Trips to Old San Juan

Plan Your Next Trip to Old San Juan and explore unforgettable sights, local flavors, and exciting experiences.

Casa TripGoGo From US $64
         

8.1 (143 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Casa Sol Bed and Breakfast From US $248
         

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10.0 (56 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Accessibility
  • Business Services
Azure Suite | Beautiful 1 Bedroom in best location in Old San Juan From US $212
         

Live Your Best Life In An Actual Palace From US $771
         

10.0 (34 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Villa Preciosa | Charming 3 BR in Best Location From US $590
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Villa Solana | Modern & Eclectic 2 Bedroom From US $583
         

10.0 (9 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Luxury Places to Stay in Old San Juan

Over 508+ Luxury Places to Stay in or Near Old San Juan
Diamond Vault Penthouse From US $2,570
         

9.0 (4 Reviews)
Apartment
  • Air Conditioner
  • TV
  • View
Tizol Historic Building 8br in Old San Juan From US $1,427
         

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8.0 (2 Reviews)
House
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  • View
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Stunning and Spacious Apartment ! From US $1,400
         

New
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  • Pet Friendly
Tizol Historic Building: 8BR in Old San Juan From US $1,268
         

10.0 (4 Reviews)
Ski Chalet
  • Air Conditioner
  • TV
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Top-Rated Vacation Rentals with a Pool in Old San Juan

Over 45+ Top-Rated Vacation Rentals with a Pool in or Near Old San Juan
Best location Old San Juan private room 9 of 11 From US $167
         

10.0 (5 Reviews)
House
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  • Pool
  • Security/Safety
Best location Old San Juan private room 5 of 11 From US $176
         

10.0 (4 Reviews)
House
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  • Pool
  • Security/Safety
Best location Old San Juan private room 6 of 11 From US $176
         

10.0 (1 Review)
House
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  • Pool
  • Security/Safety
Best location Old San Juan private room 10 of 11 From US $169
         

9.6 (13 Reviews)
House
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  • Pool
  • Security/Safety
Casa Lucienne - Adults Only From US $271
         

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9.4 (44 Reviews)
Hotel
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  • Pool
  • Balcony/Terrace
Best location Old San Juan private room 11 of 11 From US $167
         

9.4 (30 Reviews)
House
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  • Pool
  • Security/Safety
Luxury House in Old San Juan From US $643
         

9.4 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Best location Old San Juan private room 1 of 11 From US $181
         

9.4 (3 Reviews)
House
  • Air Conditioner
  • Pool
  • Balcony/Terrace

Pet-Friendly Vacation Rentals in Old San Juan

Over 97+ Pet-Friendly Vacation Rentals in or Near Old San Juan
Casa Saffra in Old San Juan 1 From US $837
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Child Friendly
153 Luna by Stay with Bear From US $208
         

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8.4 (19 Reviews)
Apartment
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  • Pet Friendly
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Fountain Mansion, Old San Juan Rooftop & Parking From US $528
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
La Sanse & Cruz #10 From US $186
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
OLD SJ 1ST fl apt ON EXCLUSIVE ST W GREAT BAY VIEW ! From US $253
         

9.6 (47 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Bi-Level w/Rooftop Terrace AC Wifi Kitchen 51 Calle Cristo From US $216
         

9.4 (20 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Old San Juan

Over 59+ Large Vacation Homes & Villas in or Near Old San Juan
Modern 2 Apts. 3-BR - 10 Guests in Old San Juan From US $537
         

10.0 (1 Review)
Apartment
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  • TV
  • Security/Safety
Modern 2 Apartments 3-Bedroom - 10 Guests in historic Old San Juan From US $481
         

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10.0 (1 Review)
Apartment
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  • Parking
  • Balcony/Terrace
Diamond Vault Penthouse From US $2,519
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • TV
  • View
Spacious and Beautiful Colonial Apartment From US $954
         

9.2 (29 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Spacious 9BR & 7BA Divided in 6 Units in La Puntilla. From US $932
         

New
Apartment
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  • Pet Friendly
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Grand Palazzo del Mar From US $700
         

New
Apartment
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  • Balcony/Terrace
Casa Saffra Old San Juan Apt #5 From US $672
         

New
Apartment
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  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Old San Juan

Over 61+ Wheelchair Accessible Vacation Homes in or Near Old San Juan
San Juan Suite | Perfect Getaway in Centric Location From US $218
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Casa Sol Bed and Breakfast From US $242
         

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9.6 (75 Reviews)
Bed & Breakfast
  • Air Conditioner
  • View
  • Wheelchair Accessible
Casa Of Essence From US $209
         

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9.0 (407 Reviews)
House
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Villa Esmeralda | Large 2 Bedroom in beautiful Old San Juan From US $341
         

9.4 (48 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Mint Suite | Beautiful 1 Bedroom in best location in Old San Juan From US $243
         

9.2 (24 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Balcony Suite | Stunning 1 Bedroom in Old San Juan From US $241
         

9.0 (26 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Old San Juan Varoom and Airbnb Places to Stay Under $200

Over 129+ Old San Juan Varoom and Airbnb Places to Stay Under $200
Tiny Cave Studio in Old San Juan/high speed WIFI/Luxury Bathroom/55” TV From US $146
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Bay apartment From US $81
         

9.7 (17 Reviews)
Apartment
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  • Parking
  • Pet Friendly
Fortaleza Suites From US $178
         

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9.0 (1221 Reviews)
House
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  • Bedding/Linens
Best Location Old San Juan private room 2 of 11 From US $179
         

9.2 (5 Reviews)
House
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  • Pool
  • Balcony/Terrace
Best location Old San Juan private room 3 of 11 From US $170
         

8.6 (9 Reviews)
House
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  • Security/Safety
  • Bedding/Linens
Best location Old San Juan private room 8 of 11 From US $170
         

6.8 (3 Reviews)
House
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  • Pool
  • Security/Safety
The LOFT in Old San Juan From US $191
         

New
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Instantly Bookable Vacation Homes in Old San Juan

Over 252+ Instantly Bookable Vacation Homes in or Near Old San Juan
Dreamscape Studio | In the Heart of It All! From US $204
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
OLD MOON OLD SAN JUAN From US $386
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Historic 2-bedroom-2 bath apartment with AC, laundry, WiFi in Old San Juan From US $360
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
San Juan Family Penthouse- 2BR & City Views From US $553
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Spacious Apartment in the Heart of San Juan From US $403
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Modern 2-BR Apt. in historic Old San Juan From US $314
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace

About Old San Juan Vacation Rentals

With more than 517 Old San Juan vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Smartours and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Old San Juan.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Smartours Old San Juan, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Old San Juan. Places to stay near Old San Juan are 636.73 ft² on average, with prices averaging $376 a night.

Smartours makes it easy and safe to find and compare vacation rentals in Old San Juan with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Old San Juan

Type Count
Holiday Apartments 363
Vacation Homes 81
Hotels with Suites 38
Villas 8
B&B 4
Ski Chalet Rentals 3
Others 2
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Old San Juan

Pro Tip: Smartours makes it easy to compare the best listings on Smartours homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Smartours homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Old San Juan.

Weather in Old San Juan

View the weather forecast for Old San Juan before booking your Old San Juan Vacation Rentals to confirm your best time to go.

December - February
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March - May
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June - August
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September - November
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