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.

Guest favorite

A colorful hot air balloon rises in the sky above a white house surrounded by landscaped gravel and vegetation. The patio features a shaded pergola and outdoor furniture, contributing to a relaxed outdoor atmosphere.

Home in Temecula

4.94 out of 5 average rating, 247 reviews

A Wine Country Comfort: In the heart of the valley

RivCo Ordinance #927 requires person responsible for making any AirBnB reservation be at least 25 yrs of age Nightly room rate is for TWO (2) adults & 2 night min Like other establishments, each additional guest (max 8)@ $30 extra per night & auto calculated when making the reservation Level 2 EV charger w/20' cord available We clean according to CDC guidelines NO smoking & NO pets Service Animal documentation required 100% Solar Powered 2-1/2 acres Most wineries and wedding venues within 15 min

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, 142 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, 206 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.

Guest favorite

A cozy outdoor deck features wooden seating arranged under a wooden pergola adorned with string lights. Potted plants add greenery on each side, creating an inviting space for relaxation. The camper is parked nearby, complementing the serene country setting at dusk.

Farm stay in Temecula

4.96 out of 5 average rating, 153 reviews

Charming rustic camper on a 22 acre private ranch

Welcome to this thoughtfully remodeled camper located just east of wine country in Temecula. Bring your kids, or have a romantic getaway to enjoy the scenery, and feed the rescue farm animals. While this farmhouse styled camper is the perfect private retreat in the country, it's conveniently located close to wineries, horseback riding, and Old Town Temecula. All of our profits go back to the animals. You are only: 5-10 mins to wineries 10 mins to horseback riding 25 mins to Old Town Temecula

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, 427 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, 127 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 stylish studio interior features a modern bathroom area with a vessel sink and illuminated mirror. The cozy sleeping space includes a spacious bed adorned with white linens, while natural light flows through the black-framed glass doors leading to the outside.

Guesthouse in Temecula

4.9 out of 5 average rating, 101 reviews

Glam Tiny House in the Country!

Unwind at this stunning Boho-Inspired studio under the stars! The studio was lovingly built with white shiplap, high ceilings, and modern details for a luxurious yet charming feel. Enjoy the stars and mountain views from our Bali-Inspired garden. The studio is located in the rural and peaceful hillside community of Rancho Spanish Hills, a quiet and serene setting for a couples getaway! Although the property feels peaceful and secluded, some of the best wineries are only 15-20 min away!

Top guest favorite

The exterior of a charming structure is surrounded by desert landscaping, featuring a mix of greenery and rock features. Warm sunset hues fill the sky, and a welcoming porch is presented under a pitched roof. Outdoor seating and games are available nearby.

Guesthouse in Temecula

4.98 out of 5 average rating, 127 reviews

The Roadhouse Follow us at @roadhousewinecountry

The RoadHouse! A cozy, stylish spot smack dab in the middle of wine country. You can walk to many wineries from our location, really! Or stay on site and enjoy the private jacuzzi spa (always hot!), have a round of mini golf or just relax on the deck. Located on a fully fenced property The Roadhouse has everything you need for a fantastic wine country getaway. Don’t forget to get up early and check out the hot air balloons. They land outside our fence most days!

Guest favorite

A welcoming covered porch features wooden decking and a metallic red roof. A white door leads into the property, complemented by a small window. Seating is provided by a wicker chair and a side table adorned with a plant. Decorative pots line the railing.

Guest suite in Temecula

4.95 out of 5 average rating, 327 reviews

Cozy casita in the heart of wine country

Take a break and relax in this rural oasis in the heart of wine country. You will enjoy the sounds of nature, the balloons drifting above and the sunsets over the vineyard. Stroll by the barn toward the corrals under the majestic eucalyptus trees while enjoying the view of the neighboring vines. Walk, bike, drive or Uber to dozens of nearby wineries. Enjoy the sights, sounds and smells of everything that Old Town Temecula has to offer. (Certificate # 000256)

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, 140 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.

Superhost

The estate is set amidst expansive vineyards, featuring a spacious layout with a combination of tile and stone pathways leading to a grand entrance. Surrounding gardens with colorful blooms and tall cypress trees add to the property's charm while showcasing its connection to the lush landscape.

Villa in Temecula

4.84 out of 5 average rating, 200 reviews

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