Best Vacation Rentals in Oak Glen

Top Vacation Rentals in Oak Glen

Plan your perfect getaway with our selection of vacation rentals in Oak Glen. Each choice offers a blend of comfort and local charm, ideal for families and groups.

Vacation Rentals in Oak Glen
Vineyard estate with pool and amazing views
House
13822 Mustard Seed Drive, Yucaipa, CA, CA 92399, USA

Providing an outdoor swimming pool, Vineyard estate with pool and amazing views offers accommodations in Yucaipa. This property offers access to a patio, a pool table, free private parking, and free Wifi. The vacation home has an outdoor fireplace and a hot tub. Offering a balcony and mountain views, the spacious vacation home includes 6 bedrooms, 2 living rooms, cable flat-screen TV, an equipped kitchen, and 4 bathrooms with a walk-in shower and a hot tub. Featuring air conditioning, this unit has a dressing room and a fireplace. The vacation home offers bed linen, towels, and laundry service. You can play table tennis at the vacation home. San Bernardino International Airport is 19 miles from the property.

Amenities:

Security/Safety • Oceanfront • Fireplace/Heating • Other • Hot Tub • Sports/Activities • View • Air Conditioner • Wellness Facilities • Internet • Pool • Barbecue/Outdoor Cooking

Vacation Rentals in Oak Glen
Vintage Mountain Cabin
Cabin
Forest Falls, California, USA

Requires 4 wheel or all wheel drive car due to snow. Take it easy at this unique and tranquil vintage getaway. Located on a dirt road at 6000 feet, by a creek and forest.
You will feel like you stepped back in time to the 1940’s cabin life. This place is not new, it is well used, the floors, stove, refrigerator, and other items are vintage and do have stains, scratches and imperfections. Two wood stoves, a beautiful stained glass window, large bedroom, a sleeping loft, bar patio with BBQ.

All wood cabin interior walls and high ceilings. There is a large bedroom with queen bed, and fold out full size couch. In the living room there is a queen size fold out couch. Upstairs there is a loft with two full mattresses. There is 1 bathroom with a clawfoot bathtub that has a shower. Three is a small dining room, kitchen, laundry room, and an attached patio with darts, and chess, and a long seating area with bar stools and a bbq grill.
There are 4 parking spots in the driveway. No other parking available on the narrow dirt road.
Big Falls waterfall is a short 15 min walk up the dirt road also Vivian creek trailhead.

Guest Reviews:

- "It was a lovely property, walkable to some fun hikes. " - "We love love this cabin It’s so beautiful and inviting a little bit of everything. Jami Is wonderful host she make sure that we have everything that we need and she responds very quickly. We highly highly recommend this beautiful, beautiful cabin."

Vacation Rentals in Oak Glen
Spacious Golf Course Retreat - with Modern Kitchen
House
Yucaipa, CA, USA

Spacious Golf Course Retreat - with Modern Kitchen is located in Yucaipa, just 29 miles from Auto Club Speedway and 8 miles from University of Redlands. The property is around 9.5 miles from Morongo Golf Club, 21 miles from Jenks Lake Junction Recreation Area, and 23 miles from Barton Flats Forest Service Station. There's an outdoor fireplace and guests can use free Wifi and free private parking. The air-conditioned vacation home also provides a flat-screen TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 4 bathrooms with a bath and a shower. The property has an outdoor dining area. Guests can also relax in the garden. San Bernardino International Airport is 13 miles away.

Amenities:

Barbecue/Outdoor Cooking • Air Conditioner • Parking • Fireplace/Heating • Balcony/Terrace • Other • Security/Safety • Pet Friendly • Guest Services • Internet • View • Child Friendly

Vacation Rentals in Oak Glen
Forest Falls Creekside Cabin
Cabin
Forest Falls, California, USA

Wake up in the forest in a cozy 1939 Vintage Cabin with the sound of running water, nestled between beautiful old growth trees. High wood beamed ceilings & a spectacular rock fireplace transport you to another time. You will truly feel you have escaped to a piece of mountain heaven. Wrap around deck with hot tub, next to the creek, will guarantee relaxation.
You will have the entire property. Private use of cabin. It has a kitchen, bath, living room, fireplace, sleeping loft, and central heat. Large driveway. Creek on property. Outdoor shower. Hot Tub. Outdoor table for 4. Outdoor couch if weather permits. 2 redwood decks. BBQ. ***SNOW and WINTER STORM ⛈ This location sometimes requires 4x4 and chairs to access!
You will have use of:
Entire cabin
Wrap around deck
Outdoor Hot Tub on the creek
Outdoor shower
Outdoor propane fire pit and seating
BBQ
Dining table on deck
Creek in yard
Driveway parking for up to 4 cars
Fire wood
Clean towels and sheets

There is one across the street neighbor who is the best neighbor on earth, please be courteous and don't play loud music after 9pm. Basic price is for 2 guest, each additional guest adds $20 per day per guest to cover added linens, cleaning, and spa maintenance

Amenities:

Hot Tub • Sports/Activities • Parking • Fireplace/Heating • Other • Security/Safety • Entertainment • Balcony/Terrace • Child Friendly • Bedding/Linens • Internet • Kitchen

Vacation Rentals in Oak Glen
Hot Tub and Views Luxe Mountain Escape in Yucaipa
House
Yucaipa, CA, USA

Offering a garden, Hot Tub and Views Luxe Mountain Escape in Yucaipa offers accommodations in Yucaipa. This vacation home provides air-conditioned accommodations with free Wifi. Providing a patio with garden views, this vacation home also provides guests with a flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 8 bathrooms with a bath and a hair dryer. The accommodation has a fireplace. San Bernardino International Airport is 24 miles away.

