Family-friendly holiday rentals in San Juan

4.84 out of 5 average rating, 193 reviews

Flat in Santurce

Water & Generator Luxury Condado Beach Apt For 8

Welcome to Casa Luna, a luxury 3BR + office, 2BA beach condo in the best location in Condado, San Juan, just 5 minutes from Old San Juan and Isla Verde. This stunning 1st floor, no stairs retreat is just one block from the beach, top restaurants, bars, boutiques, casino and kayaking. Perfect for families and groups, it comfortably sleeps up to 8 guests. Enjoy a full kitchen, TV lounge/office w/ sofa bed, high speed WiFi, free onsite parking, washer and dryer, generator and water cistern! ✨🌴🏖️

4.96 out of 5 average rating, 218 reviews

Flat in San Juan

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

An aerial view showcases a modern hacienda set on a spacious lawn surrounded by lush greenery and mountains. The property features a turquoise pool and a shaded outdoor seating area, all under a clear blue sky adorned with scattered clouds.

5.0 out of 5 average rating, 101 reviews

Hacienda w/Pool | 18 min Airport | Ocean+Mntn View

✈️ 18 minutes from the airport & 🏖️ 20 minutes from top beaches 🏡 1-acre retreat with ocean & El Yunque mountain views 🏊 35’ x 15’ pool + gazebo, BBQ & hammock 🎮 Game room with Pacman arcade, foosball & more 🛏 5 bedrooms, 7 beds, 4 bathrooms, 2 kitchens – sleeps up to 14 🍽 Fully equipped kitchen + multiple lounging areas ⚡ Fast WiFi, A/C throughout, gated parking & washer/dryer 🪑 Beach chairs, towels & cooler for your outings 📍 Minutes from restaurants, shops & top attractions

4.94 out of 5 average rating, 134 reviews

A private pool is set against a backdrop of lush greenery and a vibrant tree with red flowers. Several lounge chairs are positioned nearby, inviting relaxation. The tranquil water reflects the soft colors of the sunset, completing the serene outdoor space.

Flat in San Juan

One of a Kind Villa w/ Private Pool & Views in SJ

Escape to your own private mountain retreat where cool tropical breezes, lush surroundings, and breathtaking panoramic views create the perfect setting for an unforgettable stay. The property is perfectly tucked away in the hills while amazingly close to everything you need. It is a gem for those who wish to experience Puerto Rico on a deeper level, away from the tourist trap. Not only is it beautifully furnished, the apartment has the perfect private pool only 10mins away from SJU.

4.99 out of 5 average rating, 150 reviews

Townhouse in Santurce

Ocean Park Beachfront & Pool | Steps to the Sand

This Beach Front Townhouse is located in Ocean Park. One of Puerto Rico’s sought out locations! It is perfect for group trips as well as families looking for the perfect getaway! The Town House is in a gated community which means you will be guaranteed a safe trip. Private parking will be provided. The unit is a 10 minute drive from the airport as well as Old San Juan. You will have a private rooftop facing the ocean and a shared pool on the ground floor to use at your convenience.

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.

4.99 out of 5 average rating, 102 reviews

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.

Casa particular in Santurce

Blue lagoon

Have fun with the whole family at this stylish place to stay. Spacious and luxurious place. It has a pool, BBQ and an emergency electric generator, a dock for fishing, and views of Isla Verde. It also has a ramp to pull boats , TV in all the rooms , internet and bluetooth horns. There is a yacht at the dock that can accommodate 2 more guests for an extra cost. To add this service, contact the host. For reservations of three or more nights, you get 1 hour of free jet ski.

4.93 out of 5 average rating, 113 reviews

5.0 out of 5 average rating, 175 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

Enjoy uninterrupted water and power at Villa Jade, with a whole-house generator and 600-gallon water cistern for peace of mind. Villa Jade is a unique luxury waterfront retreat with a heated saltwater pool, jacuzzi, and private dock on a serene lagoon. Just 10 minutes from SJU Airport and the fabulous beaches of Isla Verde. Three spacious bedrooms with private baths. Fully remodeled. As a dedicated 5-star host, I’m here to ensure a smooth, relaxing stay. Welcome!

A dining area is presented with a large wooden table surrounded by six chairs. Natural light fills the space through large windows, which are dressed with sheer curtains. Green plants add a touch of vibrancy, and a pendant light hangs overhead, softly illuminating the setting.

