Vacation 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.

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Superhost

Guest suite in San Jose

4.88 out of 5 average rating, 644 reviews

Hillside Retreat Private 2-Room Guest Unit & Pool

Our home is on 1/2 acre hilltop lot, in a secluded, very quite 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 solar thermal heated pool when weather permitted.

Jul 18 – 25

R2,392 ZAR per night

Guest favorite

Home in San Jose

4.92 out of 5 average rating, 154 reviews

Splash Pad

4 BD/3.5 baths 2900 SQFT. 4 blocks from Downtown Willow Glen and Starbucks on*The Avenue* UPSTAIRS: Master*en suite*King bed and a Graco-Tot-Yard. Two Guest Bedrooms*2 queen beds. DOWNSTAIRS: Fourth Guest Bedroom*Triple Twin Adult Size Bunks*Gourmet Kitchen*LivingRoom*Formal DiningRoom*FamilyRoom*Pool Table*WIFI* SmarTVs* Detached Garage*Man Cave*Cabana*Private Toilet*Sink*ChangingRoom*Pool* Spa*Outdoor Gas Firepit*Outdoor Gas Fireplace*Entire home is for guests’ use. It is a Single Family Home.

Jan 19 – 26

R20,502 ZAR per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 reviews

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Jul 9 – 16

R6,319 ZAR per night

Guest favorite

Home in Santa Jose

4.98 out of 5 average rating, 152 reviews

SuperHosts! Walk to 49ers @ Levi! Early Check in!

Voted Best of AirBnB! Come enjoy our spacious 3 bedroom house next to Levi's Stadium 49ers North San Jose. Fast Internet. Perfect 4 biz travelers and families. Coworking space. Complete w/ 3 bedrooms & 3 bathrooms. Gated private backyard, BBQ, remodeled interior, & amenities. Everything to enjoy a working or holiday trip to the Silicon Valley. Modern kitchen. Keurig coffee. 50inch TVs in each room w/ Netflix, and YouTube TV. A fabulous and comfortable home. Guests Favorite in 2023. Superhosts!

Jun 5 – 12

R12,925 ZAR per night

Guest favorite

Guest suite in San Jose

4.94 out of 5 average rating, 108 reviews

Private Queen Suite-Private Entry, Pool & Hot Tub

Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Campbell and Willow Glen. We follow all cleaning guidelines to protect the health of all guests. 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 in our serene and safe neighborhood. Very high speed internet is included.

Oct 11 – 18

R2,757 ZAR per night

Superhost

Guest suite in Los Altos Hills

4.8 out of 5 average rating, 148 reviews

A private hillside suite nestled among oaks

Better than the Four Seasons or the Rosewood! Beautiful, compact, private in-law suite in the walk out basement of our modern home. Enter via outdoor stairs from parking area to suite. Serene bay views and lush greenery below grand oaks. Your suite has a very comfortable King bed, Japanese washlet, closet space, TV, wi-fi, private washer/dryer, fully equipped kitchen with gas stove, microwave, fridge/freezer & dishwasher. Ceiling fan, radiant in-floor cooling/heating. Private parking. 280 SF.

Jul 13 – 20

R2,852 ZAR per night

Guest favorite

Guesthouse in Monte Sereno

4.97 out of 5 average rating, 387 reviews

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.

Sep 22 – 29

R2,862 ZAR per night

Guest favorite

Guest suite in Woodside

4.89 out of 5 average rating, 408 reviews

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.

Jun 24 – Jul 1

R3,011 ZAR per night

Guest favorite

Condo in Santa Clara

4.94 out of 5 average rating, 264 reviews

La Casa de Alpaca

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.

Jan 13 – 20

R4,105 ZAR per night

Guest favorite

Apartment in San Jose

4.98 out of 5 average rating, 223 reviews

Apartment above the valley.

This 2 bedroom apartment. It has outside stairs that lead up to a large private deck (with with spectacular view of Silicon Valley). The entrance is via sliding door from the deck. There are two bedrooms, one bathroom and a combined full kitchen/living room. The ground level pool and patio are shared space with owners. Living room has couch, TV, and Roku streaming. Apartment has good WiFi. Sit on the private deck and you may see wild turkeys, deer, and even a cow!

Nov 22 – 29

R3,488 ZAR per night

Guest favorite

Bungalow in San Martin

4.99 out of 5 average rating, 105 reviews

Moose Mountain Vineyards Bungalow

Relax in an elegant 2 bed bungalow sitting atop Moose Mountain Vineyards. Enjoy the panoramic view of San Martin as well as the 13,000 grape vines growing on property. Relax in the hot tub or infinity pool, or sip estate wine on one of our four decks as the sunset takes your breath away. Enjoy a complimentary whole food plant-based breakfast with ingredients sourced onsite. This stay offers many opportunities to explore the inner workings of Moose Mountain Vineyards.

Nov 15 – 22

R8,258 ZAR per night

Guest favorite

Guesthouse in Los Gatos

4.97 out of 5 average rating, 860 reviews

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!

Jul 16 – 23

R4,215 ZAR per night