
Holiday houses in Pleasanton
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Top-rated holiday rentals in Pleasanton
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Santa Cruz A-Frame
This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame

★UNIQUE STAY in the middle of the BAY★ Wifi+MORE!
Comfortable in-law suite located in the “Heart of the Bay.” Just a 5-minute drive to downtown Hayward and BART, 25 min. from OAK Airport, and 35 min. from SFO Airport. In-N-Out, Sprouts, Raising Cane’s, Starbucks and much more are conveniently located just 4 minutes away. Our space is ideal for couples, travelers, and guests looking for a well-located home base. Enjoy easy access to nearby cities, dining, transportation, and experience the Bay Area’s energy and diversity from a central location.

Private In-Law unit in Dublin, CA
Private in-law unit is located behind the main house in a quiet neighborhood in Dublin, CA. Close to BART for an easy commute to San Francisco and near the Iron Horse trail for a morning or evening run. Along with a private entry, one bedroom and a fully equipped kitchen this unit has a sleeper sofa and could accommodate up to 3 guests. Perfect alternative to a hotel if you're travelling to the Bay Area for business or coming to visit family. NO PETS PLEASE. No children under 12 years old.

The French Door
This space is a private entry 275 square foot small studio with a private bath, connected to the main house but with no access to the main house. The unit has a standard sized mini fridge, microwave and keurig coffee maker with coffees to choose from, a very mini toaster oven for one bagel or one piece of toast, lite snacks and waters for you. Also a small table and chair set, desk and a brand new queen sized bed, the location is great if you work at the lab or if visiting family in the area.

Wine Country Craftsman Cottage
Restored Craftsman Cottage, walking distance to historic downtown Livermore. Downtown features excellent restaurants, theaters, antique stores. Short drive to Livermore wine country. Perfect for romantic getaways, wine tasting trips, antiquing, bike trails, hiking, weddings. Sleeps 2-4. Private backyard with patio, BBQ , organic garden . Charming vintage décor. Fully equipped kitchen. One bedroom with queen size bed, 2nd bedroom with queen size bed. Hardwood floors throughout.

Beautiful In-Law Unit in Dublin (Private Entrance)
Quiet, luxurious 400 square feet in-law unit (1 Bedroom/1 Bath) located in the beautiful Dublin Ranch Golf Club. The in-law suite is part of a bigger house but is completely private with a separate entrance. The studio has quality furnishings including a queen bed, dresser, office desk & chair, couch, and flat screen TV. While there is no full kitchen, we have a Keurig coffee maker, mini fridge & a microwave in the unit. We have Disney+, Hulu and Netflix for you to enjoy. No pets please.

Newly Beautiful 4 Bedroom Townhome
Beautifully upgraded 3 level townhome with open floor plan in newer complex. Lower level bedroom with attached remodeled bathroom. Upper level includes Master bedroom with attached bathroom as well as 2 extra bedrooms/1 full bathroom in a very comfortable neighborhood. Ideal for families and/or traveler groups at a reasonable price with many local restaurants, gyms, grocery markets and nearby shopping malls. Conveniently located near BART for transportation throughout the Greater Bay Area.

Quiet wine country cottage sleeps 4 - Pet Friendly
Forget your worries in this spacious and serene space. Located in the beautiful Livermore wine country just two miles from downtown. With walking/biking trails just across the street and two wineries in walking distance you won’t need to go far to enjoy your time here. This very spacious one king bed bedroom cottage (and queen Murphy bed) is just right for quiet time. Most days you can see horses and cows just out your windows with owls hooting and birds chirping for the country feel.

Cozy Modern Detached 1br Guest House, close to DT
Detached Guest House that is on the same property of the main house. It is private, safe, and cozy 1br features a "Casper" queen bed. The living room features a twin-sized sleeper sofa, smart TV, and high-speed WIFI. Self-check-in with a keypad, for contactless and flexibility in arrival. Tesla EV charger also available to share For a more personalized experience, we kindly ask our guests to share the reason for their visit at the time of booking. Dogs are allowed with pet fee

Secluded retreat/Remote office/Livermore Ranch.
Modern Retreat in Livermore Wine Country Relax and recharge in this stylish 3-bedroom, 2-bath home nestled in the rolling hills of Livermore. With a modern kitchen, spacious layout, and cozy furnishings, it's perfect for getaways, wedding prep, or small gatherings. Enjoy peaceful, semi-private surroundings with easy access to wineries, hiking, Silicon Valley, and San Francisco. Only registered guests allowed on the property.

Spacious Pleasanton Townhouse with Fenced Yard
Escape to our cozy 3-bedroom, 1.5-bath townhouse, perfect for up to 6 guests. This fully furnished home features a modern kitchen with stainless steel appliances, high-speed Wi-Fi, and 2 Smart TVs. Enjoy the convenience of a private garage and extra parking in a safe, peaceful neighborhood. Ideal for families or groups seeking a comfortable and quiet home away from home.

