
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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Highland rentals with a pool
House rentals with a pool

Tropical Paradise| cozy, fun & perfect location!
Thank you for being so quick to reply and being so kind

Very private House in Riverside! 3bedrooms w/pool
Great hosts, great house.

ā¤ļøLarge & COZY , 6 Bedrooms With 65ā Tvs + Pool ā¤ļø
I had a very pleasurable experience staying at Johnās! Itās amazing with a big group of people because there are so many rooms with huge couch space where you can hang out depending on the vibe. The place was basically spotless and was equipped with all the essentials. John was responsive and was so helpful with any requests. Would highly recommend staying here!

Spacious 3 Bedroom Home with Pool
our family had a great time it was convenient we were able to start new memories and enjoy our quality time with each other. Now we're headed into a new journey of life without my brother but we will always have the memory of this weekend. Thank you

Mid Century Modern POOL HOME w/ GAME ROOM
We had a great stay at this Airbnb! The place was clean just as expected and had a cozy, homey feel to it. The game room was definitely a fun bonus. The beds were super comfortable and the sheets were fresh and clean. Overall, a relaxing and enjoyable experience would definitely stay again!

North Upland pool home with its own private bathroom. Near Euclid Avenue walking trail 10 minutes to Claremont Colleges Non smoking No pets
The place was wonderful it was perfect for a short stay and was extremely clean. Reed had amazing communication throughout the entire trip making everything so much easier. Would recommend and stay again!

Elegant 4-Bedroom Home with Relaxing Pool
We stayed at Mimiās property for about 7 weeks. The property was clean, had a beautiful backyard and was on a nice quiet street next to UC Riverside. The neighbors were nice and friendly and the area felt super safe. We would often walk the area with our dogs and always felt safe. The inside of the home is clean, super spacious and the rooms were comfortable. The bathrooms were a nice size. They provided some of the basic materials, towels, toilet paper, dish soap, detergent and such. They have a washer dryer in the garage that was super convenient as well. Mimi and the cohost Jose checked in with us regularly to see if we needed anything. Our contact was minimal but they were very responsive and friendly if we needed to ask them any questions. We would absolutely stay here again if given the chance. Great experience! Especially when the local donkeys would stop by and say hello. 10/10.

Large Home w/ Spacious Backyard and Pool
We stayed here for a wedding and really enjoyed our stay! House is very spacious and quiet and felt very peaceful. It was very clean with good amenities, would definitely recommend!
Condo rentals with a pool

Charming Condo W/ Hot Tub & Pet Friendly
Very comfortable bed and couches nice 65 in tv also tvs in each bedroom all have prime and all the movies you want to watch. Nice bbq with patios and great pool and spa. I will definitely be staying here again when in big bear.

The Cozy Cottage Condo - Jacuzzi & Lake Access!
āThank you so much ! Everything was really clean, and all the amenities were well-organized. The pool and jacuzzi were absolutely amazing. On the first day, we asked if we could check in earlier, and they kindly agreedāmuch appreciated! It was just a one-minute walk to the karma restaurant and the best lake. Next time, weāll definitely stay here again, and Iāll also recommend this place to my friends. It was an incredible tripāthank you for your hospitality!āapperiateš¹š

Rch Cucamonga Luxury Cozy Modern Style w/Pool
The place was nice. It was in a nice quiet neighborhood. The floors were a little sticky in the kitchen but overall the place was clean. I would definitely recommend this place to anyone who is traveling to the inland empire. It was close to a big shopping center. The host was great they dropped off new towels and slippers. But she did message us before we got to the Airbnb saying there was complementary water in the fridge and there was none.

Casa De Lago - Beautifully Upgraded Lakeside Gem!
Great place to stay had an amazing time with my family. The owner was very helpful and friendly. When ask anything the responded fast.

Lakeside Lumberjack Lodge - Condo *Pool/Jacuzzi*
Love the area very clean I love the view to the lake everything I need it cook my meals.

Casita Condo | Jacuzzi | 3 miles to slopes!
Natalie was an efficient communicator and made the stay very easy. Location and amenities were very nice.

Cheerful ⢠Pet Friendly ⢠2 BR-1BA Condo
The place was very clean, very well laid out and homey, lots of closet space, and I can't say enough about how well-stocked the house was! Plenty of kitchen supplies - everything you could ever need - as well as cleaning supplies, plenty of towels, even extra toilet paper and tissues if you ran out. Office area was a great place to sit and put on my make-up and dry my hair (using the portable make up mirror provided in the bathroom) while my husband showered! Eric was very responsive to any questions. Easy check-in and check out. We would definitely stay again if in the area.

