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.

Kitchen · Family · Barbecue

Wild Olive Lodge ° Stylish & Comfy Family Getaway

★Featured in Condé Nast Traveler★ Relax and unwind in this calm, stylish, and clean Running Springs mountain cabin★Perfect for a family retreat or a romantic getaway★Newly renovated cabin offers a serene interior, vaulted A-frame loft, inviting decks & much more★IG @wild_olive_den for more • 10m to Snow Valley Ski Resort for great skiing • 15m to Lake Arrowhead • 30m to Big Bear • 10m to Sky Park & Skyforest Close to Arrowbear Lake, Lake Gregory, and Green Valley Lake. Priceless memories await!

Indoor spaces · Kitchen · Hospitality

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.

Kitchen · Family · Checkout

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!

Kitchen · Indoor spaces · Pool

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!

Family · Indoor spaces · Walkability

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!

Family · Kitchen · Comfort

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 · Family · Nearby

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

Kitchen · Indoor spaces · Air conditioning

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.

Kitchen · Indoor spaces · Walkability

Riverside Serenity Spring Oasis|Spa/Pool/Mini Golf

Welcome to our exquisite Riverside retreat, where luxury meets family fun! Here's what makes our place truly special: 🔥 Cozy Fireplace for Chilly Evenings 🌴 Tropical Oasis with a Sparkling Pool 🌟 Jacuzzi Bliss under the Stars ⛳ Mini Golf Extravaganza. 🏡 Spacious and Clean Rooms 📍 Centrally Located Convenience: Downtown Riverside, UCR, NOS Center, 210 Freeway, Yaamava, and local shops *~Fun-Filled Family Environment!~* Book now!

Kitchen · Family · Wi-Fi

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.

Kitchen · Family · Decor

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.

Indoor spaces · Family · Getting around