
Family-friendly vacation rentals in Highland
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Highland
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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

(1) Cozy Redlands Retreat with Victorian charm
Private room, entrance & restroom. Well decorated, great view of the San Bernardino Mountains. This room has everything you need for a comfortable stay! Room includes television, wifi, mini refrigerator, small table (2), work space (desk & chair), coffee machine & more. Down Town Redlands is 1 mile away. Big Bear Lake/Snow less than an hour away, & L.A about 60 miles away. Conveniently located right off the 10 fwy. Security cameras recording at all times all around the outdoors of the property.

All New cozy SUITE in Arrowhead Country Club!
SPACIOUS, BRAND NEW, INDEPENDENT SUITE in the luxurious and peaceful Arrowhead Country Club. Independent with self-check in. 1 California bed plus 1 additional bed, kitchenette and huge shower. 500 sqft by the Golf course and 20 min. away from LAKE ARROWHEAD! Great for all seasons. Trees all around, all markets and restaurants you may need. Also 10 min. from San Manuel Casino. Close to Riverside and Redlands! We will only consider bookings for Registered ID Guests with reviews. Thank you!

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!

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

#1 Cozy Tinyhouse "Route 66" container- private
Longterm Rental, peaceful, rural neighborhood- No Smoking property, no animals allowed due to health conditions. Right in the center of all: 1.5 hour to Santa Monica, Venice Beach, less than 2 hours from San Diego, 3 hours to Las Vegas, 5 min from the world famous motocross track, Glen Helen Amphitheater, Route 66, and hot spot for paragliding is close by. CozyTiny Container home is private, with all comforts. Peaceful, calm at the foot of the mountains with 1 dedicated parking spot.

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*)

Ray of sunshine Cottage.
Cozy and centrally-located home to relax, work, go to the casino, attend concerts or events near by. Down the street (1.2 miles) from Yaamava Resort & Casino. 14 min (6.8 miles) from National Orange Show Event center (NOS). 9 min (4.3 miles) from San Bernardino International Airport. 25 min (25 miles) from Ontario International Airport. Conveniently located as it’s at walking distance to restaurants, Starbucks, retail store; as well as food market, fast food places and more!

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.

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.

· Under the White Fir at The Twin Peaks Lodge ·
A short walk to the National Forest and a 10-minute drive to both Lake Arrowhead and Lake Gregory, the historic Twin Peaks Lodge offers 21 unique cabins with a top-rated restaurant on site. Our 3 rules: no smoking no pets (sorry, no exceptions) no grilling or bonfires (we're surrounded by trees!) Some things to note: we have a microwave & small fridge at the cabin, and our restaurant is open for dinner and there's a little market open late just next door!

2-King size bed: Hidden Gem
Join the fuss, come and relax in this NEW lively & stylish rear space. Here you have one master bedroom with a king-size bed and its private restroom, TV with Netflix. Send your guest to the second bedroom also king size bed & TV, and leave that one friend to sleep in the sofa bed joined by another TV. Fully stocked kitchen plus We offer free coffee ☕️ ◆15 minute drive to Yaamava' Resort & Casino ◆9 minute drive to National Orange Show (NOS) Center
Popular amenities for Highland family-friendly rentals
Family-friendly home rentals with a hot tub

A-Frame in the Sky - “Rim of the World” Views!

Casa de Agua Retreat

Palisades View - Cabin With Spa

DMO 1 Bdr+ Suite. Private Pool, Spa, Luxury & Fun

Tropical Retreat near Downtown, Pool/Spa

LUX 4BR near NOS & Yaamava w Private Backyard

Summer Oasis: Tropical Vibes + Pool & Mini Golf!

Peaceful Private Retreat In The Heart Of Town
Family- and pet-friendly home rentals

Majestic Log A-Frame | Lake Walk, Loft & BBQ Deck

The Best Views and Vintage Cozy Cabin!

Wilderness Road A Frame Mountain Cabin

Private backyard - Walk to Downtown - Pet friendly

Cozy Monthly Stay :Your Home-Entire Guest House

Beautiful private guest suite

1930 Cozy One Bedroom Lake Arrowhead Cabin

Pristine Wooded Retreat/Near SkyPark and Lakes
Family-friendly home rentals with a pool

Shalimar Serenity|Pool|Hot Tub|Fun Games|Ping Pong

Colonial Cottage Get-A-Way

Walk to Village & 5C's & Trader Joe's/Private Pool

The Cozy Cottage Condo - Jacuzzi/3mi to slopes

Ski-In/Ski-Out Remodeled Property at Snow Summit

Claremont Guesthouse 5 Min to Colleges|Non-Smokers

Beautiful home in a stress-free environment

Tranquil Retreat | Private Guest Quarters + Pool
Quick stats about vacation rentals that are family-friendly in Highland
Total vacation rentals
Explore 30 vacation rentals in Highland
Nightly prices starting at
Highland vacation rentals start at $126 CAD per night before taxes and fees
Verified guest reviews
Over 820 verified reviews to help you choose
Pet-friendly vacation rentals
Find 10 rentals that welcome pets
Vacation rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 of Highland vacation rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Highland rentals
4.9 Average rating
Highland stays are highly rated by guests—averaging 4.9 out of 5!
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