Amenities:

View • Sports/Activities • Accessibility • Security/Safety • Child Friendly • Internet • Other • Parking • Fireplace/Heating

Vacation Rentals in Oak Glen
Perfect Location! Hiker's and Dogs (2) Paradise.! Walk to Trails!
Cabin
Forest Falls, California, USA

Truly a hiker or mt. biker's paradise! Our romantic cabin is good for couples, solo adventurers, and small families. The cabin sleeps four, but we'll let you put a fifth person to sleep on the couch if you like. Many wonderful hiking trailheads are nearby, including the famous Vivian Creek Trail to the peak of Mt. San Gorgonio. Walk to nearby trailheads for a day-hike, then return for a nice hot shower! Sports fishing is 15 minutes close at Jenk's Lake! Only 43 miles away and you'll be skiing at Big Bear Lake's world-class Ski Lodges! Only 88 miles away and you can surf the Pacific Ocean at "Surf City" Huntington Beach! Do them BOTH on the same day!

More information
The space

This is a truly unique mountain home for travelers who want to experience the spirit of a bygone age. Built in 1927 by a handyman from nearby Yucaipa, the cabin is a rustic retreat. Created before the age of air conditioning, flatlanders would escape the hot summers by dashing to their cozy mountain cabins that they built themselves. Welcome to ours!

Ample parking for two cars can be found in the driveway leading uphill to the cabin. The main entrance is up a short flight of steps but there is also a side entrance off the breakfast nook with no steps.

The living room is unusually spacious for this era and features a hand-built stone hearth with a classic river rock fireplace. (No fires or candles please.) The electric reclining chair is the best seat in the house, but the "L" shaped couch is a comfy place to snooze or sleep the night.

The mini kitchen hosts a propane range and oven, a new refrigerator and microwave. A new toaster is where we do most of our cooking. Everything you need is available to cook your gourmet meals.

The breakfast nook is delightful in the morning with a huge window view straight up the mountain. Don't forget a hot cup of coffee from our coffee maker or French press. There is also tea and an electric kettle.

The bathroom has a quant clawfoot shower-tub and pedestal sink, and of course, all bathroom amenities are included for your comfort.

The cabin features a main bedroom on the first floor, which holds a cozy full-size bed for two, topped with a snuggle-down quilt cover. The bedroom door shuts with a "do not disturb sign" for your added privacy!

There is a screened-in porch off the living room with a cozy kids bunk bed. (Two twin Zinus mattresses. See photos.)

The door off the front porch will lead you to the large outside elevated deck. Patio furniture is provided for your bird watching, reading, card games, and relaxing.

The mountain air is clear and refreshing. The tap water is cold, clear, and pure from our community owned springs and wells. Drink deep! Enjoy a few days to recharge your personal battery!

Guest access

You will have complete access to the entire property except the locked storage garage below and the locked attic space above.

Interaction with guests

We want you to have a 5-star visit! We value your privacy, but we are available by email, text, and emergency phone 24/7 for your convenience.

Other things to note

Don't forget your favorite pal Fido! Dogs are always welcome. However, we do ask guests to pay an added fee of $50 per stay. (Two dog maximum. No cats, please.) This is for the additional cleaning necessary after you leave. We recommend that you bring his/her favorite bed or blanket. It calms your pet and helps us keep the fee as low as possible. Please do not allow your pet to be on the beds or couches. Never leave your dog unattended in the cabin, even for a moment. Fees for damages or carpet cleaning due to potty accidents start at $250. Thank you.

Unfortunately, we can't accept cats. There are simply too many people who are allergic, including members of our personal family.

Fill your water bottles from the kitchen sink! Forest Falls public water company is share-owned by the community landowners. We source it from local mountain springs and wells and it conforms to the highest federal and state standards. It's cold and refreshing. You will agree that it's better than any city water around! Take a gallon home!

Check-in time is 3 pm, and check out is 11 am. If the calendar is open, you can add a block of four hours before or after the standard stay for a modest charge.

You will notice "Ring" doorbells on the front and back door to the cabin. These are security cameras and are there for your safety and security. Tampering with, or attempting to disable them is against the house rules and you may be asked to leave. We value your privacy at all times.

Please do not put any biologicals down the sinks. (No food waste or coffee grounds.) The sewer is septic, so please only human waste and minimal toilet paper in the toilet.

Please take ALL trash with you when you leave. This is a county requirement. Trash bags are provided. You will be charged $20 per bag if you leave them behind. Forest Falls does not have a garbage pick-up service. Thank you.

We would like to be a quiet mountain community. Please, NO LOUD PARTIES ALLOWED, and quiet after 10 pm.

We are in extreme forest fire country. Please, no open flames. No smoking. No fires. No candles. No charcoal. The fireplace does not work. It will fill the room with smoke. Do not use.

Please note: Pet cleaning fee is $50 per stay. Two dogs maximum.
Please walk your dog regularly and kindly use your pooper-scooper.

Please be very careful on the stairs, steps, ladders, and decking. Naturally, you take full responsibility for your safety. Keep your children or elder hosts safe. The cabin is not suitable for unattended children. We sincerely care for you and do not want you to get hurt.
We have thoroughly cleaned and sanitized the cabin before your arrival. Remember however that you are in a rustic mountain environment. An occasional spider, mosquito, bug, and a little dust may blow in. Enjoy the wilderness. :)

*******SPECIAL NOTE FOR WINTER MONTHS!*******
Forest Falls does indeed get snow in the winter. (Elevation 5,700 feet) The snow can be heavy at times. The CHP will turn you around if you do not have tire chains. Snow tires are not enough. My cabin can be a fun adventure when you are snowed in, but I cannot be responsible for snow removal. I supply snow shovels for your use. You may need to dig yourself out or clear the driveway before you can pull in. I am not responsible for any damages, and you are responsible for any damages to the property. The main street is plowed by the county, but the steep driveway is not. DO NOT PARK ON THE STREET. YOU WILL BE TOWED AND FINED. There is no cancelation on account of weather. If you love adventure, you will love my cabin in the winter!
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Standard Disclaimer:

The renter(s) also hereby agree to INDEMNIFY, DEFEND AND HOLD the owners HARMLESS from any and all claims, actions, suits, procedures, costs, expenses, damages and liabilities including, but not limited to, attorney’s fees, arising from, or in any way related to rental of cabin, except for those arising out of the willful misconduct, gross negligence or intentional torts of the above parties, as applicable.

