
Vacation rentals in Highland
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Top-rated vacation rentals in Highland
Guests agree: these stays 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!

#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

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.

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 ig arbnbproperties

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.

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.

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.
Popular amenities for Highland places to stay
Other great vacation rentals in Highland

Beautiful Suburban Private Suite

Cactus Casino- w/game room-next to Yaamava Casino!

Attached back, House

Retro Retreat | Blackjack+Billiards | Vinyl Vibes

High finished ADU One queen bed and one sofa bed

B&G Studio Space Guesthouse

A Pet Friendly, Quiet Space, Imperfectly Country

3BDModern Unit-NOS/Yaamav/Mtns.
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 90 | € 95 | € 90 | € 97 | € 94 | € 97 | € 90 | € 86 | € 86 | € 88 | € 93 | € 87 |
| Avg. temp | 14°C | 14°C | 15°C | 16°C | 18°C | 20°C | 23°C | 24°C | 24°C | 21°C | 17°C | 14°C |
Frequently Asked Questions
How much does it cost to stay in house rentals in Highland?
Experience the best of Highland with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Highland?
Yes! Work meets play with ease at over 30 house rentals in Highland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Highland?
Make yourself at home in Highland by choosing from our most frequently booked neighborhoods. We have over 260 vacation rentals in Northwest Redlands, over 290 vacation rentals in North Redlands, and over 60 vacation rentals in East Highlands.
Do house rentals in Highland have wifi?
Absolutely! We offer over 60 house rentals with wifi in Highland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Highland have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Highland. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly house rentals in Highland?
Four-legged friends are welcome in Highland. Choose from more than 10 house rentals for guests traveling with pets.
Are there family-friendly house rentals in Highland?
Highland has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Highland?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with wifi, over 60 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Highland

Total vacation rentals
Explore 100 vacation rentals in Highland

Nightly prices starting at
Highland vacation rentals start at € 34 per night before taxes and fees

Verified guest reviews
Over 3,700 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
100 of Highland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Highland rentals

4.8 Average rating
Highland stays are highly rated by guests—averaging 4.8 out of 5!
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- 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
- Alpine Slide at Magic Mountain
- Mesquite Golf & Country Club
- Indian Canyons
- Palm Springs Aerial Tramway
- Tahquitz Creek Golf Resort
- Dos Lagos Golf Course
- Mountain High
- Chino Hills State Park
- Big Morongo Canyon Preserve
- Indian Canyons Golf Resort
- Big Bear Alpine Zoo
- Mt. Baldy Resort
- Palm Springs Air Museum
- Knott's Soak City U.S.A.
- Whitewater Preserve