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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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Top guest favorite
A tranquil pool surrounded by a spacious deck features lounge chairs for relaxation. The sun casts a warm glow over the water, highlighting the adjacent charming cottage and lush greenery. Tall trees provide shade, enhancing the serene atmosphere.
Guesthouse in Oakland
4.96 out of 5 average rating, 275 reviews

Pool, Jacuzzi, Sauna, Huge Views, gated, ADU

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated May 31st to October 30th. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

Top guest favorite
A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.
Guesthouse in Woodside
4.99 out of 5 average rating, 344 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.

Guest favorite
A wooden deck is framed by palm trees, featuring a round table and an adjacent chair. The view captures a sparkling pool, surrounded by lush greenery, inviting relaxation in a serene outdoor setting.
Guesthouse in Walnut Creek
4.91 out of 5 average rating, 607 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cozy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mi from Berkeley/Oakland, 50 mi from Napa Valley Wineries. Perfectly located in a quiet, safe and green neighborhood: 0.8 mi from Walnut Creek BART station and 1 mi from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big, has rustic charm and is good for couples, solo and business travelers.

Guest favorite
An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.
Home in Los Altos
4.93 out of 5 average rating, 399 reviews

Pool, Hot tub, Sauna I Your Silicon Valley Luxury

Upscale Los Altos Hills. Peaceful and spacious 1,500 sq. ft. retreat. Ideal for business travelers, couples, nature lovers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access, wildlife, serenity. Inside: workspace with fiber-optic Wi-Fi, fireplace, sauna, pool table, fully equipped kitchen and plush queen bed with guest praised mattress. Outside: exclusive access to saline heated pool and hot tub, patio with BBQ. Minutes from Stanford, Palo Alto, and top tech campuses.

Top guest favorite
The bedroom features a spacious bed with neutral bedding accompanied by vibrant accent pillows. A colorful piece of wall art adds visual interest, while two windows allow natural light to filter in. A small sitting area is present with a plant nearby, enhancing the welcoming feel.
Farm stay in Walnut Creek
4.99 out of 5 average rating, 579 reviews

Garden Oasis Studio with Spa and Pool Walnut Creek

Former Plus-rated Studio. How about a rejuvenating get-away with pool and hot tub? Picture window overlooking a garden. Sunbathe poolside. Watch TV from a comfy bed before falling into a restful sleep. 27 stairs to house, 3 stairs inside unit. Complimentary beverage for 3+ nights/return stay. After 10 stays, $100 credit. Deep cleaned. 2 separate units off same foyer; no shared walls. Private locked unit door. Shared access to spa/pool (9am-11pm) for overnight guests only. Host lives upstairs.

Top guest favorite
The cottage exterior features a charming design with a slate stone patio and a round dining table with two chairs. Glass double doors provide access, and large windows offer views of the surrounding greenery. The roof is intricately shaped, complementing the natural setting.
Guesthouse in Monte Sereno
4.98 out of 5 average rating, 446 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.

Guest favorite
The outdoor area features a spacious patio with several lounge chairs, an umbrella, and a table near the pool. Large glass doors provide access to the interior, enhancing the connection between inside and outside. Lush greenery surrounds the property, contributing to the tranquil setting.
Guesthouse in Orinda
4.87 out of 5 average rating, 377 reviews

Nature Poolside Cabana - 30+ days rental

Lovely residential location, rustic glamping. Lounge by the pool or cuddle up by the electric fireplace. Surrounded by trees, birds singing, lovely views of the hills, you will feel at ease. Open the doors - it's an outdoor living/bedroom. NOTE only Outdoor Tiki Shower, very private/hot water. Parking on the street, well lit pathway/stairs to cabana. NO PARTIES. Only children over 12. Respect neighborhood, behave responsibly. Active security. Lite cooking, no oils please.

Guest favorite
An open-concept living space is highlighted by a modern kitchen featuring light cabinetry and stainless steel appliances. Large windows provide natural light and scenic views. A cozy seating area includes a dark sectional sofa facing a television, and a colorful area rug adds warmth to the floor.
Guesthouse in Walnut Creek
4.96 out of 5 average rating, 124 reviews

The Willow Cottage

Modern Farmhouse Cottage, walking distance to downtown Walnut Creek. Recently renovated unit sits on a sprawling 5 Acres, which feels like the country but also close to shopping and amazing restaurants. Includes full access to a pool, Chef style kitchen and an outdoor lounge area. Private entrance and plenty of free parking. If Interested, please contact me with: - Occupancy (total amount of guests, pets, cars, etc) - A bit about yourself and your interest in renting

Top guest favorite
An outdoor area features a serene pool surrounded by blooming flowers and lush greenery. The distant horizon showcases a sparkling view of the city lights below, under a clear evening sky transitioning from dusk to night.
Guesthouse in Almaden Valley
4.97 out of 5 average rating, 1,001 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!

Top guest favorite
A tranquil Watsu pool is surrounded by lush greenery and vibrant plants. A fabric shade cover is suspended overhead, providing protection from the sun. Natural stone flooring complements the pool's serene ambiance, creating a peaceful retreat atmosphere.
Guesthouse in Willow Glen
4.97 out of 5 average rating, 614 reviews

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.

Top guest favorite
A shaded outdoor dining area is set beside a heated pool. The space is furnished with a table and six metal chairs, accompanied by an umbrella. Lush greenery and tall trees provide a backdrop, enhancing the private and serene atmosphere of the yard.
Home in Walnut Creek
4.97 out of 5 average rating, 310 reviews

Gated 3 BR 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. Walk to shops, restaurants, parks, hiking and biking trails. Minutes from downtown Walnut Creek, freeways and train (BART) stations to SF and Bay Area. No Guest Cleaning Tasks for check out. *NO PARTIES OR EVENTS * STRICTLY ENFORCED *

Top guest favorite
The exterior view captures a spacious waterfront home with a private dock featuring a floating pool. Palm trees line the property, and outdoor seating areas are visible. A covered section houses a boat, enhancing the serene waterfront setting.
Home in Discovery Bay
4.94 out of 5 average rating, 108 reviews

Waterfront home w/ private dock and pool

Waterfront family home with private floating pool in dock and hot tub jacuzzi. Only a short ride to the fast water to enjoy boating, fishing, wakeboarding, tubing, etc. Nearby wineries, fruit picking or scenic drives. An hour drive to San Francisco, Napa or Sacramento. Access to waterfront restaurant at the Marina by boat and 5 minute drive to shopping plaza with Safeway, CVS, Starbucks, etc.

Popular amenities for Pleasanton rentals with a pool

When is the best time to visit Pleasanton?

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Quick stats about vacation rentals with a pool in Pleasanton

  • Total vacation rentals

    Explore 40 vacation rentals in Pleasanton

  • Nightly prices starting at

    Pleasanton vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 210 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Pleasanton vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pleasanton rentals

  • 4.8 Average rating

    Pleasanton stays are highly rated by guests—averaging 4.8 out of 5!