
Pet-friendly vacation rentals in Highland
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Highland

Total vacation rentals
Explore 20 vacation rentals in Highland

Nightly prices starting at
Highland vacation rentals start at G$16,744 GYD per night before taxes and fees

Verified guest reviews
Over 1,030 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Highland vacation rentals include wi-fi 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!
Top-rated pet-friendly home rentals in Highland
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Cozy Quiet Private Rose House laundry cooking
The home is conveniently located next to Highway 210, less than 2 miles from Costco and several business districts; less than 20 minutes from the largest outlet Ten Doors, about 20 minutes from Ontario Airport, 10 minutes from Victoria Garden Mall Leisure Shopping District, 48 miles from Arrow Lake… Comfortable and beautiful garden, quiet and tidy space, fully equipped living space, fully functional private residence, super comfortable latex memory mattress from Costco, cozy rose home for two, welcome😀

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.

Fort Black Bear w/ Hot Tub - Lake Arrowhead
Our chic mountain retreat is everything you'd want in your Lake Arrowhead getaway. Beautiful wood cathedral ceilings accent the views of trees, boulders and peeks of the city lights far below. The expansive great room is anchored by a stone fireplace, wrap around sectional and large inviting dining area. A fully outfitted cook's kitchen, roman tub with picture window, king size bed and large dining table make this the ultimate retreat. Enjoy the cedar clad hot tub set next to massive boulders!

100-Mile View | Romantic Chalet • Dogs Welcome
Holly Hill Chalet is designed for romantic interludes and peaceful retreats. While the interior is stylish and cozy, the true star of the show is the view: an ever-changing masterpiece that transitions from golden sunrises to cinematic sunsets. From our expansive patios and park-like garden, you have a front-row seat to the awe-inspiring expanse below. As twilight descends, the horizon dissolves into a sea of twinkling city lights, igniting a garden of whimsical light, chandeliers, and magic.✨

Designer Cabin at LAKE Gregory- walk to shops!
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.

Beary Romantic Jacuzzi Cabin in the Woods with A/C
Enjoy our tastefully updated 1929 Cabin in the Woods near Lake Arrowhead. One of the first cabins built in the area, charming place for a romantic getaway or to enjoy with family. The ambiance of the electric fireplace, the double egg-swing chair on the deck, the relaxing hot tub overlooking a hillside of trees, the cute bedroom/loft w/cool AC, a peek-a-boo view of the lake... the perfect getaway! Come enjoy the Beary Romantic Cabin in the Woods! How many "bears" can you find at the cabin?

1965 Mid-Century A-Frame • Forest Views
Mid-Century 1960s A-Frame Cabin in Running Springs, California Escape to this stylish A-frame nestled in the trees —perfectly located just 30 minutes to Big Bear, 15 minutes to Lake Arrowhead, and minutes from SkyPark at Santa’s Village, hiking trails and cafés. Two bedrooms on the main floor plus a third bedroom in the loft. Enjoy a fully stocked kitchen and fresh linens and towels. A spacious wraparound deck with seating and a grill—ideal for morning coffee, outdoor dining, and star-gazing.

The Capricorn Cabin
Welcome to the Capricorn Cabin! Built in 1961, this cozy mid-century modern A-frame cabin in Big Bear blends historic charm with hygge comfort featuring vintage décor, a modern gel-fuel fireplace, vaulted ceilings, and king bed sleeping loft. Located in the historic Big Bear neighborhood Sugarloaf, this cabin is perfect for a romantic getaway, trip with your small family, or solo retreat. Just minutes from the lake, slopes, and village, with easy access by bus. We'd be happy to host you!

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).

Romantic Hot tub • Fireplace | Near Snow Valley
Welcome to The Den, a 1960s cabin reimagined by LBL Design Co. This moody, romantic retreat blends almond-blasted ceilings, warm wood tones, and modern finishes — complete with a private hot tub under the pines. Perfectly centered in the San Bernardino Mountains, it’s your base for snow days, trail adventures, and slow, cozy nights by the fire. Sip wine on the deck, roast s’mores under the stars, and unwind beside the glowing fireplace on our plush velvet sofa.

IncredibleCityView- Pet&FamFriendly PoolTble-games
Great View Chalet truly has a one-of-a-kind view! This 100 year old cabin boasts a modernized kitchen with a Pool and Ping Pong table for added family fun! Our cozy Chalet has an oversized bedroom with a King sized bed and soaking tub, an additional bathroom provides a shower. Close to downtown Crestline, 1 mi. to Lake Gregory, hiking-trails, off-roading activities, water park, snow sledding/skiing and only 15 minutes from Lake Arrowhead. Come enjoy our cabin!
Popular amenities for Highland pet-friendly home rentals
Pet-friendly house rentals

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

Dragonfly Landing *Lake Access *Dog Friendly*Spa*

Mountain Lake A-Frame | Forest, AC, Auto-Generator

Balsam Bungalow - Lake View 1 min to ski - Hot Tub

Forest Views | Fire Pit | BBQ Grill | Cozy Cabin

Vineyard Retreat, Pool & Amazing Views!

Hilltop Escape | Heated Pool & Epic Views

Creek House - Water Front
Pet-friendly home rentals with a pool

Log Cab-Inn | Authentic w/ Modern Luxuries & Spa!

The Cozy Cottage Condo - Jacuzzi/3mi to slopes

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

Charming 5 bed, 3 bath home with pool

Exclusive Private 1Bdr+Suite. Peaceful Luxury, Fun

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

Tranquil Retreat | Private Guest Quarters + Pool

Norco country private entrance
Private, pet-friendly home rentals

The Best Views and Vintage Cozy Cabin!

Running Wolves Lodge: Slope Views, Gym, Spa, Pets

1929 Vintage Arrowhead Villas

Dog Friendly A-Frame in the Treetops w firepit

Modern Cabin with Stunning Views, Outdoor Firepit

Cozy Updated Cabin w/ Views, Walk to Lake Gregory

Pet/Kid Friendly Retro Cabin, BBQ, Views

Mile High Haus w/ Mountain Views by @To_Dwell_Here
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$25,534 GYD | G$24,069 GYD | G$29,720 GYD | G$28,046 GYD | G$36,418 GYD | G$32,651 GYD | G$26,162 GYD | G$29,302 GYD | G$26,790 GYD | G$31,395 GYD | G$27,627 GYD | G$28,674 GYD |
| 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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- 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
- University of California Irvine
- Palm Springs Convention Center
- Mountain High
- Angel Stadium of Anaheim
- Honda Center
- Bear Mountain Ski Resort
- Yaamava' Resort & Casino
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- Snow Summit
- Great Park
- Tahquitz Creek Golf Resort
- Snow Valley Mountain Resort
- Chino Hills State Park





