Family-friendly holiday rentals in Viejo San Juan

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, 483 reviews

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.

The bedroom features a spacious bed with soft linens, complemented by a cozy armchair and a decorative area rug. Large arched windows frame the view, allowing natural light to illuminate the space while highlighting the rich wood ceiling and furnishings.

4.96 out of 5 average rating, 207 reviews

Quiet 2BR Loft · Walk Everywhere · King+Queen Beds

Quiet 2BR Loft · Walk Everywhere ❤️ Peaceful retreat in the heart of Old San Juan ❤️ Tucked away from street noise yet steps to cafés, shops, nightlife & iconic sights · Walk Score 98 ❤️ Spacious open loft layout · King & Queen beds, 1½ bathrooms & full kitchen ❤️ Ideal for families, close friends & guests comfortable sharing space ❤️ Historic 200-year-old home with soaring ceilings & Colonial charm ❤️ A/C, fast WiFi, Smart TV, washer/dryer ❤️ Guests love the quiet, comfort & unbeatable location

An open living and kitchen area features terracotta tiled flooring and wooden ceiling beams. A comfortable seating arrangement includes a sofa and a chair. A dining table is positioned near the window, which opens to the balcony, allowing natural light to illuminate the space.

4.92 out of 5 average rating, 263 reviews

1 Bdrm Colonial Style Apt w/balcony

Second-floor colonial-style apt near local bars & restaurants. A private balcony overlooks Calle de la Cruz. Features a fully equipped kitchen, internet, ac, free laundry room on ground level. Note: due to the central location, there is street noise from nearby bars throughout the day and into the night However, the bedroom is located at the back of the apartment, providing a quieter space. Check-in: from 10:00 AM to midnight. Overnight check-in is also possible if the prior night is reserved.

4.81 out of 5 average rating, 209 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.

4.92 out of 5 average rating, 275 reviews

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.

An inviting living area features a spacious white sofa, accent tables, and decorative mirrors on the golden wall. An open kitchen is visible in the background, showcasing modern appliances and a dining table with upholstered chairs, enhancing the stylish design and ambiance.

4.92 out of 5 average rating, 154 reviews

Luxury Romantic Getaway w/Patio & Backup Power

Nestled in the 500-year-old historic Spanish colonial city of Old San Juan, Casa Arcos Blancos offers a unique opportunity to live like a local while enjoying all the luxuries that make you feel right at home. Its superb central location allows you to explore the entire colonial city without having to grab a ride for anything. Conveniently located on Sol Street, you will be at walking distance from supermarkets, pharmacies, shops, restaurants, & world-renowned bars & night spots. Other details

4.91 out of 5 average rating, 459 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.

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, 125 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.

4.95 out of 5 average rating, 230 reviews

A vibrant yellow façade with classic Spanish colonial architecture is highlighted in the morning light. The entrance features an elegant archway, leading into a spacious interior. The street gently slopes down towards the water, surrounded by lush greenery and cobblestones.

Home in San Juan

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.

Superhost

4.86 out of 5 average rating, 408 reviews

Hidden Gem in Old San Juan

This is a cozy one bedroom, one bathroom apartment with a queen size bed, toiletries included and fresh clean bath towels and beach towels. It has a fully equipped kitchen with everything you need from pots & pans to oils & spices. A living / dining room area with a sofa and dining table that sits 4. A small cozy terrace with a bistro table & chairs under a nice trellis garden.

5 out of 5 average rating, 130 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

Located in the heart of Puerto Rico's lively Calle Loíza, 8-10 minutes from the airport and 8 minutes walk to the beautiful "Ocean Park beach", "Palomar" at Casa Loiz offers an authentic Puerto Rican experience with access to beaches, restaurants, and bars within walking distance. Important cultural sites, such as Old San Juan, are only a 5-10 minute drive away.

An open courtyard is featured, framed by arched doorways. Decorative potted plants and elegant ceramic vases are positioned throughout the area. A staircase leads to the upper levels. Natural light filters in, enhancing the tiled floor's neutral tones.

4.81 out of 5 average rating, 397 reviews

The Cathedral 🇵🇷 (Old San Juan)😍

This apartment is located in beautiful old San Juan, calle San José. It's a one bedroom apartment ( one queen bed and a futon in the living area) A.C in all the apartment. Walking distance to el Morro, art places, historical monuments, bars and excellent restaurants. Close to the airport, public transportation and taxis. You won't find a better location!!

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

The exterior of a colorful building showcases a blend of orange and blue facades with wooden details. A covered balcony with decorative railings extends across the front, complemented by window grilles and a wooden door. Cobblestone streets enhance the historic atmosphere.