Guest Reviews:

- "It was just right. Beds were comfortable, linens were fresh and good quality. The appliances were working. I loved the location, we found a perfect place to go snow play, which is the only reason why we went up the mountain. We enjoyed the warm cabin, the furnace worked perfectly well." - "Awesome place to stay!" - "Everything was great! Checking in was easy, great communication with the owners. They had everything we needed; extra towels, blankets, pots and pans, great WiFi and even doggie bags for the pups 🐶 . Very quiet, peaceful and relaxing. Closet city only 30 minutes away( super plus)We had an incredible time. Loved the trails and beautiful scenery. Would love to book again. Thanks for the wonderful experience 😀"

Vacation Rentals in Oak Glen
Winter Falls Cabin-Stunning Views
House
39671 Prospect Drive, Forest Falls, CA, CA 92339, USA

This vacation home offers accommodations with a balcony. The vacation home also features free Wifi, free private parking, and facilities for disabled guests. Featuring a terrace and mountain views, the vacation home includes 2 bedrooms, a living room, flat-screen TV, an equipped kitchen, and 1 bathroom with a bath and a shower. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. The vacation home has a picnic area where you can spend the day outdoors. San Bernardino International Airport is 19 miles from the property.

Amenities:

Security/Safety • Sports/Activities • Child Friendly • Wheelchair Accessible • Accessibility • Internet • Parking

Vacation Rentals in Oak Glen
New Mexican casita! Minutes from Oak Glen, fishing, hiking, parks, casinos& Mt.
House
Yucaipa, California, USA

This brand New Mexican style casita has all the handcrafted features you’re looking for. As soon you open the 100 year old wood door you will immediately walk onto the authentic Saltillo tile. You will enjoy the spacious 17 foot vaulted ceiling with a wrought iron vintage chandelier. Dark walnut live edge counters with handcrafted talavera tile backsplash in kitchen and bathroom.Full kitchen. Special loft acts as 3rd bedroom that easily sleeps 4 on 2 queen size self inflating mattresses. Two amazing comfortable bedrooms Separate temp control in each room. A beautiful authentic slice of a Mexico without the long drive. Stocked coffee and tea bar.

Literally walking distance to uptown restaurants and bars. Concerts at the performance center, market nights, regional park with fishing, minutes from Oak Glen Apple orchards and Oak Glen pumpkin / Christmas farm. Minutes from Yaamava and Morongo casinos. 1 hour from Big Bear Lake and ski resorts. Lots of Pickleball courts nearby. Hiking trails everywhere! Morton’s Peak, Zanja Peak and Mt San Gorgonio (highest peak in Ca) is only 30 minutes away!

A very warm and welcoming small town with plenty to explore. Only a 1-minute walk to Veterans memorial park. Kids playground, basketball courts, walking trails….

UPDATE: ***SPA GRAND OPENING IS JULY 4th! POOL IS OPEN NOW!!

RESORT STYLE POOL—AMAZING POOL (23’x34’ sport pool. We have water basketball and water volleyball. Entry steps on both sides, 3ft deep on each sides and 5 1/2’ ft deep in the middle. WITH TANNING LEDGE (tanning ledge is 9” deep. Perfect for kids to play or chill on the pool loungers under the 3 umbrellas. Just a gentle reminder: for everyone’s comfort, little ones who aren’t potty trained need to wear swim diapers while enjoying the pool. Thank you so much for helping us keep the water fresh and sanitary for all. Ledge measures 6’x20’) BIG ENOUGH FOR 6 CHAIRS, 8 SEAT SPA, LED LIGHTS IN POOL AND SPA, INTEGRATED SPEAKERS AND LANDSCAPE LIGHTING, FIREBOWLS TO LIGHT UP THE NIGHT!

BOOK NOW FOR SUMMER! A PARADISE AWAITS YOU! *Our pool is an Ozone pool! No salt and very little chlorine and chemicals added.

*Pool- Heating is available for $150 for the initial heating paid before arrival. $100 per day after

*Spa- Heating is $25 per day. Spa takes about 20 minutes to heat in summer. To control spa you can download the spa app or message me and I can turn it on for you.

*Firebowls- $50 for 2 hours ( includes both bowls)

*Firepit- $50 for a full 5 gallon propane tank. Use it until it’s gone (tank should last 4-5 hours). Note: We live in the main house and love it when people get to enjoy our casita and pool. Please treat our property with care and respect. NOTE: We live in the front house and may use the pool and spa occasionally as well. Of course we will make extra efforts to give you privacy when using the pool and spa. It’s a HOT summer and everyone needs an awesome way to cool off and enjoy the summers heat. However, if you feel you need complete privacy in the pool and spa area please note this upon booking.

Guest Reviews:

- "The little Spanish style casita is a hidden gem. Me and my family will always book when we come to stay in the Calimesa area. Have to book it and see for your self ....... Amazing" - "The casita is beautiful, private, comfortable and thoughtfully decorated. We had the best time and will absolutely stay again! Hosts were super helpful and easy to get ahold of. They worked with us to customize our stay and took great care of us. Thank you!!"

Vacation Rentals in Oak Glen
James apartment rental
Apartment

Boasting a garden, James apartment rental features accommodation in Yucaipa with free WiFi and garden views. Housed in a building dating from 2022, this apartment is 49 km from Auto Club Speedway and 13 km from Morongo Golf Club. The air-conditioned apartment is composed of 2 separate bedrooms, a living room, a fully equipped kitchen, and 2 bathrooms. A flat-screen TV is available. Breakfast is available each morning, and includes continental, American and Asian options. University of Redlands is 16 km from the apartment. The nearest airport is LA/Ontario International Airport, 54 km from James apartment rental.

