Holiday houses in Oak Glen

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Top-rated holiday rentals in Oak Glen

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Dome in Palm Springs
4.95 out of 5 average rating, 1,239 reviews

Christmas Celebration Large House in Palm Springs

Large Private House and Property 3 Bdrms Sleeps 7 10 min drive to Palm Springs Perfect Romantic Getaway, Destination Retreat for Friends and Family Celebrations, Business, Music, Yoga, Writing, Arts, Music, Video & Photo Shoots Amazing Photo Opportunities View of Mountains and Windmills Follow us at: Palmspringsdomehome Note Extra Fees: Each Guest over 6 total per night, for Events , Weddings, Professional Photo & Video Shoot Not safe for children under 12 and pets Check-in 4 pm Check-out 11 am

Top Guest favourite
The exterior of a striking A-frame cabin is prominently displayed, framed by snow-covered ground and bare trees. Large front windows reflect the surrounding nature, while a balcony extends from the structure, providing a vantage point over the serene landscape.
Cabin in Running Springs
5 out of 5 average rating, 188 reviews

Romantic A-Frame Cabin | Hot Tub, Fire Pit, Skiing

❤️Escape to the most romantic cabin in Southern California-featured in Dwell Magazine❤️ ★ Perfect for a couple's getaway ★ Designer furnishings, high-end linens, luxury details ★ Hot tub surrounded by boulders ★ Firepit ★ Cozy fireplace ★ Hiking out the back door ★ Nespresso Vertuo espresso, coffee ★ 55" TV, WiFi, games ★ Gas grill ★ 7 min to Snow Valley ★ 5 min to Running Springs ★ 13 min to Sky-Park ★ 19 min to Lake Arrowhead ★ 25 min to Big Bear Lake ★ We welcome people from all backgrounds

Guest favourite
An outdoor gazebo is illuminated by soft blue lights, featuring a dining set and comfortable seating area. The space is surrounded by a well-kept patio, providing an inviting atmosphere for evening gatherings under the night sky.
Guesthouse in Cherry Valley
4.96 out of 5 average rating, 106 reviews

Secluded & Quiet Guest House-Cherry Valley-Morongo

Enjoy the lovely setting of this romantic spot in nature. Secluded and located in a farm area overlooking the San Gorgonio/San Bernardino National Forest/Big Bear mountains and yet just two miles away from the freeway 10. You will love the darkness and tranquility of rural life at night. Close to Oak Glen, Yucaipa, Redlands, Beumont, Banning, San Jacinto wedding venues and outdoor activities. No more CA blackouts with our Tesla battery back up. Free 2-220v level-2 EV charging at your convenience

Top Guest favourite
The exterior of a mid-century A-frame cabin is flanked by tall trees, showcasing a modern design with large glass windows. A wooden deck leads to the entrance, creating a welcoming path amidst the natural surroundings. Warm lighting glows from within, hinting at a cozy interior.
Cabin in Running Springs
4.95 out of 5 average rating, 283 reviews

Cozy Mid Century A- Frame Cabin Romantic + Hot tub

Come Cozy up in this Mid Century A - Frame, where you can kick off your shoes , relax your feet, body, and mind. Enjoy entire Cabin peacefully. There's Central AC and Heating. Escape here to A Lookout Lodge where you will be surrounded by nature, singing birds and tall pine trees. Enjoy the sparkling hot tub, grill some food, dream away in a good books. Play classic games by the fire and create priceless memories. Picture perfect A- Frame Loft awaits you to be snuggled in and dream away...

Guest favourite
Cabin in Crestline
4.94 out of 5 average rating, 152 reviews

Designer cabin at LAKE Gregory- walk to town

A sanctuary to provide respite from the fast- paced modern lifestyle where time seems to stand still, allowing for reconnection with nature and a focus on the simple pleasures of life. Located in the mountains next to Lake Gregory. 1930s cabin filled with vintage charm, nestled admits a lush pine forest. Newly renovated fully equipped kitchen, heat/AC, wifi. Enjoy lake activities and nearby skiing and let this special cabin transport you to a bygone era while evoking nostalgia and tranquility.

Top Guest favourite
A person sits at a table with a small vase of flowers, enjoying a scenic view of rolling green mountains and a clear blue sky. The lush landscape extends into the distance, with varying shades of green and hills melting into the horizon.
Guest suite in Crestline
4.99 out of 5 average rating, 244 reviews

Breathtaking Mountain Views | Romantic Hideaway

Holly Hill Chalet is ideal for romantic interludes or peaceful retreats, we promise an unforgettable experience. Expansive patios and park-like setting for garden. The true star of the show is the view an ever-changing masterpiece that transitions from incredible sunrises to beautiful sunsets, all the while offering a front-row seat to the awe-inspiring expanse below. As twilight descends, the view transforms into a sea of twinkling city lights, igniting the atmosphere with a touch of magic

Guest favourite
An outdoor living space features a large pool surrounded by sun loungers, with a cozy fire pit area nearby. The two-story estate is visible in the background, showcasing a blend of modern and rustic elements against a backdrop of mountainous scenery.
Home in Yucaipa
4.89 out of 5 average rating, 108 reviews

Vineyard Retreat, Pool & Amazing Views!

