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Holiday 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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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
4.86 out of 5 average rating, 529 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.

Top guest favourite
A serene outdoor space features a well-maintained pool surrounded by lounge chairs and umbrellas. Stone steps lead to a home with a large patio. A gazebo is visible, enhancing the setting with additional outdoor seating.
Guest suite in Oak Hills
4.96 out of 5 average rating, 261 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.

Top guest favourite
Home in San Bernardino
4.99 out of 5 average rating, 103 reviews

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 favourite
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, 179 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 favourite
A spacious living area features a cozy, light brown couch facing a stone fireplace. Complemented by a large mirror and dining area in the background, the room is enhanced by natural light from windows adorned with dark curtains.
Apartment in Big Bear Lake
4.93 out of 5 average rating, 120 reviews

Boulder Bay cabin steps to the lake & hot tub

Upgraded condo just steps from Boulder Bay Park, the lake, hiking trails, fishing & the main boulevard. Kayak & paddle board rentals conveniently located next door. A convenience market is just around the corner to help with any last minute needs. The Village, full of shops & restaurants, is just down the road a bit. You are only a few minutes from all major snow play & skiing on the mountain. Don't feel like driving? Hop on the Mountain Transit Shuttle with a stop located near the parking lot.

Guest favourite
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.
Apartment in Downtown Riverside
4.89 out of 5 average rating, 207 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 favourite
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
4.99 out of 5 average rating, 325 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 favourite
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, 143 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!

Guest favourite
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
4.95 out of 5 average rating, 220 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 favourite
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
4.82 out of 5 average rating, 201 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.

Guest favourite
A welcoming entryway features a decorative iron door with a 'Welcome' sign. A cozy bench is positioned to the side, complemented by a small table adorned with potted plants and decorative items. A doormat invites guests with the message 'welcome to our home.'
Guest suite in Norco
4.97 out of 5 average rating, 253 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

Top guest favourite
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
4.96 out of 5 average rating, 270 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.

Popular amenities for Highland rentals with a pool

When is the best time to visit Highland?

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Avg. price$115 SGD$136 SGD$137 SGD$153 SGD$137 SGD$153 SGD$145 SGD$141 SGD$140 SGD$115 SGD$115 SGD$114 SGD
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Quick stats about holiday rentals with a pool in Highland

  • Total holiday rentals

    Explore 20 holiday rentals in Highland

  • Nightly prices starting at

    Highland holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,230 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Highland holiday rentals include wifi 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!