Amenities:

Internet • Pet Friendly • Child Friendly • Air Conditioner

Vacation Rentals in Oak Glen
Cherry Valley Guest Cottage
Cottage
Cherry Valley, California, USA

We are an established Guest Cottage (since 2008) with 100% excellent reviews at another well-known guest home rental/share site! and I am a designated Super Host and Guest Preferred Property. Finally decided to give VRBO another try!

The extensive Guest Cottage Welcome manual, should answer most questions you have, and you will receive once booked is printed and available for your convenience when you arrive at the Guest Cottage.

Please note that we are a rural Farm setting. We do have chickens, and two roosters whom will greet the morning with their cock-a-doodle-doo's! and, with five acres of farmland, there are bugs, just like most places on earth! so most likely you will see a bug during your stay! If this is intolerable to you, the Cottage may not be for you! 😅 We hire the best housekeepers and they clean and clean and clean, charging more than one night of my rental income, and inevitably an earwig or spider will try to move in to the Cottage! We do have a monthly service spray the perimeter but avoid spraying inside because of sensitivities, pets, children etc.

We have two Guest Cottages on our five-acre property - YOUR fully-furnished Cottage, a serene 2-bedroom, 1.5 bath, newly-renovated rural 1954 Guest Cottage - is completely yours, nestled in the San Gorgonio Mountain foothills at 2,800 ft. elevation.

This Cottage includes a master bedroom with queen bed and private 1/2 bath; 2nd bedroom has one twin bed, and one full bed, plus full bathroom in hallway.

Enjoy your fully-equipped kitchen - pots, pans, dishes, towels, utensils, etc. You will find a self-serve breakfast in the refrigerator, which is provided once on your first day, and may include: our own pasture farm-fresh eggs, butter, coffee, and fresh cream.

AT&T DirectTV plus Fire TV is provided in the bedroom and living room with various streaming channels which you may log into with your private accounts (be sure to log out upon your departure) plus enjoy complimentary Frontier FIOS 500/500 wireless internet.

We are a non-smoking Cottage/property. Thank you kindly for your understanding.

Guest Cottage is 30 miles from Palm Springs (be sure to visit the Living Desert Museum a bit further east); 20 minutes to the town of Redlands; less than 50 miles from Big Bear Lake, including Forest Falls just 20 miles away; and 15-20 minutes to the tranquil mountain town of Oak Glen, with excellent hiking trails! Plus we are less than 50 miles west of the incredible Joshua Tree National Park! which makes for a fabulous day trip. in addition, if you just follow the guest Cottage Street North up through the mountains to Mile High road, you will get a beautiful Vista of the entire valley! just a few miles drive!

NOTE: We do ask that our guests have complete profiles with clear photos, names of each guest planning on staying, and the purpose of the trip. It is very important for us to know a bit about the wonderful guests who are staying at our Cottage, while still maintaining privacy.

Guest Reviews:

- "We loved our stay! Everything was immaculate and felt just like home, never had that awkward “we’re sleeping in someone else’s house” feeling. The house was stocked with everything we needed and the host was just a text away. Fresh eggs, orange juice and coffee creamer were in the fridge. We arrived late so she left some lights on and turned up the heat for us. It smelled beautiful when we walked in. The backyard truly reminded me of the secret garden and we really enjoyed it. We will definitely stay here again!"

Vacation Rentals in Oak Glen
Secluded & Quiet Guest House-Cherry Valley-Morongo
House
Cherry Valley, California, USA

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
The space.

This guest house is separate from the main house and fully renovated with all brand new amenities. Please take note that the guesthouse is sharing the sliding gate in a one compound with the main house but you have your own space. The place is cute and cozy which is perfect for traveling nurses, casino lovers or anyone that wants to escape the city life.

Come and relax in a tranquil night and enjoy all the modern amenities a house could offer with a fraction of a price. One bedroom has a huge closet complete with iron and ironing board ready for formal occasions you may want to attend nearby and full sized office working desk. The other room is large enough to fit 3 twin beds, cabinetry, working desk and a power recliner sofa.

The family room has a reclining love seat with built-in body massager while enjoying the ambiance of an electric fireplace that could match your mood of the night with different settings of color, intensity & temperature. You will love the big screen TV and surround sound bar.

The galley style gourmet kitchen will entice you to take out your cooking skills with the all new stainless kitchen appliances and kitchen wares with a matching elegant refrigerator with craft ice.

Want to experience rural living at night? Spend the night at the nice gazebo outside. Grill a steak or seafood galore at the stainless barbecue grill and dine at the glass top full dining table or by the comfortable outdoor lounging furniture. Gazebo is equipped with pendant light for more formal dining and exterior decorative lights to match your mood of the night with adjustable/selectable different setting of light colors, speed, brightness or rhyme with the beat of your favorite music.

The glass top dining table is just perfect for your small group complete with all the luxurious dining wares and wine glasses.

Coffee and tea lovers? No problem, we got you covered with the mini coffee/tea bar with keurig coffee maker and a glass kettle for different mix of drinks that includes hot chocolate.

Our place is secluded and yet the amenities and complimentary things and goodies can’t be matched by a Casino suite nor a 5-star hotel. Sorry, no hot tub though :)

Staying longer or had a garment accident that needs washing? No worries, a top notch state-of-the-art washer & dryer is just right by your side and your garments will be ready in a breeze.

Guest access
The property is gated and keypad access will be provided at time of booking/reservation. You will have access to the whole guest house but stay away from the cabinets, closets and storage marked with “OFF LIMITS/STAFF ONLY” and are normally locked. Stay within the guest house perimeter.

Other things to note
You may park inside the gated property at the front of the property. Please use the back vacant lot for additional parking spaces. Keep the gate closed. You need to use same gate code to close the gate.

The gazebo and barbecue grill are provided for your enjoyment as well as the surrounding of the property with complete privacy from the neighborhood.

