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.

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 Blue Cabin

Relax at this unique, tranquil, and comfortable mini home in our backyard. Surrounded by a beautiful garden with a wide variety of succulents and a relaxing pool. With a space to enjoy reading or listening to music. Equipped with microwave, Keurig coffee machine, mini refrigerator, toaster, blender, washer/dryer, and tableware. The mini home has air conditioning and heating system for comfort and a smart TV. No parties allowed.(SPACE EQUIPPED ONLY FOR 2-3 PEOPLE *no more than 3 fit*)

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

Spacious 4 bedroom home in the heart of town!

Your entire group will enjoy easy access to everything from this centrally located home. Only one mile to the University of Redlands, and less than a mile to all the great restaurants, bars, and shopping boutiques on State St. Easy access to both on and off-ramps of the 10 freeway. Almost everything inside the house is new! With over 2 years of ALL 5-star reviews, this is hands down the best place to stay in Redlands! Don't hesitate, we book up fast.

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.

Dreamy Escape Private Entrance/pool/near Yaamava

Our location is close to dining, hiking, shopping, movie theaters, and popular attractions like the National Orange Show Event Center (NOS), Yaamava Resort & Casino, vibrant nightlife, Redlands University, and Loma Linda University. You'll love our place for its location, inviting ambiance, outdoor space, and friendly neighborhood. It's the perfect spot for couples, solo adventurers, and business travelers looking for a cozy getaway!

Sunset Bungalow

Welcome to Sunset Bungalow. A beautiful guest house located on historic Sunset Dr in the city of Redlands. Within walking distance to renowned Kimberly Crest Mansion at Prospect Park. Downtown Redlands is just a few short minutes drive away along with University of Redlands, Loma Linda University, Redlands Hospital, Loma Linda Hospital, VA Hospital and ESRI. Sit back and relax in this calm, stylish space.