Family-friendly holiday rentals in Viejo San Juan

A light-filled living area features a comfortable beige sofa adorned with colorful accent pillows. A vibrant abstract painting hangs above, complemented by a sleek glass coffee table. Contemporary decor is found nearby, enhancing the modern aesthetic of the space.

4.99 out of 5 average rating, 278 reviews

Dreamy Old San Juan Apartment

In the heart of Historic Spanish Colonial City of Old San Juan. This dreamy apartment is located at walking distance from restaurants, shopping, parks, cruise port, museums, historical sites and night live. It's a perfect mixture of antique ambient with modern comfort and amenities. The apartament has 1 bedroom, 1 spacious bathroom, totally equiped kitchen, a dining room with setting for 4 people, a living room with a very comfortable queen sofa bed and air conditioning all over the apartament.

Indoor spacesFamilyWifi

A private rooftop garden features a spacious seating area with a blue sofa next to a wooden coffee table. The area is adorned with decorative plants and a dining table surrounded by white chairs. Shade is provided by a black canopy overhead.

4.88 out of 5 average rating, 154 reviews

Penthouse w/ Private Rooftop | Old SJ | Central AC

Enjoy a stylish experience at this centrally-located PRIVATE penthouse apartment with PRIVATE rooftop (no one else has access to unit or rooftop). It is located in the heart of Old San Juan on Sol (Sun) Street, right by most of the nightlife (bars and restaurants). The apartment is close to El Morro, the fort the Spanish Crown used to defend San Juan back in the day. The unit is for six guests, and having more guests is prohibited. Additional guests who stay against the rules pay $50 per night.

KitchenIndoor spacesCondition

A spacious living room is showcased with a comfortable sofa adorned with orange cushions. An indoor balcony is visible through open doors, allowing natural light to illuminate the area. A large mirror reflects the stylish decor, enhancing the cozy ambiance.

4.92 out of 5 average rating, 279 reviews

Historic Colonial Flat, 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.

Indoor spacesKitchenSleep quality

4.81 out of 5 average rating, 216 reviews

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.

KitchenFamilySolo travel

4.96 out of 5 average rating, 216 reviews

Historic 2BR • Walk Everywhere • Quiet King Bed

Historic 2BR Spanish Colonial home in the heart of Old San Juan—walk everywhere, enjoy authentic architecture, and take in the city from balconies overlooking the street. ♦️ Just steps to restaurants, cafés, nightlife & historic sites • Walk Score 98 ♦️ Quiet King bedroom + Queen bedroom with balcony views ♦️ Soaring 18-ft ceilings, arches & authentic character ♦️ A/C & ceiling fans in every room, fast Wi-Fi, Smart TV ♦️ Great for families, couples & small groups who want to walk everywhere

Indoor spacesFamilyBathroom

4.91 out of 5 average rating, 471 reviews

An open kitchen area is framed by arches, leading to a charming interior courtyard. Green plants and a small dining set are visible, providing a serene atmosphere. The kitchen features light cabinetry and stainless-steel appliances, contributing to a bright and inviting space.

Home in San Juan

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.

Indoor spacesKitchenLocation

4.81 out of 5 average rating, 712 reviews

1 Normal water service Best Location OSJ (1 of 11)

Trotamundos... is located in the history rich Old San Juan. San Jose Street is in the nightlife epicenter of the city. It has restaurants, bars and cultural sites, just steps away. We include air conditioning, hot water, en suite bathroom, shampoo, soap, towels and beach chairs and towels. There is private small living room area. The sofa bed is for a third and/or fourth guest. In the event that two guests want to sleep apart there is a 5$ extra linen fee.This room does not have windows.

Indoor spacesKitchenOutdoor spaces

4.95 out of 5 average rating, 194 reviews

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, couples, business travelers, or families seeking a getaway. Easy, well‑lit access with no stairs — arrival will be smooth at any hour. Enjoy a spacious living room, fully equipped kitchen, brand‑new bathroom, and a tranquil interior patio/lanai for unwinding after exploring the old city. Book today!

KitchenIndoor spacesWalkability

A light-filled living area showcases a gray sectional sofa and a blue accent chair. A wooden coffee table with decorative items is centered in the space. A lush plant adds a touch of greenery, while artwork enhances the wall. The staircase leads to an upper level.

4.94 out of 5 average rating, 134 reviews

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.

KitchenIndoor spacesTV

The living area features a comfortable sofa with red accent pillows, complemented by a wall-mounted TV. Natural light filters through two wooden shuttered windows, adding to the relaxed ambiance. A large green plant is positioned near the entrance, enhancing the welcoming decor.

