Pet-friendly holiday rentals in Highland

4.95 out of 5 average rating, 494 reviews

The spacious living area features a vibrant orange sectional sofa, complemented by wooden cathedral ceilings and a large window overlooking the outdoors. Decorative elements include mounted deer heads and a selection of records on a wooden shelf, creating a cozy atmosphere.

Cabin in Rimforest

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!

4.95 out of 5 average rating, 178 reviews

The outdoor patio features a rustic fire pit surrounded by several Adirondack chairs, inviting relaxation. A wooden deck leads to the entrance of the cabin, set against lush greenery and shade provided by tall trees. The cabin's stone chimney adds character to the setting.

Cabin in Crestline

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.

Cabin in Green Valley Lake

A covered patio is displayed with a striped awning and a wooden table surrounded by colorful seating. A potted plant sits at the center of the table. The natural view of trees and distant mountains creates a serene outdoor environment.

4.94 out of 5 average rating, 163 reviews

The Best Views and Vintage Cozy Cabin!

The most stunning sunset you have ever experienced with a scenic view of Lake Arrowhead in the distance! This rustic cabin sits on the edge of the San Bernardino Mountains, and has everything you need to get away. Green Valley Lake is located at 7200 feet making it the highest village, meaning more snow in winter and cooler temps in the summer. There is a swimming beach w/ lifeguards, boats to rent, and a well-stocked fishing lake 5 minutes away. We’re close to the ski slopes and hikes too.

4.88 out of 5 average rating, 433 reviews

Cabin in Running Springs

Wilderness Road A Frame Mountain Cabin

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.

4.97 out of 5 average rating, 180 reviews

Cabin in Running Springs

A-Frame in the Sky - “Rim of the World” Views!

Breathtakingly Gorgeous Views, like nothing you've seen before. EV charger, SAUNA, spa and Views to the Pacific Ocean and Catalina Island. Golden hour sunsets that fade into the city lights for 100 mile views. AFrame in the Sky, sits up high in the clouds and is backed up to the National Forest. Hiking Trails are out your front door. Snow Valley Ski Resort is 10 minutes away and Lake Arrowhead less than five minutes away. Hot Springs, hiking, shopping, fine dining, skiing, snowboarding

4.99 out of 5 average rating, 255 reviews

A person sits at a table with a small vase of flowers, enjoying a scenic view of rolling green mountains and a clear blue sky. The lush landscape extends into the distance, with varying shades of green and hills melting into the horizon.

Guest suite in Crestline

100-Mile View | Romantic Mountain Hideaway

Holly Hill Chalet is curated 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 transforms into a sea of twinkling city lights, igniting the atmosphere with a touch of mountain magic.❤️

4.89 out of 5 average rating, 151 reviews

The living room is furnished with a dark brown sectional sofa, a white coffee table, and a pair of armchairs. A television is positioned against a gray wall, while natural light enters through the windows, which are adorned with navy blue curtains. Decorative elements enhance the space.

Home in Amber Hills

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!

Superhost

A modern living room features a sleek leather sofa and a cozy ottoman centered on a decorative area rug. A stylish light fixture hangs overhead, while a fireplace with an elegant mantel adds warmth. Large windows invite ample natural light, showcasing outdoor views.

Villa in Arrowhead

4.93 out of 5 average rating, 129 reviews

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).

4.96 out of 5 average rating, 124 reviews

A spacious deck is shown with comfortable seating arranged to enjoy expansive views of the landscape. The area is surrounded by tall trees, allowing natural light to filter through and offering a serene outdoor escape.

Cabin in Crestline

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!

A spacious living area showcases high vaulted ceilings and large floor-to-ceiling windows framing expansive views of the mountains. A leather sofa sits atop a light-colored rug, adjacent to a stone fireplace with a warm glow. Rustic chandeliers provide soft ambient lighting, enhancing the inviting space.

4.96 out of 5 average rating, 112 reviews

Modern Cabin with Stunning Views, Outdoor Firepit

“Skyridge Cabin” is a modern 3-bedroom, 2-bath A-frame retreat in Lake Arrowhead with stunning mountain and desert views. It features two king bedrooms, and a queen with a trundle, accommodating up to 6 guests. Highlights include a wood-burning fireplace (wood provided), a balcony with Adirondack chairs, a fire pit, new Nest-powered AC/heat, games for kids, Google Home, and a Frame Smart TV in the living room. Perfect for a secluded mountain getaway.

