Pet-friendly holiday rentals in Highland

4.96 out of 5 average rating, 516 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!

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.

4.95 out of 5 average rating, 210 reviews

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.

4.99 out of 5 average rating, 264 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 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.✨

An outdoor seating area features a fire pit surrounded by two lounge chairs with yellow cushions. A large dining table is positioned under strung lights, with a stone pathway leading up to the main cabin, nestled among tall trees.

5.0 out of 5 average rating, 123 reviews

Single-Story Cabin with Hot Tub, EV Charger & Yard

Welcome to Little Bearfoot Cabin! A 1925 single-story cabin with modern spa-like amenities and separate A-Frame office with fast wi-fi for digital nomads. Luxurious summer camp vibes. Cozy up by the fire pit making s'mores, enjoy al fresco dinners, and relax in the hot tub nestled under towering evergreens. If not outdoors in the amazing yard, enjoy central AC/heat. Less than a mile to lake, Village, and Lake Arrowhead Brewery. Access to walk the private trails. Dog & kid friendly. EV Charger

4.99 out of 5 average rating, 110 reviews

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

Nestled amidst breathtaking scenery, Running Wolves Lodge is a creative, unique space, immersive with nature. Prepare to be captivated by PANORAMIC MOUNTAIN/ SLOPE VIEWS that surround our lodge, providing a picturesque backdrop to your stay. Enjoy our cinema movie projector with 120 inch screen. Indulge in our wellness oasis: a private gym equipped with a sauna, hot tub, heavy bag and weights. A true haven awaits you with spa-like soaking tubs, plush bedding and more. Designed by AMABASPACES.

Home in Green Valley Lake

An A-Frame cabin is nestled among trees, featuring a vibrant red door and multiple windows that reflect the evening light. String lights adorn the space, creating a warm ambiance. A wooden deck leads to the entrance, enhancing the cabin's rustic charm.

5.0 out of 5 average rating, 106 reviews

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

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

4.95 out of 5 average rating, 101 reviews

A welcoming entrance is framed by lush green ivy climbing over a covered porch. The dark front door is adorned with a seasonal wreath. Rocking chairs and potted plants create an inviting atmosphere, while a small doormat adds a pop of color near the entrance.

Home in Redlands

Downtown Redlands Historic Wonderland

Downtown Redlands 2 Min Walk From State St. Food, Bars, Fun. Peace & Yoga I own a studio & teach private classes in the back studio- I am very quiet, you are always welcomed to join & I love helping Great for a couple/Travel Nurse & Medical/ Student or World Travelers 🧳 LAX Ontario & San Bernardino Airports within 20 minutes. Located near LLU, SB County, Káiser, Redlands Hospital & The University of Redlands, SBCU, LLUMC Valley & Crafton & of course Coachella & Bicycle Classics.

5.0 out of 5 average rating, 112 reviews

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!

4.88 out of 5 average rating, 171 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 Highland

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 San Bernardino

4.93 out of 5 average rating, 133 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).

4.99 out of 5 average rating, 178 reviews

A couple walks hand in hand on the wraparound deck, with large glass doors leading into the cozy interior. The space features a welcoming wood-beamed ceiling and a blend of natural light, contributing to the inviting ambiance of the cabin.

Cabin in Running Springs

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.

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.

4.96 out of 5 average rating, 141 reviews

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

Superhost

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

4.94 out of 5 average rating, 108 reviews

Creek House - Water Front

4.99 out of 5 average rating, 134 reviews

Home in San Bernardino

Hilltop Escape | Heated Pool & Epic Views

4.85 out of 5 average rating, 525 reviews

Natural light fills the living area through large glass doors, offering views of the surrounding trees and hills. A simple rug is placed on the floor, with two chairs and a bar area featuring tall stools visible in the space.

Home in Big Bear Lake

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

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, 186 reviews

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

4.95 out of 5 average rating, 155 reviews

A bright bedroom features a white wooden bed frame adorned with a blue and aqua bedding set. Colorful pillows add a touch of vibrancy. Soft lighting from two bedside lamps creates a warm glow, and a window with blinds allows for natural light to filter in.

