
Vacation rentals with a pool in Pleasanton
Find and book unique homes with a pool on Airbnb
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.ﺇ 184 per night before taxes and fees

Verified guest reviews
Over 650 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 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
Top-rated rentals with a pool in Pleasanton
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Private Queen Suite-Pool & Hot Tub, private entry
This is your Getaway spot! Enjoy your private suite, bathroom and large smart TV, pool and hot tub outside your door. Located within 3 miles of downtown Los Gatos and Campbell with great food options. Levi's Stadium/49ers 9.5 miles, Mountain Winery Concerts 7.5 miles, San Jose International Airport 6.5 miles, SFO 35 miles, SAP Center/NCAA/Sharks 4.6 miles. We have professional cleaning. Check-out like a hotel, no starting laundry! Hot tub and Pool are a perfect way to relax and end the evening.
ValueFamilyBreakfast

3 BR Home on Vineyard nr Palo Alto & Stanford
Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.
FamilyLocationQuiet

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.
FamilyLocationSolo travel

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.
LocationFamilyAccess

Heated Pool, Jacuzzi, Sauna, Huge Views, Chic ADU!
Tucked between pine, oak, & redwood trees is a 4 year old, high end cottage nestled with amazing views of the mountains. Peaceful, upscale gated, property. 1 mile to large regional parks for hiking, mountain biking & horse stables. Nature at its best! Pool heated to 82F 4/1-10-31. 16 miles to San Francisco, 5-10 minutes to many restaurants. Jacuzzi & barrel sauna, grill. Large patio, pool /new deck (6500 sq foot outdoor oasis shared with main house small family of 4). Own spot in driveway.
FamilyValueOutdoor spaces

Cozy BUS on Farm Animal Rescue with CITY VIEW
Stay on a farm animal rescue in a 38’ yellow school bus conversion. If you are interested we also host an Airbnb Experience called Life With Farm Animals At Rancho Roben Rescues where you get a 90-120 minute up close encounter with all of the animals - taking time to learn about each of the unique creatures that lives here and the opportunity to interact with them directly. Pet a chicken, groom a pony, feed a goat, take a walk patrolling the fields with our livestock guardian dogs.
FamilyValueQuiet

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 queen bed. 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 not heated (9am-10pm) for overnight guests only. Host lives upstairs.
FamilyValueHiking

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
FamilyValueLong stay

Views for Miles | Hot Tub | Gated Hilltop Home
Retreat above the city in this one-of-a-kind home and gaze at the sweeping view of Silicon Valley. Rancho Ruby is a revived 1950s ranch designed with a modern California style. Every amenity and detail has been thoughtfully considered for the tech-savvy travelers. The home is open, peaceful, and cool. It sits on a hilltop, situated on a secluded & gated third acre lot to allow tranquility for guests but is only a 15 minutes drive to the city center.
LocationValueAmenities

Sanctuary in Sierra Azul Open Space Preserve
Nestled in the Sierra Azul Mountain Range in Los Gatos, the Sanctuary combines rustic country decor, original art and spa amenities, providing the perfect private retreat. Surrounded by numerous hiking trails, many friendly animals, and vast wild forest all around us to explore to your liking, along with this exclusive unit serves to provide a refreshing, rejuvenating space to reconnect with your loved one, yourself and of course Mother Nature!
LocationValuePool

Luxury Silicon Valley Wellness and Work Oasis
Ideal for business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.
ValueFamilyBathroom

Hillside Wellness Retreat | Pool, Gym & A/C
Escape to your own private hillside wellness retreat in Marin. Recharge with sweeping views, a heated saltwater pool, fitness studio, air conditioning, and a peaceful standalone guesthouse all to yourselves. Perfect for couples, solo travelers, remote workers, and small families seeking relaxation, outdoor adventure, or a refreshing getaway. Minutes drive from San Francisco, Napa, Sonoma, hiking, yoga, spas, and farm-to-table dining.
FamilyLocationComfort
Popular amenities for Pleasanton rentals with a pool
House rentals with a pool

Beautiful Large 4BR Home with POOL
LocationFamilySleep quality

Pool, Hot tub SFO, Napa, Clean Home
FamilyValueAccuracy

Private cul-de-sac home in Marin with pool
ValueLocationComfort

Large Home in Palo Alto, 5 bedrooms, Pool
LocationFamilyGrill

Little Poolside House near Downtown. New AC!
FamilyLocationHospitality

Luxury 4-Suite Carbon-Neutral Home With Pool
FamilyValueHeating

Private Oasis with Pool and Fire Pit
ValueFamilyAmenities

Beautiful 4 Bedroom Hillside Retreat
LocationValueParking
Condo rentals with a pool

Lakeside Retreat (w/ private parking)
FamilyValueDecor

Modern 2‑bed, 2‑bath top‑floor apartment.
FamilyValueCondition

Quiet & Comfortable Entire Furnished Apartment
FamilyLocationHospitality

KING BED | Fully Furnished Luxury Condo Gym & Pool
ValueFamilyIndoor spaces

Downtown Modern Living Condo!
FamilyLocationOutdoor spaces

Modern 1B1B condo + quiet patio | Downtown Mt View
FamilyLocationAmenities

Penthouse with SF nightlights, gym 31 nights+ ONLY

Waterfront Retreat in Bay Area, near San Francisco
FamilyLocationBeach
Other vacation rentals with a pool

Romantic Mtn Studio - Pool, Sauna, Views!
FamilyValueLaundry

Private Garden Cottage Belmont Hills*Pool*HotTub*
LocationFamilyTV

Separate entry room near Stanford
ValueFamilyNearby

By The Bay Retreat
ValueFamilyTV

Trailside Home, Panoramic Views
FamilyLocationIndoor spaces

Beautiful Spacious Living w/Resort Like Feel
ValueLocationAccess

Apartment above Levi Stadium.
FamilyLocationTV

Resort Style Retreat -Private Pool, Hot Tub & View
FamilyLocationComfort
When is the best time to visit Pleasanton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 404 | ﺩ.ﺇ 404 | ﺩ.ﺇ 400 | ﺩ.ﺇ 400 | ﺩ.ﺇ 430 | ﺩ.ﺇ 433 | ﺩ.ﺇ 437 | ﺩ.ﺇ 433 | ﺩ.ﺇ 400 | ﺩ.ﺇ 393 | ﺩ.ﺇ 400 | ﺩ.ﺇ 400 |
| Avg. temp | 11°C | 12°C | 13°C | 15°C | 16°C | 18°C | 19°C | 20°C | 20°C | 18°C | 13°C | 11°C |
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