Please keep the gazebo furniture, dining set & barbecue grill in order and clean after each use.

NOTE: The main house is also a short term rental. Please be friendly with your neighbors :)

NON TESLA CARS:
For other EV cars , make sure to bring different 220v adapter configurations to match your car to different outlets because EV cars got their own 220v outlet configurations.

Guest Reviews:

- "Very cozy & absolutely a beautiful view. The stay was very memorable for me and my family. Enjoyed every moment in the guest house. I will definitely arrange another stay and recommend my friends and family." - "Hosts were very helpful and responsive. Good location to visit all the sites." - "Very clean, we'll maintained house." - "Very clean and comfortable place to stay. Loved that all cabinets/drawers were labeled with the contents. The gate added an extra level of safety (even though already in a safe area). Perfect set up for outside meals. "

Vacation Rentals in Oak Glen
Luxury Studio
Condo
Yucaipa, California, USA

Welcome to our new fully remodelled Studio!
Located only a couple minutes walk to restaurants , breweries, wine bars, performing arts center and the Yucaipa summer outdoor music concerts.

Regional park 5 Minutes
Oak glen 10 Minutes
Golf course 10 Minutes
Forest Falls 20 Minutes
Ontario airport 40 minutes
Big Bear 50 minutes

Guest Reviews:

- "The place was super clean and the host was very friendly and communicative. Loved that it was close to old town Yucaipa. We were able to walk down to the shops and look around. It was quiet and comfortable." - "This was a perfect place for us to stay while visiting our son. We were not familiar with Yuciapa and this was a great location. Easy walk to grab a bite or explore the shops. Short drive to Oak Glen. Liam was very easy to communicate with. We hope to stay in Liam’s studio next time we visit."

Vacation Rentals in Oak Glen
GrayHart Get Away 1 bedroom \/ 1 bathroom Cabin
Cabin
Forest Falls, California, USA

This peaceful and centrally-located place is downtown forest falls. You are a 3 minute walk to the local restaurant and general store. You are a mile in half away from the “Big Falls Waterfall” one of the largest waterfalls in San Bernardino county. This very cozy cabin is located right across from the Momyer trail head. You will experience peace and serenity within the beautiful national forest. Feels like another world but only 18 miles from Redlands and Yucaipa.

Guest access
The entire cabin is yours, free of interface and private in all respects.
Other things to note
If entering the wilderness, permits may be required for both day and overnight access.

Guest Reviews:

- "The property was just as described, great location, very clean, roomy, and just perfect for an easy getaway. Owner was very attentive and responded quickly to any questions we had. We will definitely return now that we know there's a great place to escape to!" - "Our stay was amazing. It was clean and everything we need was available. Can’t say anything bad. Owner was always in contact when I had questions. I would recommend 100%." - "The place was amazing, property manger responds quickly to any questions you might have. Would definitely recommend it to anyone."

Vacation Rentals in Oak Glen
Apartment with Yard and Porch
Condo
Yucaipa, California, USA

Welcome to our newly remodelled 1 bedroom Condo. Located only a couple minutes walk to restaurants , breweries, wine bars, performing arts center and the Yucaipa summer outdoor music concerts.
Regional park 5 Minutes
Oak glen 10 Minutes
Golf course 10 Minutes
Forest Falls 20 Minutes
Ontario Airport 40 Minutes
Palm Springs 40 minutes
Big Bear Mountain 50 minutes

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Guest Reviews:

- "We stayed at this really wonderful, perfectly located hidden gem. You won’t want or need for anything and Liam has really done a fabulous job with this place. It’s a great location very close to downtown and everything else, it’s a great size, an amazing value, super clean and the bed is so very comfortable! We really enjoyed our stay and couldn’t have been happier. If you can book this one do it you won’t be sorry. Thanks Liam" - "Excellent place to stay! Close to Palm Springs, Riverside & Redlands."

Vacation Rentals in Oak Glen
Cherry Valley Studio Guest Cottage
Cottage
Cherry Valley, California, USA

(NOTE: WE have multi-dozens of return guests - outside of this rental system - leaving fabulous reviews of their stay in our guest journal at our two Guest Cottages! Plus, we have been hosting at another popular rental site for the past 15 years and have 100% 5-star reviews! : )

You will love this quaint, private 1954 Studio/Cottage in a historic, well-established neighborhood - it is the perfect size for a single person looking for a relaxing, rejuvenating weekend, or a couple seeking a quiet getaway!

This Studio Cottage is attached to our 2-bedroom Guest Cottage, separated by an enclosed, private and locked breezeway - so if complete privacy is desired, you will be delighted! This Studio Cottage can also be used for a larger groups who wish to book the 2-bedroom Cottage and Studio Cottage together for an extra couple or family member.

Recently completely renovated, the Cottage consists of three mains rooms: one large room which includes a queen-size bed, 2 seat recliner, 1 seat recliner, dresser, storage cabinet, desk, and TV. The second room is a fully-equipped kitchen (apartment sized refrigerator, propane stove/oven, dishes, utensils, pots/pans, etc.), and the third room is a full size bath/shower, fully equipped with towels, bath wash, shampoo & conditioner. There is also a small closet. (Please note that all amenities i.e. toilet paper, dish soap etc. are provided during the first day of your visit, which should be enough for at least 3 days. We have a Walgreens and Stater Brothers a couple miles south if you need extra items during your longer stay! ) Enjoy your own private, covered shaded deck, with seating, right outside the Studio Cottage French doors!

Your stay includes a complimentary, self-served first-day breakfast selection which MAY include some or all of the following: our own farm-fresh pasture eggs, butter, and coffee plus fresh cream awaiting your arrival in the refrigerator. We also provide AT&T Direct TV, and brand new Toshiba Smart TV, and offers guests the opportunity to log into their personal NETFLIX, HBO max, Disney plus accounts, Etc . Please be sure to log out of your personal accounts upon departure ) and complimentary Frontier Wi-Fi, plus two parking spaces right outside your French door.