Superhost

A bright living area features two distinct seating arrangements, including a brown leather sofa with striped cushions and a dark blue upholstered couch. A small coffee table is centered on a neutral rug, and a potted plant adds a touch of greenery. Natural light illuminates the space.

Home in Bloomington

4.94 out of 5 average rating, 144 reviews

2 BDRM Home Spacious Lot plenty of Parking Space

Welcome to La Chiquita! You don’t want to miss this AMAZING home to relax and unwind for vacation or business. Beautiful kitchen and living room layout fabulous flow for everyday living and entertainment. Enjoy a place to cook and eat, kids have their own space to play and run, pets can enjoy the outdoor space provided. Never too late to book we welcome last minute late checkins. We welcome travel workers pls inquire for longer stay.

4.96 out of 5 average rating, 394 reviews

A charming cabin is nestled among trees, featuring a warm exterior and large windows. A wooden deck surrounds a circular hot tub, ready for relaxation. The setting sun casts a soft glow, highlighting the natural landscape surrounding the home.

Cabin in Running Springs

Glen Oak Rim | Hot Tub · Game Room · Epic Views

Couples, Families, & Mountain Peace Seekers only, please. Located at the base of a steep private drive and overlooking the San Bernardino Basin sits this stunning California family cabin. Originally constructed in 1965, the dwelling's Mid-Century details have been lovingly restored while not forgetting a single modern amenity. Brilliantly designed by SoCalSTR® | IG: @socalstr "Top 1%" local market performer according to AirDNA

Popular amenities for Highland pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.92 out of 5 average rating, 178 reviews

A unique barrel sauna is positioned on a stone path, surrounded by tall trees. Softly glowing string lights are hung above, illuminating the area near the entrance. The structure features a wooden exterior with a welcoming entryway, providing a serene atmosphere for relaxation.

Home in Running Springs

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

Home in Downtown Riverside

The blue cottage features a welcoming exterior with large windows allowing warm light to shine through in the evening. A well-maintained lawn surrounds the home, accentuated by shrubs and small trees, creating an inviting atmosphere for guests.

4.91 out of 5 average rating, 139 reviews

Private backyard - Walk to Downtown - Pet friendly

4.89 out of 5 average rating, 133 reviews

A charming two-story cabin is surrounded by trees, showcasing a large deck that wraps around the structure. Oversized windows offer views of the outdoors, allowing natural light to fill the interior. The warm wooden exterior complements the serene natural setting.

Home in Lake Arrowhead

Lakeview House

4.97 out of 5 average rating, 129 reviews

A charming blue house is surrounded by tall trees, featuring a bright red front door. An artificial grass yard offers a lush appearance, complemented by smooth stones that line the pathway. The front porch, adorned with white railings, invites relaxation and outdoor enjoyment.

Home in Big Bear Lake

Fenced Yard, Central AC, Heat, Spa, Sauna, Dogs OK

4.96 out of 5 average rating, 102 reviews

The living area features a spacious gray sectional sofa adorned with decorative pillows. A rustic chandelier hangs above, illuminating the room. Large windows offer views of the surrounding forest. A wooden dining table is visible in the background, accompanied by a warm wood railing along the staircase.

Home in Lake Arrowhead

Forest Views | Fire Pit | BBQ Grill | Cozy Cabin

4.97 out of 5 average rating, 99 reviews

A wooden picnic table is positioned beside a gently flowing creek, surrounded by lush greenery and trees. Sunlight filters through the leaves, casting dappled shadows on the rocks and water, creating a serene and inviting outdoor space.

Home in Lytle Creek

Creek House - Water Front

4.85 out of 5 average rating, 220 reviews

An entertainment area is highlighted by a billiard table centered in the space. Comfortable seating is arranged around the table, with a vintage fireplace located beside it. Natural light enters through the window, and a chalkboard and dining setup are visible in the background.

Home in Fontana

🥳Pub Style Family-Friendly Entertainment Paradise💯

4.99 out of 5 average rating, 143 reviews

The exterior of the studio is illuminated by string lights, creating a warm ambiance at dusk. A fenced area features a covered patio with dining chairs and a small table, while the structure is surrounded by natural landscaping and hills in the background.

