
Family-friendly holiday rentals in Viejo San Juan
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Viejo San Juan

Total holiday rentals
Explore 260 holiday rentals in Viejo San Juan

Nightly prices starting at
Viejo San Juan holiday rentals start at $51 SGD per night before taxes and fees

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Over 23,280 verified reviews to help you choose

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wifi availability
260 of Viejo San Juan holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Viejo San Juan rentals

4.8 Average rating
Viejo San Juan stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated family-friendly rentals in Viejo San Juan
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Colonial Old San Juan Apartment
Location The apartment is located in Puerto Rico's political and cultural capital, San Juan. It's within walking distance of the best locations Old San Juan has to offer. Great bars and restaurants, hotels, casinos, San Critobal Castle, Paseo La Princesa , plazas and the cruise terminal are only steps away. In its sorroundings there are also farmacies, transportation services, a post office, stores for shopping,beaches and Cathedrals. The apartment is a 10 minutes drive to the Convention Center and 20 minutes to the international airport,. Spaces Typical of Spanish Colonial architecture the apartment spaces include an indoor balcony, perfect for relaxing, and tall ceilings, up to 20 feet high, sporting traditional Ausubo wood beams. Amenities Full kitchen with an industrial stove and oven, microwave, refrigerator, coffee maker and dinnerware. The cozy bedroom has a comfortable queen bed, a/c and drawers for storage. Living room with Flat HDTV, Blue Ray, DVD player, WI-Fi, Satellite dish. Laundry access in the hall.

Quiet Romantic Retreat: Walk Everywhere · Historic
Quiet, romantic retreat in the heart of Old San Juan~ walk everywhere, enjoy historic charm, & come home to peace & quiet after a day exploring. ❤️ Tucked away from street noise yet steps to cafés, shops, nightlife & iconic sights • Walk Score 98 ❤️ Warm historic charm with a peaceful atmosphere ❤️ Comfy Queen bed, A/C, fast WiFi, Smart TV, kitchen & self check-in ❤️ Downstairs yoga patio adds to the building's serene atmosphere ❤️ Ideal for couples seeking charm, walkability, and restful nights

Classic Old San Juan •1rst Floor•Best Location•
Best in Old San Juan! Classy and beautifully restored colonial‑style building. Our 2BR apartment blends historic charm with modern comfort. Perfect for cruise ship visitors, vacationers, romantic couples, business travelers, or a family getaway. Easy, well‑lit access, no stairs; arrival will be smooth at any hour. You’ll find a spacious living room, fully equipped kitchen, a brand-new bathroom, and a tranquil interior patio/linai for unwinding after adventuring the old city. Book with us today!

Cozy Historic Ruin Apartment
Located in the heart of Old San Juan, this unique and special place enables you to experience a fully authentic colonial experience- the most authentic you will get in Old San Juan. This renovated ruin apartment conserves the historical architecture from Old San Juan at a maximum potency, while offering a comfortable and cozy stay. Perfect for any small family, couple or group of friends seeking to enjoy what Old San Juan has to offer, from restaurants to forts, in a fully cultural experience.

In the Heart of Old San Juan!
Experience the charm of Old San Juan in this colorful apartment, housed in a historic 17th-century building with characteristics that come with its age! To brighten the space, simply open the doors and windows to let the natural light flood in as the shutters do not open. Located just a block from the vibrant nightlife on “Calle San Sebastian” and a short stroll from the “Castillo El Morro”. Enjoy plazas, dining, and shopping all within walking distance in the heart of this famous walled city.

Quaint Colonial Home Old San Juan
Beautiful Spanish colonial home in the north side of Old San Juan where locals live, you are just steps (one block) from the ocean. Unique opportunity to explore the city while staying in an exquisite setting and enjoying the colonial architecture of this space. Discover this UNESCO World Heritage Site through a mix of historic architecture and contemporary culture. Note: This home is registered with the PR Tourism Company and strictly adheres to all established Health and Safety protocols.

Enchanting Spanish Colonial Loft in Old San Juan
Discover the enchantment of Old San Juan in this charming Spanish colonial apartment, perfectly nestled in the historic heart of Puerto Rico’s most iconic city. Walk everywhere, from historic parks and landmarks, restaurants, coffee shops, and shopping. Just steps away from Playa del Capitolio or a longer scenic walk to the Escambron beach and recreation area. The apartment is a tranquil loft insulated from the heat and busy streets when you need a break to recharge on your trip.

