Holiday rentals with outdoor seating in Highland

5 out of 5 average rating, 184 reviews

The exterior of a striking A-frame cabin is prominently displayed, framed by snow-covered ground and bare trees. Large front windows reflect the surrounding nature, while a balcony extends from the structure, providing a vantage point over the serene landscape.

Cabin in Running Springs

Romantic A-Frame Cabin | Hot Tub, Fire Pit, Skiing

❤️Escape to the most romantic cabin in Southern California-featured in Dwell Magazine❤️ ★ Perfect for a couple's getaway ★ Designer furnishings, high-end linens, luxury details ★ Hot tub surrounded by boulders ★ Firepit ★ Cozy fireplace ★ Hiking out the back door ★ Nespresso Vertuo espresso, coffee ★ 55" TV, WiFi, games ★ Gas grill ★ 7 min to Snow Valley ★ 5 min to Running Springs ★ 13 min to Sky-Park ★ 19 min to Lake Arrowhead ★ 25 min to Big Bear Lake ★ We welcome people from all backgrounds

4.99 out of 5 average rating, 104 reviews

Home in San Bernardino

Hilltop Retreat | Heated Pool + Spectacular Views

Welcome to The Vibe Estate 🌴✨ A hilltop retreat designed for meaningful moments with family and friends. Enjoy breathtaking views 🌄, a heated cocktail pool 💧, and a spacious home perfect for meals, games 🎲, and connection. A peaceful escape to unwind, recharge, and create unforgettable memories together 💛. 🆓 Enjoy the Heated Pool and Propane BBQ Grill free of charge. Everything is set up to help families and friends spend quality time together. Please message host with special requests.

Guest suite in San Bernardino

A charming exterior of a single-story house is framed by lush palm trees and vibrant greenery. The front yard showcases a variety of plants, with a well-maintained pathway leading to the entrance. Clear blue skies provide a bright backdrop to this inviting structure.

4.99 out of 5 average rating, 144 reviews

All New cozy SUITE in Arrowhead Country Club!

SPACIOUS, BRAND NEW, INDEPENDENT SUITE in the luxurious and peaceful Arrowhead Country Club. Independent with self-check in. 1 California bed plus 1 additional bed, kitchenette and huge shower. 500 sqft by the Golf course and 20 min. away from LAKE ARROWHEAD! Great for all seasons. Trees all around, all markets and restaurants you may need. Also 10 min. from San Manuel Casino. Close to Riverside and Redlands! We will only consider bookings for Registered ID Guests with reviews. Thank you!

4.98 out of 5 average rating, 104 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

Cozy hilltop Studio on 5 acres Completely private with spectacular day and night views of the valley.. Everything you need is here to enjoy a relaxing sunset or drink your favorite coffee viewing a beautiful sunrise.View the night sky while enjoying a glass of wine. You will feel miles away, yet all store conveniences are just less than 10 minutes away.Come and enjoy the relaxing quietness of Apple Valley. Relaxing little walking trail in front of house .only 4 mins. hill drive to location.

4.99 out of 5 average rating, 244 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

Breathtaking Mountain Views | Romantic Hideaway

Holly Hill Chalet is ideal for romantic interludes or peaceful retreats, we promise an unforgettable experience. Expansive patios and park-like setting for garden. The true star of the show is the view an ever-changing masterpiece that transitions from incredible sunrises to beautiful sunsets, all the while offering a front-row seat to the awe-inspiring expanse below. As twilight descends, the view transforms into a sea of twinkling city lights, igniting the atmosphere with a touch of magic

4.99 out of 5 average rating, 326 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!

Located in beautiful South Redlands near Prospect Park, this detached cottage has its own private and inviting fenced backyard, nicely landscaped with comfortable patio furniture. Inside you will find separate living and bedroom spaces, charming decor, Heating/A/C, Cable TV, WIFI, kitchenette with microwave, Keurig coffee maker and compact refrigerator, fine linens, comfortable queen sized bed, and newer bathroom. Conveniently located near Downtown Redlands, University of Redlands and ESRI!

4.95 out of 5 average rating, 221 reviews

A two-story mini home is showcased beside a refreshing swimming pool, surrounded by a neatly landscaped garden filled with various plants. The clear blue sky enhances the peaceful outdoor atmosphere, while a palm tree rises above the structure.