4.98 out of 5 average rating, 152 reviews

Rustic Modern Home |Walk 2 Beach| Close 2 Airport

Guests keep telling me the photos don't do it justice. A 4BR/2BA that actually breathes — room to spread out, plus common space where everyone lands at night. Big beds, AC throughout, 5 minutes from the airport, short walk to the beach. Calm, safe neighborhood, Old San Juan 10 minutes away. Whole-house generator and an 1,100-gallon water tank , so when the island's power goes, yours stays on. Message me and I'll send my restaurant list before you land.

A bright living area is equipped with a blue sectional sofa adorned with decorative pillows. A round coffee table sits on a soft area rug, while a wall-mounted television adds to the entertainment options. Natural light filters through sheer curtains on multiple windows.

4.91 out of 5 average rating, 278 reviews

Samoa's Boho (6 minutes from airport)+ Car Rentals

Bring the whole family to this great place with lots of room for fun. Samoa's Boho is a spacious, cosey home where you could enjoy all the amenities and more. Its also equipped with solar system and a 500 gallons water tank.Samoa's Boho is very centric, 10 minutes from the airport , 5 minutes from one of the most exclusive malls of Puertorico (The Mall of SanJuan) ,12 minutes from the beaches, 20 minutes from Old SanJuan, and 30 from El Yunque.

4.94 out of 5 average rating, 188 reviews

A bright living space features a cozy sleeping area with a spacious bed. A wooden dining table surrounded by folding chairs is visible, along with a modern television mounted on the wall. A mirror reflects the adjoining kitchen area, highlighted by sleek cabinetry.

Apartment in Carolina

Buena Vida Beach Studio, Puerto Rico

Enjoy a stylish experience at this centrally-located place just a 7-minute drive from SJU Airport. Direct access to the beach, passive park, gym, swimming pool, grill area, basketball court, tennis court, and a laundromat on the first level. It will be a pleasure to have your coffee or wine in the hanging chair of the cozy rustic-modern style balcony where you can appreciate the views of the beach and the city. Follow @buenavidabeachstudio

4.95 out of 5 average rating, 296 reviews

Flat in San Juan

Ocean View Loft Penthouse in Old San Juan

Sol 13 | Rooftop Loft Above Old San Juan Above the rooftops of Old San Juan, the city slows down. Ocean-view loft penthouse with a private rooftop terrace, soaring ceilings, a floor-to-ceiling library, and an exceptionally comfortable king bed. Sunrises, sea breezes, and space rarely found in the historic district. Third-floor walk-up (the final flight is steep), but a short climb to another world.

Popular amenities for San Juan family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 197 reviews

The two-story property is surrounded by lush greenery, featuring a serene pond reflecting the building and sky. Lounge chairs are positioned on the grass, offering a relaxing spot to enjoy the natural surroundings.

Home in Rio Grande

Hacienda Azucena, Río Grande, Yunque Rainforest

4.92 out of 5 average rating, 127 reviews

A serene view of the resort grounds is presented, featuring a winding waterway bordered by palm trees and manicured greenery. Colorful buildings are visible in the background, with pathways connecting the areas. The clear water reflects the blue sky, enhancing the tranquil ambiance.

Apartment in Vieques

Aquatika Beach & Waterpark: Garden Condo Loiza, PR

4.96 out of 5 average rating, 158 reviews

An infinity pool with illuminated edges provides a serene atmosphere during twilight. A swim-up bar is positioned at one side, while lounge chairs are visible nearby. A basketball hoop is set up next to the pool, and surrounding tropical foliage completes the tranquil outdoor space.

Home in Luquillo

Fabulous Ocean Views /Private Infinity Pool /4 BR

4.96 out of 5 average rating, 195 reviews

A two-story home sits gracefully on a gently sloping landscape, surrounded by lush greenery. The exterior features large windows that invite natural light, with vibrant flowering plants cascading along the walls. A spacious driveway leads up to the front of the house.

Home in Bayamón

Casalta: A Unique Villa Experience in Puerto Rico

4.89 out of 5 average rating, 241 reviews

A charming cottage is surrounded by lush greenery and tropical plants, with a stone path leading to its entrance. The blue sky above contrasts with the vibrant foliage, creating a serene outdoor environment, enhanced by the natural landscaping featuring various palm trees and flowering plants.

Cottage in Río Grande

Casita del Yunque, Private Heated Jacuzzi Pool!