4.92 out of 5 average rating, 212 reviews

★Rojo★In the Middle of Old San Juan Luxury Condo

Rojo is our apartment located in the heart of Old San Juan. Staying at our stylish and properly decorated all in Red 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. Very quiet and peaceful apartment. Being in the center makes this place one of the best properties in Old San Juan you can stay in.

FamilyKitchenView

4.99 out of 5 average rating, 100 reviews

A serene outdoor space presents a heated pool surrounded by lush greenery. Comfortable seating is located under an umbrella on a wooden deck, while a large planter with tropical plants adds a natural touch. The setting is enhanced by vibrant pink flowers climbing the walls.

Home in San Juan

Old San Juan Gem | Backup Power/Water, Pool + Pkg

Enjoy added peace of mind with solar power, battery backup, a private water cistern, and fiber internet, amenities rarely found in Old San Juan. Stay in a 200-year-old historic home in the heart of Old San Juan, complete with a heated private pool and dedicated parking just steps away. This spacious two-story retreat blends historic architecture, curated Puerto Rican art, and modern comfort, all within walking distance of the city’s best restaurants, shops, and landmarks.

FamilyKitchenCheck-in

A comfortable living area is furnished with a futon and an armchair adorned with bright cushions. Art on the wall adds a touch of color, and natural light filters through wooden shutters, creating a cozy atmosphere in the space.

4.88 out of 5 average rating, 361 reviews

Historic 1BR with Old San Juan at your Doorstep

Our apartment offers easy access to everything Old San Juan has to offer! It's situated a block from the Old San Juan Cathedral and El Convento Hotel, and only a couple of blocks away from the Plaza de Armas, the City Hall, the Fortaleza –Governor’s Mansion- and the famous Calle San Sebastián. It is walking distance to historic sites like the El Morro and the traditional Parque de las Palomas. A short walk will also take you to Paseo La Princesa and the Old San Juan Port.

FamilyIndoor spacesQuiet

Popular amenities for Viejo San Juan family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A view from the unit showcases the serene waters of Condado Bay, framed by large glass windows. The bright blue sky, dotted with fluffy clouds, enhances the calming atmosphere. The distant skyline of San Juan can be seen across the bay, adding a picturesque backdrop.

4.85 out of 5 average rating, 164 reviews

Pelican Suite | Ocean View | Pool | King Bed

FamilyIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 138 reviews

Stunning Getaway Penthouse @the❤of OSJ

KitchenIndoor spacesQuiet

5.0 out of 5 average rating, 139 reviews

A spacious bed is centered against a softly lit, curved wall. Woven pendant lights cast a warm glow above the bed, accompanied by decorative pillows. A cozy bench sits at the foot of the bed, while natural textures are visible in the surrounding furnishings.

Loft in Santurce

*NEW* Relax Outdoor Bathtub, Walk To Beach

KitchenIndoor spacesCheck-in

5.0 out of 5 average rating, 174 reviews

A spacious pool area features a heated saltwater pool accompanied by a jacuzzi. Comfortable lounge chairs are positioned around the pool, with lush palm trees providing shade. A modern covered terrace offers seating options for relaxation next to the scenic outdoor landscape.

Villa in Carolina

Luxury waterfront villa with dock and heated pool

KitchenFamilyAir conditioning

A balcony features a glass table set with two wine glasses and a bottle of red wine. A small vase with white flowers rests on the table. Lush palm trees and ocean waves are visible in the background under a clear blue sky.

4.82 out of 5 average rating, 312 reviews

Ocean Views Studio | Relaxing

Indoor spacesFamilyAccuracy

4.84 out of 5 average rating, 187 reviews

Flat in Cataño

Cataño Bay Escape Near Old San Juan

KitchenIndoor spacesHospitality

4.89 out of 5 average rating, 196 reviews

PH/ Water Cistern+Jacuzzi +Private Nook | Sleeps 4

KitchenIndoor spacesGrill

A private balcony features a wooden table and two matching chairs, overlooking the tranquil lagoon waters. A small plant is placed at the center of the table, with vibrant blue skies and distant city views creating a serene backdrop.

4.8 out of 5 average rating, 109 reviews

Sunrises Near Beaches+Power+Private Balcony

FamilyKitchenCleanliness

Family- and pet-friendly home rentals

A quaint indoor balcony area is showcased, featuring a round glass table surrounded by woven chairs. A vase of tropical flowers adds a touch of color. In the background, a well-lit bedroom is visible through shuttered doors.

