Sugarloaf vacation rentals

We found 19 vacation rentals — enter your dates for availability

Discover a selection of 5 homes and other vacation rentals in Sugarloaf that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the amenities you expect and more, which might include WiFi and a hot tub. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Sugarloaf

Why visit Sugarloaf

  • Family-friendly activities: Sugarloaf offers a welcoming atmosphere with various activities suitable for all ages.
  • Scenic parks: Explore nearby urban parks that provide beautiful settings for relaxation and recreation.
  • Diverse dining options: Enjoy local dining experiences that cater to a range of tastes and preferences.
  • Charming vacation rentals: Choose from cozy homes and modern apartments for a comfortable stay.
  • Vibrant shopping: Discover unique shops and boutiques in the lively Sugarloaf neighborhood.

Popular types of accommodation around Sugarloaf

Discover the perfect getaway with vacation rentals in Sugarloaf. Whether you're looking for a cozy private vacation home, a charming cottage, or a modern apartment, there's an ideal option for every traveler. Sugarloaf vacation homes offer the comfort and convenience you need for an unforgettable stay. Explore our selection of Sugarloaf cottages and find the ideal backdrop for your next adventure. Your dream vacation in Sugarloaf awaits.

  • Houses: The top choice for visitors in Sugarloaf, offering spacious and comfortable accommodations ideal for families or groups.
  • Apartments: A popular option for those seeking convenient stays, providing amenities for a home-like experience.
  • Cottages: Charming and cozy, these rentals are perfect for a romantic getaway or a peaceful retreat.
  • Condos: Offering a blend of luxury and convenience, condos are great for travelers wanting amenities and proximity to attractions.
  • Villas: These upscale properties provide an indulgent vacation experience with beautiful surroundings and ample space.**

Top attractions near Sugarloaf

Sugarloaf, located in San Mateo, California, is an ideal destination for family vacations, business trips, and city-themed getaways. Visitors can enjoy a variety of attractions, including scenic beaches, urban parks, and historic colleges. Whether you're seeking outdoor adventures, cultural experiences, or a relaxing weekend getaway, Sugarloaf offers plenty of activities and points of interest to explore, making it a perfect spot for all types of travelers.

  • Stanford University: Immerse yourself in the rich history and stunning architecture of this prestigious institution. Explore beautiful gardens, art installations, and the iconic Hoover Tower while soaking in the vibrant campus culture.
  • San Francisco Bay: Experience the bustling energy and picturesque views of this iconic bay area. Enjoy waterfront dining, scenic walks, and a variety of recreational activities, all set against the backdrop of the stunning Golden Gate Bridge.
  • San Mateo County Event Center: Engage in a diverse range of events in this versatile venue. Whether it's a trade show, concert, or community gathering, you'll find a dynamic atmosphere perfect for networking and entertainment.

Things to do recommended for couples

Looking for a romantic getaway in Sugarloaf? Indulge in relaxation at Oceanic Foot Spa, enjoy live music at Bing Concert Hall, or embrace adventure with water sports at University of Surfing. Each experience is designed to create unforgettable memories together.

Things to do recommended for families

Families visiting Sugarloaf can enjoy exciting experiences like the sports atmosphere at Stanford Stadium, splash around at Parkside Aquatic Park, or have fun skating at the Ice Center in San Mateo, all within a short distance from their stay.

Things to do recommended for groups

Explore the Hillsdale Shopping Center for a mix of shopping and entertainment just 2 miles from Sugarloaf. Enjoy a round of golf at Crystal Springs Golf Course, located 4 miles away, or catch a show at the Shoreline Amphitheatre, a cultural gem 15 miles from your base.

*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 Sugarloaf

If you're traveling with a group, family, or pets, or if you're considering extended stays, be sure to prioritize your search accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Sugarloaf with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Sugarloaf with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Sugarloaf: For many families, a trip wouldn’t feel complete without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly options come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Sugarloaf: If you're searching for vacation rentals with discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Sugarloaf

Explore the charming neighborhood of Sugarloaf, San Mateo, where family-friendly activities and a warm, welcoming atmosphere await. Enjoy nearby parks, local dining, and vibrant shopping options that cater to all ages. With easy access to vacation homes and rentals, Sugarloaf serves as the perfect base for your getaway, allowing you to experience the blend of urban excitement and cozy community vibes. Discover the best of California while making lasting memories with loved ones.

