Woodside holiday rentals

We found 621 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Woodside that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, including air conditioning and Wi-Fi. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

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Why visit Woodside

  • Scenic Woodside Hills: Experience breathtaking views and enjoy outdoor activities in the picturesque Woodside Hills.
  • Leisurely strolls at Woodside Plaza: Relax and explore vibrant community spaces perfect for families and couples alike.
  • Natural reserves and parks: Discover lush urban parks and natural reserves that provide a serene retreat from city life.
  • Charming neighbourhood vibe: Immerse yourself in the friendly community atmosphere that Woodside is known for.
  • Accessible nearby beaches: Take a short trip to nearby beaches for sunbathing and coastal exploration.

Popular types of accommodation around Woodside

Discover Woodside in Redwood City, California – a charming neighbourhood offering a range of holiday rental options. Enjoy the comfort of private holiday homes, apartments, and cottages, ensuring a delightful stay. Explore local attractions and landmarks unique to Woodside, and make the most of your visit with woodside holiday rentals, woodside apartments, redwood city holiday rentals, redwood city rentals, and woodside apartments redwood city.

  • Private Holiday Homes: These exclusive self-catering residences are the top choice for a Woodside escape.
  • Apartments: Stylish, independent flats provide a cosy retreat in the heart of Woodside.
  • Cottages: Quaint, charming cottages offer a traditional and intimate setting for a peaceful break.
  • Condos: Modern, well-appointed condominium units promise a comfortable stay in Woodside.
  • Cabins: Rustic cabins deliver a unique and relaxed experience amidst nature.**

Top attractions near Woodside

Woodside, nestled within Redwood City, offers a delightful blend of outdoor and family-friendly experiences. Visitors can explore the scenic urban parks, reserves, and nearby beaches, all perfect for a leisurely city holiday. Ideal for those seeking tours that highlight the natural beauty and vibrant community, Woodside promises a memorable retreat filled with picturesque landscapes and a plethora of activities for all ages.

  • San Francisco Bay: Experience the stunning views and vibrant atmosphere of this iconic bay area, perfect for exploring local culture, dining, and recreational activities.
  • Miramar Beach: Enjoy the serene sandy shores and picturesque ocean views at this beautiful beach, ideal for sunbathing, picnicking, and leisurely strolls along the coastline.
  • Hakone Gardens: Discover tranquil Japanese-inspired landscapes in this private garden, featuring lush greenery, koi ponds, and serene pathways, perfect for families and nature lovers.

Things to do recommended for couples

Discover Woodside's charm with a stroll through its scenic paths paired with quaint cafés. Enjoy a cosy boat ride along the nearby stream, sharing intimate moments that create lasting memories for both of you.

Things to do recommended for families

Families visiting Woodside can explore the enchanting Filoli Estate with its beautiful gardens and historical tours, or enjoy a day at the nearby Huddart Park, where children can play and picnic amidst nature. Redwood City's lively downtown offers family-friendly dining and entertainment options, ensuring a delightful experience for all.

Things to do recommended for groups

Groups visiting Woodside can enjoy scenic countryside walks and local farm tours, sampling fresh produce and exploring historic sites in Redwood City. Enjoy the relaxed, community feel and authentic Californian charm during your group holiday.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Woodside

Whether you’re travelling with a group, as a family, with your pets, or seeking longer stays, be sure to select the appropriate filters. Here are some Stayz booking tips to help you.

  • Traveling to Woodside with a group: Consider the amount of bedrooms required, along with facilities like a fully-equipped kitchen or an outdoor area suitable for a group gathering. Fortunately, Stayz allows you to filter for all these features and more.
  • Traveling to Woodside with young kids: Traveling with young children can be challenging. It is essential to prioritise their comfort and safety, and to secure amenities suited to their age, such as a private swimming pool. Additionally, it is wise to consider your closeness to attractions that cater to families.
  • Taking your pets with you to Woodside: For some, a family holiday is not complete without the company of their four-legged companion. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring a comfortable stay for all.
  • Planning for a long term stay visiting Woodside: If you’re in search of holiday accommodation with exclusive offers for extended stays of a month or more, you’ve come to the right destination. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. You might also consider including additional features such as parking, a well-equipped kitchen, or a private pool in your search.