Home in Apple Valley

Studio in Apple valley

Pet-friendly home rentals with a pool

4.94 out of 5 average rating, 123 reviews

A private swimming pool is surrounded by a stone patio and secured by transparent fencing. A sun lounger is positioned beside the pool, offering a place to relax. Bright blue water reflects the clear skies above, enhancing the outdoor ambiance.

Home in Ontario

Charming 2BR 1BA Private pool Self check-in

4.86 out of 5 average rating, 559 reviews

Cabin in Big Bear Lake

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

4.95 out of 5 average rating, 149 reviews

A spacious outdoor pool is surrounded by a concrete patio and palm trees, providing a relaxing area for guests. The lush greenery and well-maintained landscaping enhance the outdoor setting, while the house features a tiled roof and large windows that allow natural light.

Home in Canyon Crest

Charming 5 bed, 3 bath home with pool

4.96 out of 5 average rating, 284 reviews

A serene outdoor space features a well-maintained pool surrounded by lounge chairs and umbrellas. Stone steps lead to a home with a large patio. A gazebo is visible, enhancing the setting with additional outdoor seating.

Guest suite in Oak Hills

DMO 1 Bdr+ Suite. Private Pool, Spa, Luxury & Fun

4.89 out of 5 average rating, 110 reviews

An outdoor living space features a large pool surrounded by sun loungers, with a cozy fire pit area nearby. The two-story estate is visible in the background, showcasing a blend of modern and rustic elements against a backdrop of mountainous scenery.

Home in Cherry Valley

Vineyard Retreat, Pool & Amazing Views!

4.9 out of 5 average rating, 221 reviews

The guest house features a welcoming entrance with a decorative front door and a small chair positioned by the entrance. Lush greenery surrounds the exterior, with tropical plants and palm trees enhancing the natural landscape. A clean pathway leads to the doorway.

Guest house in Colton

Oasis in the canyon

4.99 out of 5 average rating, 333 reviews

The outdoor space features a sparkling swimming pool surrounded by a landscaped patio. The cottage is seen in the background with large glass doors, inviting natural light. Beautiful plants and greenery enhance the serene atmosphere, providing a pleasant space for relaxation.

Guest house in Redlands

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

4.93 out of 5 average rating, 182 reviews

A serene pool area is illuminated by soft blue lights under a night sky, surrounded by lush greenery and potted plants. Comfortable seating options are available, enhancing the inviting ambiance created by string lights overhead.

Guest suite in Riverside

Tranquil Retreat | Private Guest Quarters + Pool

Private, pet-friendly home rentals

A charming cabin exterior is framed by a lush, wooded landscape. The structure features a dark wood exterior with red accents, including windows and a front door. A wooden deck extends from the entrance, nestled beside a large, aged tree.

4.98 out of 5 average rating, 116 reviews

Pet friendly, Romantic, Fast WiFi, 1m from Village

4.91 out of 5 average rating, 113 reviews

Chalet in Crestline

Lake Chalet- Walk to Lake and Town.

Superhost

The A-Frame structure, framed by tall trees, showcases a spacious deck illuminated by soft string lights. The large glass windows reflect a warm glow from inside, inviting guests to enjoy the surrounding nature and direct access to the outdoor space.

4.94 out of 5 average rating, 250 reviews

A-Frame of Mind • Fenced Yard - Lake Access - AC

4.98 out of 5 average rating, 172 reviews

The Lazy Bear Lodge

4.93 out of 5 average rating, 137 reviews

A modern fireplace in turquoise and black stands at the corner of a wooden room, contributing to a cozy ambiance. A comfortable chair, adorned with decorative pillows, is placed nearby, with a textured pouf positioned on the floor. Large windows provide a view of the surrounding trees.

Cabin in Big Bear Lake

NEW! ModernRusticLogCabin-RARE SkiView-Spa-Firepit

A charming 1929 cabin is nestled among tall trees, showcasing a light green exterior and inviting front door. The stairs lead up to the cabin's entrance, surrounded by natural foliage, providing a sense of privacy in a serene woodland setting.

4.99 out of 5 average rating, 284 reviews

Beary Romantic Jacuzzi Cabin in the Woods

Guest suite in San Bernardino

A modern kitchen and dining area features sleek white cabinetry and stainless steel appliances. A spacious island with seating for four stands at the center. Light wood flooring complements the area, while large windows allow natural light to brighten the space.

4.92 out of 5 average rating, 74 reviews

3BDModern Unit-NOS/Yaamav/Mtns