. We offer complimentary parking on the premises. If you're traveling with furry friends, we're happy to welcome them for a deep-clean fee of $300 per pet. Please note our quiet hours are from 10:00 PM to 7:00 AM to ensure a peaceful environment for all. Pool heating is available for an additional fee. From May 1st to October 1st, the cost is $200 per day, and otherwise, it's $300 per day. Let us know in advance if you'd like to heat the pool. Please be aware that parties and events are not permitted. The maximum occupancy is 19 guests. For any assistance during your stay, contact us via the platform's messaging system. At Kenwood Family Estate, we're dedicated to making your stay seamless and enjoyable. Our team at LegacyRnR is available to assist you throughout your visit. We're generally available from 24/7 to answer any questions or address concerns. The best way to reach us is through the platform messaging system, where we aim to respond within one hour. For urgent matters, you can also contact us via the platform, and we'll do our best to assist you as quickly as possible. We're here to ensure you have a memorable Wine Country experience!

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
May 18, 2026$1,200Not Available1
May 19, 2026$1,200Not Available1
May 20, 2026$1,511Not Available1
May 21, 2026$3,068Not Available1
May 22, 2026$4,647Not Available6
May 23, 2026$4,850Not Available6
May 24, 2026$4,109Not Available6
May 25, 2026$3,516Not Available6
May 26, 2026$1,250Not Available1
May 27, 2026$1,250Not Available1
May 28, 2026$1,250Available1
May 29, 2026$1,250Available1
May 30, 2026$1,250Available1
May 31, 2026$1,250Not Available1
Jun 1, 2026$2,475Not Available1
Jun 2, 2026$2,178Not Available1
Jun 3, 2026$2,272Not Available1
Jun 4, 2026$2,745Not Available1
Jun 5, 2026$3,720Not Available1
Jun 6, 2026$1,500Available2
Jun 7, 2026$1,500Available2
Jun 8, 2026$1,500Available2
Jun 9, 2026$1,500Not Available2
Jun 10, 2026$2,000Not Available2
Jun 11, 2026$2,000Available2
Jun 12, 2026$2,000Not Available2
Jun 13, 2026$3,823Not Available1
Jun 14, 2026$2,864Not Available1
Jun 15, 2026$2,482Not Available1
Jun 16, 2026$2,190Not Available1
Jun 17, 2026$2,277Not Available1
Jun 18, 2026$3,129Not Available1
Jun 19, 2026$4,299Not Available1
Jun 20, 2026$4,451Not Available1
Jun 21, 2026$2,918Not Available1
Jun 22, 2026$2,555Not Available1
Jun 23, 2026$2,052Not Available1
Jun 24, 2026$2,174Not Available1
Jun 25, 2026$2,638Not Available1
Jun 26, 2026$3,549Not Available1
Jun 27, 2026$3,643Not Available1
Jun 28, 2026$2,800Not Available1
Jun 29, 2026$2,800Not Available1
Jun 30, 2026$2,800Available1
Jul 1, 2026$2,800Not Available1
Jul 2, 2026$2,748Not Available3
Jul 3, 2026$4,248Not Available3
Jul 4, 2026$4,165Not Available3
Jul 5, 2026$3,163Not Available3
Jul 6, 2026$2,000Available1
Jul 7, 2026$2,000Available1
Jul 8, 2026$2,000Available1
Jul 9, 2026$2,000Not Available1
Jul 10, 2026$3,200Not Available3
Jul 11, 2026$3,200Not Available3
Jul 12, 2026$2,500Available1
Jul 13, 2026$2,500Not Available1
Jul 14, 2026$2,234Not Available2
Jul 15, 2026$2,348Not Available2
Jul 16, 2026$2,818Not Available3
Jul 17, 2026$3,902Not Available3
Jul 18, 2026$2,000Available1
Jul 19, 2026$2,000Available1
Jul 20, 2026$2,000Not Available1
Jul 21, 2026$4,194Not Available2
Jul 22, 2026$4,194Not Available2
Jul 23, 2026$4,194Not Available2
Jul 24, 2026$4,194Not Available2
Jul 25, 2026$4,194Not Available2
Jul 26, 2026$3,171Not Available3
Jul 27, 2026$2,200Available2
Jul 28, 2026$2,200Available2
Jul 29, 2026$2,200Not Available2
Jul 30, 2026$3,043Not Available3
Jul 31, 2026$3,951Not Available3
Aug 1, 2026$3,406Not Available1
Aug 2, 2026$3,406Not Available1
Aug 3, 2026$3,406Not Available3
Aug 4, 2026$3,406Not Available3
Aug 5, 2026$3,406Not Available3
Aug 6, 2026$3,406Not Available3
Aug 7, 2026$3,406Available1
Aug 8, 2026$3,406Not Available1
Aug 9, 2026$2,805Not Available3
Aug 10, 2026$2,399Not Available2
Aug 11, 2026$1,600Not Available5
Aug 12, 2026$1,600Not Available5
Aug 13, 2026$2,602Not Available3
Aug 14, 2026$3,535Not Available3
Aug 15, 2026$3,108Available3
Aug 16, 2026$3,108Not Available3

Amenities

Pool outdoor
Hot tub
Gym
Fire pit
Fire place
Patio
Mountain view
Garden view

4.8 · 15 reviews

A
Anonymous
2 weeks ago

Excellent host.

Lindsey
Lindsey
January 2026

The place was amazing for our large group! The amount of bedrooms and large living and dining room were so enjoyable. The host was incredibly responsive when we did have a few questions. Would 10/10 recommend!

Aldo Enrique Balarezo
Aldo E.
January 2026

Great place to stay, recommend.

Where you'll be

Kenwood, California, 95452, United States

Wander Kenwood Retreat is nestled in Sonoma County’s picturesque Kenwood region, offering an idyllic escape amid rolling vineyards, oak-studded landscapes, and wine country tranquility. From this serene location you’re just minutes from exceptional wineries like Benziger, Ledson, and Chateau St. Jean, where tasting experiences and vineyard vistas await. Nature lovers can explore scenic trails, including those in Jack London State Historic Park, or take leisurely drives through the Sonoma Valley with stops at local farmstands, tasting rooms, and charming village shops. When the mood strikes, savor acclaimed culinary offerings at nearby restaurants or unwind back at the retreat as night falls, enjoying the fresh air and starlit skies in this peaceful countryside setting.

Things to know

Cancellation policy

Contact us for cancellation policy details prior to booking.

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
Pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 19 guests.