
House vacation rentals in Highland
Find and book unique houses on Airbnb
Quick stats about house rentals in Highland

Total vacation rentals
Explore 70 vacation rentals in Highland

Nightly prices starting at
Highland vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

Verified guest reviews
Over 2,620 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Highland rentals

4.8 Average rating
Highland stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated house rentals in Highland
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

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.

Mountain Lake A-Frame | Forest, AC, Auto-Generator
This enchanting A-Frame cabin offers the perfect blend of adventure and tranquility. Explore trails, mountain towns, or unwind in the hammocks. Sits on a double lot, so you have space to yourself. Cutest small mtn town & 30 min to Big Bear 🔸Auto Generator (no worrying @ blackouts summer or winter, happens often) 🔸NEW AC mini split 🔸 NEW cozy couch 🔸Propane BBQ & Fire Pit (with tanks) 🔸Private acre of forest 🔸 5-minute walk to lake 🔸 Hammocks & swing 🔸 Fireplace 🔸 Washer/Dryer BYOD

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!

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.

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.

Magical lake house with spectacular views
Gorgeous, tranquil retreat with enriching views of the lake and nature. A storybook bridge with the soothing flow of the stream beside it sets the mood for relaxation, inspiration and/or romance immediately. The home opens to captivating views of the entire lake from the curated, open floor plan. Ideal for cooking, quality dining, working on something creative or simply a peaceful escape from the city. Multiple terraces and balconies to enjoy the crisp air and setting.

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

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!

Charming 3 BR Home - Near NOS Center/Mountains
Welcome to this beautifully renovated 900 sq. ft. home, carefully designed to be your home away from home. Inside you will find a full kitchen, washer/dryer, and three bedrooms (full beds, TVs, desks). Only 10–15 mins to NOS Event Center, plus easy drives to Big Bear, Palm Springs, and beaches. For your peace of mind, the property has 3 exterior cameras which actively record audio/video and are monitored 24/7 for security.

Private Casita with Jacuzzi, newly remodeled.
Enjoy a stylish experience at this centrally-located home with its own private basketball half court (ball not included) hot tub, and grill. Close to downtown San Bernardino, where you will find great eating places, close to mountains, casinos, The NOS Center, National Orange Show(7 minute drive.) Less than 1 hour from Lake Arrowhead & Big Bear Lake. p.s if you don't like neighbors, this is the house for you.

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 house rentals
House rentals with a pool

One In A Trillion • 32+ Private Acres!

Charming 5 bed, 3 bath home with pool

Vineyard Retreat, Pool & Amazing Views!

CHARMING POOL HOME BY DOWNTOWN *FAMILY GETAWAYS*

Luxury 5BR Pool Home | ONT, Victoria Gdns & Mills

Pool|Jacuzzi|Arcade|Game Room|2 BBQ Grill|Fire Pit

Peaceful retreat in Upland!

North Upland House with a Pool
Weekly house rentals

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

Peaceful A-Frame-Walk to Village & Lake - New AC

Mtn. Hideaway: Your Relaxing Escape (Sauna & Cozy)

Cozy Quiet Private Rose House laundry cooking

Perfect Weekend Retreat | Hot Tub+Firepit+Games

Creek House - Water Front

Cottage Grove Haus

So. Cal. Living near Redlands-Beautiful 3,000+Home
Private house rentals

The Redlands Retreat | Near Downtown & University

Perfect home for large groups! Newly remodeled

Cozy, Romantic Cabin for Two | The Squirrel House

Valle de Guadalupe Escape gem

Entire house near Redlands

Backyard Paradise – Pool, Firepit & Outdoor Dining

ThE FuN FaCtOrY

Lake Arrowhead Luxury Chalet
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 448 | ﺩ.ﺇ 466 | ﺩ.ﺇ 547 | ﺩ.ﺇ 452 | ﺩ.ﺇ 466 | ﺩ.ﺇ 481 | ﺩ.ﺇ 499 | ﺩ.ﺇ 544 | ﺩ.ﺇ 470 | ﺩ.ﺇ 481 | ﺩ.ﺇ 426 | ﺩ.ﺇ 430 |
| 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 |
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- Rentals with a patio Highland
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- Rentals with a fire pit Highland
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- Family-friendly rentals Highland
- Rentals with pools Highland
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- House rentals San Bernardino County
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- Disneyland Park
- Knott’S Berry Farm
- Disney California Adventure Park
- Pechanga Resort Casino
- National Orange Show Events Center
- Anaheim Convention Center
- Big Bear Mountain Resort
- Disneyland Resort
- Palm Springs Convention Center
- Mountain High
- Angel Stadium of Anaheim
- University of California Irvine
- Honda Center
- Bear Mountain Ski Resort
- Palm Springs Aerial Tramway
- Indian Canyons
- Yaamava' Resort & Casino
- Glen Ivy Hot Springs Spa
- Snow Summit
- Tahquitz Creek Golf Resort
- Irvine Spectrum Center
- Snow Valley Mountain Resort
- Chino Hills State Park
- Whitewater Preserve





