Holiday rentals in Glenoak Hills

Red Cabin Ranch Temecula Wine Country

Welcome to Red Cabin Ranch! Our cozy retreat provides natures serenity nestled in a 300 year old oak grove for the ultimate get-away-from-it-all experience in the true heart of wine country. We are a 3 minute drive to De Portola Wine Trail near Cougar and Masia de la Vinya and just steps to Estate Vinyard 2156 with exclusive tours available with its award winning vintner, upon request. Miles of walking & bike trails await or enjoy a leisurely swing in the shade & a friendly game of horseshoes.

Family · Location · View

Coyote Crossing Casita

Welcome to Coyote Crossing Casita! We are a pet-friendly destination! Drive up the long driveway & enter your own carport to the right of the casita. Once inside you’ll see a large bedroom, bathroom and walk-in closet. Continue into the living room & kitchen while noticing an enclosed patio/dog run for your pets! Enjoy being minutes from Temecula’s Wine Trail w/ amazing wineries within 5-10 minutes! Visit the lower property to visit our 21 chickens and enjoy fresh eggs daily during your stay!

Family · Value · Walkability

Romantic, private and surrounded by best Wineries!

Isolate in your hot tub overlooking a private vineyard in the heart of Wine Country! Wine theme decor throughout this cottage. Bedroom simulates a barrel room, sleep on unique bed of wine boxes and barrels. Full kitchen plus BBQ grill to create your own fine gourmet meals or visit local fine dining. Enjoy gazing at the magical starry Temecula skies from the comfort of a private custom cedar hot tub. Bring your horse for $50/night. Safe Driver discounts for same day bookings as schedule permits.

Family · Location · Wifi

Private Guesthouse overlooking vineyards & hills

Rogers Ranch once a racing quarter horse ranch, is now a place where we welcome visitors to enjoy the spectacular views of the Temecula Valley. We recently remodeled the guest home inside and out. Within walking/biking distance of 11 of Temecula's finest wineries on the De Portola Trail, and also close to many wedding venues. You will wake up to a sky filled with hot air balloons, and enjoy peaceful evenings with only a coyote howl in the distance Great hiking in the nearby hills and vineyards.

Location · Value · Check-in

Olive Manor - Luxury in the Heart of Wine Country

Romantic, English elegance in the heart of the Temecula Wine Country. Enjoy European ambiance in this beautiful, Tudor manor with lush gardens and a 70 tree olive grove. Olive Manor is the quintessential wine country getaway. This captivating estate features European architecture and provides perfect privacy and tranquility in southern California's Tuscany. Escape the city for a week or weekend and lounge poolside in Olive Manor's backyard oasis with waterfalls, birds of paradise and hot tub.

Family · Value · Shared spaces

Private 1 Bedroom Villa Overlooking the Vineyards

Enjoy the Quiet and Peaceful Serenity overlooking the Temecula Valley Wine Country in your Luxurious Private Villa with a Comfy Pillow Top King Size Bed, Fully Equipped Kitchen, Private Covered Patio and Unobstructed Views of the Wine Country and local mountain ranges. Located in the Glen Oaks Hills just a two minute drive from the De Portola Wine Trail and within 5 to 10 minutes from over 40 Wineries. Less than 10 minute Drive to CRC, Galway Downs and Green Acres and 15 minutes to Old Town.

Location · Value · View

Gorgeous Wine Country Home with 4 Master Suites

Welcome to Belle Volte Estate, a stunning 5,000 sq ft luxury estate set on 5 private acres in the heart of Temecula Wine Country. Ideally located just minutes from Temecula’s renowned wineries and Galway Downs, this expansive property offers breathtaking rolling views, resort-style amenities, and flexible sleeping accommodations for large groups. This Estate includes 4 Primary Suites all with own private bathroom and TV. Pool, Spa, & Fire Pit. Great for 4 to 8 to 17 guests.

Value · Family · Indoor spaces

♥ Of Wine Country | Privacy+, Gazebo, BBQ, Jacuzzi

Private, 3-BR, single-level home on 5 acres in the heart of Wine Country is a resort-style paradise. Self check-in. If you're looking for a party or large gathering this home is NOT for you. • Grill + Seasonal Pool (saltwater) + Jacuzzi. Pool toys on site. • Gazebo • Smart TVs • Work stations in two bedrooms • Fully equipped + stocked kitchen • On-site washer + dryer • 5 min drive to most wineries • Ping pong table • Pets allowed, with notice and additional fee.

Family · Location · Beach

Wine Country Retreat | Pool, Spa, Views

Escape to your private retreat in the heart of Temecula Wine Country. Perched on a peaceful hilltop, this elegant getaway features sweeping wine country views, unforgettable sunsets, a resort-style pool and spa, and four beautifully appointed king bedrooms. Just minutes from award-winning wineries, Old Town Temecula, Pechanga, and premier wedding venues. Perfect for wine country escapes, family getaways, girls' weekends, wedding stays, and relaxing retreats.

Value · Location · Access

The Love Shack -Temecula Wine Country

This private cheerful 1-bedroom apartment is nestled in the Temecula wine country. This property is just minutes from over 40 Temecula wineries. Have a glass of wine and BBQ your favorite meal on the porch while watching the beautiful sunset. In the morning, have a cup of coffee and wave to hot air balloons flying overhead. Enjoy the grounds, with a fishpond, succulent garden and fire pit. For extra fun, play a game of Pickleball, horseshoes or cornhole.

Family · Location · Bathroom

De Portola Vineyard and Retreat House-39950S

- Located on De Portola Wine Trail in the heart of Temecula Wine Country with 8 acres of Italian varietal mature grape. - adjacent to Cougar Winery & Frangipani Estate Winery - Pool and Spa with vineyard view. - Gentle slope upward creating the most amazing views from the hilltop estate built in 2015 - 3,800 square feet of living space and an additional 1,573 square feet of covered outdoor living and entertaining space - 5 Bedrooms 4.5 Bath & 7 beds

Family · Value · Check-in

Cavallini Family Vineyard Estate in Wine Country

Enjoy the great views on this 5 acre hill top property. You will have a 360 degree view of the city and hills of Temecula. Relax and soak in some sun on the patio or drive a short distance to the local wineries. This property is very private and has the most unbelievable views. The fireplace inside cannot be used also outdoor fire bowls next to the pool are not to be used due to very high risk fire zone. No events or parties.

Value · Family · Access