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Holiday rentals in San Juan

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Top-rated holiday rentals in San Juan

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Guest favourite
An outdoor terrace features a covered seating area with a sectional sofa and a dining table surrounded by four wicker chairs. String lights enhance the ambiance, while the view includes surrounding rooftops and clear blue skies.
Apartment in San Francisco
4.9 out of 5 average rating, 178 reviews

Historic Tropical Terrace -PH - Cozy for Two

A perfect getaway for a couple seeking to relax in a very well maintained, historic PH. The 3rd floor (42 steps) apartment is one of three in a Spanish Colonial building which includes an open air courtyard along the walkway from the bedroom to the two restrooms (not suitable for children). The PH comfortably sleeps two in a queens sized bed with A/C in the bedroom. A full kitchen & living room come equipped with Free Wi-Fi and TV. However, one should take full advantage of the outdoor terrace which provides year-round outdoor sitting, table & chairs usable as work space, no desk available. A perfect getaway apartment for a couple seeking to relax in a very well A perfect getaway apartment for an individual or couple seeking to relax and immerse in Old San Juan life and living. Enjoy your stay in a very well maintained penthouse apartment in an historically and tastefully remodeled Spanish Colonial 3-story corner building. Located on one of the most charming streets of Old San Juan nestled among homes, restaurants, and cafes along Calle Sol, the building is just two blocks away from commercial streets like Calle San Francisco which have pharmacies, supermarket, boutiques, and retail stores and restaurants. Also just one block away from the nightlife of Calle San Sebastian and a few blocks from the ocean, museums and historical fort! Read all our reviews as the vast majority love the experience of living in a traditional Spanish Colonial building. Ours is a corner building which allows for lots of sunlight and includes windows in the kitchen, living room and bedroom, as well as an authentic courtyard that opens onto all three apartments. Note that the courtyard does have a hallway going to the bathroom that is visible to all three apartments, though all the rooms are private including a large outdoor terrace which provides year-round outdoor sitting, dining and naps on the hammock, and a great breeze coming off the ocean two blocks away. This penthouse apartment comfortably sleeps two in a queen sized bed in an air-conditioned room; the air-conditioner can easily cool off the living room too. A full kitchen opens to the terrace as does the living room and both are charming, cozy and equipped with necessities and items for your comfort and relaxation. Free WiFi and TV (including NetFlix) are included and also a washer/dryer which is located in an over-sized and beautifully designed bathroom; toilet and additional sink in adjoining bathroom. We certainly hope you will take advantage of this special, sunny and very well maintained apartment and have an ideal getaway in an authentic Old San Juan home. We are available before, during and after your stay for any question you may have. Check-in Information: One of our team will personally welcome you in front of the Condo at the moment of your arrival. Please confirm your arrival time including flight info and the phone you are traveling with a few days before traveling so we can schedule your check-in. On the day of arrival you will call us as soon as you are leaving the airport in your taxi or rental car and while you are driving in to Old San Juan we will walk over and meet you at the rental. Old San Juan is few blocks of unique colonial style architecture and offers a great selection of restaurants, bars, cafes, shops, galleries, music, and paths to walk by the port. Taxi, Buses, Rental Cars TIPS FOR BETTER LIVING IN THE TROPICS First of All: Be Happy, Relax & Enjoy - you are on a beautiful, sunny, tropical Island, which requires an open heart and mind to be fully enjoyed! Stay happy! - even if anything is missing or broken. Simply contact us immediately and we will be glad to help. Remember you are renting a Home away from Home and no one likes a stinky apartment: Therefore the garbage goes out daily. And the dishes are specially made to break after 2 hours of being used unless they get cleaned. To avoid any extra charges for broken dishes simply clean them. We are in the tropics and if you want to have your food and drinks for yourself, store almost everything in the fridge. If not you might have to share it with unwanted animals or the humidity and heat may destroy some foods. The plumbing system on tropical Islands appears to be delicate. Therefore it is important not to throw any sanitary items, Condoms and not even a lot of toilet paper at the same time in the toilet. Misuse may end in clogged toilets and extra charges!, if misuse would be proven by Plumber. It also rains on a sunny island. Please close all doors and windows while exploring “paradise”. If you don't the apartment may get flooded and you would have a lot of extra work. !!!Please be environmentally friendly!!! We are a small Island in the middle of the Atlantic Ocean with limited access to resources! PLEASE do not waste fresh water! Only turn on A/C while being at home. Turn off A/C when leaving the apartment. Close all windows and doors while running the A/C. You have chosen to stay in a condo with real neighbors that are unfortunately not on vacation and deserve their good night sleep. Please keep the volume down after 10PM and before 9AM. Please make arrangements for your check-in or out a few days before it actually happens, so we can prepare for a smooth arrival and departure. In case of EMERGENCY please call 911! And please inform us as well - send a text message or call to the following numbers: (PHONE NUMBER HIDDEN) and (PHONE NUMBER HIDDEN)

