
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.

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! 🏳️🌈

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!

All-in-One Pool Guest House w Private Backyard!
We’d love to host you at our cozy and fully equipped guest house—perfect for families and friends! Located in a quiet, premiere gated community, just 6 min off the 60 fwy. You'll have the guest house all to yourself!This private guest house has its own entrance, pool, and private backyard, offering 600+ sqft of space, including a studio layout, 1 bathroom, and all the essentials you need for a comfortable stay. We can accommodate up to 4 guests and always do our best to meet your needs!

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.

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.

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

Shalimar Serenity |Pool|JacuzziGames|Massage Chair

Perfect home for large groups! Newly remodeled

Entire House in Moreno Valley

Valley of Guadalupe Escape gem

Modernized condo in the Arrowhead Village with spa

The MazeHouse 3— Movie Theatre & pool

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

Scenic views pool/spa/bbq/karaoke/games No Parties
Apartment rentals with a pool

Charming Condo W/ Pool, Hot Tub & Pet Friendly

Fully Upgraded Lakeside Hideaway for Quiet Escapes

Lakefront Walk 2 Village w/ Dock Access & Pets

Lagonita Lodge - Full Lake View Villa Guaranteed!

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

Amazing New Condo (Victoria Garden/Ontario Mills)

Lakeside condo

Big Bear 2BR Condo on Beautiful Resort
Other holiday rentals with a pool

Modern Studio Near LLU Hospital

Pool Home w/ Game Room near NOS Center

Summit Solace, Steps to Snow Summit w/ Hot tub

New Clean Safe 4BR*Pool*Jacuzzi*BBQIslandBar*King

Two Trees Tiny House

SoCal Base Camp

Full Condo in Ontario

Luxurious, Private 1 Bedroom Guest House 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 | ₹7,989 | ₹9,442 | ₹9,533 | ₹10,622 | ₹9,533 | ₹10,622 | ₹10,078 | ₹9,805 | ₹9,714 | ₹9,896 | ₹9,533 | ₹8,262 |
| 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 ₹3,632 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 & 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!
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- Disneyland Park
- Big Bear Mountain Resort
- Knott’S Berry Farm
- Bear Mountain Ski Resort
- Anaheim Convention Center
- Snow Summit
- Palm Springs Convention Center
- Disney California Adventure Park
- Pechanga Resort Casino
- Mountain High
- Honda Center
- Disneyland Resort
- Angel Stadium of Anaheim
- Palm Springs Aerial Tramway
- National Orange Show Events Center
- Alpine Slide at Magic Mountain
- Indian Canyons
- Tahquitz Creek Golf Resort
- Snow Valley Mountain Resort
- Chino Hills State Park
- Big Bear Alpine Zoo
- Mt. Baldy Resort
- Whitewater Preserve
- Big Morongo Canyon Preserve




