Holiday rentals in Glenoak Hills

4.99 out of 5 average rating, 189 reviews

A cozy red cabin is showcased with a covered porch and wooden steps leading up. Two black adirondack chairs sit on the porch, complemented by a small table. Large windows provide natural light, while surrounding oak trees offer shade and a serene setting.

Cabin in Temecula

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.

4.99 out of 5 average rating, 101 reviews

A welcoming living space is displayed with a comfortable sofa facing a large window that provides views of rolling hills. Two bar stools are positioned at a high table beside the window, while decorative elements enhance the room's character.

Guest suite in Temecula

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!

4.99 out of 5 average rating, 412 reviews

A bright living area features a yellow sofa adorned with colorful cushions. Natural light enters through multiple windows, illuminating the wooden floors and a cozy stone fireplace. A wooden coffee table is surrounded by art pieces, creating a welcoming space for relaxation.

Cottage in Temecula

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.

A spacious pool area features a clear blue pool complemented by a rock formation with a water slide. A covered pavilion with seating is visible nearby, set against a backdrop of rolling hills under a bright blue sky.

4.89 out of 5 average rating, 213 reviews

Wine Country Retreat-Pickleball, Expansive Acres

Welcome to Temecula Wine Country Retreat. Tucked away in the hills of wine country, this five-acre retreat is a one-of-a-kind property and the perfect escape for all families, wine-goers, golfers, and those searching for peace and serenity. Our custom home offers seven bedrooms*, an in-ground spa, a pool slide, and a custom pavilion with three TVs. We also have a pickleball court, horseshoe pit, soccer goals, dart board, Bocce Ball court, and ping pong table! Let us cater to you and your family!

A serene outdoor seating area features four gray chairs arranged around a fire pit, with decorative cushions adding a pop of color. Rolling hills and vineyards are visible in the background, under a cloudy sky with a hint of blue.

4.99 out of 5 average rating, 113 reviews

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.

A spacious living area is furnished with brown leather seating, arranged to encourage conversation. A wooden coffee table sits in the center, complemented by large windows that offer views of the surrounding greenery.

4.89 out of 5 average rating, 230 reviews

Coyote den in wine country (3br/2bath)

Why coyote den? Because they live at the edge of the property! You have nothing to worry about though...they tend to shy away from people. But you may hear them and may see them. Your place is located on top of a hill on 2 1/2 acres. This is an older home in a great location. You are a bike ride distance to all the wineries and walking distance to a few. Pechanga Casino and Old Town Temecula are 15 minutes away. There are 2 queen beds, 1 king and a double sofa bed. 50in smart TV. Kitchen

5.0 out of 5 average rating, 155 reviews

A colorful hot air balloon hovers above a spacious villa with a stone-accented entrance. The structure features a tiled roof, arched windows, and a sandy driveway, set against a clear blue sky.

Guest house in Temecula

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.

4.86 out of 5 average rating, 138 reviews

Villa in Temecula

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.

A serene outdoor area features a sparkling saltwater pool surrounded by palm trees and tropical landscaping. The pool area is complemented by a spa and patio space, with the main house visible in the background against a vibrant sky.

4.98 out of 5 average rating, 256 reviews

♥ 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.

4.9 out of 5 average rating, 124 reviews

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.

A porch area is shown with a small table and two chairs. The view reveals lush greenery and a spacious outdoor area, including trees and seating arrangements. Natural light fills the scene, highlighting the peaceful ambiance of the surroundings.