4.8 out of 5 average rating, 114 reviews

Home in Luquillo

Luquillo Beach Beauty

4.97 out of 5 average rating, 506 reviews

Cabin in San Juan

Hidden Paradise Cabin | Romantic Forest Retreat

4.97 out of 5 average rating, 106 reviews

A spacious living area features large glass doors that provide views of the surrounding greenery. A comfortable gray sofa is positioned near a circular mirror, with a decorative pouf and a small plant nearby. Natural light brightens the open space.

Home in Toa Alta

Hacienda Lucero: Your Tropical Lakefront Escape

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 113 reviews

Tropical Pool * 5 Min Beach & Airport/Backup Water

Superhost

A private swimming pool is framed by sleek gray tiles, with clear blue water reflecting the sky above. Nearby, a shaded patio area includes a seating arrangement, providing a space for relaxation. Lush greenery can be seen in the background, enhancing the tranquil setting.

4.89 out of 5 average rating, 153 reviews

Casa Va-Le | 4BR | Private Pool | 2 King Beds

4.92 out of 5 average rating, 178 reviews

A wide view of Playa Azul showcases soft, sandy shores bordered by lush green palms. The calm turquoise waters gently meet the beach, with several figures visible enjoying the sun and water. A clear blue sky stretches overhead, contributing to the serene coastal scene.

Home in Luquillo

Renovated Beach House on BEST beach in Puerto Rico

4.95 out of 5 average rating, 166 reviews

An open living and dining area features a circular glass table surrounded by four white chairs. A sectional sofa with light upholstery is positioned near a flat-screen TV, while a kitchenette is visible in the background. Large windows allow natural light and views of the outdoors.

Flat in Loíza

2 Bedroom 2 Bathroom Penthouse

4.99 out of 5 average rating, 164 reviews

The property is nestled on a hillside, surrounded by lush greenery and tropical plants. The building features a rooftop terrace with sweeping views of the landscape and clouds above, showcasing the natural beauty of the coastal region.

Cottage in Ceiba

My Estela

4.9 out of 5 average rating, 355 reviews

A two-story vacation home features a light-colored exterior with decorative balconies. The entrance is marked by a central door flanked by two smaller doors. Lush greenery surrounds the property, enhancing the welcoming appearance. A paved pathway leads to the home, with a well-maintained lawn visible.

Home in Fajardo

ONE STOP VACATION HOME, w private pool and jaquzzi

4.82 out of 5 average rating, 134 reviews

A panoramic view of the ocean is captured from a height, showcasing the rolling waves and sandy beach below. The coastline is lined with palm trees, and the clear blue sky complements the shimmering water.

Apartment in Santurce

Ocean & City View Studio in Condado, San Juan

4.91 out of 5 average rating, 585 reviews

Flat in Carolina

#1 IslaVerde Beach (Cistern/Generator/Airport)

Family-friendly home rentals with a pool

A private outdoor area is illuminated by string lights, creating a warm ambiance at night. The pool, featuring shimmering blue lights, is bordered by sleek lounge chairs. A modern barbecue grill is visible in the distance, surrounded by lush greenery and a clean, well-maintained pathway.

4.95 out of 5 average rating, 138 reviews

Casa Kenia

An outdoor area features a private pool adjacent to a covered terrace. A billiard table and comfortable seating are visible, with ceiling fans providing airflow. The space is surrounded by greenery and offers easy access to the kitchen through large glass doors.

4.92 out of 5 average rating, 222 reviews

Casa Caliad • Pool House • San Juan

4.95 out of 5 average rating, 104 reviews

A spacious living area features large glass doors that invite natural light and provide views of palm trees outside. A sectional sofa is paired with accent chairs and a geometric coffee table, while a wall art piece adds subtle visual interest.

Apartment in Río Grande

Pristine 4 bdrm (all private) steps to beach/golf

4.99 out of 5 average rating, 299 reviews

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.

Flat in Santurce

Best location with pool, steps from beach!

4.97 out of 5 average rating, 271 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!

4.9 out of 5 average rating, 165 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

An aerial view captures a private pool surrounded by a tiled patio. The pool, featuring steps for easy access, is bordered by fencing for safety. Two reclining chairs are positioned nearby, with lush greenery visible beyond the pool area.

4.96 out of 5 average rating, 120 reviews

Traveler’s cozy house | Private Pool Near Airport

A serene outdoor space features a private pool with tranquil blue water, surrounded by lounge chairs and lush greenery. An inviting seating area is visible, alongside a bar with high stools. A well-lit space creates an atmosphere for relaxation and enjoyment.