Family-friendly holiday rentals in Redlands

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.

2-BDR attached apt in rural Redlands neighborhood.

“RURAL REDLANDS” has a quiet neighborhood with a few creatures (coyotes, rabbits and squirrels). Although other hosts welcome pets, we request “no pets” (returning guests with allergies). Older 60’s home; not fancy but comfortable. Two bedrooms, kitchenette and living room. Private entrance; we share a living room wall and A/C. We are near U of Redlands, Downtown Redlands, restaurants, Oak Glen apple farms. . We’re 60-70 miles from Palm Springs, Casinos, BigBear Mtns, Disneyland, & beaches

Bright Vibes Home|Sleeps 8|1Blk to Univ|Pacman+BBQ

Step into our inviting Redlands home full of bright vibes and fun! Centrally located near the University, this lively gem features an indoor gym, playful outdoor spaces with Tic-Tac-Toe, fire pit + BBQ, and a lively atmosphere. Whip up culinary delights in the fully equipped kitchen, unwind in cozy bedrooms, and enjoy modern amenities. Explore downtown's lively scene, indulge in local attractions, and create unforgettable memories at our spirited Redlands retreat! 30+ day/ insurance stays okay.

Yucaipa's Cottage on a Hill

Welcome to our quiet country cottage located on top of a hill overlooking the canyon and City of Yucaipa. With all the amenities you'll need during your stay, you will feel right at home. Less than five minutes to the freeway, your home away from home will be the perfect place to rest your head at the end of the day. The Cottage is the central location to LA, the beaches, Disneyland, Palm Springs, San Diego and the mountains. And if you don't want to leave, there's plenty to do right here!

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

Located in beautiful South Redlands near Prospect Park, this detached cottage has its own private and inviting fenced backyard, nicely landscaped with comfortable patio furniture. Inside you will find separate living and bedroom spaces, charming decor, Heating/A/C, Cable TV, WIFI, kitchenette with microwave, Keurig coffee maker and compact refrigerator, fine linens, comfortable queen sized bed, and newer bathroom. Conveniently located near Downtown Redlands, University of Redlands and ESRI!

Peaceful Private Retreat In The Heart Of Town

Meticulously designer-renovated modern home “The Nest “is surrounded by mature tree and nestled beneath the mountains in South Redlands. Whether you’re looking to spend time with loved ones, vacationing or work remotely in a peaceful environment, this is the place to do it all. Relax by the fireplace while light pours in from the wall of windows, with pleasant sparkling pool, grill and chill on the backyard, and explore nature right outside your front door. Conveniently located in Redlands!

The Capricorn Cabin

Welcome to the Capricorn Cabin! Built in 1961, this cozy mid-century modern A-frame cabin in Big Bear blends historic charm with hygge comfort featuring vintage décor, a modern gel-fuel fireplace, vaulted ceilings, and king bed sleeping loft. Located in the historic Big Bear neighborhood Sugarloaf, this cabin is perfect for a romantic getaway, trip with your small family, or solo retreat. Just minutes from the lake, slopes, and village, with easy access by bus. We'd be happy to host you!

The Far Out - A Frame cabin in the woods

The Far Out is a classic A-frame cabin nestled in the beautiful woods of Idyllwild in the San Jacinto Mountains. This mountain retreat sits on an acre of land, complete with a 1200 sq ft wooden deck and semi-sunken hot tub. The interior décor is impeccably curated, blending vintage character with modern design for a distinctly cool cabin vibe. Set far back from the road, the cabin and the grounds offer a magnificent private space for a relaxing getaway. Beauty abounds at The Far Out!

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.

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

Private Cozy Suite & Bath | Self Check-In

Private-entry guest suite with keypad access, private attached bathroom, Wi-Fi, workspace, TV with streaming, mini fridge, and microwave. Cozy and ideal for 1–2 guests. Located in a historic 1895 home—updated with a few quirks: toilet paper goes in trash (older pipes), shower is simple and functional (not luxury). Climate control is via a portable AC unit and small heater (not central), which comfortably does the job. Quiet space, no parties.

Casa Mariposa: Airstream in Downtown Riverside

Step inside Casa Mariposa, a vintage Airstream thoughtfully redesigned for modern comfort while keeping its timeless charm. Whether you’re here for a weekend escape, a business trip, or a Riverside adventure, this cozy home-on-wheels offers the perfect mix of style, comfort, and convenience. Enjoy your own private retreat while still being just steps away from Riverside’s vibrant restaurants, coffee shops, and local attractions.