Cozy Loft in Old San Juan – Prime Location!
Immerse yourself in the charm of Old San Juan in this stunning Spanish colonial loft! Featuring classic architecture, exposed beams & vibrant tile work, this space offers serenity. Nestled on the cobblestone streets, you're steps from iconic landmarks, exceptional dining & the ocean's edge. Enjoy year round tropical weather and an unbeatable location where culture, beauty and tranquility come together to create unforgettable memories. Come experience the beauty of Old San Juan!

★Dorado★ History & The City Luxury Condo
Dorado is our apartment located in the heart of Old San Juan. Staying at our stylish and properly decorated all in Golden you will enjoy the old city experience. Our apartment is very convenient when it comes to accommodation since it has a separate bedroom with a queen bed, Smart TV on living room and bedroom, dedicated workspace and a balcony that overlooks the Cathedral. Being in the center makes this place one of the best properties in Old San Juan you can stay in.

Old San Juan Ocean View With Outstanding Location
Welcome to “Casa Azulia”, Old San Juan, Puerto Rico. Newly restored luxury apartment, PRIME LOCATION, within a short walking distance to: • 3 min walk to Saint Cristobal Fort. • 10 min walk to El Morro Fort. • 2 min away from the most renowned local bars, restaurants and hangouts. • Just steps away from the apartment the most impressive ocean view walk in the whole city. • Around the corner from where the viral “Despacito” music video was filmed.

Casita del Sol☀️couples’ HOUSE-rooftop, water views
Casita del Sol offers a rare opportunity to rent an entire house in Old San Juan. Classic Spanish colonial architecture with multiple water views and huge rooftop deck. With an entirely removed secondary suite, it can be spacious enough for two couples or cozy enough for one. On a quiet and peaceful residential block, it is still just a short walk from the liveliest restaurants, bars, and shops and offers the best of life in Old San Juan.

Old San Juan Historic Loft 4 The Adventurous
Stay in the Heart of Old San Juan – Now with Reliable Backup Power and Fiber optic internet connection ! DISCOUNTS AVAILABLE FOR EXTENDED STAYS: 3-6 nights= regular price ; 7 nights =12% ; 14 nights = 18% DISCOUNTS Enjoy this 280-year-old historic building, and walk to iconic places such as El Morro, La Factoria (known worldwide) & many other restaurants, plazas, & arts + culture centers. You'll have access to public transportation.
Popular amenities for Viejo San Juan family-friendly rentals
Family-friendly home rentals with a hot tub

*NEW* Relax Outdoor Bathtub, Walk To Beach

Stunning Penthouse @the❤of OSJ

Sunset & Ocean View | Pool | 2 Qn Beds | Centric

Ocean Views Studio 1| 4 Guests | Relaxing

Luxury waterfront villa with dock and heated pool

Sunrises Near Beaches+Power+Private Balcony

King Bed Loft | by Old SJ & Escambrón Beach | Pool

Studio A Few Steps from San Juan Bay
Family- and pet-friendly home rentals

La Garita Ocean View at Old San Juan

Hidden Gem in Old San Juan

Historic 1BR with Old San Juan at your Doorstep

San Sebastian and Cruz Apt. 10

Retro 1BR w/ Disco Ball | MOOD HAUS by DW

Sunrise Loft: King Bed, Washer-Dryer & Ocean Views

Rare Beachfront Getaway w Pool, Gym, + Balcony!

#1 Isla Verde Private Apt-breakfast/beach/airport
Family-friendly home rentals with a pool

Best location with pool, steps from beach!

Condado Beach Views by Cesar 2501

Villa Estrella PR (near Airport & Beach)

Jungle Bungalow | 1BR Suite | Private Plunge Pool

Hilltop Cabin w/ Pool & Views – 18 Mins to Airport

Beach Walk / Pool / Backup Power & Water

Mid-Century Modern house

Sleek & Chic Studio in amazing location in Condado
When is the best time to visit Viejo San Juan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $479 SGD | $382 SGD | $406 SGD | $353 SGD | $303 SGD | $288 SGD | $314 SGD | $336 SGD | $295 SGD | $279 SGD | $321 SGD | $368 SGD |
| Avg. temp | 25°C | 25°C | 26°C | 27°C | 28°C | 28°C | 28°C | 29°C | 29°C | 28°C | 27°C | 26°C |
Destinations to explore
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- Family-friendly rentals Puerto Rico
- El Yunque National Forest
- Liquillo Beach
- Playa las Picuas, Rio Grande
- Distrito T-Mobile
- Puerto Rico Convention Center
- Rio Mar Village
- Playa Puerto Nuevo
- José Miguel Agrelot Coliseum
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- Museo de Arte de Ponce
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