Family-friendly holiday rentals in San Bernardino

House & Barn Historic Beauty •Events & gatherings!

A block from downtown State street. Tall trees line the streets of the historical magic that is Redlands 🍊 ✨I have a sister house! Next door is The Olive Branch. This is perfect for larger parties An inground fire pit is the perfect way to get everyone together & cuddle. Or maybe just night under the stars as the sound from The Redlands Bowl Plays into the yard Spend the day playing poker downstairs in the Carriage house or make your way up the stairs and drift away in to hippie land.

Family · Indoor spaces · Walkability

Guesthouse with Loft & ICE COLD AC

This private and stylish guest house is perfect for group trips or the single traveler. Will sleep 4 adults and 1 kid with a Q bed, Q leather sofa fold out and a D futon. Quality bedding and pillow top mattress are very comfortable. K-Cups of coffee are provided along with bath sheets. Work at the desk or watch the game on the 50" big screen. Close to Yaamava Casino, Glen Helen Amphitheatre, Crestline, and three major hospitals. It's quiet and peaceful. Smoke outside only. Ice-cold A/C

Indoor spaces · Kitchen · Cleanliness

North Upland House with a Pool

Your space has a private entrance and its own bedroom, bathroom and kitchenette with a SINK induction burner & countertop . There is a large workspace perfect for remote work. WiFi is FAST. The space is secluded at the end of the main house with its own private entrance. There are no shared living spaces and you have access to the REFRESHING PRIVATE POOL, shaded, and sunny patios, and a large yard. There are table and chairs in a beautiful setting perfect for a relaxing meal

Indoor spaces · Kitchen · Hiking

Stunning 4BR near NOS & Yaamava with Private Yard

Nestled on the foothills of the San Bernardino Mountains is our luxurious 4BR house, boasting a professionally designed interior that will capture your heart immediately! Only 5-minute drive to downtown, while the top destinations of Lake Arrowhead, Disneyland, and Palm Springs are within an hour's journey. 2300 sq. ft. of space awaits – a 55” HDTV, a foosball table, ultra-fast 500 MB/s Wi-Fi, and access to a private backyard with jacuzzi and BBQ (extra fee need to apply).

Kitchen · Indoor spaces · Value

Bright Modern 2-Bd House in Quiet neighborhood!

This bright modern house was recently remodeled and it's ready for you to enjoy! The home is situated in a very quiet and safe neighborhood at the end of a cul-de-sac in the foothills of the San Bernardino mountains. This house is the perfect place to use as a basecamp when exploring San Bernardino (Yaamava Resort and Casino, NOS, the first McDonald's museum, Big Bear, Lake Arrowhead, Joshua Tree, Palm Springs, Orange County (Disneyland, Knotts), LA and so many more places.

Kitchen · Indoor spaces · Quiet

Valley of Guadalupe Escape gem

We are bringing Valle de Guadalupe to you in our own backyard, without you having to leave the country for it. Our space was created specifically to give you a taste of Mexico's beautiful wine country Valle de Guadalupe Baja California, which is why we created #VallevibesSB. Our home is fully equipped with everything you need to get away for the week(end) all that's missing is you! For safety and security reasons, we do have EXTERNAL cameras on premises and a ring door bell.

Family · Kitchen · Check-in

Hot Tub, Fire Pit/Game Room/ Near NOS Center

Welcome to our meticulously clean three-bedroom, two-bath haven in San Bernardino! This gorgeous house is designed for comfort and entertainment. Unwind in the game room with a pool table or gather around the patio's fire pit. Experience the charm of our outdoor space, featuring a second fire pit in the grass area. Create lasting memories surrounded by freshly painted murals near the inviting pool and brand-new Jacuzzi – perfect for starlit evenings with friends and family.

Family · Indoor spaces · Amenities

Amazing Large 1 Bedroom, No Chores Home

Bring the whole family to this wonderful place in the heart of Loma Linda. The bedroom has its own retreat with a sleeper sofa for the kids or friends. Within a couple of miles you have Loma Linda University and Loma Linda VA. A couple miles East and you are in Downtown Redlands where you have entertainment, plentiful restaurants, and nightlife. Or enjoy the peaceful citrus trails this beautiful neighborhood offers which lead you to large parks where you can enjoy a picnic.

Kitchen · Indoor spaces · Layout

Clean Modern ADU Close to NOS/ Yaamava/ Big Bear

This beautiful ADU-full-home is perfect for families or groups of up to 6 guests. With a private entrance and free parking, you’ll enjoy the freedom to come and go as you please. This home is minutes from Yaamava, NOS Event Center, Big Bear, or Mount High Ski Resort for summer/winter activities. Great for those going to Coachella, Los Angeles, Anehiem, or Orange County. Smart TV. WiFi. A/C. Washer and Dryer. Kitchen. Self Check-in. Close to freeways.

Indoor spaces · Kitchen · Nearby

Private Casita with Jacuzzi, newly remodeled.

Enjoy a stylish experience at this centrally-located home with its own private basketball half court (ball not included) hot tub, and grill. Close to downtown San Bernardino, where you will find great eating places, close to mountains, casinos, The NOS Center, National Orange Show(7 minute drive.) Less than 1 hour from Lake Arrowhead & Big Bear Lake. p.s if you don't like neighbors, this is the house for you.

Indoor spaces · Family · Accuracy

Entire home near campus - private yard

Entire house with private yard and parking 1/4 mile from the U of Redlands. Built in 2022, this home with no shared walls offers two bedrooms, 1.5 bathrooms + a hot/cold outdoor shower, a fully equipped kitchen, and a washer/dryer. 50 AMP outlet for EV charging onsite. The home is 2 miles from downtown Redlands, 1.2 miles from Casey Orchards and The Grove, and 2 miles from Hanger 24 Craft Brewery.

Kitchen · Indoor spaces · Amenities

Casa de Agua Retreat

Modern Hacienda themed house in a quiet neighborhood with low traffic. Cozy and with a pool so families and friends can have fun, connect, and create life-long memories. Conveniently located near some hot spots like; downtown Riverside 2.5 miles, freeway 1 mile, and UCR is 3 miles, Ontario airport is 17 miles, and if you like tennis, there are free open courts at a 5-minute walk.

Indoor spaces · Kitchen · Quiet