
Holiday 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.

Villa del Sol in La Verne, CA Private Home
Beautiful Mediterranean guest house located on large lot that shares space with another home that also may hosts guests. Bedroom has a queen size bed. Private entrance with use of the pool. Parking provided on the street with a parking pass. Walking distance to Old Town La Verne and the ULV. 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!

Gorgeous Resort Style Mountain view Pool Villa
Gorgeous 3 bed/2 bath single floor home with PRIVATE Heated POOL that feels like a 5 Star resort with FREE EV charging for your car. Beautiful backyard, BBQ grill and 12 seater lounge, pool & hot tub with water slide. Fireplace, 85” OLED TV, work space, High speed Wi-Fi , Gym. Fully equipped kitchen, 6-burner gas range stove, rice cooker, coffeemaker etc. Laundry room with washer/dryer, iron/board, air conditioning, heating, linens/towels, Pack & play. Digital door lock, Driveway for 4 vehicles.

Adorable Back House w/Secluded Garden & Yard
Stylish private pool house available with queen bed, kitchen, bathroom, desk and working area, patio, heated pool*, and garden. The unit is self-contained and opens onto a private, secure, and fenced backyard shared with the main house. Lots of great details, pet friendly, kitchen and bath, vaulted ceilings, laundry, high-speed internet, and EV car charging, in a peaceful quiet area just at the edge of Pasadena. 20 minutes to downtown LA, 7 mins to downtown Pasadena. *extra fee to heat pool

Modern Guesthouse in Highland Park: Pool & Parking
Relax in this serene, private Los Angeles retreat in Highland Park, set on a large, gated property near Pasadena and surrounded by a Mediterranean garden under the California sun. This beautifully designed, recently constructed modern guest studio is a separate, stand-alone structure from the primary residence, offering access to a shared swimming pool and dedicated off-street parking on a secure property. A curated original collection of art and photography books is available for guest use.

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!

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!

Mountain View Retreat w/ Private Pool & Backyard
Escape to this stunning 3-bedroom, 2-story home in a quiet, upscale neighborhood. Enjoy breathtaking mountain views from the private balcony and relax in your own backyard oasis with a sparkling pool and shaded patio. Inside, the open-concept layout features a luxurious master suite, gourmet kitchen, and cozy living spaces. Located near Mt Baldy , dining, and local attractions, this home combines comfort, style, and convenience. Book your perfect retreat today for an unforgettable stay!

Charming 2BR 1BA Private pool Self check-in
Private pool house in City of Ontario CA is a perfect place for your family getaway or business trip. This is the main house with 2 bedrooms, two queen beds, 1 air mattress (queen), 1 bathroom, 4K TV, living room, Dinning room, Full size kitchen, covered patio, private pool (not heated), working desk, FREE 100mbps WIFI, & more. 开车10分钟到华人超市, 餐厅。 Our house is cleaned and sanitized thoroughly w/ CDC-approved cleaning products. No street parking on Mondays from 12:00 PM to 5:00 PM.

Private studio, pool, kitchen & bath.
** READ ALL ** New Luxury, Modern, beautiful, cozy stylish mini private studio in exclusive area of Phillips Ranch. Studio has bath, 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

Walk to Village & 5C's & Trader Joe's/Private Pool
Welcome to our little casita! With a private side entrance, the space has an open living and sleeping area with a queen bed. The kitchen has granite counters, a microwave and a two-burner stove. It's not huge, but it's clean and the location is great -- walking distance to the Claremont Village and the 5 Claremont Colleges. People from all backgrounds are welcome in our casita. City of Claremont Short Term Rental Permit Number: STR-005

Relaxing 3 Bedroom Home 15 min from ONT Airport
Experience ultimate luxury at our 3BR/2BA single-story home with a stunning open floor plan, central AC, and a sparkling pool. Conveniently located close to shopping and restaurants, just 10-15 min from Ontario Airport, a short drive to Padua Wedding Venue, and 33 miles from Disneyland. Perfect for families, couples, and business travelers seeking a relaxing getaway. Book now and indulge in the ultimate luxury retreat!

Mountain Serenity!
Beautiful and cozy one bedroom unit located in a great neighborhood! This spacious unit is completely separate from the main house with a private entrance door, backyard, patio set and BBQ. The kitchen is fully furnished and there is a washer & dryer in the unit as well. There is a crib (pack’n play) upon guest’s request.
Popular amenities for Upland rentals with a pool
House rentals with a pool

Last-Min Deal Feb 24–28 • Near Disneyland

Private Oasis &Disney /Heated Pool & Gym&Arcade

Casa de Agua Retreat

Charming 5 bed, 3 bath home with pool

Peaceful Home In Central Location | Netflix 4K TV

| Vacation Home | 8’ TO Disney

Stunning, Cozy, Private Backyard Oasis with Pool!

Riverside Serenity Winter Oasis|Spa/Pool/Mini Golf
Apartment rentals with a pool

Relaxing Resort Next to Disneyland*1 bedroom suite

Disneyland + LA main attractions

Chic & Cozy Condo Near Disney - Pool & Gym

Amazing New Condo (Victoria Garden/Ontario Mills)

Entire 1-Bd Gated Condo (30-40mins from Disney)

Los Angeles Pool Home by Disneyland Hollywood DTLA

Resort-Style Suite with Fantastic Views near DTLA

Shortest Walk Across Street to Disney Pool & Spa
Home rentals with a private pool

The Naples Island Pool House

Mid Mod Pool Haus by Disney I Anaheim I Chapman U

Your Private Resort in Southern California

1 Mile to Disneyland + Pool & Game Room

Walk to Disney! Large yard. Resort-Style Pool Home

Walkable to Disney! Pool, Spa, Game Room

Your Private Resort Near the Rose Bowl Awaits

Roomy Family Home with Heated Pool Option
When is the best time to visit Upland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $231 SGD | $229 SGD | $189 SGD | $199 SGD | $212 SGD | $257 SGD | $189 SGD | $239 SGD | $225 SGD | $201 SGD | $190 SGD | $190 SGD |
| Avg. temp | 14°C | 14°C | 16°C | 17°C | 19°C | 20°C | 23°C | 24°C | 23°C | 20°C | 17°C | 14°C |
Quick stats about holiday rentals with a pool in Upland

Total holiday rentals
Explore 60 holiday rentals in Upland

Nightly prices starting at
Upland holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 1,540 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Upland holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Upland rentals

4.8 Average rating
Upland stays are highly rated by guests – averaging 4.8 out of 5!
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- Rentals with pools San Bernardino County
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- Rentals with pools United States
- Venice Beach
- Disneyland Park
- Los Angeles Convention Center
- Santa Monica Beach
- Crypto.com Arena
- SoFi Stadium
- University of Southern California
- University of California - Los Angeles
- Universal Studios Hollywood
- Rose Bowl Stadium
- Santa Monica State Beach
- Big Bear Mountain Resort
- Knott’S Berry Farm
- Bear Mountain Ski Resort
- Santa Monica Pier
- Anaheim Convention Center
- Snow Summit
- Los Angeles State Historic Park
- Long Beach Convention & Entertainment Center
- Disney California Adventure Park
- Beach House
- The Grove
- Mountain High
- Hollywood Walk of Fame




