Holiday rentals in San Juan

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Top-rated holiday rentals in San Juan

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
A serene balcony features a hammock and a small dining set with two chairs, all placed on lush green turf. A telescope is positioned for panoramic views of the ocean and surrounding landscape, complemented by bright sunlight streaming in.
Place to stay in Port of Spain
4.92 out of 5 average rating, 136 reviews

Enchanted Forest:Projector/Pool/Jacuzzi/King Bed

Step into the enchanting embrace of our forest-themed villa nestled in the heart of Port of Spain. Elegance meets adventure in this central haven, where captivating ocean views and stunning sunsets, with boats dotting the horizon, await your arrival. This space promises an experience beyond the ordinary. With proximity to shopping malls, restaurants, nightlife and more. Our villa is the perfect blend of convenience and serenity, making it an ideal retreat for travelers seeking the extraordinary.

Top guest favourite
An open floor plan reveals a spacious bedroom with a large bed and a cozy armchair, surrounded by expansive windows that provide views of the lush rainforest. A modern dining table is situated nearby, while natural light filters through the space, highlighting the wooden floors.
Place to stay in Paramin
5 out of 5 average rating, 202 reviews

Paramin Sky Studio

A luxurious observatory for experiencing nature like never before. Wake up to clouds and birds soaring beneath your feet. Have a one-of-a-kind bath experience, 1524 ft above the Caribbean Sea, lathered with bubbles and surrounded by humming birds. See the mist roll over the forest canopy and submerse you completely. Explore Paramin community and fall in love with its people & culture. Whether for remote work, a romantic get away, creative inspiration, or lazy days, Paramin Sky welcomes you!

Top guest favourite
A compact kitchen area features wooden cabinetry and a tiled countertop. Essential appliances including a refrigerator, microwave, and electric kettle are arranged for convenience. A bar-height seating area with a round stool complements the space, inviting casual dining or coffee breaks.
Guest suite in San Juan
4.99 out of 5 average rating, 67 reviews

RAP's Cozy Getaway Your home away from home.

One bedroom self contained flat with en suite bathroom. Brightly decorated, with essential amenities. It is conveniently located with easy access to gyms, savannahs, and for the more religious guests there are many places of worship.. It is accessible to the city, the north coast beaches, Mount St Benedict , the Caroni Bird Sanctuary and the south of Trinidad by public transportation. The space can accommodate 2 persons. Fans are provided . No pets. No smoking . Yes to Hot and cold water.

Superhost
A heated plunge pool is framed by lush greenery and potted plants, with a clear blue sky above. The pool area is surrounded by a light-colored wall, offering an inviting space for relaxation.
Serviced apartment in Lower Santa Cruz, San Juan,
4.96 out of 5 average rating, 102 reviews

Riverside Bed & Breakfast Poolside

* Fully air-conditioned bedroom situated on the ground floor * Private entrance * Queen-size bed, mini refrigerator, microwave, hot water kettle, mini coffee/tea station, iron and ironing board * Bathtub in spacious bathroom (requires stepping into high bathtub), bathtub pillow * Towels & toiletries * Wifi-ready desk with office chair, free high speed internet * 55" HD Smart TV, free Netflix, Standard Cable TV * Heated plunge pool available until 12am Essentially clean, cozy, homey....

Guest favourite
A bright living area features a comfortable seating arrangement with a neutral-toned sofa and decorative pillows. Large windows provide an unobstructed view of the surrounding landscape. A ceiling fan adds to the airy feel, while a doorway leads to an outdoor space.
Flat in San Juan
4.91 out of 5 average rating, 88 reviews

Peaceful 1BR apt in San Juan

Enjoy spectacular views at this Fully Equipped 1 bedroom natural oasis nested in the beautiful and secluded hills of Petit Bourg, San Juan. You'll have a complete apartment outfitted with a full kitchen (dishwasher too), a laundry with a stacked washer-dryer and a King-sized bed that can be separated into 2 single beds. Enjoy the best of worlds with a peaceful retreat that's conveniently 15 minutes away from the city and only 8-10 minutes away from supermarkets, parks and restaurants.

Guest favourite
A modern kitchen features sleek white cabinetry and a minimalist design. Counter space is utilized for food preparation, complemented by gray patterned backsplash tiles. Two place settings are arranged, with matching plates and mugs. Stainless steel appliances, including a microwave and refrigerator, are also visible.
Guest suite in San Juan
4.91 out of 5 average rating, 142 reviews

Oasis, Your home away from home.

Nestled at the foothills of the Northern Range in the lush, peaceful valley of Santa Cruz, this property offers the beauty of nature - birds chirping in the morning, fruit trees. as well as the comforts of modern day life. Only 30 minutes drive from the beautiful beaches of the north coast in general and Maracas Beach in particular, this modern property is also in walking distance of supermarkets, pharmacies and local food joints. It's a mere 20 from the Queen's Park Savannah

Guest favourite
A balcony area features a metal railing and is furnished with two black chairs and a small table. The view captures rooftops of neighboring buildings and green trees, with a cloudy sky above, reflecting the island's scenic environment.
Flat in San Juan
5 out of 5 average rating, 51 reviews

BRAND NEW Tropical Haven Island Getaway

A Welcoming light open concept two bedroom apartment, with a large fully equipped kitchen and well appointed living and dining spaces. There are both a front and rear balcony allowing for the enjoyment of the free flowing island breeze and the panoramic views of the island. You will find several tropical fruit trees from which you are welcome to part take and enjoy when in season. This brand new construction ticks all the boxes of meeting the needs of Tropical Island Getaway.

