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Vacation rentals with a pool in Pleasanton

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pleasanton

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

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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 21 – 28

G$26,709 GYD per night

Cabin in Oakland

4.97 out of 5 average rating, 185 reviews

Spa style cottage! Jacuzzi, Sauna, Pool, Views!

POOL HEATED MAY 1st! Stunning, detached cottage w/ higher end finishes. Endless views of mountains set on beautiful, peaceful, upscale property. Very close to regional parks for hiking. Quiet & set amongst over an acre of land with redwood, pine, & oak trees. Pool heated 81F May 1st-October 31st. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (4000 sq ft) is shared with main house (small family of 4). Secured driveway gate.

Jun 26 – Jul 3

G$54,307 GYD per night

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 22 – 29

G$70,234 GYD per night

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 9 – 16

G$30,642 GYD per night

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 19 – 26

G$31,813 GYD per night

Guest suite in Walnut Creek

4.99 out of 5 average rating, 534 reviews

Garden Oasis Suite with Spa and Pool, Walnut Creek

How about a rejuvenating get-away with a pool and spa? Bask in the late afternoon sun on a patio lounger overlooking a serene pool and tropical garden. Enjoy an evening snack while watching a movie or enjoy a good read. Luxuriate in a deluxe spa before falling into a comfy bed. Keep your work area separate from the bedroom. Brand new split AC/heater! Deep cleaning. 2 Airbnb units off same foyer. 27 steps. Neighborhood annexed to Lafayette. $25/person for additional guests or early check-in.

Aug 17 – 24

G$34,637 GYD per night

Home in Walnut Creek

4.97 out of 5 average rating, 225 reviews

Gated Home. Heated Pool. Top Location.

Fully remodeled gated home on exclusive private lane in the heart of Walnut Creek. 2000" ft, single story. Pool heated 365 days. Fully landscaped 1/2 acre Yard. Short walk to shops, restaurants, trails & famous Bancroft Gardens. Access 2 BART (train) stations, downtown Walnut Creek and freeways in minutes. Transparent pricing & 5 Star Amenities. No Guest Cleaning Tasks for check out. All Fees and Taxes included in nightly rate. *NO PARTIES OR EVENTS * STRICTLY ENFORCED *

Dec 28 – Jan 4

G$75,549 GYD per night

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!

Mar 27 – Apr 3

G$38,763 GYD per night

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.

Feb 24 – Mar 3

G$90,837 GYD per night

Guesthouse in Los Gatos

4.97 out of 5 average rating, 862 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 20 – 27

G$48,783 GYD per night

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 502 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cosy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mile from Berkeley/Oakland. Perfectly located in a quiet, safe and green neighborhood: 0.8 mile from Walnut Creek BART station and 1 mile from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big and is good for couples, solo and business travelers

Nov 16 – 23

G$26,849 GYD per night

Guesthouse in Monte Sereno

4.9 out of 5 average rating, 187 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

Dec 20 – 27

G$38,591 GYD per night

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Popular amenities for Pleasanton rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in El Sobrante

4.99 out of 5 average rating, 177 reviews

Zen Meets Pool Retreat!

Oct 8 – 15

G$94,871 GYD per night

Home in Mountain View

4.88 out of 5 average rating, 112 reviews

Little Poolside House near Downtown Mountain View!

Jul 4 – 11

G$37,713 GYD per night

Home in Concord

4.91 out of 5 average rating, 175 reviews

Pool, Hot tub, Napa, SFO Clean

Aug 7 – 14

G$98,346 GYD per night

Home in Portola Valley

4.92 out of 5 average rating, 137 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

Jun 1 – 6

G$119,043 GYD per night

Home in Santa Jose

4.98 out of 5 average rating, 152 reviews

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

Aug 13 – 20

G$143,652 GYD per night

Home in San Rafael

4.9 out of 5 average rating, 443 reviews

MCM Waterfront Pool/Hot Tub between SF and Napa

Oct 29 – Nov 3

G$96,935 GYD per night

Home in Menlo Park

4.85 out of 5 average rating, 155 reviews

Modern French Country Style Home

Feb 20 – 27

G$239,521 GYD per night

Home in San Jose

4.8 out of 5 average rating, 279 reviews

Downtown Oasis with Heated Pool near Whole Foods

Oct 16 – 23

G$89,974 GYD per night

Condo rentals with a pool

Condo in Oakland

4.91 out of 5 average rating, 246 reviews

Lakeside Retreat (w/ private parking)

Jul 6 – 13

G$28,559 GYD per night

Condo in Santa Clara

4.94 out of 5 average rating, 264 reviews

La Casa de Alpaca

Dec 1 – 8

G$44,862 GYD per night

Condo in Mountain View

4.95 out of 5 average rating, 122 reviews

Spacious Top Floor Condo Retreat

Oct 4 – 11

G$57,612 GYD per night

Condo in San Ramon

5.0 out of 5 average rating, 8 reviews

La Casa de Maya

Jul 22 – 29

G$56,649 GYD per night

Condo in Emeryville

4.83 out of 5 average rating, 24 reviews

Furnished 1 bedroom Apartment, Pool, Gym - Monthly

May 24 – 31

G$29,366 GYD per night

Condo in Cupertino

4.84 out of 5 average rating, 64 reviews

WFH from Penthouse with View and location!

May 22 – 29

G$46,850 GYD per night

Condo in Antioch

4.5 out of 5 average rating, 14 reviews

🌈A Travelers Dream💤Second Floor Condo Pool💦

Nov 29 – Dec 6

G$36,016 GYD per night

Condo in East Palo Alto

4.9 out of 5 average rating, 29 reviews

PA Home Theatre & Full Office Setup Great for WFH

Nov 23 – 30

G$36,877 GYD per night

Quick stats about vacation rentals with a pool in Pleasanton

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
180 reviews

Destinations to explore