Top guest favourite
A spacious open-concept living area features a comfortable sofa with a light throw blanket. The area is illuminated by natural light from large sliding glass doors that lead to a balcony with scenic views. Modern furnishings include a dining table with bar stools and a television mounted on the wall.
Home in Carolina
4.99 out of 5 average rating, 161 reviews

Chic cabin-Ocean&Yunque view-Peace&Relax/Free prkg

Enchanting modern wooden house located in the serene countryside of the greater San Juan Metro Area (Carolina). If you're seeking a harmonious blend of comfort, nature & breathtaking views, look no further! Situated on a countryside hill, but close to everything: San Juan (20 mins), airport (15 mins), beaches (15 mins) and El Yunque Rainforest (45 mins). The scent of fresh wood greets you as you step into the open-concept house. With attention to detail, this home exudes warmth & sophistication.

Top guest favourite
A comfortable living area features a beige sofa with decorative pillows, complemented by a light green accent chair. A low coffee table sits in the center, adorned with a small plant and a candle. Natural light filters in through white shutters, enhancing the calm atmosphere.
Flat in Santurce
4.97 out of 5 average rating, 245 reviews

Bright, Spacious, Central Condado Home, Steps from the Beach

An uncluttered aesthetic boasts fresh pastel and coastal hues, peppered with greenery. A green marble vanity hugs the corner of a white tile-clad bathroom. It is one of the few remaining period style houses in Condado, located on a quiet residential street. The 1 bedroom apt located off the main house, imbues a light-hearted yet thoughtfully designed home that is more reminiscent of the classical Puerto Rico. With its own entrance, the quaint apt is located on a 2nd floor & has a gated parking.

Guest favourite
Flat in San Cristóbal
4.91 out of 5 average rating, 253 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.

Guest favourite
A spacious living area is highlighted by large corner windows that allow abundant natural light. A sectional sofa is complemented by an accent chair and a small side table. Decorative pieces are arranged on shelves, and sliding glass doors provide access to a balcony.
Apartment in San Juan
4.9 out of 5 average rating, 257 reviews

A Gem of a 2 bedroom condo unit close to the beach

This luxurious unit is located in a modern high rise building in an up and coming area in the isle of Old San Juan just one mile from the old Spanish town and near Condado. The location is perfect to access the famous beach of El Escambron (just 1 block away!) very popular among surfers. It´s a newly reformed gem of a condo unit loft-like style with exposed concrete ceilings and beams with floor to ceiling north looking windows in a corner unit with ample sun light all through the day-time.

Top guest favourite
An outdoor terrace features a wooden deck with a table and chairs, providing ample seating. A cozy swing chair hangs nearby, surrounded by lush greenery and expansive views of the mountainous landscape. Decorative string lights add warmth to the inviting setting.
Shipping container in Gurabo
4.98 out of 5 average rating, 241 reviews

Vista Linda Haus

At Vista Linda Haus, from the moment you start the journey to the beautiful town of Gurabo, the adventure begins. A unique experience towards the favorite destination. You will find panoramic landscapes, lakes, mountains, farms, cities, and a community with the Puerto Rican warmth of our mountains. Just 35 minutes from the Luis Muñoz Marín International Airport, over 1,000 feet above sea level, you will breathe freedom and peace, in a harmonious environment full of energy and pure nature.

Top guest favourite
A contemporary house is positioned atop a hill, surrounded by lush greenery and palm trees. A winding pathway leads to the entrance, while panoramic ocean views extend in the background, highlighting the beauty of the surrounding landscape.
Home in Ceiba
4.98 out of 5 average rating, 132 reviews

La Casita: Private Heated Pool W/ Ocean Views

Nestled atop a lush hill at the beachfront town of Ceiba, this 2-bedroom house is a haven of luxury & tranquility, offering a spectacular panoramic view of the ocean, the rainforest, mountains & neighboring islands. As you approach the property, a winding driveway bordered by vibrant, blooming flowers leads you to the entrance, setting the tone for the enchanting retreat that awaits. Just a 1-hour drive from SJU's International Airport & half hour ride from El Yunque National Rainforest.

