Holiday houses in Isla de Cabras

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.

4.99 out of 5 average rating, 101 reviews

Quiet 3BR: Walk Everywhere · 2000 sqft · King Beds

Huge 3BR Spanish Colonial home in the heart of Old San Juan—walk everywhere, enjoy historic charm, and sleep peacefully in quiet bedrooms away from the street. ♦️ Walk to restaurants, cafés, nightlife & historic sites • Walk Score 98 ♦️ Huge 2,000-sqft layout ideal for families & groups ♦️ Quiet bedrooms for restful sleep ♦️ 2 King beds + 1 Queen ♦️ 3 balconies with vibrant street views ♦️ 18-ft ceilings, arches, terracotta floors & original character ♦️ A/C, fast Wi-Fi, full kitchen & laundry

4.96 out of 5 average rating, 252 reviews

Loft in San Juan

San Juan, Ocean views, Luxury LOFT,

Your search is over!!!! You have found the perfect place for your staycation in this 989 sqft. (largest in the condo), centrally-located, open space luxury Loft in SAN JUAN, PR. Indulge yourself in an Exquisite and tastefully decorated loft. with many unique pieces of art. Also, NO need to worry about power or water outages that occur on the island, this condo is backup with power generators and cisterns, so your visit should not be interrupted. Everything you need is here ! See you soon🙏🏻

4.84 out of 5 average rating, 192 reviews

Apartment 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! ✨🌴🏖️

4.81 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.

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.

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.

4.89 out of 5 average rating, 503 reviews

The Balconies, Old San Juan Best location!!

Beautiful second floor apartment in the heart of the Old San Juan. A spacious one bedroom apartment with a mezzanine that works as a open extra bedroom. One bed, two sofa beds. One full kitchen, and one bathroom. From the balcony you can get a breathtaking view of the Atlantic Ocean. Excellent location! 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!!

4.95 out of 5 average rating, 193 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!

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.

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.