Vacation rentals in Oak Glen

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oak Glen

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Cabin in Running Springs

4.95 out of 5 average rating, 192 reviews

Cozy A-Frame Cabin Nestled In The Mountains

An hour and a half away from Los Angeles, enjoy a cozy, modern A-Frame cabin steps away from seasonal Arrowbear Lake. Outfitted with lightning-fast WiFi, heat, A/C, a bidet, rainfall shower and vaulted ceilings. The Lazy Loft is perfect for a couple's or family getaway. Enjoy a centrally-located taste of the mountains! During the Winter: → 5 mins from Snow Valley → 30 mins from Bear Mountain / Snow Summit During the Summer: → 10 minutes to swimming, fishing and hiking → 20 minutes to Big Bear

Guest favourite

Home in Yucaipa

4.89 out of 5 average rating, 95 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!

Guest favourite

Home in Cherry Valley

4.96 out of 5 average rating, 68 reviews

Secluded/Quiet Home-CherryValley

Fully remodeled home with mini golf. No more California blackouts with our Tesla Powerwall battery back up. Free 2-220v level-2 EV charging at your convenience. 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 FWY 10. You will love the darkness and tranquility of rural life at night. Close to Oak Glen, Yucaipa, Redlands, Beaumont, Banning, San Jacinto wedding venues and outdoor activities.

Top guest favourite

Guest suite in Yucaipa

4.96 out of 5 average rating, 56 reviews

Cozy Master Studio w/ Private Entrance

Cozy and comfortable master suite with private entrance. New french doors open into a private bedroom with a newly remodeled bathroom, small kitchenette, 2 large closets, and a quaint outdoor area that extends the living area. Smart television mounted to the wall and a ceiling fan to keep guests cool. Property located in Upper Yucaipa only 5 minutes from downtown Yucaipa, YPAC, restaurants, the regional park and 10 minutes from Oak Glen Preserve, 15 minutes from Historic Redlands.

Superhost

Guest suite in Beaumont

4.96 out of 5 average rating, 24 reviews

The Beau Cottage | Beautiful and Private Stay

Welcome to The Beau Cottage! This petite home is perfect for someone needing a quiet space to work, relax or visit family & friends. Beaumont is also about an hour away from most destinations in SoCal. The cottage has its own private entrance, full kitchen, living room, big bedroom & bathroom. There is also a stove with full oven, microwave, toaster oven and coffee maker to enjoy your home cooked meals. There may be guests staying in other separate units during your stay.

Superhost

Loft in Banning

4.86 out of 5 average rating, 111 reviews

Apartment w/ Kitchen 8 min to Casino & 10-Freeway

A beautiful apartment with a cozy one-bedroom and bathroom. Enjoy a relaxing and exclusive vacation in this apartment with a kitchen, kitchen appliances (stove, microwave, fridge), dining table, and living room. One loveseat that converts to a bed. Also a washer/dryer at no extra cost! In the city of Banning, a perfect area near, Cabazon Outlet is 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

Top guest favourite

Home in Yucaipa

4.96 out of 5 average rating, 129 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

Guest favourite

Cabin in Forest Falls

4.91 out of 5 average rating, 216 reviews

Forest Falls Creek side hot tub & vintage Cabin

This location is phenomenal located right on a freshwater creek. The sound of the water from creek and the views of the water below the deck are amazing. 1939 rustic original Vintage Cabin with stone fireplace. Deck with hot tub overlooking creek. Very simple camp stove, rustic feel. TV only plays DVD’s. Verizon cell service phone for you use w/wifi hotspot. Another cabin across the road to rent for added space: airbnb.com/h/vintage-mountain-cabin-with-hot-tub

Guest favourite

Home in Oak Glen

4.88 out of 5 average rating, 43 reviews

The Garden House in Oak Glen

The Garden House is nestled among the San Bernardino Mountains in beautiful Oak Glen! The Oak Hollow property is walking distance to the Oak Glen Steak House and the Oak Glen store, as well as a short drive to Oak Tree Mountain, Los Rios Rancho Wilshires Apple Shed, and Riley's Farm. We are also within minutes of Serendipity and the Homestead wedding venues. The Garden House puts you in the perfect spot to enjoy Oak Glen and all apple country has to offer!

Top guest favourite

Cabin in Forest Falls

4.99 out of 5 average rating, 268 reviews

Palisades View - Cabin With Spa

This cabin has central air conditioning and 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 This cabin was recently remodeled and modernized with: - 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.

Top guest favourite

Guesthouse in Yucaipa

5 out of 5 average rating, 60 reviews

"The Olive Branch"

"The Olive Branch" is located in upper Yucaipa. Minutes away from beautiful Oak Glen, Forest Falls, and Historic Uptown Yucaipa. "The Olive Branch" is a stylish one bedroom, one bath, living area and kitchenette casita, attached to the main home with its own private entrance. "The Olive Branch" is in a great location for attending weddings in beautiful Oak Glen. No children, pets, or smoking permitted.

Superhost

Home in Yucaipa

4.76 out of 5 average rating, 75 reviews

Cheerful 5 Room Home w/ Salt Water Pool & Hot Tub

Forget your worries in this spacious and serene space. No parties and no speakers are allowed in the house or yard! The single air mattress can be used anywhere. Most people choose to use it in the upstairs den or the office room. Early check-in and/or late check-out is $55 per hour extra and also depends on availability.