Guest house in Fontana

The Blue Cabin

Relax at this unique, tranquil, and comfortable mini home in our backyard. Surrounded by a beautiful garden with a wide variety of succulents and a relaxing pool. With a space to enjoy reading or listening to music. Equipped with microwave, Keurig coffee machine, mini refrigerator, toaster, blender, washer/dryer, and tableware. The mini home has air conditioning and heating system for comfort and a smart TV. No parties allowed.(SPACE EQUIPPED ONLY FOR 2-3 PEOPLE *no more than 3 fit*)

5 out of 5 average rating, 282 reviews

The Black A-Frame cabin is nestled among tall trees, surrounded by snow. Warm string lights illuminate the inviting exterior, enhancing the tranquil evening setting. A hammock is positioned on the deck, inviting relaxation while enjoying the serene winter landscape.

Cabin in Running Springs

Mid-Century Cabin Perfect for Romantic Getaway

This Black A-Frame style cabin nestled in the trees of Running Springs. Surrounded by grand pine and cedar trees, it makes you feel like you are exploring tree tops. This cabin has decks on each of its 3 levels to appreciate it even more. You are greeted with a mid-century modern styling throughout the home that take you back to a golden era of design. Enjoy snuggling in the A-frame loft, get lost in a good book, enjoy some classic music, or enjoy a film in the secret cinema room...

4.89 out of 5 average rating, 121 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!

4.82 out of 5 average rating, 201 reviews

An outdoor space is presented, featuring a sparkling pool and a relaxing Jacuzzi under a wooden gazebo. Colorful murals adorn the surrounding wall, with warm light illuminating the area at dusk. Comfortable lounge chairs are positioned around the pool for leisure.

Home in Wildwood Park

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.

4.96 out of 5 average rating, 270 reviews

A charming guesthouse exterior is presented with a paved patio featuring potted plants. A comfortable seating area is visible, along with glass doors that allow natural light into the space. Lush palm trees surround the area, enhancing the inviting atmosphere.

Guest house in Highland

Serene Escape Tiny House Living/pool/near Yaamava

We are located close to dining , hiking, shopping, movie theaters, National Orange Show Event Center (NOS Events), Yaamava Resort and Casino, some nightlife, Redlands University and Loma Linda University. You’ll love my place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. Our place is good for couples, solo adventurers, and business travelers. Perfect little getaway! I have another listing-click on my photo to view.

4.93 out of 5 average rating, 426 reviews

The cabin's interior features high vaulted ceilings with exposed wooden beams. A sunlit seating area includes a blue sectional sofa and a rustic table set for dining. Large windows illuminate the space, providing views of the surrounding nature.

Cabin in Running Springs

Rocky Top Retreat- Amazing Views!

You will love the peacefulness of this cozy hilltop cabin. This cinder block home sits in a quaint Arrowbear community just up the hill from a seasonal lake. Trees & large boulders abound on the property, provide surroundings you are sure to appreciate. Situated between Lake Arrowhead & Big Bear you are just a short drive to either. Relax on the front deck or enjoy the serenity of the back patio with amazing views.

Popular amenities for outdoor seating rentals in Highland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.94 out of 5 average rating, 363 reviews

A round wooden dining table is surrounded by six upholstered chairs featuring a light fabric design. The table is set with six plates and a centerpiece of natural elements, including a candle. Soft lighting enhances the warm interior with earthy tones.

Home in Fontana

DJ's Bed & Bistro (Xmas decor after thxsgiving!)

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.

4.9 out of 5 average rating, 126 reviews

Private backyard - Walk to Downtown - Pet friendly

4.93 out of 5 average rating, 389 reviews

A comfortable living room features a gray sectional sofa adorned with colorful patterned pillows. Natural light enters through two large windows, illuminating a vibrant floral area rug. Potted plants and fresh flowers add a touch of greenery to the inviting space.

Home in Rialto

Private HOME AWAY Cozy 2Bedrms 1Ba Ktch Lvg Rm Pkg

4.97 out of 5 average rating, 114 reviews

A charming white cottage is surrounded by a blanket of fresh snow, with trees dusted in white. The entrance is framed by a picket fence and features two inviting outdoor chairs by the door. Shadows and sunlight play across the snow-covered path.

Home in Cedar Glen

The Maple Cottage: family cabin by @themaplecabins

4.97 out of 5 average rating, 207 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

4.97 out of 5 average rating, 228 reviews

A dining area features a wooden table surrounded by four padded chairs. The walls are adorned with three large artworks depicting serene landscapes. A light-colored rug lies beneath the table, and a potted plant adds a touch of greenery to the space.

Home in Upland

Mountain Serenity!

4.98 out of 5 average rating, 125 reviews

A cozy bedroom features a spacious bed with a navy blue blanket and decorative pillows. Light wood flooring complements the minimalist decor. A large window with sheer curtains opens to a private patio, while a wall-mounted TV adds modern convenience.

