Discover Your Perfect San Mateo Vacation Homes

San Mateo Pet Friendly Vacation Rentals

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9.8 (178 Reviews)
Bed & Breakfast
Grand Gables Inn Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in San Mateo on PetFriendly.io

Why Choose Rent By Owner for your San Mateo Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit San Mateo

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit this destination can enhance your experience and ensure you enjoy the best weather and local events in the area.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination experiences milder weather, making it an ideal time for outdoor activities and exploring the region in comfort.

Average Temperature Daytime: high 60s to low 70s °F - Nighttime: mid 40s to mid 50s °F
spring
Spring (March to May)

Spring offers pleasant temperatures and blooming scenery, attracting visitors seeking a vibrant and comfortable environment for outdoor adventures.

Average Temperature Daytime: mid 70s to low 80s °F - Nighttime: mid 50s to mid 60s °F

Off-Season Highlights

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Summer (June to August)

Summer months tend to be hotter and more humid, but they also bring fewer visitors, allowing you to enjoy the area’s natural beauty with less crowding.

Average Temperature Daytime: high 80s to low 90s °F - Nighttime: mid 70s to low 80s °F
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Fall (September to November)

Autumn features cooler temperatures and less tourist activity, providing a peaceful setting to experience the region's tranquility before the winter rush.

Average Temperature Daytime: mid 70s to high 70s °F - Nighttime: mid 50s to mid 60s °F

Weekly Weather Forecast for San Mateo

How to Book Your San Mateo Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in San Mateo

More Top-Rated Vacation Rentals in San Mateo Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor seating areas such as patios or verandas to relax and soak in the scenic views of the region.
  • Take advantage of private or shared pools that provide a refreshing escape during warm days in this destination.
  • Experience outdoor dining setups perfect for family barbecues or al fresco meals with picturesque surroundings.
  • Make use of well-maintained gardens or landscaped yards that offer tranquil spots for unwinding amid nature.
  • Utilize outdoor fire pits or fireplaces ideal for cozy evenings and social gatherings under the stars.
  • Access to outdoor recreational facilities like sports courts or playing fields can enhance your stay here.
  • Benefit from covered porches or gazebos that provide shaded outdoor living spaces, ideal for relaxing regardless of the weather.

Top Attractions Around San Mateo

What attractions are nearby?

Nearby, you can explore a variety of outdoor activities, scenic parks, and local attractions that showcase the natural beauty and charm of this destination, making it an ideal spot for relaxing and memorable experiences during your stay.

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Family Activities

  • Hiking at the San Mateo Nature Preserve: Explore scenic trails and enjoy outdoor adventures amidst the lush landscapes unique to this region.
  • Visiting Riverside Park: Spend quality time with your family by the water, engaging in picnicking, playing, or relaxing in a serene setting.
  • Fishing at local lakes: Experience the tranquility of fishing in nearby lakes, perfect for bonding and creating lasting memories.
  • Discovering local wildlife refuges: Observe native birds and animals in their natural habitat, offering an educational experience for all ages.
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Adult Activities

  • Fishing at Lake City: Enjoy a relaxing day casting your line at the nearby lake, renowned for its abundant freshwater fish and scenic surroundings.
  • Golfing at Silver Lake Golf Course: Tee off amidst beautifully maintained greens that cater to all skill levels, providing an ideal backdrop for a leisurely round of golf in this area.
  • Exploring Nature Trails: Immerse yourself in the region’s natural beauty by hiking along well-marked trails that showcase the local flora and fauna.
  • Visiting Local Wineries: Experience the region's burgeoning wine scene with tastings at charming wineries that highlight the area's unique flavors and craftsmanship.

San Mateo Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Explore local parks and outdoor spaces to fully enjoy the natural beauty of this destination, ensuring a memorable stay.
  • Choose a Prime Location: Select vacation rentals close to key attractions or scenic spots to maximize your leisure time and convenience here.
  • Engage with Local Cuisine: Take advantage of nearby eateries and markets to experience authentic regional flavors during your visit.
  • Utilize Reliable Transportation Options: Arrange for trusted transportation services or rent a vehicle to easily navigate the area and access all that the region offers.

Transportation Options

  • San Mateo Transit System: This local transit service provides convenient bus routes that help you explore the area without hassle.
  • Driving Your Own Vehicle: Renting a car gives you flexibility and ease to access the region’s scenic spots and nearby attractions at your own pace.
  • Taxi and Ride-Sharing Services: Reliable cab companies and ride-sharing options are readily available for quick, comfortable trips around town.
  • Nearby Airports: The close proximity of regional airports offers effortless connections for travelers arriving from afar, making your journey to this destination smooth and straightforward.

Local Customs Options

  • Southern Hospitality:** You will notice the warm and welcoming attitude that reflects this region’s friendly and community-oriented spirit.
  • Local Festivals:** Participating in local festivals offers a glimpse into the regional culture and traditions that are cherished here.
  • Traditional Cuisine:** Enjoying regional dishes at local eateries allows you to experience authentic flavors unique to this destination.
  • Respect for Nature:** The community emphasizes outdoor conservation practices, encouraging visitors to preserve the natural beauty of the area.

Frequently Asked Questions About San Mateo?

1. What are the top vacation rentals in San Mateo?

There are a lot of options in San Mateo. If you plan on staying in the San Mateo area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in San Mateo:

2. Which vacation homes in San Mateo are best for families?

If you are looking for a family-friendly vacation home in San Mateo, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in San Mateo:

3. How many Rentbyowner vacation rentals are available in San Mateo?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 67 in the San Mateo area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in San Mateo. 

4. What is the cancellation policy for vacation rentals in San Mateo, Florida?

Cancellation policies vary by property, so it’s important to review the specific listing details or contact the property owner directly to understand the terms and any associated fees or refund policies.

5. How do I find vacation rentals with flexible booking options in San Mateo?

You can filter search results based on flexibility in your preferred booking dates or cancellation terms. Reviewing the listing descriptions and contacting owners can also help you confirm available options before booking.

6. Are there any house rules I should be aware of when staying in a vacation rental here?

Yes, each property typically has its own set of house rules regarding check-in/out times, pet policies, noise restrictions, and other guidelines. Be sure to read the listing thoroughly and reach out to the owner if you need clarification.

7. What amenities are usually included in vacation rentals in this region?

Most properties offer essential amenities such as Wi-Fi, parking, and kitchen facilities. Specific amenities can vary, so it's best to carefully review the listing details or contact the owner for confirmation.

8. How do I ensure my stay complies with local regulations in this area?

Check the property listing for compliance information and ask the owner about any local regulations or permits. It's important to adhere to community guidelines during your stay for a smooth experience.