Cozy Bungalow near Bart to SF, SJ, & Hwy 238 & 580
Welcome to this charming Bungalow 2-bedroom 1-bath single family home that offers you a fully equipped nice stay with comfort in the neighborhood of Castro Valley, conveniently commute to many central locations, and minutes to Bart station to S.F., S.J., Oakland, and other destinations. (Station map and location details available inside the house).
Popular amenities for Pleasanton holiday rentals
Other great holiday rentals in Pleasanton

Private ADU on 1/2 acre property near wineries

Hillside Haven - East Bay

Downtown Darling

Sweet Zen: 1 BR/1 BA Luxe Suite w/ Pvt. Courtyard

New to Livermore California, The Acacia House

Bungalow Guest House

Pretty 4B2B Pleasanton House

Walk to Downtown | Workspace + Pet Friendly
When is the best time to visit Pleasanton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $197 NZD | $209 NZD | $199 NZD | $197 NZD | $167 NZD | $192 NZD | $192 NZD | $184 NZD | $182 NZD | $182 NZD | $182 NZD | $194 NZD |
| 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 |
Frequently Asked Questions
What are the best places to stay in Pleasanton?
Many travelers choose accommodations near downtown Pleasanton for walkable dining, shopping, and cultural attractions. Suburban neighborhoods around parks are also frequently suggested for quieter stays with easy access to outdoor spaces.
What are the best things to do in Pleasanton with kids?
Families often explore parks, try hands-on activities at local museums, or enjoy playful afternoons at playgrounds around Pleasanton. Occasional seasonal events, farmers markets, and interactive workshops are also frequently suggested for children.
What are some of the best things to do in Pleasanton?
Explore Main Street's shops, cafés, and art galleries, or relax in family-friendly parks like Shadow Cliffs Regional Recreation Area. Seasonal farmers markets and local wineries invite visitors to discover Pleasanton's flavors and traditions.
How is the weather in Pleasanton?
Pleasanton experiences mild, wet winters around 43–59°F (6–15°C) and warm, dry summers near 57–77°F (14–25°C). Spring and autumn bring moderate temperatures and occasional rain, so layering is recommended year-round.
When is the best time to visit Pleasanton?
Late spring and early summer are frequently suggested for comfortable temperatures and lively festivals, while autumn brings harvest celebrations and mild weather. Winters are cooler and wetter, popular for quieter visits and holiday activities.
What are the best places to visit in Pleasanton?
Shadow Cliffs Regional Recreation Area and downtown Pleasanton are often recommended for their outdoor trails, community events, and historic architecture. Art galleries and neighborhood parks invite relaxed exploration.
What are some hiking trails in Pleasanton?
Shadow Cliffs Regional Recreation Area has popular nature trails winding past lakes and open spaces, while Pleasanton Ridge Regional Park features rolling hills and oak woodlands for longer hikes. Neighborhood paths and creekside walks invite easy exploration.
What are some family activities we can do in Pleasanton?
Families often spend time at parks, splash pads, and playgrounds, or attend family movie nights and craft workshops hosted by local venues. Seasonal fairs and nature walks in recreation areas are frequently suggested experiences.
What are some of the best day trip ideas from Pleasanton?
Explore nearby wine country with vineyard tours, wander through historic neighboring towns, or venture to regional nature reserves for hikes and wildlife watching. City art galleries and outdoor gardens are also around Pleasanton.
Are there any pet friendly accommodations available in Pleasanton?
Many hosts in Pleasanton welcome pets, especially in neighborhoods near parks and trails. Community green spaces and walking paths around the area make it easy to explore with your dog or companion animal.
What are some local tips for visiting Pleasanton?
Locals enjoy early mornings in downtown cafés, walkable art murals, and sunsets at neighborhood parks. Bring layers for changing temperatures, try regional produce at markets, and check out community events for a sense of the area's traditions.
What is Pleasanton known for?
Pleasanton has a vibrant downtown area, parks with spacious green spaces, and a history rooted in agriculture and railway traditions. Seasonal festivals and a welcoming community atmosphere are frequently highlighted by visitors.
What are the best hidden gems to explore in Pleasanton?
Discover local art murals tucked along side streets, picnic spots in lesser-known parks, and smaller family-owned shops downtown. Occasional pop-up markets and neighborhood walking tours unveil Pleasanton's quieter character.
What are the best foods to try in Pleasanton?
Pleasanton has local California cuisine with fresh produce, farm-to-table menus, and diverse tastes from regional wine and craft breweries. Bakeries, global eateries, and seasonal farmers markets introduce visitors to the area's flavors.
What should I bring for a trip to Pleasanton?
Pack comfortable walking shoes and layers, as temperatures vary from cool mornings to warm afternoons. A light rain jacket is helpful in winter and spring, while sun protection is useful during drier summer months.
What is the nightlife in Pleasanton like?
Pleasanton has a relaxed nightlife scene, with neighborhood bars, casual lounges, and wine bars around downtown. Live music and community events occasionally liven up evenings, especially on weekends.
What are the most popular events or festivals in Pleasanton?
The Alameda County Fair is one of Pleasanton's most popular annual events, usually held in early summer with rides, exhibits, and performances. Downtown street festivals, art walks, and farmers markets are also frequently suggested.
Are there family friendly vacation rentals in Pleasanton?
Pleasanton has family friendly vacation rentals in residential neighborhoods near downtown and parks, providing spacious layouts with kitchens and living areas. Many hosts welcome children and offer amenities for family gatherings.
Quick stats about holiday rentals in Pleasanton

Total holiday rentals
Explore 160 holiday rentals in Pleasanton

Nightly prices starting at
Pleasanton holiday rentals start at $33 NZD per night before taxes and fees

Verified guest reviews
Over 2,700 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 60 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
160 of Pleasanton holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Pleasanton rentals

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