There are many local hikes, or just walk out your Cottage door and head west and enjoy the mountain views/roads/trails and fresh air! Local drives are spectacular - Big Bear(53 miles); Palm Springs(30 miles); Forest Falls(30 miles) ; or Oak Glen(6 miles) are just minutes away.

This is a Non-Smoking Cottage and Property. Thank you for your consideration. If you are a smoker, and wish to rent my Cottage, please message me directly to discuss and I am sure we can work something out.

NOTE: We do require our guests to have complete profiles, with photos, some information on each guest planning on staying, and the purpose of the trip. It is very important for us to know a bit about the wonderful guests staying at our Studio Cottage, while still maintaining your privacy.

Guest Reviews:

- "Very relaxing stay at a gorgeous and perfectly appointed cottage. We were greeted by an air conditioned breeze, ambient music, and moody salt lamps. We had eggs and squeezed orange juice from the farm for breakfast both mornings. In the evenings we heard owls and coyotes. I stayed here to attend a wedding just ten minutes up into the mountains at Serendipity Gardens, and it was very easy to call a Lyft to get there. The area immediately around the property isn't the best for walking, but there are so many lovely hikes a short drive away (with suggestions and directions thoughtfully provided in binders by the host). We really loved the Oak Glen Preserve for the hiking, dining, and shopping (and it's a great spot for anyone whether you have kids, dogs, or are just traveling solo). Such a relaxing weekend -- thanks for a lovely getaway!"

Vacation Rentals in Oak Glen
Vineyard villa w/pool & amazing views
Villa
Yucaipa, California, USA

Escape to your private vineyard oasis perched on a scenic hillside in Yucaipa. This stunning 6-bedroom villa combines the charm of a working vineyard with luxurious amenities, making it perfect for family gatherings, retreats, or special events. Enjoy breathtaking mountain views and spectacular sunsets from your exclusive hilltop vantage point.

The Space:

This expansive estate features elegant indoor and outdoor living spaces designed for both comfort and entertainment. The heart of the home is a grand living room with an 80" TV and cozy fireplace, flowing into a chef's dream kitchen and a magnificent dining area that seats 10. Let your creativity flow in the spectacular music room with a grand piano – perfect for everything from impromptu sing-alongs to memorable musical evenings.

Indoor Amenities:

‣ 6 bedrooms including two luxury suites
‣ 1st floor wheelchair accessible king bedroom
‣ 2nd floor king suite with luxury bathroom
‣ 4.5 bathrooms in total w/ bath tubs
‣ Fully equipped kitchen with modern appliances
‣ Billiards & ping pong table
‣ Dedicated workspaces w/ fast WiFi
‣ Laundry room with washer and dryer
‣ Living room with 80" TV & streaming services

Outdoor Living:

‣ Private vineyard with scenic walking paths
‣ Large pool & hot tub for year-round enjoyment
‣ BBQ station for outdoor cooking
‣ Cozy firepit for evening gatherings
‣ Complete privacy from neighbors
‣ Stunning mountain vistas and sunset views

* Perfect for Events *

This estate is ideal for special occasions, with ample space and available event furniture rental. Just 4 minutes from Serendipity Garden Wedding venue, it's perfect for wedding parties and family gatherings.

Location:

Ideally situated in Yucaipa's wine country, you're minutes away from:

‣ Oak Glen apple orchards (10 min)
‣ Snow Line Orchard and Winery (10 min)
‣ Yucaipa Rodeo (8 min)
‣ Yucaipa Performing Arts Center (10 min)
‣ Historic Yucaipa Uptown District with dining and entertainment (10 min)

Accessibility:

We pride ourselves on being welcoming to all guests:

‣ Wheelchair accessible entrance to the house
‣ First-floor accessible bedroom with king bed
‣ Bathroom with fixed grab bars
‣ Wide doorways and hallways

Whether you're planning a family reunion, corporate retreat, or special celebration, this unique vineyard estate offers the perfect blend of luxury, privacy, and convenience.

Guest Reviews:

- "This was the perfect location for our family. Our beautiful daughter married at Serendipity Garden Weddings which is just six minutes away. Ann, the owner, is an excellent communicator. " - "We had a wonderful stay in this beautiful home! The home is spacious and lovely! The five bedrooms fit our family of 13 perfectly. The views of the hills are beautiful and the pool was a great hit with the family. The patio was perfect for hanging out while food was cooking on the BBQ grill. There was plenty of parking and communication with the host, Ann, was easy. Ann, thank you for sharing this lovely home! This was a fantastic vacation for our family."

Vacation Rentals in Oak Glen
15 Acre Estate - Family Reunions, Corporate Retreats.n STR PERMIT # 002356
House
Cherry Valley, California, USA

Big groups can spend quality time at our family-friendly estate nestled against the backdrop of epic mountains. Our endless variety of activities, 12 bedrooms of regal splendour & iconic French architecture guarantee an unforgettable experience. There’s entertainment for everyone; whip up a BBQ while the kids play basketball, tennis or go horse riding. Host a retreat at our luxury mansion & 15 acres of lush gardens 30-minutes from Palm Springs.

The Space
With 8 charming bedrooms in the 3-story Mansion and 4 cosy cottages just a 2-minute walk away, we have a total of 12 bedrooms on the enormous estate grounds that can accommodate up to 20 guests. Each cottage comes with its own bathroom, kitchenette, aircon, heating, and patio spread around the property. Our pastel blue window shutters, splendid lawns, and architectural grandeur are reminiscent of a classic home in the French Countryside.

Indoors
The estate features a carefully curated selection of fine and contemporary art and a variety of inviting and dreamy spaces that are tastefully decorated with gold and oak-wood finishings to feel palatial yet homey. The living and dining room are adorned with world maps, antique clocks, and golden candelabras; an eclectic collection of hidden gems. Our kitchen is professionally stocked, bathed in natural light, with sunny yellow walls and a welcoming breakfast table to seat 6.

