
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.

Oasis in the canyon
This charming guest house is well lit located on a quiet neighborhood easy access from two mayor interstates and shopping a 15 min drive to Redlands and 7 min to Loma Linda hospital what ever the reason of your stay if you want peace and quiet and a fun place to enjoy the cool evenings this is it. Don’t forget the pool to relax during hot days of summer we have a piece of tropical paradise on our backyard also we are at the guest request only 30 feet and a knock on our back door! WE HAVE DOGS!

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! 🏳️🌈

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.

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.

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

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.

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.
Popular amenities for Highland rentals with a pool
House rentals with a pool

Feel the Tropics: Stunning Getway Free Spa Heating

Pool Home w/ Game Room near NOS Center

Charming 5 bed, 3 bath home with pool

Golden Hour Oasis~MovieTheater~Hot Tub

The Maze House—Pool & Theatre Room

Summer Oasis: Tropical Vibes + Pool & Mini Golf!

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

Cheerful 5 Room Home w/ Salt Water Pool & Hot Tub
Condo rentals with a pool

Lakefront Walk 2 Village w/ Dock Access & Pets

Next to Lake. Close to Village and Slopes. BBQ.

Rch Cucamonga Luxury Cozy Modern Style w/Pool

Amazing New Condo (Victoria Garden/Ontario Mills)

The Adler's Nest | Lakefront w/ Pool & Spa

Lakeside condo

Big Bear 2BR Condo on Beautiful Resort

1BedrmCondo-Kitchen-WiFi-2Bathrms-King+Sofabed GSL
Other vacation rentals with a pool

Relaxing Poolside Getaway Guest House

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

Valley of Guadalupe Escape gem

Golden - 1bd Condo

Exquisite Comfort Stay

SoCal Base Camp

Honey Bee Hideaway

Spacious 3 Bedroom Home with Pool
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ323 | ﺩ.ﺇ382 | ﺩ.ﺇ386 | ﺩ.ﺇ430 | ﺩ.ﺇ386 | ﺩ.ﺇ430 | ﺩ.ﺇ327 | ﺩ.ﺇ323 | ﺩ.ﺇ320 | ﺩ.ﺇ323 | ﺩ.ﺇ323 | ﺩ.ﺇ320 |
| 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 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 1,230 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!
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