Best Vacation Homes in Old San Juan
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Old San Juan Luxury Rentals
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Old San Juan Pet Friendly Vacation Rentals
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Old San Juan Large Vacation Homes
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Why Choose Rent By Owner for your Old San Juan Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Old San Juan Vacation Rentals
Where are the best neighborhoods to stay in Old San Juan?
When choosing where to stay in Old San Juan, youโll want to explore neighborhoods that offer a perfect blend of historic charm and vibrant local culture. Each area provides its own unique atmosphere, from colorful streets filled with colonial architecture to lively districts buzzing with authentic Puerto Rican flavor. Staying in these neighborhoods ensures youโre immersed in the rich history and lively ambiance that make Old San Juan a truly unforgettable destination. Whether you prefer the intimacy of a cozy rental or the convenience of being close to popular sites, selecting the right neighborhood will enhance your experience of this historic city.
Puerta de Tierra
Located just outside the historic core, this neighborhood offers convenient access to Old San Juan's main attractions while providing a quieter, residential atmosphere for your stay.
View 124+ Rentals in Puerta de TierraMarina
This waterfront area is perfect for travelers seeking scenic views and easy access to Puerto Ricoโs vibrant port life, making it an ideal spot for exploring the regionโs maritime charm.
View 1098+ Rentals in MarinaCatedral
Nestled near historic sites, this neighborhood places you within walking distance of iconic landmarks and lively streets filled with local shops and dining options.
View 133+ Rentals in CatedralSan Francisco
Known for its charming streets and cultural vibrancy, here youโre close to historic architecture and bustling squares that capture the essence of this coastal city.
View 198+ Rentals in San FranciscoMercado
A lively hub where local markets and authentic eateries invite you to experience the flavors and sounds of Puerto Rico, all within a short stroll from your accommodation.
View 43+ Rentals in MercadoSan Cristobal
Home to one of the most formidable fortresses, this neighborhood provides a glimpse into the area's rich history and offers stunning views of the surrounding cityscape.
View 1140+ Rentals in San CristobalLa Puntilla
With scenic ocean vistas and tranquil surroundings, this area is perfect for relaxing by the water while remaining close to the heart of Old San Juan.
View 1073+ Rentals in La PuntillaBallaja
Once the site of a historic military barracks, today it encompasses cultural spaces and parks, making it a great choice for those interested in both history and outdoor leisure.
View 742+ Rentals in BallajaBest Times to Visit Old San Juan
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this vibrant destination can enhance your experience and ensure you find the perfect vacation rentals that suit your preferences during your stay.
Peak Season Highlights
December through April
During these months, the area experiences its busiest period with warm, sunny days ideal for exploring historic sites and enjoying outdoor activities. Expect lively atmosphere and higher prices for vacation rentals.
June through August
Summer time here attracts visitors seeking vibrant nightlife and beachside relaxation, making it a popular peak season for booking your stay in the region. Accommodations tend to fill quickly, so early reservations are recommended.
Off-Season Highlights
May and November
These shoulder months offer a more relaxed visitor flow, providing a quieter experience while still enjoying warm weather. It's an excellent time to find better rates for your vacation rentals in this destination.
September and October
During the early fall months, the region sees fewer travelers, offering an ideal opportunity for budget-conscious visitors to secure affordable vacation rentals while avoiding the peak crowds.
Weekly Weather Forecast for Old San Juan
How to Book Your Old San Juan Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
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Explore and book the perfect rental in Old San Juan
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 private outdoor patio or terrace to relax and unwind after exploring the region.
- Take advantage of a swimming pool or rooftop pool with scenic views of the historic cityscape.
- Make use of outdoor dining areas for alfresco meals in the warm Caribbean breeze.
- Experience outdoor lounge spaces perfect for socializing or enjoying sunset evenings.
- Benefit from lush landscaped gardens that add privacy and tranquility to your stay.
- Utilize shared outdoor amenities such as grilling stations or BBQ areas for casual cookouts.
- Stroll through nearby courtyards or open-air communal spaces designed for relaxation and social activities.
Top Attractions Around Old San Juan
What attractions are nearby?
Nearby, you can explore vibrant cultural sites, enjoy scenic waterfront promenades, and indulge in local cuisineโall just steps from your vacation rental in this historic part of San Juan.
