Apartment holiday rentals in San Juan

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.

Location · Family · Condition

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! ✨🌴🏖️

Location · Value · Decor

3 Habitacion Loiza · The Modern Tropic Nest/Near T

Welcome to your vibrant home away from home.This spacious 3-bedroom, 2-bath apartment features a modern, stylish design with a bright open layout, fully equipped kitchen, laundry area, and a large private balcony. Perfectly located just 10 minutes from the airport and Old San Juan, and steps from the beach and a lively street filled with restaurants, bars, and shops. Whether you’re relaxing or exploring, this is the perfect base. Book now and experience the best of San Juan in comfort and style

Family · Value · Amenities

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

Family · Value · Getting around

Limón by VP - Apartment 4

Enjoy a stylish experience at this centrally-located place. Large two bedroom two bath loft like apartment. Featuring two en-suite bedrooms with king beds and large bathroom. The apartment also has a full size pullout couch. Guests can enjoy sunsets on the shared rooftop deck. The apartment is centrally located right off of Calle Loiza and 4 blocks from the Ocean Park beach. Enjoy the many restaurants and bars that the area has to offer in our newly remodeled space. Your own private oasis.

Value · Family · Kitchen

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.

Family · Location · Cleanliness

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.

Value · Location · Sleep quality

A view like no other in the Center of Condado.

Talk about beach front! Want to go to the beach? Check. Want to be walking distance away from all the nightlife, restaurants and bars? Check. Just want to sit back, relax and enjoy the view? Check. Located in the Condado shoreline, this apartment is fully equipped and air conditioned. Itchecks all the marks for a perfect dream getaway. Close to the airport, Old San Juan and all things San Juan Metro Area. For everything else, we'll let the pictures and virtual tour do the talking!

Value · Family · Biking

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!

Location · Family · View

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.

Value · Family · Check-in

Amazing City and Bay Views San Juan Art District

YES WE HAVE WATER 😊 Enjoy a stylish experience at this centrally-located place in Santurce, San Juan. Experience true authentic Puerto Rican culture in this urban apartment located in the art district. A short walk to many restaurants, rooftops, and bars and a short drive to the beach. Only 10 min from SJU airport and Old San Juan. With stunning views overlooking the city and bay. Brand new fully renovated, open kitchen and living room concept layout with 3 bdrms.

Family · Value · Kitchen

Ocean Park 2BR Penthouse Beach Pool

Bright top-floor penthouse just steps from Ocean Park Beach. Enjoy ocean views from your private rooftop terrace, perfect for morning coffee or evening dining. This modern 2-bedroom retreat comfortably sleeps 4 and is located in a quiet, gated community just a 2–5 minute walk to Calle Loíza’s restaurants and shops. Free parking included. Guests also have access to the shared pool. Pool use requires signed waiver per administration rules.

Value · Location · Getting around