Superhost
A serene balcony view is presented, featuring two white lounge chairs positioned for relaxation. A small table sits between them, adorned with a potted plant. The expansive ocean stretches out in the background, framed by a railing and bright blue skies with scattered clouds.
Apartment in Santurce
4.86 out of 5 average rating, 104 reviews

Ocean View Bliss / Condado

Beautiful ocean view apartment located in the heart of Condado with direct access to the Condado Lagoon (ideal for snorkling and Paddle Boarding). Minutes away from all the Luxury shopping, fine dinery and lots of fun that Condado provides. Walking distance to all the famous Hotels of the area such as Marriot and Vanderbilt. Minutes Taxi or Uber Rides to the beautiful and legendary Old San Juan and to many other great places for fun such as Distrito T-Mobile and Coca Cola Music Hall.

Top guest favourite
Two people are seen enjoying a natural swimming area beneath a waterfall, surrounded by lush greenery and rocky terrain. The cascading water creates a serene atmosphere, and sunlight filters through the foliage, reflecting off the surface of the water.
Cabin in San Juan
4.98 out of 5 average rating, 460 reviews

Cabin hidden paradise, cozy & romantic loft cabin

Experimenta unos dias de la serenidad única de la naturaleza en nuestra cabaña con vistas a las montañas y junto al río, a pasos de la impresionante cascada "El Salto en Charco Prieto". Embárcate en una emocionante aventura río arriba hacia un paraíso escondido. Disfruta de noches tranquilas con cielos estrellados, fogatas y la melodía relajante de la naturaleza. Ven, hospédate y vive momentos que te dejarán sin palabras. ¡Te invitamos a disfrutar de esta experiencia inolvidable!

Guest favourite
A modern living area is highlighted by a wall adorned with vertical wooden slats. A flat-screen TV is mounted above a minimalistic black media console. A comfortable gray sofa and a stylish armchair are positioned around a dark dining table, with decorative plants adding a touch of greenery.
Apartment in San Juan
4.9 out of 5 average rating, 166 reviews

Luxury Loft in Central San Juan with Free Parking

Enjoy a relaxing experience in this centrally located modern loft between Old San Juan and Condado, near restaurants, bars, and attractions. Just a 10-minute drive from San Juan airport, this spacious loft offers lagoon views, a 24-hour concierge, free parking, and a gym. The stylish space includes a fully equipped kitchen, high-speed Wi-Fi, and a comfortable workspace, perfect for leisure or business travelers. The building provides round-the-clock security for peace of mind.

Top guest favourite
An open-concept kitchen features modern appliances, including a refrigerator and stacked washer-dryer. A wooden island with shelves provides additional workspace. A dedicated desk sits beside a window, while a small plant adds a touch of color to the light-filled area.
Home in Santurce
4.99 out of 5 average rating, 138 reviews

Walk 2 Beach! Gated prkg |Renovated! Bright & Cozy

Experience a cozy stay in our renovated 1-bedroom house, just a 5-minute walk to Ocean Park Beach and half a block from vibrant Calle Loíza. Enjoy free gated parking, a modern kitchen, washer-dryer, AC, ceiling fans, and a dedicated workspace. With two TVs, excellent internet, and beach essentials included, you'll have everything you need. Immerse in local culture and conveniently explore nearby attractions. If you don’t want to rent a car, you can easily walk or use Uber.

Guest favourite
Home in San Francisco
4.94 out of 5 average rating, 101 reviews

Casa Azul | Nightlife & Terrace in Old San Juan

Colorful three-level home in the heart of Old San Juan. Located on Callejón El Tamarindo, this colonial-modern home sits within the historic district, surrounded by restaurants, nightlife, and cultural landmarks. Features a cozy private terrace ideal for sunny days or romantic evenings. The property includes a Tesla-powered backup system, providing comfort and peace of mind during power outages. A vibrant stay in one of Puerto Rico’s most iconic neighborhoods.

Popular amenities for San Juan holiday rentals

When is the best time to visit San Juan?

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Frequently Asked Questions

  • What are the best places to stay in San Juan?

    San Juan has lively neighborhoods for different interests—Old San Juan is known for historic charm, Condado for a relaxed beach atmosphere, and Santurce for arts and nightlife. Isla Verde is frequently suggested for easy beach access and a resort-like vibe.

  • What are the best things to do in San Juan with kids?

    Families often explore El Morro for its broad lawns and history, enjoy playtime at Condado Lagoon, or discover interactive exhibits at local museums. Beaches with calm water, like those near Isla Verde, are frequently suggested, and guided tours can create engaging experiences for children.

  • What are some of the best things to do in San Juan?

    Explore the colorful streets of Old San Juan, tour historic forts such as El Morro, or relax on city beaches like Escambrón. Santurce has vibrant street art, galleries, and live music for those interested in culture.