Experience luxury in this 6-bedroom vineyard estate with a grand pool, hot tub, and breathtaking views. Perfect for family gatherings or quiet retreats, our home offers a wheelchair accessible King suite, a music room with a grand piano, a dining area and billiards. Minutes from Serendipity Garden and historic Yucaipa Uptown, this property also features a full kitchen, outdoor BBQ and a full living room with 80" TV. Event chairs and tables available—ideal for celebrations or serene getaways!

Superhost
The exterior of a historic two-story house is visible, surrounded by well-kept grass and mature trees. A porch extends across the front, and multiple windows offer glimpses into the interior. The building reflects classic architecture with a subtle, inviting color palette.
Guest suite in Downtown Redlands
4.88 out of 5 average rating, 469 reviews

(2) Downtown Redlands Retreat: Cozy Master Suite

This is a nice master bedroom, converted to a guest suite. The room has a private entrance, and private bathroom. Walls were recently torn down & made sound proof so as to not disrupt our guest with noises inside the house. This house has a lot of history, it’s over 120 years old. It’s perfectly situated about a minute away from the freeway is a central locations, in the beautiful & historic city of Redlands. Security cameras recording at all times all around the outdoors of the property.

Guest favourite
A cozy sleeping area is presented with a spacious bed dressed in white linens and accented by decorative pillows. Black and gold patterned curtains frame the window, while a mirror reflects the inviting design. Nightstands with lamps are positioned on either side of the bed.
Guest suite in Banning
4.84 out of 5 average rating, 158 reviews

Cozy Suite w/ Kitchen 8 min to Casino & 10-Freeway

Welcome to our stunning studio retreat in the heart of Banning! Immerse yourself in relaxation and luxury in this cozy one-bedroom. The studio features a private layout, with a kitchen, dining table, and its own bathroom. All supplies needed to cook, with spices, pans, cups, plates and more. Near the city of Banning you'll find: 10-Freeway 5 min Cabazon Outlet 8 min Morongo Casino 11 min Palm Springs 31 min Joshua Tree Park 56 min Agua Caliente Casino 31 min Riley’s Farm 23 min

Guest favourite
A rustic living area features warm wood paneling and a high, sloped ceiling with exposed beams. A spacious bed is adorned with colorful textiles, while a cozy couch invites relaxation amidst plush pillows. Large windows provide natural light and views of the surrounding landscape.
Cabin in Forest Falls
4.91 out of 5 average rating, 233 reviews

Forest Falls Creek side hot tub & vintage Cabin

Located at 6000 feet on a remote dirt road, you will need 4 wheel drive or all wheel drive and chains to get here if there is snow. Location is phenomenal on a freshwater creek. 1939 rustic original Vintage Cabin with stone fireplace. Deck with hot tub overlooking creek and outdoor shower. Very simple camp stove, rustic feel. TV only plays DVD’s. Verizon cell phone w/wifi hotspot. Another cabin across the road to rent: airbnb.com/h/vintage-mountain-cabin-with-hot-tub

Top Guest favourite
A serene exterior view of a white two-story home is presented, with a wide driveway leading toward the entrance. To the left, rows of grapevines are visible, framed by mountainous greenery under a clear blue sky.
Home in Yucaipa
4.96 out of 5 average rating, 142 reviews

Quiet Vineyard View 2-bedroom Home Near Oak Glen

This 1700sqft spacious vineyard-view home is nestled on Yucaipa's North Bench in a peaceful, rural cul-de-sac. Close proximity to Oak Glen and Yucaipa's dedicated open space make this home a perfect landing spot for comfort and safety. Beautiful views of the mountain and vineyards. Centrally located to Oak Glen, Big Bear, Palm Springs. Bedroom 1: CalKing Bed Bedroom 2: Queen Bed Additional Beds: (2) Twins and pack-n-play upon request No parties/events are permitted

Top Guest favourite
An open layout private suite is depicted, featuring a spacious bed with a light blanket and a small kitchenette area. A countertop, microwave, and refrigerator are visible. Ceiling fans provide airflow to the light-filled room, enhancing comfort with warm wooden flooring throughout.
Guest suite in Beaumont
4.96 out of 5 average rating, 110 reviews

Quiet and cozy guest suite

Our private suite is clean & welcoming with a private studio-like floor plan with its own entrance. My wife and I are working professionals who love to host and meet new people. Our home is located within one hour of 36 hospitals & one hour to several universities including Riverside, Redlands, and CBU. Cabazon shopping outlets are 15 minutes away. Lovely Palm Springs about 38 minutes. Golfing, shopping, desert, mountains, food and more is at your fingertips!

Popular amenities for Oak Glen holiday rentals

Quick stats about holiday rentals in Oak Glen

  • Total holiday rentals

    Explore 10 holiday rentals in Oak Glen

  • Nightly prices starting at

    Oak Glen holiday rentals start at $150 AUD per night before taxes and fees

  • Verified guest reviews

    Over 320 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Oak Glen holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Oak Glen rentals

  • 4.9 Average rating

    Oak Glen stays are highly rated by guests—averaging 4.9 out of 5!