Holiday rentals in Pleasanton

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Top-rated holiday rentals in Pleasanton

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Top guest favourite
An A-Frame cabin is surrounded by lush greenery, positioned on elevated ground. A stone pathway leads to the entrance, flanked by wooden railings. The cabin features large glass panels on its façade, allowing natural light to flood the interior. A deck with seating overlooks the nature surroundings.
Cabin in Felton
4.97 out of 5 average rating, 147 reviews

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

Top guest favourite
A modern living space showcases a comfortable gray sofa with decorative pillows. A wall-mounted TV is positioned across from the seating area, with a dining table and bar stools visible in the open kitchen. Light wood flooring complements the bright, airy atmosphere.
Guest suite in Hayward
5 out of 5 average rating, 242 reviews

★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.

Top guest favourite
A bright living area features a spacious gray sofa adorned with yellow accent pillows. A circular coffee table sits on a patterned rug, and a flat-screen TV is mounted on the wall. Natural light floods in through large sliding doors leading to a private outdoor space.
Guest house in Dublin
5 out of 5 average rating, 169 reviews

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.

Top guest favourite
The private entry to the studio is framed by beige walls and features a white door with large glass panels. A small table with potted plants is positioned beside the entrance, while a covered patio area can be seen in the background, offering outdoor space.
Home in Livermore
4.98 out of 5 average rating, 290 reviews

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.

Top guest favourite
A shaded patio features a round table surrounded by four metal chairs. An umbrella provides protection from the sun, while lush greenery surrounds the outdoor space, including trees and shrubs. The patio is paved with stone, creating a comfortable area for relaxation.
Bungalow in Livermore
4.99 out of 5 average rating, 197 reviews

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.

Guest favourite
A cozy sleeping area is presented with a queen bed dressed in soft linens. Two bedside tables hold modern lamps, illuminating the space with a warm glow. Elegant curtains frame the window, while decorative pillows and a small vase add a touch of comfort and sophistication.
Guest suite in Dublin
4.94 out of 5 average rating, 178 reviews

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.

Top guest favourite
The kitchen features white cabinetry and a large central island with a marble countertop. Natural light is focused through three windows adorned with blinds. Modern appliances, including a black refrigerator and oven, complement the streamlined design, creating a functional cooking space.
Townhouse in Dublin
4.98 out of 5 average rating, 161 reviews

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.

Top guest favourite
A glimpse into the living space is provided, showcasing a bright area with wooden floors and a dining table surrounded by chairs. A shower stall can be seen through an open door, adding to the cottage's functionality. A mirror hangs near the entrance, enhancing the welcoming feel.
Guest house in Livermore
5 out of 5 average rating, 102 reviews

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.

Guest favourite
Guest house in Livermore
4.97 out of 5 average rating, 151 reviews

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

Top guest favourite
A spacious studio is highlighted by a comfortable king bed with quality linens and a cozy seating area featuring a brown sofa. A ceiling fan provides airflow, while natural light filters through the large windows covered by soft curtains. A small dining table adds functionality to the room.
Guest house in Livermore
4.97 out of 5 average rating, 303 reviews

Cozy Livermore Studio *KING BED* Close to DOWNTOWN

Firefly Guesthouse presents our cozy studio which is located only two blocks from charming downtown Livermore. Please read the entire listing before booking, as we want to ensure our studio is the right fit! If your dates are not available please reach out to us at the Livermore Firefly Guesthouse as we may be able to accommodate you in one of our other homes on the property. Early check-in or late check-out are an extra cost of $10 per hour, however approval is based on availability.

Top guest favourite
Home in Livermore
4.89 out of 5 average rating, 263 reviews

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.

Top guest favourite
A coastal cabin is situated on rugged cliffs overlooking the ocean. The structure features large windows, allowing for expansive views of the water. Lush greenery surrounds the home, highlighting its natural setting against a cloudy sky.
Home in Montara
4.99 out of 5 average rating, 124 reviews

Sea Wolf Bungalow

If you're looking for the most spectacular views on the San Mateo Coast, come to Sea Wolf Bungalow. Located just 20 minutes southwest of San Francisco and 7 miles north of Half Moon Bay, this historic cabin sits on its on own point with sweeping views of the Pacific. Enjoy whale watching, the beach, surfing, fishing, golf, hiking and the fabulous dining of the coastal area.

Popular amenities for Pleasanton holiday rentals

When is the best time to visit Pleasanton?

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Avg. price$165 SGD$160 SGD$165 SGD$150 SGD$127 SGD$146 SGD$146 SGD$140 SGD$139 SGD$139 SGD$139 SGD$148 SGD
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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 $25 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    160 of Pleasanton holiday rentals include wifi 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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