4.85 out of 5 average rating, 308 reviews

Luxury House in Old San Juan

Superhost

Flat in Cataño

4.84 out of 5 average rating, 181 reviews

Studio A Few Steps from San Juan Bay

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.

4.81 out of 5 average rating, 305 reviews

Ocean Views Studio 1| 4 Guests | Relaxing

Serviced apartment in Carolina

An outdoor space is presented with a structured wooden pergola and a circular hot tub at its center. The surrounding gravel floor is complemented by potted plants. A vibrant mural featuring the Puerto Rican flag decorates the wooden fence, creating a lively backdrop.

4.93 out of 5 average rating, 181 reviews

5 minutes from airport outdoor bathtub, sleep 3

4.88 out of 5 average rating, 189 reviews

Penthouse Jacuzzi Retreat |Private Nook | Sleeps 4

5 out of 5 average rating, 165 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

An outdoor hot tub is surrounded by a natural bamboo fence, providing privacy and a serene atmosphere. A wooden stool and a small red step stool are positioned nearby, while lush greenery enhances the relaxing environment.

4.95 out of 5 average rating, 108 reviews

Hidden Paradise w/HotTub >NEAR Airport & Beaches<

4.84 out of 5 average rating, 350 reviews

Hopesdate here San Juan

Family- and pet-friendly home rentals

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, 357 reviews

Historic 1BR with Old San Juan at your Doorstep

Serviced apartment in Santurce

An inviting outdoor nook features a circular entryway leading to a cozy sleeping area. The space is adorned with soft bedding and minimalist decor, creating a tranquil atmosphere. Surrounding greenery enhances the connection to nature, offering a serene retreat.

4.9 out of 5 average rating, 113 reviews

Loft w/ Outdoor Bath, Walk To Beach | ROSA by DW

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, 276 reviews

San Sebastian and Cruz Apt. 10

4.92 out of 5 average rating, 476 reviews

A spacious living area is highlighted by a large sectional sofa and a cozy armchair. A sleek dining table and four chairs sit adjacent to a flat-screen television mounted within a wooden cabinet. Natural light filters through large windows, enhancing the open design.

Apartment in Santurce

Luxurious beach apt/ w to beach/ and FP generator

5 out of 5 average rating, 28 reviews

Historic Old San Juan Gem w/ Balcony & King Suite

An inviting living space is captured within an arched entrance. A yellow sofa complements the light-filled area, accompanied by a round coffee table and stylish chairs. Large windows allow natural light to illuminate the room, while decorative elements enhance the modern aesthetic.

4.96 out of 5 average rating, 105 reviews

Don Charlie Building Apartment 3

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, 135 reviews

La Garita Ocean View at Old San Juan

A spacious bedroom features a large bed with a soft, textured grey blanket. An abstract artwork hangs above the headboard, complementing the light-colored walls. A full-length mirror is positioned to the left, enhancing the room's openness.

4.87 out of 5 average rating, 291 reviews

One bedroom Apartment - Miramar/Convention Center

Family-friendly home rentals with a pool

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, 288 reviews

Best location with pool, steps from beach!

4.88 out of 5 average rating, 117 reviews

A swimming pool is illuminated with soft blue lights, surrounded by vibrant mural artwork featuring tropical plants and flowers. The pool area is partially enclosed, offering a sense of privacy, while a gentle water feature is visible, adding to the serene atmosphere.

Home in Carolina

Villa Tropical Piscina privada Wifi y Neflix

A light-filled sleeping area features a spacious bed with crisp linens and a decorative pillow. Large windows provide views of the surrounding area, while sheer curtains allow natural light to filter in. A bedside lamp and a small table add functional decor to the space.

4.97 out of 5 average rating, 236 reviews

King Suite Steps from the Beach w/ Parking

4.98 out of 5 average rating, 220 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)

4.85 out of 5 average rating, 406 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!

4.98 out of 5 average rating, 106 reviews

Villa in Santurce

Beach Walk / Pool / Backup Power & Water

4.97 out of 5 average rating, 121 reviews

A serene outdoor space features a private pool surrounded by palm trees and vibrant seating. The clear water reflects the blue sky, while a lush green lawn extends toward a calm body of water in the background, enhancing the tranquil setting.

Home in Toa Baja

Lake Villa House in Toa Baja, Puerto Rico

A serene resort-style pool is surrounded by landscaped gardens and palm trees, reflecting the calm waters of the lagoon. Lounge chairs are positioned along the deck, inviting relaxation beneath the clear sky, while the distant city skyline adds a modern touch to the tranquil setting.