
Vacation rentals in Highland
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Top-rated vacation rentals in Highland
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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.

A-frame backs the forest,Walk to Slopes, Hot Tub!
This perfect little Aframe cabin backs the forest! Hiking, biking & the view is what you'll have direct access to at this mountain retreat. Located on a quiet street near Bear Mt. Ski Resort,tucked into the trees, you'll find this mid-century modern cabin.If you are looking for a romantic hide-away,a double couple adventure or a place for your besties to re-connect & unwind, this truly is the coolest cabin in Big Bear Lake.Highly sought after cabin, it will book up fast!Not for children under 6.

Adorable Cozy Cottage, base of Beautiful Mountains
This adorable cottage is located at the base of the San Bernardino mountains where you have views of the snow-capped mountains in the colder seasons & views of the beautiful sunsets all year! Close to freeways, malls & hiking trails. Relax poolside as the cottage doors open to the pool & outdoor BBQ & fire pit. It's a great get-away location with all newly remodeled amenities for a comfortable stay. Plenty of parking. NEW onsite DAY SPA services! THIS SPACE IS NOT SUITABLE FOR SMALL CHILDREN

Romantic A-Frame Cabin | Hot Tub, Fire Pit, Hiking
❤️Escape to the most romantic cabin in Southern California-featured in Dwell Magazine❤️ ★ Perfect for a couple's getaway ★ Designer furnishings and high-end linens ★ Hot tub surrounded by boulders ★ Firepit ★ Cozy fireplace ★ Hiking out the back door ★ Nespresso espresso, coffee ★ 55" TV, WiFi, games ★ Gas grill ★ 7 min to Snow Valley ★ 5 min to Running Springs ★ 13 min to Sky-Park ★ 19 min to Lake Arrowhead ★ 25 min to Big Bear Lake ★ We welcome people from all backgrounds No pets permitted

Cozy independent Studio in Arrowhead Country Club!
SPACIOUS, BRAND NEW, INDEPENDENT STUDIO 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!

Designer Cabin at LAKE Gregory- walk to town
A sanctuary to provide respite from the fast- paced modern lifestyle where time seems to stand still, allowing for reconnection with nature and a focus on the simple pleasures of life. Located in the mountains next to Lake Gregory. 1930s cabin filled with vintage charm, nestled admits a lush pine forest. Newly renovated fully equipped kitchen, heat/AC, wifi. Enjoy lake activities and nearby skiing and let this special cabin transport you to a bygone era while evoking nostalgia and tranquility.

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

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!

LUX 4BR near NOS & Yaamava with Private Backyard
Nestled on the foothills of the San Bernardino Mountains is our luxurious 4BR house, boasting a professionally designed interior that will capture your heart immediately! Only 5-minute drive to downtown, while the top destinations of Lake Arrowhead, Disneyland, and Palm Springs are within an hour's journey. 2300 sq. ft. of space awaits – a 55” HDTV, a foosball table, ultra-fast 500 MB/s Wi-Fi, and access to a private backyard with jacuzzi and BBQ (extra fee need to apply).

Bright Modern 2-Bd House in Quiet neighborhood!
This bright modern house was recently remodeled and it's ready for you to enjoy! The home is situated in a very quiet and safe neighborhood at the end of a cul-de-sac in the foothills of the San Bernardino mountains. This house is the perfect place to use as a basecamp when exploring San Bernardino (Yaamava Resort and Casino, NOS, the first McDonald's museum, Big Bear, Lake Arrowhead, Joshua Tree, Palm Springs, Orange County (Disneyland, Knotts), LA and so many more places.

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

Mountaintop Pool Paradise | Mins to NOS Center

Log Cabin w/Gorgeous Views, Hot Tub+King Beds

The Capricorn Cabin

King Bed -THE URBAN NEST-

Cozy and serene ADU retreat home

Cozy Updated Cabin w/ Views, Walk to Lake Gregory

Redlands Cozy One Bedroom Suite w/Access to a park

Luxury Tropical Modern Pool Estate/NO PARTIES
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ386 | ﺩ.ﺇ404 | ﺩ.ﺇ386 | ﺩ.ﺇ411 | ﺩ.ﺇ400 | ﺩ.ﺇ411 | ﺩ.ﺇ408 | ﺩ.ﺇ408 | ﺩ.ﺇ393 | ﺩ.ﺇ419 | ﺩ.ﺇ386 | ﺩ.ﺇ389 |
| 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 $40 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 40 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 300 vacation rentals in North Redlands, over 280 vacation rentals in Northwest Redlands, and over 50 vacation rentals in East Highlands.
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.
Are there pet-friendly house rentals in Highland?
Four-legged friends are welcome in Highland. Choose from more than 20 house rentals for guests traveling with pets.
Are there Highland house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Highland, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Highland have air conditioning?
Absolutely! We offer over 70 house rentals with air conditioning in Highland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Highland have wifi?
Absolutely! We offer over 70 house rentals with wifi in Highland. Enjoy a tailored experience with all the comforts you desire.
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 ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 4,050 verified reviews to help you choose

Family-friendly vacation rentals
40 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
- Knott’S Berry Farm
- Big Bear Mountain Resort
- Bear Mountain Ski Resort
- Anaheim Convention Center
- Disney California Adventure Park
- Palm Springs Convention Center
- Snow Summit
- Pechanga Resort Casino
- Mountain High
- National Orange Show Events Center
- Honda Center
- Palm Springs Aerial Tramway
- Angel Stadium of Anaheim
- Disneyland Resort
- Indian Canyons
- Tahquitz Creek Golf Resort
- Glen Ivy Hot Springs Spa
- Snow Valley Mountain Resort
- Chino Hills State Park
- Big Bear Alpine Zoo
- Alpine Slide at Magic Mountain
- Palm Springs Air Museum
- Whitewater Preserve




