
Holiday rentals with a pool in Milpitas
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Milpitas
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

The Alpaca House
Welcome to La Casa de Alpaca. Our home is located in the beautiful Rivermark community of Santa Clara. The space consists of 2 bed / 2 bath located on the top floor, with access to a pool, hot tub, gym, and yoga room. Local Destinations: Santa Clara Convention Center Great America Theme Park Downtown San Jose Levi's Stadium SAP Center Oracle Rivermark shopping area: restaurants and groceries AMC Mercado 20 Plaza: restaurants and movies We are business traveler ready with high-speed Internet.

Quiet Poolside Cottage for Solitude
New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

Quiet Santana Row LUXE with Mt View
Quiet, luxurious loft on Santana Row. Recently remodeled. New LG WashTower. Sleep Number Bed. Full Kitchen w/ Nespresso, smart kettle, Vitamix Blender. Lululemon MIRROR. Theragun Mini. Best upscale dining & shops downstairs. Valley Fair Mall across the street. Underground parking. Security 24/7. 70 in TV. Electronic standing desk w/ Herman Miller Aeron Chair. Ideal for business/leisure. EXCLUSIVE select dining & shopping discounts Tesla Level 2 charging + Supercharging @ Winchester Garage

Beautiful Large 4BR Home with POOL
Need a vacation or a great place to stay in the Bay area in San Jose? Look no further as you'll love this "Resort" style, very spacious 4 BR home with large in-ground pool- beautifully remodeled and furnished with plush furniture, art deco, comfy beds, upgraded modern amenities and beautiful landscaped garden. Family and business friendly. Conveniently located minutes to downtown San Jose, Trains, Malls, SAP & Levi's Stadium, SCU, SJSU and SJC. Highways 87-280-101. Book your escape today!

Private Queen Suite-Pool & Hot Tub, private entry
Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Los Gatos, Campbell and Willow Glen. Great for Mountain Winery Concerts, 49ers/Levi's Stadium and SJC. We have a professional cleaning crew, so just relax and enjoy. Check-out like a hotel, no starting laundry! You will enjoy a well designed private room with queen bed, private entrance and connected private bathroom. Hot tub and Pool are a perfect way to relax and end the evening.

Separate entry room near Stanford
This separate entry room opens to a beautiful one-acre garden with a pool, jacuzzi, cable TV/wireless, and parking. We are just off 280 and Woodside Rd., 4 miles from Stanford. It is peaceful and quiet and we are hands-off hosts. There is no access to the house and the room does not have a frig, microwave or dishes. We are set up for independent guests who want to come and go on their own and enjoy local restaurants in Woodside, Palo Alto or RWC. Please note the very short entry door.

Hillside Retreat Private 2-Room Guest Unit & Pool
Our home is on 1/2 acre hilltop lot, in a secluded, very quiet cul-de-sac, with easy access to major freeways, minutes from SJC airport, downtown, SAP, SJSU, convention center. This listing is for an entire separate unit, attached to main house. It features 2 rooms with private yard and pool to yourself. You are free to relax in the back yard with view, surrounded by mature trees, hummingbirds, butterflies while surf the net, or swim in our private pool when weather permitted.

Luxury Silicon Valley Work & Wellness Oasis
PLEASE CONTACT US FOR SUN–THU DISCOUNTS (2+ NIGHTS). Peaceful upscale 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve with private trail access. Ideal for business travelers, couples, and nature lovers. Fast fiber Wi-Fi, dedicated workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, heated saline pool May–Oct. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Cabana in Sierra Azul Open Space Preserve
Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Spacious & Luxurious 1 BR w/Pool & Free Parking
Welcome to our Luxurious 1 bedroom located in Menlo Park! Our unit is situated in the luxurious Anton Menlo Apartments, which boasts a range of amenities for our guests to enjoy during their stay. Our unit features a spacious and fully furnished living area, comfortable Queen size bed, with a large modern bathroom, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.

Cabana with Warm Watsu Pool
Our guests best describe it as: ‘Like luxury hotel meets Zen retreat meets Day Spa meets Bali rain forest meets mom and pop warm hospitality’. A private cabana close to shops and restaurants in downtown Willow Glen. You’ll love our place because of the tranquil setting, warm watsu pool, Finlandia sauna, hot plunge, and beautiful gardens. Our place is good for couples, solo adventurers, and business travelers.

Private Oasis with Pool and Fire Pit
Escape to our private oasis where every detail is designed for your ultimate comfort. Indulge in a refreshing swim in our pool. Unwind and relax in our outdoor lounge area complete with a cozy firepit, perfect for savoring a glass of wine with your loved ones. Whether it’s a family retreat, a couples getaway or a work gathering, your ideal stay begins here! ** We do not offer pool heating **
Popular amenities for Milpitas rentals with a pool
House rentals with a pool

Stunning Group Retreat w/Pool!

Little Poolside House near Downtown Mountain View!

Spacious 4BR Home w/Pool, A/C & Multiple KingBed

Silicon Valley Executive home in Santa Clara

Modern Retreat in the Heart of Silicon Valley

Modern Spacious 3 BD/2.5 BA | King Suite | Office

Country Club Living on Golf Course & amazing views

3 BR Home on Vineyard nr Palo Alto & Stanford
Apartment rentals with a pool

Charming Luxury 2BR w/ Monitor and Adjustable desk

KING BED | Fully Furnished Luxury Condo Gym & Pool

Luxury 2BR Condo Pool, & Gym | Near Levi’s Stadium

Entire Condo - comfy and central

Entire 1BR Apt•Bright, Clean, Spacious & All Yours

Waterfront Condo! Great for Month rentals!

Lovely 1B1B condo with patio near downtown MTV

Spacious, luxury condo in downtown San José, CA
Other holiday rentals with a pool

Retreat @ Oasis Pool/Hot Tub/Billiards/Game SF Bay

Livermore Cottage, Pets ok.

Peaceful Large Suit1, 3 min Santana Row

Retromodern | Pool | Games | 2LV

Luxury 4-Suite Carbon-Neutral Home With Pool

Casita Luna- Pool house 19 mins to Stanford

2 BR/2 full bath Modern Santana Row Condo sleeps 6

Guesthouse in woodside -
When is the best time to visit Milpitas?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £52 | £52 | £52 | £52 | £56 | £58 | £57 | £65 | £58 | £52 | £52 | £52 |
| Avg. temp | 10°C | 12°C | 13°C | 15°C | 17°C | 19°C | 20°C | 20°C | 20°C | 18°C | 13°C | 10°C |
Quick stats about holiday rentals with a pool in Milpitas

Total holiday rentals
Explore 150 holiday rentals in Milpitas

Nightly prices starting at
Milpitas holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 1,280 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
140 of Milpitas holiday rentals include wifi access

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

4.7 Average rating
Milpitas stays receive an average rating of 4.7 out of 5 from guests
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- Castro Street
- Levi's Stadium
- Moscone Center
- Santa Cruz Beach
- Stanford University
- Golden Gate Park
- Capitola Beach
- Baker Beach
- Muir Woods National Monument
- Oracle Park
- Las Palmas Park
- Rio Del Mar Beach
- Golden Gate Bridge
- Seacliff State Beach
- Twin Peaks
- SAP Center
- Santa Cruz Beach Boardwalk
- Mission Dolores Park
- Henry Cowell Redwoods State Park
- Pier 39
- University of California-Berkeley
- Montara Beach
- Palace of Fine Arts
- Charles Lee Tilden Regional Park




