Family-friendly holiday rentals in San Juan

Historic 2BR~Walk Everywhere• Balconies • 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. ♦️ Walk to restaurants, cafés, nightlife & historic sites • Walk Score 98 ♦️ Quiet King bedroom + Queen bedroom with balcony views ♦️ Soaring 18-ft ceilings, arches, beams & original character ♦️ A/C, fast Wi-Fi, workspace, full kitchen & nearby laundry ♦️ Great for families, couples & small groups who want to walk everywhere

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.

Hacienda Lucero: Your Tropical Lakefront Escape

Amazing views from our two bedroom lake house in Toa Alta, Puerto Rico. The house is on a hill overlooking Lake La Plata and surrounded by 12 acres of private rain forest. It is a quiet place perfect for nature lovers, bird watchers and photographers. There are about two miles of hiking trails as well as lookout points where you can enjoy sunsets and sunrises. If you use a 4x4 vehicle you can drive down to the floating dock to drop in your kayak or use ours. Please enjoy the trails and hikes.

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

✈️ 18 min to airport & 🏖️ top beaches 🏊 Private pool, loungers & hammocks 🌿 Peaceful countryside, just 5 min to city 🌴 45 min to El Yunque & Luquillo Beach 🏡 Hilltop cabin with ocean & mountain views 🛏 Queen bed + full pull-out bed (sleeps 4) 🍽 Indoor + outdoor dining for 4 with views 🚿 Outdoor shower (perfect after the beach) 🌅 Stunning sunrise views from elevated setting ⚡ Fast WiFi, A/C, Smart TV & gated parking 🪑 Beach chairs, cooler & beach towels

Best location with pool, steps from beach!

Wake up in a luxurious king bed with premium bedding, gazing out at your private pool framed by lush palm trees. Start the day with breakfast from the fully equipped kitchen, then catch up online with blazing-fast Wi-Fi under the shaded pergola. Cool off in the pool or rinse in the outdoor hot shower before walking just 50 yards to San Juan’s best beach. Ideal for couples, solo travelers, remote workers, or small families seeking comfort and style.

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.

Hidden Paradise Cabin | Romantic Forest Retreat

Descubre la serenidad de la naturaleza en nuestra acogedora cabaña a pasos de la impresionante cascada “El Salto en Charco Prieto”. Disfruta de noches bajo las estrellas, fogatas, privacidad, mañanas con café y el relajante sonido del bosque tropical. Perfecta para escapadas románticas, senderismo, desconectarse de la rutina y vivir una experiencia única rodeada de montañas, naturaleza y tranquilidad en el corazón de Puerto Rico.

*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.

Villa Estrella PR (near Airport & Beach)

Diviértete con toda la familia en este alojamiento con estilo. Esta cerca de todo lo esencial como el Aeropuerto y Playas (5 minutos), Viejo San Juan, Plaza Las Américas (15 minutos). Localizado cerca de varios restaurantes con prestigio como Bebo’s BBQ, Metropol, y el área turística de Piñones donde podrán encontrar comida típica de nuestra isla.

Old San Juan PH with Ocean View Private Terrace

Ocean Terrace Sanctuary in the Heart of Old San Juan Ocean-view terrace penthouse in the heart of Old San Juan. Sunrises, sea breeze, and silence above the city. Bright, air-conditioned loft with a king bed and a bookshelf that steals scenes. Third-floor walk-up (steep last flight), a short climb to another world.

El Yunque Retreat - Rainforest

“Our enchanting "El Yunque Retreat" is nestled within the lush and vibrant El Yunque National Rainforest, a true paradise for nature enthusiasts and tranquility seekers. Spend a relaxing time with friends and family while enjoying the breathtaking mountain views and amazing sunsets from our two spacious terraces.