
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!

Adorable Cozy 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

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.

California Modern Guesthouse in LA, Pool & Parking
Relax in this serene, private Los Angeles retreat in Highland Park, set on a gated property near Pasadena and surrounded by a Mediterranean garden. Ideal for guests seeking a quiet stay in a residential setting. This modern guest studio is a separate, stand-alone structure on an owner-occupied property, with access to a shared swimming pool and dedicated off-street parking. Thoughtfully furnished with art, photography books and modern interiors, it offers a comfortable base for exploring LA.

Newly Remodeled Philips Ranch vacation home w Pool
Beautifully remodeled & decorated vacation home. Featuring outdoor pool and spacious outdoor dining area. Multiple lounging areas with 4 bedrooms, 3 full bathrooms and functional working spaces. Peaceful neighborhood, surrounded by local shops and restaurants. Only 12 miles from Ontario International Airport and convention center. 21 miles from Disneyland. 9 miles from Chino Hills state park with lots of hiking trails. 2000sqft of living space provides plenty of space for the whole family.

Private Saltwater Pool * Hot Tub *Disney* LA
Live the indoor/outdoor SoCal lifestyle at Villa Covina, where you’ll enjoy a private midcentury corner-lot home with a saltwater pool, and mountain and garden views. You’ll have 3 bedrooms, 2 baths, and 5 beds—perfect for families or groups. Relax in a stylish Scandinavian mid-century interior and cook in a chef’s kitchen with high-end appliances. Centrally located between LA and Orange County, you'll be +/- 30 min to Disneyland, 40 mins to Universal, 40 mins to LAX, and 20 mins to ONT.

Pool • Garden Patio • 5 Min to Village & Colleges
This peaceful garden guesthouse feels worlds away while still being just minutes from the Claremont Colleges and Village. Start your mornings with coffee on the private patio, open the French doors to fresh air and garden views, then unwind beneath the trees after a day of hiking, exploring, or visiting campus. Guests love the soaring ceilings, newly renovated kitchen, pool, thoughtful details, and the calm atmosphere throughout the property. Claremont Short Term Permit Number: STR-001

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.

North Upland House with a Pool
Your space has a private entrance and its own bedroom, bathroom and kitchenette with a SINK induction burner & countertop . There is a large workspace perfect for remote work. WiFi is FAST. The space is secluded at the end of the main house 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 relaxing meal

Pool and Historical Swiss Chalet in Los Angeles
The Swiss Chalet is a historic home featuring original architecture and design. The Chalet also features lush gardens, a pool, and a hot tub on the private upper terrace. Enjoy the view of the mountains, bask in the sun by the pool, take in the sunset over a glass of wine from the veranda, and stargaze from the hot tub nestled between majestic pines and picturesque Californian oaks. Please note: no kitchen, and no parties. Glendale Home-Sharing License: HS-003915-2025

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!
Popular amenities for Upland rentals with a pool
House rentals with a pool

Casa de Agua Retreat

| Vacation Home | 8’ TO Disney

Relaxing Spanish Stunner House near the Queen Mary

Tropical Escape in the ❤️of Southern California

Riverside Serenity Spring Oasis|Spa/Pool/Mini Golf

CHARMING POOL HOME BY DOWNTOWN *FAMILY GETAWAYS*

"Angels Landing" Chic L.A Getaway w/ pool & spa

Private Pool/HeatedJacuzzi /BBQ Grill/Disney Land
Apartment rentals with a pool

Modern, Spacious 1 Bd Loft in DTLA - FREE Parking

⁎ArtDeco ⁎ Condo⁎ pool⁎ Gym⁎Free Parking⁎Jacuzzi

Skyline view Condo, Free Parking, Jacuzzi

Brand-New, Deluxe Hollywood Studio

Beautiful 2-BR Loft in DTLA w/ Rooftop Pool

Los Angeles Pool Home by Disneyland Hollywood DTLA

The Lofts: Rooftop Pool & Spa, Free Parking, DTLA

5 stars 2 BR condo with pool&gym
Home rentals with a private pool

The Naples Island Pool House

Mid Mod Pool Haus by Disney I Anaheim I Chapman U
Beautiful Guest Cottage with Private Pool (Rancho)

Pool Oasis in Vintage Craftsman House

Designer’s Dream Oasis with Lap Pool & Hot Tub

Private Chic Guest Suite Beachwood Canyon Pool/Spa

Your Private Resort in Southern California

Walk to Disney! Large yard. Resort-Style Pool Home
When is the best time to visit Upland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €134 | €150 | €190 | €137 | €146 | €177 | €130 | €165 | €155 | €139 | €131 | €131 |
| 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 70 holiday rentals in Upland

Nightly prices starting at
Upland holiday rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 2,310 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 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
- Disneyland Park
- Venice Beach
- Universal Studios Hollywood
- Beach House
- SoFi Stadium
- Santa Monica Beach
- University of California - Los Angeles
- Los Angeles Convention Center
- University of Southern California
- Crypto.com Arena
- Knott’S Berry Farm
- Dodger Stadium
- Rose Bowl Stadium
- Disney California Adventure Park
- Long Beach Convention & Entertainment Center
- Anaheim Convention Center
- National Orange Show Events Center
- Big Bear Mountain Resort
- Huntington Beach, California
- Disneyland Resort
- Santa Monica Pier
- The Queen Mary
- San Clemente State Beach
- Mountain High





