
Family-friendly holiday rentals in Highland
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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

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!

#2 Cozy Tinyhouse"Route 66" Container- private
Longterm rental, peaceful, rural neighborhood, if you’re looking to get just outside of the city. No smoking , NO animals due to health conditions. 1.5 hour or less 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 just 5 minutes away! CozyTiny Container home is private, with all comforts. Relax at the foot of the mountains with 1 parking spot.

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

(2) Downtown Redlands Retreat: Cozy Master Suite
This is a nice master bedroom, converted to a guest suite. The room has a private entrance, and private bathroom. Walls were recently torn down & made sound proof so as to not disrupt our guest with noises inside the house. This house has a lot of history, it’s over 120 years old. It’s perfectly situated about a minute away from the freeway is a central locations, in the beautiful & historic city of Redlands. Security cameras recording at all times all around the outdoors of the property.

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.

Serene Escape Tiny House Living /pool/near Yaamava
We are located close to dining , hiking, shopping, movie theaters, National Orange Show Event Center (NOS Events), Yaamava Resort and Casino, some nightlife, Redlands University and Loma Linda University. You’ll love my place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. Our place is good for couples, solo adventurers, and business travelers. Perfect little getaway! I have another listing-click on my photo to view.

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

Tropical Oasis Heated Pool & Spa/Firepit/Game Room
Pool HEATER and Jacuzzi HEATER HAVE SEPERATE ADDITIONAL FEES READ UNDER OUR POOL INFORMATION Experience a resort-style retreat nestled against the breathtaking backdrop of mountains and palm trees. Indulge in a rejuvenating stay at our home, designed to provide the perfect blend of relaxation and excitement. Located in the serene north part of San Bernardino, our inviting home is ideal for intimate getaways or gatherings with family and loved ones.
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!

Mid-Century Cabin Perfect for Romantic Getaway

Tropical Retreat near Downtown, Pool/Spa

Summer Oasis: Tropical Vibes + Pool & Mini Golf!

Romantic A-Frame Cabin | Hot Tub, AC, Fire Pit

Peaceful Private Retreat In The Heart Of Town

Golden's Pool Home |Jacuzzi|Game Room|BBQ|Near UCR

Glen Oak Rim | Hot Tub · Game Room · Epic Views
Family- and pet-friendly home rentals

Breathtaking Mountain Views | Romantic Hideaway

Wilderness Road A Frame Mountain Cabin

Private backyard - Walk to Downtown - Pet friendly

Cozy Monthly Stay :Your Home-Entire Guest House

Snow Valley Retreat W/ Spa!

Beautiful private guest suite

1930 Cozy One Bedroom Lake Arrowhead Cabin

Twin Pines A-Frame Cabin - Scenic Forest Views
Family-friendly home rentals with a pool

Colonial Cottage Get-A-Way

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

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

Norco country private entrance

Casita Condo | Jacuzzi | 3mi to slopes
Quick stats about holiday rentals that are family-friendly in Highland
Total rentals
30 properties
Nightly prices starting at
£67 before taxes and fees
Total number of reviews
820 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
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- Family-friendly rentals San Bernardino County
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- Family-friendly rentals United States
- Disneyland Park
- Big Bear Mountain Resort
- Bear Mountain Ski Resort
- Knott’S Berry Farm
- Snow Summit
- Disney California Adventure Park
- Pechanga Resort Casino
- Honda Center
- Angel Stadium of Anaheim
- Downtown Disney District
- Alpine Slide at Magic Mountain
- Mesquite Golf & Country Club
- Indian Canyons
- Palm Springs Aerial Tramway
- Temecula Creek Inn
- Tahquitz Creek Golf Resort
- Dos Lagos Golf Course
- Mountain High
- Big Morongo Canyon Preserve
- Big Bear Alpine Zoo
- Indian Canyons Golf Resort
- Chino Hills State Park
- Mt. Baldy Resort
- Palm Springs Air Museum