Superhost
A bright bedroom features a queen bed with a mix of white and dark linens. Adjacent is a small side table with a tray. A single armchair with colorful cushions sits nearby, and a window allows natural light to fill the space.
Flat in San Juan
4.8 out of 5 average rating, 10 reviews

1Bed/1bath Private suite; Nice Mango @ Red Door

Enjoy easy access to virtually everywhere from this centrally located suite. A short trip to hospitals, banks, grocery stores, shopping centers, conference centers, universities, beaches, nature sites, worship centers, public transit, international airport, downtown Port of Spain, and nightlife. For breakfast, doubles on Irving St corner. Enjoy this apartment, one of two, nestled below street level and surrounded by lush vegetation—experience living like a Trini.

Guest favourite
A cozy sleeping area features a spacious bed draped with a delicate canopy. Large windows provide views of the surrounding trees and distant sea. A chair is positioned nearby, with soft curtains allowing natural light to filter through, enhancing the serene ambiance.
Treehouse in Port of Spain
4.84 out of 5 average rating, 152 reviews

Private treehouse, cozy space, spectacular views

Enjoy the sounds of birds and the rustle of wind through the leaves of a 100-year-old nutmeg tree in this cozy treehouse. Surrounded by trees with stunning views of the surrounding forest, lush mountains and the Caribbean Sea this wood and glass treehouse is a great space to escape the hustle and bustle of city life. Access via a short hike but on arrival relax and enjoy the quiet, comfort and modern amenities while immersing yourself in the raw beauty of nature.

Superhost
Flat in San Juan
5 out of 5 average rating, 4 reviews

Modern 2BR | Free Parking | Full AC | Ground Unit

Welcome to your perfect getaway! Nestled in the heart of San Juan, this cozy retreat offers the perfect blend of comfort and convenience. Relax in the thoughtfully designed space equipped with all modern amenities. Located just minutes from Port of Spain, it’s the ideal base for exploring the island or unwinding after a busy day. Whether you’re traveling for work or leisure, enjoy a serene and memorable stay with easy access to everything you need.

Guest favourite
A spacious bedroom is furnished with a neatly made bed featuring patterned linens and pillows. A grey sofa chair is positioned beside a light-colored desk, while a tasteful painting adorns the wall. Soft natural light enters through the window, framed by patterned curtains.
Flat in San Juan
4.83 out of 5 average rating, 53 reviews

Budget Trini Homestay - Room A

deal for your BASIC ACCOMMODATION, The apartment is simply decorated and conveniently located ten minutes from the Capital and twenty minutes to the Airport. Busy with morning traffic, the neighborhood is generally quiet with the faint sounds of traffic going by and children from a nearby school on a school day. Most days, I usually come out with my coffee and watch the hustle and bustle and tend my herb garden, various other plants, and my dog.

Top guest favourite
A restful sleeping area is featured with a spacious bed adorned in soft linens and a patterned throw. A wooden headboard adds a touch of warmth, while bedside lamps provide gentle illumination. A tray holds beverages and snacks, complemented by a vase of colorful flowers.
Flat in Belmont
4.94 out of 5 average rating, 102 reviews

-20% Convenient Studio Queens Park Savannah Getway

Location, Location, Location – mins from everything in a super safe and convenient area. Newly remodeled, very clean, studio apartment with a private bathroom, kitchenette, and private workspace. Superfast WIFI and Netflix included This studio is centrally located steps off the Queens Park Savannah and just up the road from the heart of the city We are happy to share our well-proved insider tips with our guests to enjoy Trinidad at its best!

Popular amenities for San Juan holiday rentals

When is the best time to visit San Juan?

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Avg. price$109 SGD$131 SGD$131 SGD$108 SGD$108 SGD$108 SGD$111 SGD$108 SGD$108 SGD$112 SGD$112 SGD$108 SGD
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Frequently Asked Questions

  • Do apartment rentals in San Juan have air conditioning?

    Absolutely! We offer over 80 apartment rentals with air conditioning in San Juan. Enjoy a tailored experience with all the comforts you desire.

  • Are there San Juan vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in San Juan, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in San Juan?

    San Juan has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in San Juan have free parking?

    Absolutely! We offer over 20 house rentals with free parking in San Juan. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in San Juan have wifi?

    Absolutely! We offer over 80 apartment rentals with wifi in San Juan. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in San Juan?

    Yes! Work meets play with ease at over 40 vacation rentals in San Juan featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for Apartment Rentals in San Juan?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 80 homes with air conditioning, over 80 homes with wifi, over 70 homes with free parking, over 80 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in San Juan have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in San Juan. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in San Juan

  • Total holiday rentals

    Explore 170 holiday rentals in San Juan

  • Nightly prices starting at

    San Juan holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,490 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    170 of San Juan holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across San Juan rentals

  • 4.7 Average rating

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