Relax in our airy and light bedrooms that each come with their own queen or king bed, TV, access to wifi, wardrobe, bathroom, shower, and peaceful view of the outdoors. Indulge in the elegance and comfort of our home fit for royalty characterised by our sparkling chandeliers, stunning grand piano, fine china, and other treasures.

After a long day lay back on our library’s plush leather couch and lose yourself in a captivating book, Netflix movie, or your favourite sports program on our 65-inch TV. Enjoy conversation over a drink at our speakeasy bar or by the warmth of our fireplace while taking in sweeping city views. All rooms are professionally sanitized to ensure a safe and comfortable stay.

Outdoors
Immerse yourself in nature as you stroll around our enchanting gardens, lake, and fields that are spacious enough to find a serene area to relax in peace and quiet. Pet, feed, and take photos with our horses at our rustic ranch’s farm house in the afternoon under the supervision of our groundskeeper for safety purposes or watch him milk our goats in the mornings.

Our magnificently landscaped gardens, breathtaking outdoor pavilion, courtyard, and sun-drench veranda are perfect for hosting an unforgettable meal. Marvel at the vivid sunset as you enjoy an evening gathered around the fire pit with a glass of wine or cook dinner on our stainless steel BBQ and smoker.

Guest Reviews:

- "my family loved staying at this property for our Oak Glen wedding! spacious, so much to do, and such a beautiful property! the owner was fabulous and so attentive when needed. highly recommend!" - "W e had a group of 23 friends for a weekend NYE stay here and we all had an amazing time! Between the main house and 5 cottages there was plenty of space for everyone. We were able to cook multiple gourmet meals using food we brought and the supplies in fully-stocked kitchen. Half of our group went on a very nice and fairly challenging hike along the mountain ridge surrounding the property, while the other half enjoyed the afternoon playing full court basketball, flying our drone around the property, and watching the sunset on the patio with amazing views. It was a wonderful place for us to celebrate the new year and we would definitely come back. There were no complaints among the group at all!"

Vacation Rentals in Oak Glen
4 bedroom, 3 bath cabin with stunning views in Forest Falls
Cabin
Forest Falls, California, USA

Welcome to our serene and spacious A-frame cabin in a peaceful mountain town. This 4 bedroom, 3 bathroom cabin boasts stunning views of the mountain ridge from its large windows. With two living spaces and a tranquil yoga room with natural light, this cabin is perfect for families or groups of friends seeking a refreshing retreat in nature. Whether you're looking to relax and recharge, or explore the beauty of the surrounding mountains, this A-frame cabin has something for everyone to enjoy.

Guest Reviews:

- "The View from Main living room is Breath taking and the house is very spacious, perfect for families. Warm and cozy nights"

Vacation Rentals in Oak Glen
Hot Tub + Views: Luxe Mountain Escape in Yucaipa
House
Yucaipa, California, USA

16,274 Sq Ft | Play Billiards | Home Gym | Day Trip to Big Bear Lake

Spend your next stop in the San Bernardino Mountains at this stunning Yucaipa vacation rental home! Featuring a scenic hilltop setting and an expansive interior complete with 5-bedrooms, 6 full baths, and 2 half baths, ‘Eagle Crest’ makes the perfect spot for a memorable retreat with family or friends. Be sure to explore some of the surrounding hiking trails before ending the night with a favorite movie in the theater room.

-- THE PROPERTY --

CESTRP-2023-01651

SLEEPING ARRANGEMENTS
- Bedroom 1: 1 king bed
- Bedroom 2: 1 queen bed
- Bedroom 3: 1 queen bed
- Bedroom 4: 1 queen bed
- Bedroom 5: 1 queen bed
- Additional Sleeping: queen air mattresses, 1 portable crib

INDOOR LIVING
- Private hot tub, pool table
- Fireplaces & wood-burning stoves (bring your own firewood)
- Smart TVs, theater room w/ projector screen
- Dining tables, high chair
- Home gym, sauna
- En-suite bathrooms, walk-in closets

OUTDOOR LIVING
- Private garden, mountain views, wildlife spotting
- Outdoor kitchen w/ gas grill
- Covered patio w/ outdoor dining set
- Gazebo, private balconies

KITCHEN
- Refrigerator, stove/oven, microwave, dishwasher
- Toaster, cooking basics
- Island, dishware & flatware

GENERAL
- Keyless entry, self check-in, free WiFi
- Multiple washer & dryer sets, trash bags/paper towels
- Towels/linens, complimentary toiletries, hair dryer
- Central heating & A/C

FAQ
- Quiet hours (10:00 PM-7:00 AM)
- 4WD recommended in winter
- 1 exterior security camera (facing out)

ACCESSIBILITY
- 3-level house, 3 steps required to enter
- Bedroom & full bathroom on main level

PARKING
- Garage (3 vehicles)
- Driveway (7 vehicles)

-- THE LOCATION --

- Hiking trails & wildlife spotting on-site
- 7 miles to Wildwood Canyon State Park
- 11 miles to Yucaipa Valley Golf Club
- 3 miles to Oak Tree Mountain
- 28 miles to Lake Parris
- 27 miles to SBD Int’l Airport

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome--because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Outdoor fires are prohibited
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- Please observe quiet hours from 10:00 PM to 7:00 AM

ADDITIONAL INFORMATION
- This 3-level house requires using stairs to enter. It offers a bedroom and full bathroom on the main level
- Four-wheel drive may be necessary to access the property in winter months
- Your safety matters. This property features 1 exterior security camera located above the garage facing the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion

Amenities:

Internet • Bedding/Linens • Air Conditioner • Security/Safety • Laundry • Tv • Balcony/Terrace • Child Friendly • Other • Kitchen • Wellness Facilities • Fireplace/Heating

Vacation Rentals in Oak Glen
Cozy Cottage near historic uptown Yucaipa CA,
Cottage
Yucaipa, California, USA

The property is located conveniently near historic Yucaipa uptown. Uptown has old town feel with good restaurants, microbreweries and wine tasting rooms. The cottage has lovely views of snow capped San Gorgonio from the living room. Two sets of stairs access either the kitchen or the living room. The apartment is in 1950s style with lots of wood and classic mid century modern tile. There is a small Breakfast nook to enjoy your coffee with a view of Bryant Street. The unit has modern upgrades, such as ultra quiet mini split air conditioning and heating. The furnishings are brand new designed by La-Z-Boy furniture for comfort and style.

