Vacation rentals in Glenoak Hills

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.

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.

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.

Private Vineyard Estate Casita

Enjoy this magical experience as you immerse yourself in the heart of wine country in Temecula, CA where you wake up every morning to a sky full of hot air balloons! You can relax in your very own Casita and enjoy access to a 30ft. Infinity pool and jacuzzi that overlooks the vineyard and mountains. BBQ area with TV and lounge area. Beautiful working vineyard and gardens to walk and enjoy. Pool is not heated. Sit and read, sip wine, watch the sunset in one of our handcrafted Adirondack chair.

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.

Private Romantic Escape | Hot Tub | Endless Views

Escape to your private hilltop retreat & relax in your very own hot tub. Set on a beautiful 5-acre gated estate, this romantic getaway is located in the heart of the Temecula Wine Country offering the perfect combination of privacy, comfort, & unforgettable views. You’ll be centrally located just a few minutes from Temecula’s award-winning wineries, exceptional restaurants, Pechanga Resort Casino, Galway Downs, Old Town Temecula yet tucked away enough to feel like your own peaceful escape.

Luxury Cabin - Cedar Tub, Seasonal Creek & Views

Haven is Idyllwild's answer to mountain cabin luxury. Set overlooking a peaceful seasonal creek flowing winter and spring. A custom built inspirational hideaway, nestled in the mountains near LA. Immerse in nature with the creature comforts of a curated modern cabin. This spacious cabin sits in a forested valley overlooking a seasonal stream with a cedar hot tub. Ceiling to floor windows look out at the surrounding mountains & jaw-dropping rock cliffs. An expansive, open cabin feel.

Serene Spanish Villa | Vineyard | Near Wineries!

Enjoy your Temecula adventures from this centrally-located, luxurious and professionally-designed spanish masterpiece home, complete with quality finishes, chef's kitchen, wine cellar, valley views, lush garden, Cabernet Sauvignon vineyard encircling the home, and seasonal fruit orchard (fruit not always available). Inviting and unique outdoor seating areas with propane fire pit will invite you to enjoy our beautiful Temecula sunsets or observing the sunrise hot air balloons.

Modern New Home •Quiet Escape with Panoramic Views

Discover a modern retreat set on Bonsall’s rolling hills, offering sweeping views, glowing city lights, and vivid fall/winter sunsets. This newly built open-concept home features floor-to-ceiling windows and a spacious deck ideal for taking in the breeze, sunbathing, or stargazing. Private, peaceful, and thoughtfully designed for families and friends. Secluded in feel yet minutes from freeways, Oceanside beaches, dining, shops, wineries, wedding venues, and Frontwave Arena.

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.

Villa Artemis

Villa Άρτεμις is a luxurious villa located in Temecula's Wine Valley, with picturesque views of rolling hills & vineyards. Re-imagined in Aug 2023 with a focus on incorporating natural and organic materials, fragrant gardens, and culminating in an overall blissful space that bridges nature with luxury. The villa is located within 10 minutes of many of the region's award-winning wineries, equestrian activities, hot air ballooning, golfing, hiking and more!

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