Best Vacation Homes in San Mateo
10.0
Private Pool
Oceanfront
Pool
Ocean View
10.0- Oceanfront
Parking- Ocean View
Balcony/Terrace
10.0- Balcony/Terrace
Kitchen
Air Conditioner
Internet
10.0- Air Conditioner
- Internet
Child Friendly
Security/Safety
10.0- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
10.0- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
10.0- Parking
- Kitchen
- Internet
- Child Friendly
San Mateo Luxury Rentals
- Air Conditioner
- Child Friendly
Laundry
Bedding/Linens
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Private Pool
- Hot Tub
- Pool
View
- Private Pool
Breakfast- Pool
- Ocean View
- Private Pool
- Oceanfront
- Pool
- Ocean View
San Mateo Pet Friendly Vacation Rentals
10.0- Parking
- Ocean View
- View
- Kitchen
10.0- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
10.0- Parking
- Ocean View
- Balcony/Terrace
- View
10.0- Parking
- Balcony/Terrace
- Air Conditioner
Pet Friendly
10.0- Private Pool
- Oceanfront
- Parking
- Pool
10.0- Parking
- Ocean View
- Balcony/Terrace
- View
10.0- Parking
- Ocean View
- Balcony/Terrace
- View
San Mateo Large Vacation Homes
10.0- Kitchen
- Air Conditioner
- Internet
- Child Friendly
9.1- Parking
- Balcony/Terrace
- Air Conditioner
- Pet Friendly
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
10.0- Parking
- Kitchen
- Air Conditioner
- Internet
10.0- Ocean View
- Balcony/Terrace
- View
- Kitchen
10.0- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
10.0- Kitchen
- Air Conditioner
- Internet
- Child Friendly
Why Choose Rent By Owner for your San Mateo Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for San Mateo Vacation Rentals
Where are the best neighborhoods to stay in San Mateo?
When choosing where to stay in San Juan, Puerto Rico, exploring neighborhoods like San Mateo offers a convenient and culturally rich experience. This area provides a blend of local charm and accessibility, making it an ideal base for discovering the vibrant city. Located close to key attractions and amenities, San Mateo allows you to enjoy the authentic atmosphere of San Juan while providing comfortable options for your stay. Whether you're seeking a quiet retreat or a lively neighborhood atmosphere, this area ensures a seamless and enjoyable vacation experience in Puerto Rico.
Sagrado Corazon
In this vibrant neighborhood, you’ll find convenient access to local amenities and a lively atmosphere that caters to travelers seeking comfort and convenience. It’s an ideal area to stay for those wanting to explore the city’s cultural charm while enjoying modern conveniences.
View 4609+ Rentals in Sagrado CorazonHipodromo
Known for its central location and easy accessibility, Hipodromo offers a peaceful retreat close to key attractions and transportation hubs. This area is perfect if you desire a tranquil setting with quick connections to the region’s highlights.
View 41+ Rentals in HipodromoParque
Surrounded by lush greenery and scenic views, Parque provides a relaxing environment where you can unwind after exploring the bustling streets nearby. It’s an excellent choice for travelers who appreciate outdoor spaces and a serene neighborhood ambiance.
View 132+ Rentals in ParqueBest Times to Visit San Mateo
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here can enhance your experience, as this destination offers different charms depending on the season and climate conditions in the region.
Peak Season Highlights
December to April
During these months, you'll experience the region’s warm and dry weather, ideal for enjoying outdoor activities and beach excursions in San Juan. This is the most popular time for visitors seeking a sunny escape to this Caribbean destination.
July to August
The peak summer months draw many travelers who want to make the most of the lively local culture and vibrant festivities. Expect busy streets and high demand for vacation rentals here during this lively season.
Off-Season Highlights
May to June
As the weather begins to warm, this shoulder period offers fewer crowds and more availability for your stay. It’s an excellent time to enjoy a quieter visit while still benefiting from pleasant temperatures.
September to November
Late fall marks the off-peak season with lower visitor numbers, providing a more relaxed atmosphere. Be mindful of occasional showers, but the region remains inviting for those looking for a peaceful retreat in Puerto Rico.
Weekly Weather Forecast for San Mateo
How to Book Your San Mateo Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in San Mateo
Common Vacation Rentals Amenities
What amenities can you expect?
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 a sunny outdoor dining area perfect for meals with a view of the surrounding landscape.
- Relax in a private swimming pool that offers a refreshing escape during warm days.
- Benefit from landscaped gardens or lush yards ideal for outdoor activities and leisure.
- Take advantage of a spacious patio or terrace suitable for entertaining guests or unwinding.
- Utilize outdoor grilling facilities to prepare delicious meals amidst scenic surroundings.
- Experience the comfort of shaded lounging areas to relax after exploring the area.
- Make use of available outdoor showers or rinse stations for convenience after beach trips or outdoor adventures.
Top Attractions Around San Mateo
What attractions are nearby?
Within this vibrant area, you can enjoy a variety of nearby activities such as exploring local beaches, experiencing cultural sites, and indulging in delicious Puerto Rican cuisine, all easily accessible from your San Mateo vacation rental in San Juan.
