Holiday rentals in Viejo San Juan

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Top-rated holiday rentals in Viejo 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 quaint indoor balcony area is showcased, featuring a round glass table surrounded by woven chairs. A vase of tropical flowers adds a touch of color. In the background, a well-lit bedroom is visible through shuttered doors.
Apartment in San Juan
4.9 out of 5 average rating, 469 reviews

Colonial Old San Juan Apartment

Location The apartment is located in Puerto Rico's political and cultural capital, San Juan. It's within walking distance of the best locations Old San Juan has to offer. Great bars and restaurants, hotels, casinos, San Critobal Castle, Paseo La Princesa , plazas and the cruise terminal are only steps away. In its sorroundings there are also farmacies, transportation services, a post office, stores for shopping,beaches and Cathedrals. The apartment is a 10 minutes drive to the Convention Center and 20 minutes to the international airport,. Spaces Typical of Spanish Colonial architecture the apartment spaces include an indoor balcony, perfect for relaxing, and tall ceilings, up to 20 feet high, sporting traditional Ausubo wood beams. Amenities Full kitchen with an industrial stove and oven, microwave, refrigerator, coffee maker and dinnerware. The cozy bedroom has a comfortable queen bed, a/c and drawers for storage. Living room with Flat HDTV, Blue Ray, DVD player, WI-Fi, Satellite dish. Laundry access in the hall.

Guest favourite
The living area features a large white leather sofa paired with a unique side table made of natural wood. An elegant lamp provides soft lighting, while expansive windows showcase panoramic views of the surrounding landscape, including the evening sky transitioning to twilight.
Loft in San Juan
4.95 out of 5 average rating, 139 reviews

Sunrise Loft: King Bed, Washer-Dryer & Ocean Views

Welcome to the Sunrise Loft! Enjoy your stay in San Juan in a tropical boho-chic corner loft condo. Start your day with sunrise in bed and amazing views of Escambron Beach, El Yunque, Condado and Miramar boroughs. Relax winding down to sunsets and night sklyline. Located in the of heart of SJ, walking distance to the beach, Old San Juan, LMM Park, Condado and Convention Center, and short drives to, Santurce, Miramar and SJU and SIG Airports. Generators; w/ washer and dryer; high-speed internet.

Guest favourite
The living room features a sectional sofa and a round coffee table, complemented by colorful wall art. Large arched windows allow natural light to fill the space, with a door leading to a balcony that overlooks the vibrant streets of Old San Juan.
Flat in San Francisco
4.96 out of 5 average rating, 183 reviews

Colonial Gem- Walk Everywhere, King Bed +Balconies

Elegant 2BR Colonial · Walk Everywhere ❤️ Authentic Spanish Colonial gem in the heart of Old San Juan ❤️ Steps to restaurants, shops, nightlife & historic sights (Walk Score 98) ❤️ Soaring 18 ft. ceilings, arched doors & 3 balconies with vibrant views ❤️ Peaceful king bedroom + queen bedroom with balcony ❤️ A/C & ceiling fans in every room, fast WiFi + workspace. ❤️ Equipped kitchen, 43" Smart TV, washer/dryer access ❤️ Guests rave about spotless comfort, walkable location & attentive Superhosts

Top guest favourite
A cozy living area is highlighted by two comfortable leather sofas and a wooden coffee table adorned with books and decorative items. A staircase leads to the upper level, while colorful artwork brightens the wall above. Accent lamps provide warm lighting throughout the space.
Loft in San Francisco
4.99 out of 5 average rating, 306 reviews

Artsy Loft at Old San Juan PR

The charm of Old San Juan is unique! This cozy artsy loft is in a historic building. 20 ft. high ceilings, very fresh and naturally illuminated. It has marble floors in the lower level and hard wood stairs takes you to the second level where the beautifully designed kitchen, dining area and bedrooms are located. The bedrooms overlook the interior patios of the building. Quiet, comfortable and spacious. It can't be beat! Walking distance to all you need! And keyless entry for a worrisome stay!

Top guest favourite
Loft in San Juan
4.95 out of 5 average rating, 222 reviews

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🙏🏻

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.

Guest favourite
A spacious bedroom features a wooden bed with a white quilt and decorative pillows. Yellow walls provide a bright backdrop, while framed artworks add character. A mirror and a blue nightstand are present, alongside a small basket and a white rug, with natural light filtering through the window.
Apartment in San Juan
4.93 out of 5 average rating, 158 reviews

Colonial Luxury in the Heart of the Old San Juan

Live in the heart of the colonial city of the historic Old San Juan. Explore its narrow streets with centuries of history while enjoying of all the day and night life in this touristic zone. This apartment has an enviable location in the center of all points of interest, restaurants, bars and even night life. From this apartment you may walk to all points in the zone from El Morro Castle to the Cruise port and more. This luxury like apartment offer a colonial style with modern amenities.

Top guest favourite
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 Francisco
4.91 out of 5 average rating, 440 reviews

Quaint Colonial Home Old San Juan

Beautiful Spanish colonial home in the north side of Old San Juan where most residents live. One block (steps) from the ocean. Unique opportunity to discover the city while staying in an exquisite setting and enjoying the colonial architecture of this space. Old San Juan is a UNESCO World Heritage Site where colonial architecture mixes with contemporary Puerto Rican culture. “My house is registered at the PR Tourism Company and follows the Health and Safety measures enacted in May 2020"

Top guest favourite
A vibrant yellow façade with classic Spanish colonial architecture is highlighted in the morning light. The entrance features an elegant archway, leading into a spacious interior. The street gently slopes down towards the water, surrounded by lush greenery and cobblestones.
Home in San Juan
4.95 out of 5 average rating, 218 reviews

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.

Top guest favourite
A row of beautifully restored colonial-style buildings is lined along a quiet street. The architecture features arched entryways and intricate wrought iron balconies. Bright colors and textures of the façades create an inviting atmosphere under clear blue skies.
Flat in San Francisco
4.94 out of 5 average rating, 145 reviews

Classic Old San Juan; Best Location

Experience Old San Juan from this beautifully restored colonial-style building. Our cozy 2-bedroom apartment offers charm, comfort, and an unbeatable location—perfect for vacationing, a romantic getaway, a business trip, or a quick escape. Enjoy a spacious living room, a fully equipped kitchen, a comfortable bathroom, and a tranquil interior patio where you can relax and unwind. Book your stay today and make your visit truly unforgettable!

Popular amenities for Viejo San Juan holiday rentals

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Quick stats about holiday rentals in Viejo San Juan

  • Total holiday rentals

    Explore 650 holiday rentals in Viejo San Juan

  • Nightly prices starting at

    Viejo San Juan holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 57,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    260 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 110 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wifi availability

    640 of Viejo San Juan holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Viejo San Juan rentals

  • 4.7 Average rating

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

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