Discover Your Perfect San Mateo Vacation Homes

Best Vacation Homes in San Mateo

10.0
Exceptional
(7 Reviews)
980 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
GB £146/Night For 7 Nights GB £1,025
10.0
Exceptional
(3 Reviews)
1302.43 ft² 8 Guests 3 Bedrooms 2 Bathrooms
House
  • Balcony/Terrace
  • Pet Friendly
  • Parking
GB £220/Night For 7 Nights GB £1,539
9.2
Exceptional
(649 Reviews)
1 Bedroom 1 Bathroom
Family Friendly Hotel
  • Pool
  • Breakfast
  • Kitchen
GB £115/Night For 7 Nights GB £804
10.0
Exceptional
(4 Reviews)
4 Guests 2 Bedrooms 2 Bathrooms
Couples Retreat House
  • Child Friendly
GB £88/Night For 7 Nights GB £613
10.0
Exceptional
(3 Reviews)
1399.31 ft² 10 Guests 3 Bedrooms 2 Bathrooms
House
  • Fireplace/Heating
  • Balcony/Terrace
  • View
GB £207/Night For 7 Nights GB £1,446
10.0
Exceptional
(3 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Kitchen
  • Parking
GB £96/Night For 7 Nights GB £673
10.0
Exceptional
(2 Reviews)
270 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
GB £126/Night For 7 Nights GB £882
10.0
Exceptional
(1 Review)
650 ft² 3 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
GB £140/Night For 7 Nights GB £983

San Mateo Luxury Rentals

10.0
Exceptional
(19 Reviews)
8 Guests 4 Bedrooms 3 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
GB £640/Night For 7 Nights GB £4,478
New
6426.05 ft² 19 Guests 8 Bedrooms 7 Bathrooms
Free Cancellation House
  • Fireplace/Heating
  • Pet Friendly
  • Parking
GB £495/Night For 7 Nights GB £3,464
10.0
Exceptional
(8 Reviews)
6425 ft² 19 Guests 8 Bedrooms 6 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
GB £462/Night For 7 Nights GB £3,232
10.0
Exceptional
(16 Reviews)
7 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
GB £318/Night For 7 Nights GB £2,224
9.4
Exceptional
(38 Reviews)
1500 ft² 10 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Cabin
  • Fireplace/Heating
  • Balcony/Terrace
  • View
GB £287/Night For 7 Nights GB £2,008
8.5
Fabulous
(2 Reviews)
2647.92 ft² 8 Guests 4 Bedrooms 3 Bathrooms
Family Friendly House
  • Pet Friendly
  • Internet
  • Child Friendly
GB £259/Night For 7 Nights GB £1,816
9.8
Exceptional
(87 Reviews)
2456 ft² 12 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
GB £252/Night For 7 Nights GB £1,764
10.0
Exceptional
(168 Reviews)
10 Guests 4 Bedrooms 3 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
GB £251/Night For 7 Nights GB £1,759

San Mateo Pet Friendly Vacation Rentals

9.0
Exceptional
(14 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
GB £101/Night For 7 Nights GB £707
10.0
Exceptional
(1 Review)
2604.87 ft² 8 Guests 4 Bedrooms 2 Bathrooms
Free Cancellation House
  • View
  • Pet Friendly
  • Parking
GB £217/Night For 7 Nights GB £1,517
9.8
Exceptional
(178 Reviews)
1 Bedroom 1 Bathroom
Family Friendly Bed & Breakfast
  • Fireplace/Heating
  • Balcony/Terrace
  • Breakfast
GB £169/Night For 7 Nights GB £1,184
New
2 Guests 1 Bedroom 1 Bathroom
Couples Retreat House
  • Fireplace/Heating
  • Pet Friendly
  • Air Conditioner
GB £106/Night For 7 Nights GB £742
New
947.22 ft² 8 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • View
  • Pet Friendly
  • Parking
GB £94/Night For 7 Nights GB £658
10.0
Exceptional
(19 Reviews)
925 ft² 8 Guests 3 Bedrooms 1 Bathroom
Ocean View House
  • Fireplace/Heating
  • Ocean View
  • Balcony/Terrace
GB £185/Night For 7 Nights GB £1,293
10.0
Exceptional
(7 Reviews)
6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
GB £157/Night For 7 Nights GB £1,102
9.8
Exceptional
(25 Reviews)
8 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Cabin
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
GB £166/Night For 7 Nights GB £1,162

San Mateo Large Vacation Homes

9.8
Exceptional
(6 Reviews)
1360 ft² 10 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
GB £159/Night For 7 Nights GB £1,110
New
1496.18 ft² 10 Guests 3 Bedrooms 2 Bathrooms
House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
GB £193/Night For 7 Nights GB £1,353
9.2
Exceptional
(11 Reviews)
1300 ft² 11 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
GB £200/Night For 7 Nights GB £1,402
10.0
Exceptional
(6 Reviews)
50000 ft² 20 Guests 7 Bedrooms 6 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
GB £702/Night For 7 Nights GB £4,918
New
10 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Cabin
  • Fireplace/Heating
  • Pet Friendly
  • Air Conditioner
GB £168/Night For 7 Nights GB £1,177

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

winter
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

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.

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.
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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?

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.

San Mateo Top Rated Vacation Rentals

8.6
Fabulous
(141 Reviews)
20 Guests 63 Bedrooms 1 Bathroom
Family Friendly Hotel
  • Pool
  • Parking
  • Child Friendly
GB £100/Night For 7 Nights GB £703
8.2
Excellent
(1002 Reviews)
1 Bedroom 1 Bathroom
Family Friendly Hotel
  • Pool
  • Balcony/Terrace
  • Breakfast
GB £79/Night For 7 Nights GB £554
8.0
Excellent
(640 Reviews)
1 Bedroom 1 Bathroom
Family Friendly Hotel
  • Pool
  • Breakfast
  • Kitchen
GB £87/Night For 7 Nights GB £609
7.9
Very Good
(511 Reviews)
362.13 ft² 49 Guests 389 Bedrooms 14 Bathrooms
Ocean View Hotel
  • Oceanfront
  • Fireplace/Heating
  • Pool
GB £82/Night For 7 Nights GB £574
7.9
Very Good
(188 Reviews)
285.24 ft² 22 Guests 53 Bedrooms 1 Bathroom
Free Cancellation Hotel
  • Fireplace/Heating
  • Pool
  • Parking
GB £103/Night For 7 Nights GB £721