Home in Hesperia

Palm Paradise, Private Studio

4.98 out of 5 average rating, 326 reviews

The master bedroom features a soft pink color palette, complemented by elegant decor. A clawfoot tub is positioned beside the bed, while large windows allow natural light to illuminate the space. Luxurious bedding and coordinated furnishings enhance the cozy atmosphere.

Home in Crestline

Unique mountain lake victorian pink bedroom home

Apartment rentals with outdoor seating

4.96 out of 5 average rating, 72 reviews

The exterior of a newly built home is shown, featuring a warm beige facade complemented by stone accents. A clear sky serves as a backdrop, while a neatly paved walkway leads to the entrance. Soft landscaping surrounds the pathway, enhancing the overall appeal.

Flat in Highland

Beautiful Suburban Private Suite

Flat in Downtown Riverside

A modern living area features a gray sofa adorned with decorative pillows, complemented by a wooden coffee table. Warm lighting is provided by a standing lamp. The space includes a dining set and a fully equipped kitchen area, with a large wall-mounted TV for entertainment.

4.84 out of 5 average rating, 249 reviews

✹ Beautiful Downtown Riverside Apt ✹

Flat in Downtown Riverside

A landscaped pathway is framed by lush greenery and a variety of plants, leading towards a tranquil fountain. Palm trees rise against a vibrant sunset sky, creating a serene outdoor environment that invites relaxation.

4.98 out of 5 average rating, 122 reviews

Historic Mission Bungalows 2

4.86 out of 5 average rating, 95 reviews

The exterior of a charming two-story house is showcased, blanketed in fresh snow. The green siding is complemented by white framing around the windows, with a white picket fence surrounding the front yard. Snow rests on the roof and the surrounding trees.

Flat in Big Bear Lake

#1 separate bedroom & full kitchen NEW BATHROOM

4.89 out of 5 average rating, 71 reviews

A modern kitchen space features a sleek countertop with a round woven basket holding a potted plant. In the background, subtle cabinetry and a bar-style seating area create a functional and welcoming atmosphere. Natural light filters through a nearby window.

Flat in Ontario

Exquisite Comfort Stay

A bright studio living space features a comfortable gray sofa adorned with orange cushions, a small dining area with sleek black chairs, and a light-colored table. Natural light enters through a large window, highlighting the neutral color palette and modern decor.

Flat in Fontana

Secure Studio • Private Entry • Near Shops & Eats

5 out of 5 average rating, 3 reviews

A covered porch area features a comfortable seating space and a stylish lantern near the entrance. The outdoor space is surrounded by trees, providing a serene view of the landscape and nearby water, enhancing the sense of tranquility.

Flat in Cedar Glen

Quiet getaway with a great view

Flat in Big Bear Lake

Edge of the Run at Snow Summit, Walk to the Lifts

Apartment rentals with outdoor seating

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.

4.94 out of 5 average rating, 109 reviews

Lakefront Walk 2 Village w/ Dock Access & Pets

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, 193 reviews

The Cozy Cottage Condo - Jacuzzi/3mi to slopes

The cabin's exterior is characterized by a two-story design with a combination of light yellow siding and wooden accents. A private balcony is visible on the second floor. Tall pine trees provide shade and enhance the cabin's natural surroundings.

4.87 out of 5 average rating, 93 reviews

Kuma Lodge, Walk to Snow Summit

The exterior of a green cabin is surrounded by tall trees, with a snow-covered ground creating a serene ambiance. A picnic table is positioned on the snow, accompanied by an umbrella. Steps lead to the cabin's entrance, set against a clear blue sky.

4.87 out of 5 average rating, 183 reviews

lakeside hideaway walk to ski resorts and village

A view from a private deck showcases trees with bare branches and a glimpse of the lake in the background. A nearby cottage can be seen, blending harmoniously with the surrounding nature under a clear blue sky.

4.81 out of 5 average rating, 21 reviews

Lakeside condo

An outdoor balcony features a table and four chairs, complemented by a gas grill. Scenic views of Big Bear Lake and surrounding trees provide a serene backdrop, enhancing the outdoor dining experience.

4.91 out of 5 average rating, 22 reviews

The Adler's Nest | Lakefront w/ Pool & Spa

The bedroom features a queen bed with a red and black checkered blanket. A mirror wardrobe is visible, reflecting light from the nearby window. Wooden floors add warmth, and a wooden side table holds two lamps. A rustic decorative element is mounted on the wall above the bed.

4.92 out of 5 average rating, 197 reviews

Lakeside Lumberjack Lodge - Condo *Pool/Jacuzzi*

The living area features a combination of leather and upholstered seating, arranged around a coffee table. A large wall-mounted TV is visible, along with a decorative fireplace. Natural light enters through windows dressed in light curtains, creating a cozy ambiance.