Vacation rentals in Oak Glen

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Top-rated vacation rentals in Oak Glen

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

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Top guest favorite
Dome in Palm Springs
4.95 out of 5 average rating, 1,253 reviews

Seasonal Adventure Entire House with Amazing Views

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 favorite
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, 195 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 favorite
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 favorite
A covered patio is displayed with a striped awning and a wooden table surrounded by colorful seating. A potted plant sits at the center of the table. The natural view of trees and distant mountains creates a serene outdoor environment.
Cabin in Green Valley Lake
4.94 out of 5 average rating, 156 reviews

The Best Views and Vintage Cozy Cabin!

The most stunning sunset you have ever experienced with a scenic view of Lake Arrowhead in the distance! This rustic cabin sits on the edge of the San Bernardino Mountains, and has everything you need to get away. Green Valley Lake is located at 7200 feet making it the highest village, meaning more snow in winter and cooler temps in the summer. There is a swimming beach w/ lifeguards, boats to rent, and a well-stocked fishing lake 5 minutes away. We’re close to the ski slopes and hikes too.

Guest favorite
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!

Top guest favorite
A spacious living area features a comfortable gray sofa, a patterned rug, and large windows allowing natural light. A dining table for four is visible, with shelving displaying decorative items. The kitchen includes modern appliances, and a brightly painted door adds a pop of color.
Cabin in Sugarloaf
4.95 out of 5 average rating, 422 reviews

Amazing Cozy Cabin In Big Bear with Hot Tub!

Beautiful, relaxing two bedroom cabin in the woods. Enjoy the Fireplace while you watch TV or read. Need to soothe the body after a day of Mountain Biking or Skiing? Enjoy the Hot Tub and deck surrounded by towering Pines. Feel like cooking? Prepare your favorite meals in the kitchen or on the Grill. Added a cool deck hangout area last summer as well, a very relaxing and enjoyable space. Plus a fenced yard for Dogs! Pets OK with extra cleaning fee. Check out time 11am. Check in 4pm.

Guest favorite
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, 160 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 favorite
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, 236 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 favorite
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, 114 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!

Top guest favorite
The cabin, set among tall trees, features a gray exterior with warm, glowing windows. A stone pathway leads to the entrance, framed by natural landscaping. The tranquil setting hints at a peaceful atmosphere, ideal for a quiet getaway, especially during evening hours.
Cabin in Forest Falls
4.99 out of 5 average rating, 297 reviews

Palisades View - Cabin With Spa

This cabin was recently remodeled and modernized with: - Air conditioning (central AC) - Spa/hot tub on the deck with great view - Electric car charging station (L2, fast charger) - High speed internet - Laundry washer and dryer - Smart TV with YouTube TV included. You can log in with your NetFlix, etc. This cabin is located... 1/2 mile from Forest Home. 20 minutes from Oak Glen. 20 minutes from Redlands 15 minutes from Yucaipa 60 minutes from Big Bear

Guest favorite
The exterior view features a modern retreat set against a desert sunset. The house blends with the landscape, surrounded by boulders and desert vegetation. An inviting pool area is visible, complemented by outdoor seating arrangements, showcasing the seamless integration of architecture and nature.
Home in Yucca Valley
4.98 out of 5 average rating, 133 reviews

Rock Reach House | Featured in Forbes + Dwell

Welcome to Rock Reach House by Fieldtrip.  Discover this extraordinary and private retreat nestled in the breathtaking Southern California desert. This modern architectural masterpiece is perched amidst an unspoiled high desert landscape, surrounded by majestic weathered boulders, ancient juniper, pinón, and desert oak trees. Located in a private community, Rock Reach House offers an unparalleled blend of luxury, style, and tranquility.

Top guest favorite
A modern cabin is positioned on a raised deck, surrounded by tall trees. Warm lighting from the exterior illuminates the entrance, enhancing the cozy atmosphere as the dusk sets in. Stairs lead up to the deck, providing access to the inviting space.
Cabin in Running Springs
4.98 out of 5 average rating, 150 reviews

Peaceful A-Frame Cabin with Hot Tub Escape

Welcome to the Running Springs Tree House! Nestled in nature, our cozy retreat is the perfect getaway. Ski at Snow Valley—just a 10-minute drive away—or explore trails and seasonal creeks with a short walk to the San Bernardino National Forest. Visit Santa’s Village at Sky Park nearby. After a day of adventure, unwind in the hot tub or cook a meal in our fully equipped kitchen. Relax and rejuvenate!

Popular amenities for Oak Glen vacation rentals

Quick stats about vacation rentals in Oak Glen

  • Total vacation rentals

    Explore 10 vacation rentals in Oak Glen

  • Nightly prices starting at

    Oak Glen vacation rentals start at ﺩ.ﺇ367 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 vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oak Glen rentals

  • 4.9 Average rating

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