Vacation rentals with a pool in Upland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Upland

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Glendora

4.95 out of 5 average rating, 221 reviews

Petite Style Studio

This petite, small (tiny & cute) apartment studio is attached to main house. Guest have the whole place to themselves with private entrance. Brand new furniture & appliances. Bright, classy and charming, you won't want to leave this gorgeous studio. Small design custom kitchen with all necessities. This is a small studio with self check-in (arrive any time after 3:00 p.m). IMPORTANT:Airport LAX distance 45 min. It's an easy drive to main Los Angeles attractions. Location is safe & excellent.

Dec 25 – Jan 1

G$23,260 GYD per night

Guest favorite

Guest suite in Oak Hills

4.99 out of 5 average rating, 145 reviews

D.M.O. Private Studio Suite w/ Private Pool & Spa

Serenity, cleanliness, & privacy are just 3 of many desireable reasons to stay at the DMO Private Studio Suite in prestigious West Oak Hills. Just 1.5 miles from 15 freeway, the 99% sound-proofed, 540sf studio suite, has a private entrance that welcomes guests with with a king bed (or 2 twins), queen sleeper sofa, fully functional kitchenette, and a luxurious bathroom with a Jacuzzi tub. Your suite features a scenic, resort type setting, with a private patio, Pool (Open), Spa, Fire pit, & BBQ.

Nov 29 – Dec 6

G$19,322 GYD per night

Guest favorite

Cottage in San Bernardino

4.94 out of 5 average rating, 270 reviews

Adorable Cottage, base of Beautiful Mountains

This adorable cottage is located at the base of the San Bernardino mountains where you have views of the snow-capped mountains in the colder seasons & views of the beautiful sunsets all year! Close to freeways, malls & hiking trails. Relax poolside as the cottage doors open to the pool & outdoor BBQ & fire pit. It's a great get-away location with all newly remodeled amenities for a comfortable stay. Plenty of parking. NEW onsite DAY SPA services! THIS SPACE IS NOT SUITABLE FOR SMALL CHILDREN

Nov 6 – 13

G$34,744 GYD per night

Guest favorite

Home in Phillips Ranch

4.95 out of 5 average rating, 118 reviews

Private guest house, pool, kitchen & bath.

** READ ALL ** New Luxury, Modern, beautiful, cozy stylish mini private studio in exclusive area of Phillips Ranch. Studio has bath & kitchen, big closet, dining table, study desk. The studio is attached to the main house with its own Private entrance. Beautiful and unheated pool. Situated in a cul-de-sac. Quiet neighborhood. Close to all freeways, schools, hospitals. shopping, parks, restaurant. *Please review studio description and house rules. Then text me with agreed before booking. Ty

Apr 24 – May 1

G$31,117 GYD per night

Guest favorite

Guest suite in Norco

4.98 out of 5 average rating, 168 reviews

Norco country private entrance

~dog friendly ~Located in “Horse Town USA”. Riding trails located throughout the city. ~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 our bedroom. ~outdoor spaced space ~Farmhouse porch, back yard covered patio, pool, spa, large grass area & arena. 1941 farmhouse complete remodel. A lot of dirt & animals. If you want a city experience this place is not for you.

Jul 15 – 22

G$25,001 GYD per night

Guest favorite

Guesthouse in Redlands

4.99 out of 5 average rating, 278 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!

Feb 15 – 22

G$23,195 GYD per night

Guest favorite

Guesthouse in Claremont

4.97 out of 5 average rating, 194 reviews

Claremont Guesthouse 5 Min to Colleges|Non-Smokers

Beautiful getaway in the lovely town of Claremont. Spend a relaxing day, or return to after a day of exploring. Enjoy a bakery in the morning and then hike the Claremont 5-mile loop less than a mile away. You'll be 5-7 minutes from the Claremont Village and the Claremont Colleges (Pitzer College, Pomona College, Scripps College, Harvey Mudd College and Claremont McKenna College). A beautiful Mediterranean patio and pool area await you to enjoy your morning coffee or evening glass of wine.

Nov 10 – 17

G$30,892 GYD per night

Guest favorite

Place to stay in La Verne

4.98 out of 5 average rating, 294 reviews

Villa del Sol in La Verne, CA Private Home

Beautiful mediterranean style house located on large lot that shares space with another home occupied by host. Bedroom has a queen size bed. Private entrance with use of the pool. Parking for one vehicle in the driveway. Walking distance to Old Town and the University of La Verne. 2 miles from the Claremont Colleges. 25 miles to downtown LA. Near to train station, public transportation and freeways. Approx. 30 miles to Disneyland. Foothills close with hiking, horse riding, biking!

Oct 23 – 30

G$30,865 GYD per night

Guest favorite

Home in Upland

4.94 out of 5 average rating, 550 reviews

North Upland pool home with its own private bathroom. Near Euclid Avenue walking trail 10 minutes to Claremont Colleges Non smoking No pets

Your space has a private entrance and its own bedroom, bathroom and kitchenette. There is a large workspace perfect for remote work. WiFi is FAST. The space is secluded, with its own private entrance. There are no shared living spaces and you have access to the REFRESHING PRIVATE POOL, shaded, and sunny! patios, and a large yard. There are table and chairs in a beautiful setting perfect for a BBQ meal from the available pellet smoker or a sumptuous meal delivered in.

Oct 12 – 19

G$22,538 GYD per night

Guest favorite

Guest suite in Riverside

4.93 out of 5 average rating, 151 reviews

Private & Secluded Guest Quarters w/ Pool in SoCal

Escape to our tranquil Guest Quarters nestled in the serene surroundings of Jurupa Valley. With its own private entrance and seamless self check-in, this peaceful retreat offers a large, private, lush outdoor patio and pool, perfect for solo adventurers, couples, and business travelers. Situated on a secluded cul-de-sac, yet conveniently just 10 minutes from Ontario Airport, UCR, and CBU, with easy freeway access for exploration. Discover your ultimate #SoCalEscape.

Oct 17 – 24

G$24,102 GYD per night

Guest favorite

Guesthouse in Fontana

4.95 out of 5 average rating, 109 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. (SPACE EQUIPPED ONLY FOR 2-3 PEOPLE *no more than 3 fit*)

Oct 6 – 13

G$27,907 GYD per night

Guest favorite

Guesthouse in Highland

4.96 out of 5 average rating, 228 reviews

Serene Escape Tiny House Living with pool access

Close to dining , hiking, shopping, movie theaters, National Orange Show Event Center NOS, Yaamava Resort and Casino, and some nightlife. 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.

Jun 7 – 14

G$19,067 GYD per night