Quaint Farmhouse Getaway - Entire Place (Condo)
Our stay was very short, over just the weekend, but the location is great, right across the street from a park and we noticed a lot of hikers would park their cars close by at the park and hike up the hill which seemed very popular. We wished we had been able to spend a little more time at the condo as it was decorated very nicely and had a nice little sitting area in a private courtyard outside. The whole place was very cozy. And it was conveniently located near downtown Riverside where there were several restaurants. The garage was a nice bonus to be able to park the car and have it in a safe location with direct access to the condo. We would definitely stay there again if we came to the area.
Quick stats about vacation rentals with a pool in Highland
Total rentals
30 properties
Nightly prices starting at
ļŗ©.ļŗ73 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Destinations to explore
- Palm SpringsĀ Vacation rentals
- AnaheimĀ Vacation rentals
- StantonĀ Vacation rentals
- Joshua TreeĀ Vacation rentals
- Los AngelesĀ Vacation rentals
- San Fernando ValleyĀ Vacation rentals
- Southern CaliforniaĀ Vacation rentals
- Santa MonicaĀ Vacation rentals
- San DiegoĀ Vacation rentals
- La JoyaĀ Vacation rentals
- Channel Islands of CaliforniaĀ Vacation rentals
- Las Vegas StripĀ Vacation rentals
- Cabin rentalsĀ Highland
- Rentals with a patioĀ Highland
- Rentals with a washer and dryerĀ Highland
- Pet-friendly rentalsĀ Highland
- Cottage rentalsĀ Highland
- Beachfront rentalsĀ Highland
- Rentals with a fire pitĀ Highland
- House rentalsĀ Highland
- Rentals with a fireplaceĀ Highland
- Family-friendly rentalsĀ Highland
- Rentals with outdoor seatingĀ Highland
- Rentals with poolsĀ San Bernardino County
- Rentals with poolsĀ California
- Rentals with poolsĀ United States
- Yurt RentalsĀ United States
- Yurt RentalsĀ United Kingdom
- Castle RentalsĀ United States
- HouseboatsĀ United States
- Holiday CaravansĀ United Kingdom
- Private Island RentalsĀ United States
- Farm HousesĀ United States
- Farm CottagesĀ United Kingdom
- Cabin RentalsĀ Australia
- Luxury CabinsĀ United Kingdom
- Luxury CabinsĀ United States
- Holiday ChaletsĀ United Kingdom
- Cottage RentalsĀ United States
- Holiday CottagesĀ United Kingdom
- Mansion RentalsĀ United States
- Villa RentalsĀ United Kingdom
- Holiday BungalowsĀ United Kingdom
- Bungalow RentalsĀ United States
- Condo RentalsĀ United States
- Holiday ApartmentsĀ Australia
- Holiday HousesĀ United States
- Holiday HousesĀ United Kingdom
- Private Holiday RentalsĀ United Kingdom
- Big House RentalsĀ United States
- Big CottagesĀ Australia
- Large VillasĀ United Kingdom
- House Rentals with a PoolĀ United States
- Cabin Rentals with a PoolĀ United States
- Villas with a PoolĀ United Kingdom
- Apartments with a Hot TubĀ United States
- Holiday Cottages with a Hot TubĀ United Kingdom
- Beach CabinsĀ United States
- Beach CondosĀ United States
- Beachfront RentalsĀ United States
- Beach HousesĀ United Kingdom
- Beach VillasĀ United Kingdom
- Coastal CottagesĀ United Kingdom
- Pet-Friendly Vacation RentalsĀ United States
- Pet-Friendly Beach RentalsĀ United States
- Pet-Friendly Cabin RentalsĀ United States
- Dog-Friendly CottagesĀ United Kingdom
- Luxury Dog-Friendly CottagesĀ United Kingdom
- Disneyland Park
- Big Bear Mountain Resort
- Bear Mountain Ski Resort
- Big Bear Alpine Zoo
- Disney California Adventure Park
- KnottāS Berry Farm
- Angel Stadium of Anaheim
- Alpine Slide at Magic Mountain
- Mountain High
- Chino Hills State Park
- Pechanga Resort Casino
- Honda Center
- Downtown Disney District
- Indian Canyons
- Tahquitz Creek Golf Resort
- Palm Springs Aerial Tramway
- Temecula Creek Inn
- Big Morongo Canyon Preserve
- Dos Lagos Golf Course
- Indian Canyons Golf Resort
- Mesquite Golf & Country Club
- Mt. High East - Yetis Snow Park
- Boulder Bay Park
- Mt. Baldy Resort