Family Activities
- San Juan Bay Kayaking Tours: Explore the calm waters of San Juan Bay with your family on a guided kayak adventure that offers stunning views and outdoor fun for all ages.
- Condado Lagoon Wildlife Refuge: Visit this protected area to enjoy birdwatching, paddleboarding, and nature walks, providing engaging outdoor activities right in the heart of the city.
- Old San Juan Historic Walking Tour: Stroll through the colorful streets, discovering historical forts and landmarks, perfect for families interested in local culture and history.
- Plaza Las Américas Shopping Mall: Spend quality time shopping, dining, and enjoying entertainment options suitable for children within this bustling regional mall.
Adult Activities
- Sailing Tours: Embark on a scenic sailing adventure to explore the stunning coastlines and hidden coves of this vibrant destination.
- Old San Juan Exploration: Spend your day wandering through historic streets filled with colorful colonial architecture and charming plazas.
- Beach Relaxation: Unwind on pristine beaches where you can soak up the sun and enjoy the tranquil turquoise waters surrounding the area.
- Dining Experiences: Indulge in authentic Puerto Rican cuisine at local restaurants that highlight the region’s rich culinary heritage.
Other Places to Stay in San Mateo
San Jorge Children's Hospital
Santurce
San Mateo Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take the time to indulge in authentic Puerto Rican cuisine at nearby eateries to truly experience the region's culinary delights.
- Plan outdoor activities: Make the most of the area's pleasant climate by enjoying outdoor excursions such as walking along scenic streets or relaxing at nearby parks.
- Discover cultural sites: Immerse yourself in the rich history and vibrant culture by visiting accessible museums, galleries, or historical landmarks within reach.
- Utilize local transportation: Maximize your stay by familiarizing yourself with available transport options to conveniently explore the region's attractions at your own pace.
Transportation Options
- Public Transit (Bus and Rail): You can explore the area conveniently using the local bus and rail services that connect key parts of San Juan and nearby regions, making it easy to reach your vacation rental with minimal hassle.
- Taxis and Rideshare Services: Taxis and popular ridesharing options like Uber provide a reliable and flexible way to navigate around San Mateo and the surrounding areas at your convenience.
- Car Rentals: Renting a car offers you the freedom to discover hidden gems and enjoy the diverse landscape here at your own pace, with numerous rental agencies available nearby.
- Private Shuttle Services: Private shuttle options are available for direct transfers between the airport, the region, and your vacation rental, ensuring a comfortable start and end to your trip.
Local Customs Options
- La Perla Cultural Expression: Here, locals embrace vibrant street art and colorful murals, reflecting the region's lively artistic spirit.
- Festivals and Parades: Participating in lively parades and festivals demonstrates a deep appreciation for community celebrations that are central to this destination's culture.
- Traditional Music and Dance: The area's residents often enjoy lively salsa and bomba performances, showcasing Puerto Rican musical traditions.
- Religious Celebrations: Religious festivals and processions, especially during patron saint days, are significant cultural events you might witness here, highlighting local faith and customs.
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:
- Luxury 4000 sq ft Luxury Beach Villa Azure/Pool, Ocean Views & more
- Paradis - Luxurious Apartment with Ocean View and Balcony.
- Local Experience! 5 Minutes to Beach; Solar + Cistern & 4 AC Units
- Classic, Cozy & Gorgeous Apt. close to Condado beach 5B,3B&1parking
- 1058 Modern Apt 7
- Luxe Colonial Home near La Placita with Generator!
- NEW cozy & Spacious 5B, 3B, 1 parking close to Condado Beach
- Ocean Park Lovely Apartment – Your Urban Beach Escape high speed internet 200 mb
- Room 1 - Stylish Accessible Suite
- Room 14: Chill City Veranda Near Miramar
2. How many vacation rentals have private pools in San Mateo?
There are 15 vacation rentals with private pools near San Mateo. Top-rated RBO homes that have access to a swimming pool include:
- Casa Saffra @ La Placita 6/7 For Friends & Family
- Moderno Apartamento para parejas San Juan Puerto Rico
- Casa Saffra @ La Placita 4&5
- Welcome to La Perla Roja! Includes 3 units sharing gated courtyard, minutes to the airport & Old San Juan. Walk to Ocean Park beach, Ultimo Trolley beach, Isla Verde beach. Includes dedicated off-street parking and laundry.
3. 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:
4. 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 1057 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.
5. What is the cancellation policy for vacation rentals in San Mateo, San Juan, Puerto Rico?
6. Are there any additional fees I should be aware of when booking a rental here?
7. How do I contact the property owner for questions about my stay?
8. Is there a minimum stay requirement for rentals in this destination?
9. What amenities are generally included with rentals in this area?
San Mateo Top Rated Vacation Rentals
10.0- Private Pool
- Parking
- Pool
- Balcony/Terrace
9.6- Pool
- Ocean View
- Balcony/Terrace
- View
9.2- Oceanfront
- Parking
- Pool
- Ocean View
9.2- Private Pool
- Oceanfront
- Parking
- Pool
9.1- Hot Tub
- Parking
- Pool
- Balcony/Terrace
9.0- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
9.0- Private Pool
- Parking
- Pool
- Balcony/Terrace