  • How is the weather in San Juan?

    San Juan has consistently warm temperatures, typically ranging from 72–89°F (22–32°C) throughout the year, with higher humidity and more rain during summer and early fall. Light clothing and protection from sun and showers are usually recommended.

  • What are the best places to visit in San Juan?

    Old San Juan and its historic forts, such as Castillo San Felipe del Morro and Castillo de San Cristóbal, are frequently suggested. The Condado area, with its beach and dining spots, and the Museum of Art of Puerto Rico offer more ways to experience the city.

  • What are some hiking trails in San Juan?

    San Juan has natural areas like Piñones with boardwalk trails through mangroves, and Parque Luis Muñoz Rivera for shorter urban walks. For more extensive routes, El Yunque National Forest can be found just outside the city for rainforest hikes.

  • What are some family activities we can do in San Juan?

    Families can explore El Morro’s expansive greens, visit the Carolina Children’s Museum, or enjoy water activities at Condado Lagoon. City beaches provide space for swimming, sand play, and picnics.

  • What are some of the best day trip ideas from San Juan?

    Many visitors enjoy guided excursions to El Yunque National Forest, day trips to historic towns like Loíza, or boat tours to nearby islands such as Culebra or Vieques. Bioluminescent bay tours in Fajardo are also frequently suggested for a unique family-friendly experience.

  • Are there any pet friendly accommodations available in San Juan?

    Many accommodations in San Juan welcome pets, especially in neighborhoods like Condado, Santurce, and Isla Verde. Beach areas and city parks make it easy to spend time outdoors with your dog.

  • What are some local tips for visiting San Juan?

    Embrace walking in Old San Juan’s blue cobblestone streets, stay hydrated in the humid climate, and sample fresh fruit from street vendors. Tipping is customary in restaurants, and knowing a few Spanish phrases is appreciated.

  • What is San Juan known for?

    San Juan is known for its well-preserved colonial architecture, historic forts, and lively arts and music culture. The city’s beaches, traditional food, and Caribbean heritage contribute to its distinct identity.

  • What are the best hidden gems to explore in San Juan?

    La Placita de Santurce has a lively local atmosphere and open-air eateries, while Casa Blanca stands out for its layered colonial history. Discover street art along Santurce’s alleys and enjoy tucked-away cafes that invite quieter exploration.

  • What are the best foods to try in San Juan?

    San Juan is known for dishes such as mofongo, arroz con gandules, and lechón, with street vendors serving alcapurrias and tostones. Flan and tembleque are popular local desserts, and fresh seafood is often featured in coastal restaurants.

  • What should I bring for a trip to San Juan?

    Light clothing, comfortable walking shoes, and sun protection are practical for San Juan’s warm and humid climate. A swimsuit, rain jacket, and a reusable water bottle help ensure comfort for both city and outdoor adventures.

  • What is the nightlife in San Juan like?

    San Juan’s nightlife has a vibrant mix of music venues, salsa clubs, and open-air bars, especially around Santurce and La Placita. Expect a welcoming atmosphere, with many places hosting live bands and locally-inspired cocktails.

  • What are the most popular events or festivals in San Juan?

    San Juan hosts the San Sebastián Street Festival in Old San Juan each January, known for music and parades. Locals also gather for Noche de San Juan celebrations in June and colorful carnival events in late winter.

  • Are there family friendly vacation rentals in San Juan?

    Many vacation rentals in San Juan cater to families, with options in neighborhoods like Isla Verde, Condado, and Ocean Park providing beach access and convenient amenities. Look for listings with kitchens and multiple bedrooms for added comfort.

  • When is the best time to visit San Juan?

    Late winter through early spring is often recommended for milder temperatures and fewer showers. Summer and fall bring more rain and humidity but can be lively with festivals and events.

Quick stats about holiday rentals in San Juan

  • Total holiday rentals

    Explore 8,430 holiday rentals in San Juan

  • Verified guest reviews

    Over 566,560 verified reviews to help you choose

  • Family-friendly holiday rentals

    3,320 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 2,080 rentals that welcome pets

  • Holiday rentals with a pool

    2,230 properties feature pools

  • Rentals with dedicated workspaces

    4,470 properties have a dedicated workspace

  • Wifi availability

    8,260 of San Juan holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Monthly stays and Beachfront across San Juan rentals

  • 4.7 Average rating

    San Juan stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    San Juan’s top spots include Distrito T-Mobile, Paseo de la Princesa and Museo de Arte de Puerto Rico

Destinations to explore

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  2. Puerto Rico
  3. San Juan Region
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