Some info has been automatically translated. Show original language

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.

%{current} / %{total}1 / 1
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
4.87 out of 5 average rating, 135 reviews

Gorgeous Resort Style Mountain view Pool Villa

Gorgeous 3 bed/2 bath single floor home with PRIVATE Heated 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” OLED TV, work space, High speed Wi-Fi , Gym. 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.

Guest favorite
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
4.93 out of 5 average rating, 181 reviews

Tranquil Retreat | Private Guest Quarters + Pool

Escape to our tranquil Guest Quarters retreat, nestled in the serene rural surroundings of Jurupa Valley. With its own private entrance and seamless self check-in, this peaceful retreat offers a large, completely private, lush outdoor patio space, with a shared pool/backyard space. The estate is situated on a secluded cul-de-sac 10 minutes from Ontario Int. Airport, UCR, and CBU, with easy freeway access. In-N-Out Burger, Raising Cane's, Chipotle, & Aldi’s Grocery walking distance away! 🏳️‍🌈

Guest favorite
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.
Condo in Big Bear Lake
4.87 out of 5 average rating, 369 reviews

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

Enjoy a Santa Fe vibe with hand painted murals and other unique interior details. Play with dimmable lights to create the perfect mood. Gather by the spacious kitchen countertop. Sit by the wood burning fireplace or relax on the balcony facing the pool. Enjoy the heated spa or walk 100 yards to the picturesque Boulder Bay to fish, swim, rent a kayak or a paddle board. The popular Castle Rock trail is a walking distance away. Big Bear Village is only 2miles away and it is 4 miles to the slopes.

Superhost
A dining area is visible with a wooden table surrounded by four chairs, positioned against a green accent wall. Near the table, a television is mounted on a light-colored wall unit that features decorative items and small plants, enhancing the welcoming ambience of the space.
Condo in Downtown Riverside
4.88 out of 5 average rating, 220 reviews

Quaint Farmhouse Getaway - Entire Place (Condo)

Enjoy your stay at this farmhouse style 2 bed 2 bath condo! Extremely clean and well maintained, this space is conveniently located a few minutes from the downtown area, Central Plaza, and walking distance from Riverside's well known Mt. Rubidoux Hike; a 1-mile trek that gives a stunning view of the entire city. There is a park across the street that kids love which also has a nice walking path. The neighborhood is very quiet and peaceful. Access to Wifi, washer/dryer, 2 car garage, and more!

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, 333 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
A spacious living room features high cathedral ceilings and large windows allowing natural light to enter. Modern blue sofas are arranged around a glass coffee table, complemented by stylish accent chairs. A lush indoor plant adds a touch of greenery, enhancing the warm atmosphere.
Villa in Redlands
4.92 out of 5 average rating, 149 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
4.95 out of 5 average rating, 236 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
An outdoor space features a fire pit surrounded by multiple lounge chairs. In the background, a pool is illuminated as the sun sets. Vibrant murals decorate the area, and trees frame the scene, enhancing the inviting atmosphere.
Home in Wildwood Park
4.81 out of 5 average rating, 210 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 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.
Guesthouse in Highland
4.96 out of 5 average rating, 271 reviews

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.

Guest favorite
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.
Condo in Big Bear Lake
4.94 out of 5 average rating, 180 reviews

Casita Condo | Jacuzzi | 3mi to slopes

Completely renovated with a unique style and trendy touches, the Casita Condo features Spanish accents throughout the home, with arches and terra-cotta details. Enjoy the brand new kitchen, with all upgraded appliances, including a wine fridge. Gather around the fireplace and Smart TV where you can access all your favorite streaming services. The two bed/two bath layout is ideal for small families or two couples looking to enjoy a mountain getaway.

Guest favorite
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.
Condo in Big Bear Lake
4.89 out of 5 average rating, 199 reviews

The Cozy Cottage Condo - Jacuzzi/3mi to slopes

This newly decorated home is the perfect mix of modern, boho, and mountain! Wood and greenery accents remind you that you're on a mountain retreat, while all new furnishings ensure your stay will be cozy and comfortable. Take advantage of the 2 minute walk to the lake! Our home is equipped with high speed internet, a Smart TV, wood-burning fireplace, and a Keurig coffee maker with complementary coffee, tea, and hot cocoa.

Top guest favorite
Home in San Bernardino
4.99 out of 5 average rating, 114 reviews

Skyline Escape | Heated Pool & Epic Views

Welcome to The Vibe Estate 🌴✨ A hilltop retreat made for meaningful moments with family and friends. Enjoy stunning views 🌄, a heated cocktail pool 💧, and a spacious home for dining, games 🎲, and connection. Relax, recharge, and make lasting memories 💛. 🆓 Heated pool and propane BBQ included. Message the host for any special requests.

Popular amenities for Highland rentals with a pool

When is the best time to visit Highland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ323ﺩ.ﺇ382ﺩ.ﺇ386ﺩ.ﺇ430ﺩ.ﺇ386ﺩ.ﺇ430ﺩ.ﺇ408ﺩ.ﺇ397ﺩ.ﺇ393ﺩ.ﺇ323ﺩ.ﺇ323ﺩ.ﺇ320
Avg. temp14°C14°C15°C16°C18°C20°C23°C24°C24°C21°C17°C14°C

Quick stats about vacation rentals with a pool in Highland

  • Total vacation rentals

    Explore 20 vacation rentals in Highland

  • Nightly prices starting at

    Highland vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 1,320 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Highland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Highland rentals

  • 4.9 Average rating

    Highland stays are highly rated by guests—averaging 4.9 out of 5!