Pet-friendly holiday rentals in Highland

4.88 out of 5 average rating, 104 reviews

Home in Redlands

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.

Cottage in San Bernardino

4.94 out of 5 average rating, 338 reviews

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

4.95 out of 5 average rating, 497 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!

5 out of 5 average rating, 167 reviews

An open-plan living area features a plush sectional sofa adorned with a striped blanket. A circular dining table sits nearby, illuminated by sunlight streaming through large windows that showcase natural surroundings. A wood-burning stove provides warmth in the corner, enhancing the cozy ambiance.

Cabin in Banning

Boulderland A-frame on 8 acres / 4 miles from Town

Welcome to our cozy A-frame cabin nestled on the outskirts of Idyllwild California. This secluded retreat is the perfect place to escape the hustle & bustle of the city and reconnect with nature. The open-plan living area features a fully equipped kitchen, comfortable seating, and a wood-burning stove, perfect for cozy nights in. Step outside & you'll be greeted by the beautiful natural surroundings. Relax on the spacious deck & take in the views of the surrounding trees, valley & mountains.

4.95 out of 5 average rating, 185 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.

4.97 out of 5 average rating, 181 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.❤️

Superhost

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

4.86 out of 5 average rating, 152 reviews

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, 130 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, 225 reviews

A spacious terrace extends alongside the home, offering unobstructed views of the lake and surrounding hills at sunset. Subtle lighting illuminates the area, while a pair of outdoor chairs provides a cozy spot to enjoy the serene backdrop.

Home in Crestline

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.

4.96 out of 5 average rating, 128 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.

4.97 out of 5 average rating, 119 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.

Popular amenities for Highland pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

Superhost

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

4.91 out of 5 average rating, 181 reviews

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, 141 reviews

Private backyard - Walk to Downtown - Pet friendly

4.95 out of 5 average rating, 151 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

4.95 out of 5 average rating, 140 reviews

The exterior of the A-frame cabin is showcased amid tall trees, with large windows reflecting natural light. A wooden deck is visible, enhancing the connection to the surrounding landscape, while fall foliage adds warmth to the scene.

Home in Lake Arrowhead

Dragonfly Landing *Lake Access *Dog Friendly*Spa*

4.96 out of 5 average rating, 103 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, 133 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, 188 reviews

A spacious living area is bathed in natural light from large windows, revealing stunning lake views. The modern kitchen features sleek cabinetry and high-end appliances. An inviting game room offers a variety of entertainment options, while the outdoor deck showcases comfortable seating for enjoying the scenery.

Home in Fawnskin

✧ PANORAMIC Views, Pet/Child Friendly, Gameroom! ✧

4.99 out of 5 average rating, 151 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

Apartment in Big Bear Lake

An open kitchen features modern cabinetry and stainless steel appliances, including a microwave and refrigerator. A breakfast bar with four stools provides seating. Pendant lights hang above the counter, while a wooden shelf displays potted plants. Light colors and wood accents create a welcoming atmosphere.

4.89 out of 5 average rating, 208 reviews

The Cozy Cottage Condo - Jacuzzi/3mi to slopes

Apartment in Big Bear Lake

The living room features a comfortable seating area with a natural stone fireplace and a media console. A large flat-screen TV displays a serene lake view. Natural light floods the space through sliding glass doors leading to a balcony with lakefront views.

4.95 out of 5 average rating, 117 reviews

Lakefront Walk 2 Village w/ Dock Access & Pets

4.94 out of 5 average rating, 125 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, 562 reviews

Cabin in Big Bear Lake

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

4.96 out of 5 average rating, 291 reviews

A refreshing pool reflects the clear blue sky, surrounded by a spacious deck. Colorful lounge chairs and umbrellas provide shaded seating areas. Steps lead from the pool to a welcoming green building, framed by trees and decorative landscaping.

Guest suite in Oak Hills

Exclusive Private 1Bdr+Suite. Peaceful Luxury, Fun

4.89 out of 5 average rating, 112 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 Yucaipa

Vineyard Retreat, Pool & Amazing Views!

4.91 out of 5 average rating, 222 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

4.94 out of 5 average rating, 186 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 wooden dining table is positioned near large sliding glass doors, revealing views of Lake Arrowhead and surrounded by tall trees. Natural light fills the space, enhancing the inviting atmosphere of the dining area with a neutral table runner and decorative plant.

4.94 out of 5 average rating, 304 reviews

Lake View, Hot Tub, Fire Pit, Love Pets, Walkable

The vintage cabin features a welcoming exterior with a wooden porch, large windows, and a flag displayed prominently. Surrounded by lush greenery and tall trees, the entrance is accessible via a small set of steps leading to the front door.

5 out of 5 average rating, 266 reviews

1929 Vintage Cabin in Arrowhead Villas

4.96 out of 5 average rating, 146 reviews

The interior of the A-frame cabin showcases high ceilings and a spacious open-concept layout. A spiral staircase leads to the loft above. A cozy seating area is complemented by a unique hanging chair. The kitchen, equipped with seating, invites shared meals and conversations.

Cabin in Running Springs

Couple's Retreat Modern Mountain Chalet + Hot Tub

A charming cabin exterior is framed by towering trees, featuring a dark wood finish and red accent windows. A welcoming front porch is adorned with a bench, inviting relaxation amidst the serene woodland setting.

4.98 out of 5 average rating, 116 reviews

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

4.91 out of 5 average rating, 115 reviews

Chalet in Crestline

Lake Chalet- Walk to Lake and Town.

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, 253 reviews

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

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, 286 reviews

Beary Romantic Jacuzzi Cabin in the Woods

The living area features a unique triangular design with large windows providing scenic mountain views. A comfortable brown sectional sofa is arranged around a glass coffee table, and a spiral staircase leads to an upper level, enhancing the open and airy atmosphere.