Amenities:

Bedding/Linens • Fireplace/Heating • Internet • Security/Safety • Air Conditioner • Laundry • Child Friendly • Kitchen

Oak Glen Family Friendly Vacation rentals

Oak Glen Pet Friendly Vacation rentals

Oak Glen Vacation rentals with Parking

Oak Glen Vacation rentals with Entertainment

Oak Glen Vacation rentals with Private Pool

Oak Glen Vacation-Rentals on the Map

Compare the Best Vacation-Rentals in Oak Glen – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Vineyard estate with pool and amazing views 13822 Mustard Seed Drive, Yucaipa, CA, CA 92399, USA 1200 4.0 9.5 2 Click here
Vintage Mountain Cabin Forest Falls, California, USA 311 2.0 10.0 2 Click here
Spacious Golf Course Retreat - with Modern Kitchen Yucaipa, CA, USA 487 3.0 1 Click here
Forest Falls Creekside Cabin Forest Falls, California, USA 369 2.0 1 Click here
Hot Tub and Views Luxe Mountain Escape in Yucaipa Yucaipa, CA, USA 2221 3.0 1 Click here
Perfect Location! Hiker's and Dogs (2) Paradise.! Walk to Trails! Forest Falls, California, USA 174 9.6 20 Click here
Winter Falls Cabin-Stunning Views 39671 Prospect Drive, Forest Falls, CA, CA 92339, USA 358 9.0 1 Click here
New Mexican casita! Minutes from Oak Glen, fishing, hiking, parks, casinos& Mt. Yucaipa, California, USA 290 9.2 13 Click here
Cherry Valley Guest Cottage Cherry Valley, California, USA 153 10.0 11 Click here
Secluded & Quiet Guest House-Cherry Valley-Morongo Cherry Valley, California, USA 171 10.0 6 Click here
Luxury Studio Yucaipa, California, USA 180 10.0 6 Click here
GrayHart Get Away 1 bedroom \/ 1 bathroom Cabin Forest Falls, California, USA 124 9.6 5 Click here
Apartment with Yard and Porch Yucaipa, California, USA 131 9.4 3 Click here
Cherry Valley Studio Guest Cottage Cherry Valley, California, USA 183 10.0 3 Click here
Vineyard villa w/pool & amazing views Yucaipa, California, USA 843 9.4 3 Click here
15 Acre Estate - Family Reunions, Corporate Retreats.n STR PERMIT # 002356 Cherry Valley, California, USA 4455 10.0 3 Click here
4 bedroom, 3 bath cabin with stunning views in Forest Falls Forest Falls, California, USA 311 10.0 1 Click here
Hot Tub + Views: Luxe Mountain Escape in Yucaipa Yucaipa, California, USA 1988 10.0 1 Click here
Cozy Cottage near historic uptown Yucaipa CA, Yucaipa, California, USA 73 1 Click here

Note: The prices for each Vacation-Rentals in Oak Glen do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Vacation rentals in Oak Glen that include a pool include:

  • Vineyard estate with pool and amazing views.- Review Count: 2, Rating: 9.5
  • New Mexican casita! Minutes from Oak Glen, fishing, hiking, parks, casinos& Mt..- Review Count: 13, Rating: 9.2
  • Vineyard villa w/pool & amazing views.- Review Count: 3, Rating: 9.4

Family-friendly vacation rentals in Oak Glen include:

  • Vineyard estate with pool and amazing views.- Review Count: 2, Rating: 9.5
  • Vintage Mountain Cabin.- Review Count: 2, Rating: 10.0
  • Spacious Golf Course Retreat - with Modern Kitchen.- Review Count: 0, Rating: 0.0

Pet-friendly vacation rentals in Oak Glen include:

  • Vineyard estate with pool and amazing views.- Review Count: 2, Rating: 9.5
  • Vintage Mountain Cabin.- Review Count: 2, Rating: 10.0
  • Spacious Golf Course Retreat - with Modern Kitchen.- Review Count: 0, Rating: 0.0

Vacation rentals in Oak Glen that include breakfast options include:

  • Perfect Location! Hiker's and Dogs (2) Paradise.! Walk to Trails!.- Review Count: 20, Rating: 9.6

Vacation rentals in Oak Glen with private or on-site parking include:

  • Vineyard estate with pool and amazing views.- Review Count: 2, Rating: 9.5
  • Vintage Mountain Cabin.- Review Count: 2, Rating: 10.0
  • Spacious Golf Course Retreat - with Modern Kitchen.- Review Count: 0, Rating: 0.0

Some of the best Vacation Rentals in Oak Glen are:

  • Vineyard estate with pool and amazing views.- Review Count: 2, Rating: 9.5
  • Spacious Golf Course Retreat - with Modern Kitchen.- Review Count: 0, Rating: 0.0
  • Hot Tub and Views Luxe Mountain Escape in Yucaipa.- Review Count: 0, Rating: 0.0

Some of the popular Vacation Rentals in Oak Glen are:

  • Perfect Location! Hiker's and Dogs (2) Paradise.! Walk to Trails!.- Review Count: 20, Rating: 9.6
  • New Mexican casita! Minutes from Oak Glen, fishing, hiking, parks, casinos& Mt..- Review Count: 13, Rating: 9.2
  • Cherry Valley Guest Cottage.- Review Count: 11, Rating: 10.0