Family Activities
- Castillo San Felipe del Morro: Discover the historic fortress that offers breathtaking views and engaging history lessons for the whole family to enjoy in this vibrant destination.
- Old San Juan Walking Tour: Explore the colorful streets and colonial architecture, providing an educational experience that immerses your family in the region's rich cultural heritage.
- San Juan Cathedral: Visit this stunning cathedral featuring impressive architecture and historical significance, perfect for a family outing that combines learning with leisure.
- La Fortaleza Gardens: Stroll through the lush gardens around the historic residence, offering a relaxing outdoor activity for families seeking serenity amidst scenic beauty.
Adult Activities
- Exploring Historic Forts: Discover the impressive San Juan National Historic Site, where you can walk through centuries of history and enjoy panoramic views of the coastline.
- Strolling Through Calle del Cristo: Wander along this charming street lined with local shops, cafes, and art galleries that capture the vibrant spirit of the area.
- Sampling Local Cuisine: Indulge in authentic Puerto Rican dishes at renowned restaurants, offering a taste of the regionโs rich culinary traditions.
- Enjoying Sunset Views from Paseo de la Princesa: Relax along this scenic promenade as you take in breathtaking sunsets over the historic city walls and harbor.
Other Places to Stay in Old San Juan
Old San Juan Travel Tips
How Can You Make the Most of Your Stay?
- Explore the Historic District: Make sure to stroll through the cobblestone streets to fully experience the charm and history that make this destination unique.
- Book Early for Prime Locations: Secure your vacation rentals in the most desirable areas here well in advance to enjoy easy access to local attractions and vibrant nightlife.
- Sample Local Cuisine: Take advantage of your stay by trying authentic Puerto Rican dishes at nearby eateries, which add flavor to your trip.
- Plan Indoor and Outdoor Activities: Balance sightseeing with relaxing moments on scenic patios or beaches in the area to make the most of your time here.
Transportation Options
- Walking: Exploring the historic district on foot is ideal here, allowing you to immerse yourself in the charming streets and discover local shops and cafes at your own pace.
- Public Transit (bus): The regional bus service offers an affordable and convenient way to navigate the area, connecting major attractions and neighborhoods within easy reach.
- Taxis and Rideshare Services: Taxis and ride-hailing apps provide flexible and quick transportation options to comfortably reach destinations around this vibrant region.
- Car Rentals: Renting a car gives you the freedom to explore beyond the immediate area and visit nearby sites at your leisure, all while enjoying the comfort of your vacation rental.
Local Customs Options
- La Bomba Dance: You might experience lively traditional Puerto Rican dance performances, which are an integral part of the area's vibrant cultural expressions.
- Puerto Rican Cuisine Etiquette: When enjoying local cuisine, itโs customary to share dishes and embrace the warm hospitality that defines this destination's culinary culture.
- Religious Festivities: Participating in or observing colorful religious festivals reveals deep-rooted traditions that are celebrated with reverence and community spirit here.
- Casa Blanca Customs: Visiting historic homes offers insight into the regionโs colonial history and the customs of gracious hosting that continue today.
Frequently Asked Questions About Old San Juan?
What are the top vacation rentals in Old San Juan?
There are a lot of options in Old San Juan. If you plan on staying in the Old San Juan area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Old San Juan:
- One Bedroom Spacious Apartment
- Bayfront Oasis in Old San Juan's safest neighborhood!
- Casa Sol Bed and Breakfast
- Spectacular 4000 ft2 Renovated Luxury Beach Villa Azure Stunning Interior Design
- Live Your Best Life In An Actual Palace
- Live Your Best Life In An Actual Palace
- Vintage 2BR/2Ba Apt. w/Fiber Optic on Main Plaza, Min. 1-Month!
- Castillo View | Spacious Penthouse with terrace!
- Villa Preciosa | Charming 3 BR in Best Location
- Villa Solana | Modern & Eclectic 2 Bedroom
How many vacation rentals have private pools in Old San Juan?
There are 7 vacation rentals with private pools near Old San Juan. Top-rated RBO homes that have access to a swimming pool include:
Which vacation homes in Old San Juan are best for families?
If you are looking for a family-friendly vacation home in Old San Juan, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Old San Juan:
How many Rentbyowner vacation rentals are available in Old San Juan?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 551 in the Old San Juan 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 Old San Juan.โฏ
Old San Juan Top Rated Vacation Rentals
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