Where to stay near Woodside

Woodside, nestled in Redwood City, California, offers a delightful blend of outdoor adventures and serene landscapes. Visitors can explore the majestic Woodside Hills, enjoy leisurely strolls through Woodside Plaza, or bask in the scenic beauty of Redwood Shores. This charming neighbourhood is perfect for families and couples alike, providing a relaxing atmosphere and a friendly community vibe, making it an ideal destination for those seeking both adventure and tranquility.

  • Farm Hills: Farm Hills is a charming neighbourhood just 3km from Woodside, offering a rich blend of cultural, family, and outdoor experiences. The area is dotted with educational facilities and recreational spaces, making it ideal for visitors seeking a diverse travel itinerary. You can explore a historic college university, enjoy a leisurely stroll in the urban park, or relax by the beach. Whether you’re indulging in a day of shopping at the local mall centre or experiencing the vibrant local culture, Farm Hills promises a well-rounded visit.
  • Sharon Heights: Sharon Heights, also only 3km from Woodside, provides a dynamic mix of culture, business, and family attractions. The neighbourhood is home to educational institutions and bustling shopping centres, perfect for those who appreciate both heritage and modernity. Key attractions include a historic college university, a prominent research facility, and a nearby beach ideal for a seaside retreat. The area’s blend of traditional and contemporary experiences makes it a versatile destination for all travellers.
  • Emerald Hills: Situated 5km from Woodside, Emerald Hills is a picturesque neighbourhood celebrated for its cultural, outdoor, and family-oriented offerings. The region features educational venues, expansive recreational areas, and a golf course that invites both novice and seasoned players. Visitors can explore landmarks such as a historic college university, enjoy the refreshing coastal breeze at the beach, or wander through an urban park. Emerald Hills is a destination that beautifully marries scenic beauty with engaging local attractions.

Booking with Stayz is a breeze

Looking to reduce your travel expenses? Consider keeping your travel dates flexible, as prices can vary. Additionally, booking a longer stay often leads to significant savings. To find the ideal Stayz property that fits within your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz's Trip Board provides a dedicated space for you to plan new trips, manage your ongoing arrangements, or review and organise your bookings efficiently. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To explore the Trip Boards further, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

When is the best time to visit Woodside for a holiday rental?
The most popular time to visit Woodside is during the peak season from May to July when the weather is at its finest, making it great for outdoor enthusiasts and those seeking a tranquil retreat. This period sees a delightful mix of warm temperatures, typically ranging from 15 to 25 degrees Celsius, allowing visitors to fully enjoy the expansive hiking trails and picturesque landscapes of the area.July stands out as the peak month, bustling with activity as travellers flock to enjoy the lush scenery and partake in various outdoor pursuits. Whether you're hiking through the redwood forests or exploring the charming local shops, there's an invigorating atmosphere that makes Woodside an ideal destination for relaxation and adventure.For those who prefer a quieter experience and are looking for more economical options, December presents a wonderful opportunity. While it may be off-peak, visitors can still appreciate the serene beauty of the winter landscape, complete with crisp air and the chance for peaceful walks along the scenic routes.
What are the top attractions in Woodside, California, United States of America?
In Woodside, California, visitors can enjoy a blend of natural beauty and cultural attractions. One of the top highlights is the stunning Huddart Park, which offers serene hiking trails, picnic areas, and a chance to immerse oneself in California's coastal redwoods. The park is a fantastic spot for those looking to explore the outdoors.Another popular attraction is the Filoli Historic House and Garden, a magnificent estate that features beautifully manicured gardens and a grand mansion, showcasing the area's rich history and stunning landscaping. The estate often hosts seasonal events and tours, providing a glimpse into its historical significance.For those interested in equestrian activities, Woodside is known for its horse culture, and there are several stables and riding trails in the vicinity. The local community often hosts equestrian events, making it a vibrant spot for horse lovers.Additionally, the nearby Skyline Boulevard offers breathtaking views of the Bay Area and is great for scenic drives or leisurely walks.
Are all fees included in the Woodside holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Woodside holiday homes with parking?
Stayz offers a wide selection of holiday homes in Woodside with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Woodside holiday homes?
You can find great discounts on holiday homes in Woodside on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Woodside holiday home booking on Stayz?
To find Woodside holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Woodside?
A long-stay holiday home in Woodside is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Woodside holiday home?
Book your Woodside holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Woodside?
Prices for holiday homes in Woodside vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Woodside to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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