Vacation rentals in Glenoak Hills

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Top-rated vacation rentals in Glenoak Hills

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Top guest favorite

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

4.99 out of 5 average rating, 378 reviews

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.

Top guest favorite

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

4.99 out of 5 average rating, 141 reviews

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.

Guest favorite

An open-air deck frames sweeping views of the surrounding hills and mountains. The space features wooden beams, a barbecue grill, and seating areas, with soft natural lighting illuminating the terrace. Details of the rocky landscape can be seen in the distance.

Tiny home in Aguanga

4.92 out of 5 average rating, 200 reviews

High Desert Tiny Home w/ Sauna

The Rambler is tucked amidst boulder strewn hills in the high desert with sweeping views of the hills and mountains beyond. With 12’ ceilings and thoughtful layout, this tiny home provides 2 sleeping areas (queen/twin), open concept living+kitchen, bathroom w/composting toilet, and a 10’ counter perfectly positioned to enjoy the peaceful scenery. This is paired with a spacious deck, bbq, and sauna. Step away. Reconnect. Come discover a different way of doing things. Welcome to The Rambler.

Top guest favorite

A private patio area is presented with a round table and two chairs, surrounded by potted greenery. Double glass doors provide entrance to the interior, with light-colored walls complementing the outdoor space. The setting is open, featuring a clear sky in the background.

Guest suite in Temecula

4.98 out of 5 average rating, 425 reviews

Celestial Moments of Temecula - Casita Cosmos

At Casita Cosmos, you will enjoy the pastoral valley and rolling hills from the private patio outside your entrance, highlighted by the Palomar Mountains and the Observatory domes in the distance. This is the the inspiration for the Space related wall decor throughout the casita, which is set up for comfort and relaxation. It's a short drive to Temecula Wine Country and event venues, and a great jumping off spot for other attractions, but note that Old Town & shopping can take 20+ minutes...

Top guest favorite

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.

Guesthouse in Temecula

5 out of 5 average rating, 126 reviews

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.

Guest favorite

A cozy living area features a reclining loveseat adorned with a soft blanket. A dining table with black chairs is set near a small refrigerator. Artwork hangs on the walls, and natural light filters through the window with white blinds.

Cottage in Temecula

4.9 out of 5 average rating, 106 reviews

Rejuvenation Cottage -Wine Country Tranquility

Rejuvenate your spirit at this newly renovated cottage with privacy and tranquility on a large lot in the heart of the wine country, right behind Wilson Creek and Monte de Oro winery. Whether it's a spirit rejuvenation or a romantic getaway, this is the ideal place. Wake up and see the hot air balloons flow by, or enjoy the tranquility with a glass of wine on the front porch in the afternoon. With only one other house on this massive 4.6-acre lot, this is an experience unlike any other.

Guest favorite

The entrance to the casita features a welcoming white door flanked by potted plants and a decorative wreath. A wooden porch with two chairs provides a cozy outdoor seating area, while a mat lies in front of the door, inviting guests to step inside.

Guest suite in Temecula

4.98 out of 5 average rating, 266 reviews

Spacious casita in the heart of Wine Country

Get comfortable and enjoy plenty of extra room in this spacious casita. This large space is family friendly with plenty of room for two adults and one or two young children. It features a queen bed, futon, kitchenette, eating area and attached bath. Stroll the 4.36 acre property, enjoy the views of neighboring vineyards and balloons floating above. Walk, drive or Uber to dozens of nearby wineries. Enjoy the sights, sounds, restaurants, and shopping in Old Town Temecula. (Permit #000256

Top guest favorite

A charming cabin is set in an open landscape, featuring a spacious deck with wooden railings and steps leading up to it. The exterior is constructed of wood, with large windows allowing natural light to enter. Surrounding vegetation and a gravel path enhance the rustic feel.

Ranch in Hemet

4.98 out of 5 average rating, 246 reviews

Cabin Retreat at BigD'sX2 Ranch

Enjoy the view and relax at this unique-tranquil glamping cabin getaway. Located in Sage 17 miles from Temecula wineries, local lakes include, Diamond Valley, Skinner, and Hemet Lake. Local casinos, Romona Bowl, hiking, horse trails & room for RV parking. Relax on the deck or covered patio with a beautiful view, or head to your favorite activity. No guest service fee(s), no cleaning fees, and farm fresh eggs included. Nightly discounts when booking 3 or more nights.

Top guest favorite

The exterior of the single-family home is shown, featuring a covered porch with potted plants lining the entrance. The light-colored building has windows on either side of the front door, with a gravel driveway leading up to the residence against a clear blue sky.

Home in Temecula

4.97 out of 5 average rating, 194 reviews

The Arena in Temecula Wine Country

This single-family home, on the eastern edge of wine country, sits on a 5-acre piece of property, on a hill in a quiet neighborhood with a beautiful view of the countryside, San Jacinto, and San Bernardino mountains. Close to the wineries, but secluded. A nice quiet, relaxing property. This is the perfect house for work from home or a weekend getaway. There is a Starlink satellite dish for Wi-Fi and Netflix, but no local TV. The house has everything you'll need.

Top guest favorite

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.

Home in Temecula

5 out of 5 average rating, 139 reviews

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.

Guest favorite

A cozy outdoor fire pit area is surrounded by light-colored Adirondack chairs, set on a gravel surface. A small patio with a table and umbrella is visible, and the cottage in the background features large glass doors that lead to a picturesque hillside.

Guesthouse in Temecula

4.97 out of 5 average rating, 181 reviews

The Cottage Overlooking Wineries-Panoramic Views

Welcome to The Cottage at Mira Bella Ranch! Sit back and enjoy panoramic views of beautiful Temecula Wine County from the guesthouse on this 10 acre, off-grid, family ranch. Located within 0.8-1.5 miles of 7 of the most popular wineries along the De Portola Wine Trail. Also within a 10 mile radius of Old town Temecula, Pechanga, Vail Lake, and Lake Skinner. Experience all the charm and serenity of countryside living without sacrificing convenience.

Guest favorite

A bright, open interior features a spacious bed with white linens and a minimalist design. A cozy area rug complements the terracotta tiled floor. A compact kitchenette is visible in the background, with shelves adorned with plants and decorative items creating a welcoming ambiance.

Guest suite in Hemet

4.9 out of 5 average rating, 251 reviews

Sycamore Hill Casita on 80 acre Horse Ranch

This quaint casita is located on an 80 acre horse ranch in the rural community of Sage. Quiet and peaceful but just a 15 minute drive to the very popular Temecula Wine Country and 25 minutes to Old Town Temecula. Old town Temecula has great restaurants, bars & a fun night life. The ranch as well as the casita patio have views that are unbelievable from every angle. You are also welcome to bring your horse to stay in a stall or pasture!