
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.

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.

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.

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.

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!

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!

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!

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*)

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.

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.

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!

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!

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
House rentals with a pool

3 BD |Large Pool|Spa|Basketball|Backyard|Ping Pong

Mountaintop Pool Paradise | Mins to NOS Center

Charming 2BR 1BA Private pool Self check-in

Perfect home for large groups! Newly remodeled

Valley of Guadalupe Escape gem

Modernized condo in the Arrowhead Village with spa

Mountain Serenity!

BOHEMIAN AND MODERN SERENE HOME WITH POOL
Condo rentals with a pool

Charming Condo W/ Pool, Hot Tub & Pet Friendly

Lakefront Walk 2 Village w/ Dock Access & Pets

Lagonita Lodge - Full Lake View Villa Guaranteed!

Amazing New Condo (Victoria Garden/Ontario Mills)

Lakeside condo

Big Bear 2BR Condo on Beautiful Resort

The best memories are made here.

Lakeview Getaway | Game Rm, Pool, Spa, Sauna!
Other holiday rentals with a pool

All-in-One Pool Guest House w Private Backyard!

Modern Studio Near LLU Hospital

Entire House in Moreno Valley

The MazeHouse 3— Movie Theatre & pool

Two Trees Tiny House

Golden - 1bd Condo

So. Cal. Living near Redlands-Beautiful 3,000+Home

Gated Suite - King Bed, Cozy, Quiet, Kitchen, Pool
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | 14°C | 14°C | 15°C | 16°C | 18°C | 20°C | 23°C | 24°C | 24°C | 21°C | 17°C | 14°C |
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!
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- Rentals with pools San Bernardino County
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- Rentals with pools United States
- San Bernardino National Forest
- Disneyland Park
- Big Bear Mountain Resort
- Bear Mountain Ski Resort
- Knott’S Berry Farm
- Snow Summit
- Anaheim Convention Center
- Pechanga Resort Casino
- Disney California Adventure Park
- Big Bear Snow Play
- Honda Center
- Mountain High
- Disneyland Resort
- Angel Stadium of Anaheim
- Palm Springs Aerial Tramway
- Alpine Slide at Magic Mountain
- Indian Canyons
- Tahquitz Creek Golf Resort
- National Orange Show Events Center
- Snow Valley Mountain Resort
- Chino Hills State Park
- Big Bear Alpine Zoo
- Mt. Baldy Resort
- Whitewater Preserve