  • San Francisco: San Francisco is a vibrant metropolis known for its stunning views, iconic landmarks, and diverse culture. Located a short distance from Sugarloaf, this city offers a plethora of family-friendly activities, outdoor adventures, and urban exploration. Visitors can indulge in shopping at popular centers, explore educational venues, or catch a game at the local sports facilities. Don't miss the chance to stroll along the picturesque bay, where you can enjoy breathtaking views of the Golden Gate Bridge and Alcatraz Island, making it a perfect destination for sightseeing enthusiasts.
  • Beresford Park: Beresford Park is a charming neighborhood located just a mile from Sugarloaf. It provides a delightful blend of business, family, and outdoor experiences. The area features a variety of shopping centers and educational venues, making it an excellent spot for both leisure and productivity. Visitors can enjoy the serene atmosphere of the urban park, perfect for a family picnic or a leisurely walk. Additionally, the nearby beach offers a great escape for sunbathers and water sports enthusiasts alike, making Beresford Park a well-rounded destination for relaxation and recreation.
  • Highlands-Baywood Park: Highlands-Baywood Park is a scenic neighborhood located a mile away from Sugarloaf, appealing to sports lovers and culture enthusiasts. The area boasts beautiful golf courses and offers a variety of outdoor activities, making it ideal for those who enjoy an active lifestyle. Visitors can immerse themselves in local culture by visiting nearby natural history museums or exploring event venues that host various exhibitions. With its inviting atmosphere and recreational opportunities, Highlands-Baywood Park is a fantastic place to unwind and experience the beauty of the California landscape.

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, if you book a longer stay, you may unlock even more substantial savings. To discover a Vrbo property that meets your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash on your total booking amount. It’s definitely rewarding to take on the planning role. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up where you left off, or manage and organize your travel plans. You can easily access properties you've saved or booked in your Potential, Upcoming, or Current Trips sections. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a vacation home in Sugarloaf?
Prices for vacation rentals in Sugarloaf 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Sugarloaf to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Sugarloaf vacation house rentals?
You can find great discounts on house rentals in Sugarloaf on Vrbo, 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.
Are there any Sugarloaf vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Sugarloaf with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
Can I find long-stay vacation rentals in Sugarloaf?
A long-stay vacation rental in Sugarloaf is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Sugarloaf for a vacation rental?
The peak season for visiting Sugarloaf is from May to July, with July being the most popular month among travelers. This vibrant period draws outdoor enthusiasts eager to experience the beauty of the San Bernardino Mountains, where hiking, biking, and other adventures abound. With warm temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, visitors can comfortably explore the area's stunning landscapes and enjoy a variety of outdoor activities.

During this time, Sugarloaf buzzes with excitement as families and friends gather for summer fun. Whether you're planning a scenic hike to discover local flora and fauna or enjoying a picnic by the lake, the options for outdoor enjoyment are plentiful. It's also a great time for stargazing, as the clear summer nights offer breathtaking views of the night sky.

For those mindful of their budget, consider planning your visit in December. While this month falls into the low season, it provides a unique opportunity to experience a different side of Sugarloaf, often adorned with beautiful winter scenery. Plus, you can enjoy a quieter atmosphere and find some excellent rental deals.

Ultimately, your choice of when to visit Sugarloaf will depend on whether you prefer the lively summer activities or the tranquil beauty of winter.
How early should I book a Sugarloaf vacation rental?
Book your Sugarloaf vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Sugarloaf, California, United States of America?
In Sugarloaf, California, visitors can enjoy a variety of attractions centered around the natural beauty of the San Bernardino National Forest. This quaint mountain community is known for its proximity to outdoor recreational activities. Lake Arrowhead and Big Bear Lake are just a short drive away, offering opportunities for boating, fishing, and hiking. The area features beautiful trails like the Pacific Crest Trail, which is great for both hiking in the summer and snowshoeing in the winter.

Additionally, the local ski resorts in nearby Big Bear provide excellent winter sports options, including skiing and snowboarding, attracting enthusiasts from all over. Sugarloaf itself has a cozy atmosphere with charming cabins and vacation rentals, making it an ideal base for exploring the surrounding natural attractions.
Can I change or cancel my Sugarloaf home rental booking on Vrbo?
To find Sugarloaf vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Sugarloaf vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

More Vacation Ideas