Vacation rentals with a pool in Highland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Highland

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

The living room features a comfortable sectional sofa with a neutral palette, facing a stone fireplace. Large glass doors allow natural light and provide a view of the outdoors. A wooden coffee table sits at the center, complemented by a cozy area rug.

Cabin in Big Bear Lake

4.87 out of 5 average rating, 519 reviews

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

Experience the best of Big Bear with this remodeled townhouse, only a two-minute walk from the top snowboarding destination in town! Located adjacent to Snow Summit Ski Resort, you can enjoy skiing/snowboarding in the winter and mountain biking once summer arrives. Fantastic amenities including private parking, air conditioning, a rare gem in Big Bear. Community amenities, such as barbecue area, sauna and a seasonal pool to make your stay more enjoyable. The ultimate ski and ski out experience.

Guest favorite

The image presents a serene dusk view of a swimming pool surrounded by a landscaped yard. The pool reflects the soft evening light, with a gazebo and lounge chairs visible nearby. Lush greenery and potted plants add natural accents, contributing to a tranquil outdoor setting.

Guest suite in Oak Hills

4.96 out of 5 average rating, 243 reviews

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

Located in canyon country near the Cajon Pass, where rural serenity meets comfort, charm & luxury, all enhanced by the DMO's famous top-tier privacy, views and quiet surroundings. The Suite's Double French Door entry is accessed within a guest only area where a scenic, 5-star resort type setting, that includes a private patio, Deck, Gazebo, Pool & Spa. Inside is a Queen Bed, Queen sofa, kitchen, dining table, games, 75" TV, and a Luxurious 5-star bath. The separate Bedroom includes a King bed.

Guest favorite

A refreshing private pool is surrounded by a spacious yard, featuring a lounging area with chairs visible nearby. The structure showcases a sturdy diving board at the far end and is framed by trees and sunlit patios, creating a relaxed outdoor environment.

Home in Upland

4.93 out of 5 average rating, 692 reviews

North Upland pool home with its own private bathroom. Near Euclid Avenue walking trail 10 minutes to Claremont Colleges Non smoking No pets

Your space has a private entrance and its own bedroom, bathroom and kitchenette. There is a large workspace perfect for remote work. WiFi is FAST. The space is secluded at the end of the main house with its own private entrance. There are no shared living spaces and you have access to the REFRESHING PRIVATE POOL, shaded, and sunny patios, and a large yard. There are table and chairs in a beautiful setting perfect for a BBQ meal from the available pellet smoker or a sumptuous delivered meal.

Superhost

A private pool area features a natural stone water slide, surrounded by lush greenery and palm trees. A hot tub is positioned beside the pool, with colorful flowers in a planter nearby. Vibrant patio furniture adds a touch of comfort to the outdoor setting.

Villa in Rancho Cucamonga

4.85 out of 5 average rating, 123 reviews

Gorgeous Resort Style Pool Home + free EV Charging

Gorgeous 3 bed/2 bath single floor home with PRIVATE POOL that feels like a 5 Star resort with FREE EV charging for your car. Beautiful backyard, BBQ grill and 12 seater lounge, pool & hot tub with water slide. Fireplace, 85” LED TV, work space, High speed Wi-Fi , treadmill. Fully equipped kitchen, 6-burner gas range stove, rice cooker, coffeemaker etc. Laundry room with washer/dryer, iron/board, air conditioning, heating, linens/towels, Pack & play. Digital door lock, Driveway for 4 vehicles.

Top guest favorite

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.

Guesthouse in Redlands

4.99 out of 5 average rating, 311 reviews

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!

Guest favorite

Villa in Redlands

4.92 out of 5 average rating, 137 reviews

Peaceful Private Retreat In The Heart Of Town

Meticulously designer-renovated modern home “The Nest “is surrounded by mature tree and nestled beneath the mountains in South Redlands. Whether you’re looking to spend time with loved ones, vacationing or work remotely in a peaceful environment, this is the place to do it all. Relax by the fireplace while light pours in from the wall of windows, with pleasant sparkling pool, grill and chill on the backyard, and explore nature right outside your front door. Conveniently located in Redlands!

Top guest favorite

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.

Guesthouse in Fontana

4.96 out of 5 average rating, 212 reviews

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*)

Guest favorite

Home in San Bernardino

4.81 out of 5 average rating, 194 reviews

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.

Top guest favorite

A vibrant outdoor space features a pool with a unique shape, surrounded by sun loungers and tropical greenery. Tall palm trees provide shade, while a spacious patio area invites relaxation. Well-maintained plants enhance the inviting atmosphere of the shared outdoor setting.

Guest suite in Norco

4.97 out of 5 average rating, 243 reviews

Norco country private entrance

~Dog friendly - No cats ~Gated acre of property with secure parking. ~Extra large bedroom w/private entrance & full Bathroom. Mini fridge/microwave, for reheating. No kitchen or sink ; no cooking in bedroom. ~No smoking anywhere on property. ~outdoor shared space ~ porch, back yard covered patios, pool, spa, large grass area. ~registered guest only. No visitors. 1941 farmhouse complete remodel. A lot of dirt & animals. If you want a city experience this is not for you

Guest favorite

An inviting outdoor space features a well-maintained pool surrounded by palm trees. A putting green is present in the foreground, along with lounge chairs and a slide nearby. The space provides opportunities for relaxation and recreation, all under a soft evening sky.

Home in San Bernardino

4.89 out of 5 average rating, 120 reviews

Tropical Oasis Heated Pool & Spa/Firepit/Game Room

Pool HEATER and Jacuzzi HEATER HAVE SEPERATE ADDITIONAL FEES READ UNDER OUR POOL INFORMATION Experience a resort-style retreat nestled against the breathtaking backdrop of mountains and palm trees. Indulge in a rejuvenating stay at our home, designed to provide the perfect blend of relaxation and excitement. Located in the serene north part of San Bernardino, our inviting home is ideal for intimate getaways or gatherings with family and loved ones.

Top guest favorite

A spacious sleeping area features a queen-size bed adorned with blue and white linens. Adjacent, a small dining table with two chairs is positioned near a window dressed with dark curtains. A flat-screen TV is mounted on the ceiling, enhancing the room's comfort.

Guesthouse in Highland

4.93 out of 5 average rating, 157 reviews

Dreamy Escape Private Entrance (pool) near Yaamava

Our location is close to dining, hiking, shopping, movie theaters, and popular attractions like the National Orange Show Event Center (NOS), Yaamava Resort & Casino, vibrant nightlife, Redlands University, and Loma Linda University. You'll love our place for its location, inviting ambiance, outdoor space, and friendly neighborhood. It's the perfect spot for couples, solo adventurers, and business travelers looking for a cozy getaway!

Guest favorite

An inviting outdoor area includes a spacious swimming pool surrounded by illuminated pathways and lush greenery. A cozy seating area is visible beneath a gazebo, while the backdrop features a scenic view of mountains under a colorful twilight sky.

Home in San Bernardino

4.9 out of 5 average rating, 130 reviews

Mountain Oasis: Pool Home Sleeps 10 People

Welcome to our exquisite 4-bedroom, 3-bath, 2-story retreat with a refreshing pool—ideal for up to 10 guests. Minutes from NOS Center, Cal State SB, Redlands, Yamava Casino, and the San Bernardino Mountains, our fully-equipped haven offers modern comforts. Pet friendly (fee applies). No parties/events. Pool isn’t heated. Bring your own propane for BBQ.