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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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Superhost
Cabin in Big Bear Lake
4.9 out of 5 average rating, 340 reviews

Feet Away From Slopes Modern Snow Summit Cabin

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 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.
Condo in Big Bear Lake
4.93 out of 5 average rating, 122 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 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, 368 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, 218 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.
Guesthouse in Redlands
4.99 out of 5 average rating, 331 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, 147 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 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.
Guesthouse in Fontana
4.95 out of 5 average rating, 233 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 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, 208 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 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, 177 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.

Top Guest favourite
A well-maintained yard is shown, featuring a small wooden bridge leading over a stream. Lush green grass contrasts with the surrounding autumn foliage, including tall trees and bushes. Clear blue skies create a serene backdrop to the peaceful outdoor space.
Townhouse in Big Bear Lake
4.84 out of 5 average rating, 108 reviews

Falcon’s Nest, on the lake!

Relax with the whole family at this peaceful Boulder Bay Condo! Steps from the lake, and a short walk to Pleasure Point Marina to jump on a boat or jet ski. The rear deck looks over the lake and a big wilderness area, that is quiet and peaceful. There are TV’s in every room to keep everyone entertained. An open kitchen and living/dining area makes room for the whole crew.Located near the village, ski resorts, hiking trails and off road adventures!

Top Guest favourite
Guesthouse in Highland
4.93 out of 5 average rating, 163 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 favourite
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, 196 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.

Popular amenities for Highland rentals with a pool

When is the best time to visit Highland?

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Avg. price$153 NZD$181 NZD$183 NZD$204 NZD$183 NZD$204 NZD$193 NZD$188 NZD$186 NZD$153 NZD$153 NZD$152 NZD
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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 $70 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,320 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Highland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Highland rentals

  • 4.9 Average rating

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