4.9 out of 5 average rating, 489 reviews

Colonial Old San Juan Apartment

FamilyIndoor spacesWalkability

A scenic waterfront walkway is shown, featuring a wide grassy area bordered by a low stone wall. The ocean extends to the horizon under a clear blue sky, with some clouds scattered overhead. Buildings are visible in the background, adding a colorful urban touch.

4.81 out of 5 average rating, 136 reviews

La Garita Ocean View at Old San Juan

KitchenFamilyBeach

A vibrant street view reveals charming buildings painted in yellow and other pastel colors, framed by fluffy clouds in a blue sky. The cobblestone road runs through the scene, showcasing parked cars and a glimpse of local life.

4.91 out of 5 average rating, 280 reviews

San Sebastián y Cruz Apt. 10

KitchenIndoor spacesLocation

4.86 out of 5 average rating, 413 reviews

Hidden Gem in Old San Juan

FamilyKitchenParking

Serviced apartment in San Juan

The exterior of a charming two-story building is displayed, featuring vibrant yellow walls. The entrance showcases a large wooden door with a decorative barred window beside it. Two balconies adorned with wooden railings overlook the street, and a vintage street lamp casts a warm glow on the façade.

4.87 out of 5 average rating, 149 reviews

Villa Old San Juan escape 2 adults. we have water

Indoor spacesKitchenAmenities

4.99 out of 5 average rating, 148 reviews

Townhouse in Santurce

Ocean Park Beachfront & Pool | Steps to the Sand

KitchenIndoor spacesView

4.98 out of 5 average rating, 154 reviews

A vibrant outdoor space features a blend of blue and orange walls adorned with decorative elements. Green plants and hanging decorations create a lush ambiance, while a small table with chairs provides a cozy seating area. The ground is painted in a warm red tone.

Guest suite in Santurce

Cozy apartment with patio

FamilyKitchenLocation

The living room is furnished with two accent chairs featuring colorful cushions, complemented by a glass coffee table at the center. A television is visible in the background, while bright leaf-patterned wall art adds a vibrant touch to the space. Natural light streams in through the nearby windows.

4.81 out of 5 average rating, 130 reviews

Spacious Apartment on Calle Cerra Santurce/Miramar

Indoor spacesKitchenDecor

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 236 reviews

A refreshing pool area is surrounded by natural greenery, with stone accents and a sunlit patio. The pool features clear water and a small seating area, creating an inviting outdoor space. Lush foliage frames the scene, enhancing the serene atmosphere.

Home in Carolina

Villa Estrella PR (near Airport & Beach)

Indoor spacesFamilyWifi

A tranquil private pool reflects the clear blue sky, surrounded by lush greenery and palm leaves. The modern apartment's large glass windows allow for abundant natural light, while a shaded outdoor seating area and hammock can be seen beside the pool.

4.99 out of 5 average rating, 296 reviews

Best location with pool, steps from beach!

KitchenIndoor spacesWalkability

4.97 out of 5 average rating, 270 reviews

A balcony view is presented, featuring two chairs and a small table. The vivid blue ocean stretches beyond the sandy beach lined with palm trees. The scene offers a serene atmosphere with direct access to the beach visible below.

Flat in Carolina

Beach Vacay!

FamilyKitchenAmenities

4.9 out of 5 average rating, 163 reviews

A serene outdoor seating area is seen through an open patio. A large hammock is suspended nearby, while palm trees sway gently in the breeze. In the background, the sparkling ocean is visible beyond a grassy area, creating a tranquil beachfront atmosphere.

Flat in Carolina

Beach Front, Ocean View & Direct Access to D Beach

FamilyKitchenCondition

4.91 out of 5 average rating, 446 reviews

Direct beach access... best spot in Condado

Indoor spacesFamilyAir conditioning

4.85 out of 5 average rating, 414 reviews

A spacious studio apartment is shown with a queen Murphy bed in the foreground, covered with a light comforter and arranged with two pillows. A twin Murphy bed is visible in a separate area, framed by light-filtering window shades. Decorative wall art complements the minimalist decor.

Apartment in Santurce

Beautiful apartment in Condado with beach access!

Indoor spacesKitchenDecor

4.99 out of 5 average rating, 143 reviews

A bright outdoor area features a rectangular pool surrounded by light-colored tiles. White walls enhance the spacious feel, while an adjoining open-air space reveals a modern kitchen area with a shaded seating area. Lush greenery provides a natural accent, complemented by a clear blue sky.

Home in Santurce

Casa Reyes

FamilyKitchenAmenities