Home in North Fontana

Cozy Quiet Private Rose House laundry cooking

4.97 out of 5 average rating, 188 reviews

An A-frame cabin is surrounded by tall trees, featuring large windows that invite natural light. A welcoming entrance is framed by a stone path leading to two outdoor chairs placed on the porch. Nearby, bushes and greenery contribute to the serene outdoor setting.

Home in Wrightwood

The BobKat LodgeRomantic A-Frame Mountain Getaway

4.96 out of 5 average rating, 110 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

4.95 out of 5 average rating, 147 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*

Pet-friendly home rentals with a pool

4.99 out of 5 average rating, 336 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!

4.97 out of 5 average rating, 115 reviews

A spacious pool area is showcased with a clear blue pool reflecting the evening sky. Surrounding the pool are lounge chairs and a dining table with an umbrella for shade. The house features large windows that invite natural light, enhancing the outdoor living experience.

Home in Riverside

Tesla EV Charger, 2 KING BEDs, 3 minute to UCR

4.95 out of 5 average rating, 165 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 Riverside

Charming 5 bed, 3 bath home with pool

4.94 out of 5 average rating, 188 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

An inviting living area features a large, down-filled sofa adorned with decorative pillows and a cozy throw. A stone fireplace is central, with a fire burning brightly. A smart TV is positioned on a console, while natural light filters through the windows, highlighting wooden beams and rustic decor.

4.97 out of 5 average rating, 235 reviews

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

4.9 out of 5 average rating, 363 reviews

Feet Away From Slopes Modern Snow Summit Cabin

Apartment in Big Bear Lake

A cozy living area is displayed with a stone fireplace, flickering with flames. A circular wooden coffee table, featuring a plant in a terracotta pot, is positioned in front. Brown and beige decor elements add warmth to the space, complemented by patterned wall art.

4.88 out of 5 average rating, 382 reviews

Lakeside Condo 2B/2B - Jacuzzi, 3mi to slopes

Apartment in Big Bear Lake

A comfortable living area features a brown sofa and two green chairs arranged around a circular black table. Light streams through sheer curtains, enhancing the warmth from a fireplace. Decorative plants and a subtle lamp complete the inviting space.

4.94 out of 5 average rating, 193 reviews

Casita Condo | Jacuzzi | 3mi to slopes

Private, pet-friendly home rentals

Cabin in Green Valley Lake

4.94 out of 5 average rating, 174 reviews

The Best Views and Vintage Cozy Cabin!

4.98 out of 5 average rating, 109 reviews

Cozy Updated Cabin w/ Views, Walk to Lake Gregory

4.96 out of 5 average rating, 141 reviews

Secluded A-Frame, Hot Tub, Lake Access

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, 297 reviews

Beary Romantic Jacuzzi Cabin in the Woods with A/C

4.99 out of 5 average rating, 335 reviews

An aerial view highlights a modern cabin surrounded by towering pine trees. A spacious outdoor deck features a sunken seating area, while a hammock is positioned nearby on a natural ground surface, inviting relaxation in a serene, wooded setting.

Cabin in Wrightwood

Insta famous 70’s Escape, Hot tub • EV • Pets

4.88 out of 5 average rating, 385 reviews

Mountain A-Frame | Hot Tub+Views | 90 Min from LA

A spacious living area features high, sloped ceilings and is anchored by a stone fireplace. Large windows allow natural light to fill the room, offering views of the surrounding trees. A leather couch, a round pouf, and a wooden dining table define the welcoming space.

4.96 out of 5 average rating, 453 reviews

Idyllic A-Frame - Lake rights - Hot tub

The exterior of the cabin is surrounded by trees and features a wooden deck leading to the entrance. A propane grill is positioned nearby, and two lounge chairs are visible on the deck, with a clear view of the natural landscape beyond.