Holiday rentals with a pool in San Juan

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Juan

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Superhost

Holiday home in Port of Spain

4.88 out of 5 average rating, 128 reviews

Jungle Oasis: Sea&City Views with Ruby Sunsets

Experience the ultimate escape at our luxurious villa. With breathtaking views of the Caribbean Sea, a serene environment, and fully-equipped amenities, this is the perfect getaway for couples, families, and business professionals. Let the cool windward breezes rejuvenate your soul while gazing upon the majestic boats sailing towards the horizon, painting the sky with a stunning array of ruby hues during the unforgettable sunsets. Book now and indulge in the tranquility of this tropical paradise

Superhost

Apartment in Petit Valley

4.87 out of 5 average rating, 15 reviews

VClose to POS Home away from H :Peaceful 2BR Apt

Nestled in the hills yet close to the city, unwind at our cozy, peaceful oasis with hill views, beautiful sunsets &ocean views.. Modern Ground floor apartment: 2 bedrooms each with its owndesignated workspace , Queen beds , 2 full baths, fully air conditioned, fully equipped kitchen. Washing machine & dryer, Open living space which opens on to pool deck. Ping-Pong Table, Board Games. Close proximity to POS, shopping malls, banks, cinema, grocery, Pharmacy. Access to Food delivery services

Top guest favourite

Apartment in Port of Spain

5 out of 5 average rating, 110 reviews

Contemporary Port of Spain Condo

Enjoy a stylish experience at this centrally located place. The unit it located steps away from any amenity you can think of. The best restaurants the island has to offer, banking, supermarkets, pharmacy, recreation, hospitals and much more. You can’t ask for a better or safer location. Perfect for your visit to Trinidad or for a luxury staycation. This unit aims to cater to your every need so your vacation or business trip is an enjoyable one. You will feel totally relaxed at this unit .

Guest favourite

Townhouse in San Juan-Laventille Regional Corporation

4.84 out of 5 average rating, 19 reviews

Beautiful Villa w/Spa Pool in safe gated Mt Hope

Villa Halcyon is a spacious fully furnished home in a secure gated community in Mt. Hope. The 2nd floor features a main bedroom with ensuite bathroom and balcony, plus 2 more bedrooms and a modern bathroom. All bedrooms have air conditioning. The 1st floor features an open living/dining room, 1/2 bath, kitchen, pantry, breakfast banquette and porch. Down the spiral stairs to the ground level is the Spa Pool, 4th bedroom (bonus) suite, kitchenette, bar area, wet bathroom and laundry area.

Top guest favourite

Apartment in Piarco

4.95 out of 5 average rating, 130 reviews

Modern Condo in Piarco Trinidad (With Pool)

The Pad: Modern Condo Near Piarco International Airport Dive into a realm of elegance and ease at "The Pad at Piarco" – our contemporary 2-bedroom condo nestled within a secure gated community. Situated just a stone's throw away from Piarco International Airport. This refined haven is crafted for those with an eye for luxury. Cool off at the swimming pool or relax in the plush interiors. The Pad at Piarco is in close proximity to 24hr gas stations, groceries, and vibrant malls.

Guest favourite

Guest suite in San Juan

4.91 out of 5 average rating, 130 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.

Top guest favourite

Flat in Port of Spain

4.96 out of 5 average rating, 26 reviews

Perfect location/ Pool - White Sand Apt

Welcome to “Sands of Time”, a secure compound with beautiful apartments. This apartment, which is named “White Sand” is perfect if you like a little bit of everything. Top-tier location. Comfortable living. Stylish and modern amenities. A place to retreat. You can choose to enjoy coffee on your private patio or lounge by the poolside. Also, if you are a nature lover, take advantage of the patio between 4:30 -5:30 pm as you see flocks of birds returning to their homes.

Guest favourite

Villa in Diego Martin Regional Corporation

4.94 out of 5 average rating, 36 reviews

Garden Oasis 1: Villa with Private Pool

A stylish and spacious 3 bedroom villa located in one of the most desirable neighbourhoods in Trinidad. This duplex villa is fully serviced, and designed to define opulence. It awaits guests in a completely private and serene setting, where the only desire is to never leave. This property is located close to shopping, attractions, and an array of dining options. It is outfitted with five star furnishings, has a private pool, and BBQ grill to enhance the overall experience

Guest favourite

Guest suite in Loango

4.86 out of 5 average rating, 21 reviews

Vista Stays ....Bamboo View

Need to get away for that much needed staycation or from the hustle and bustle of everyday living. Look no further, this modern self contained space captures the tranquility and beauty of the rainforest and affords the conveniences that you are used to at home. Leave the cooking to our Chef, as we serve up breakfast, lunch and fine dining dinner experiences. It gets even better as our massage therapist pamper you with massage and spa treatments tailored for you.

Superhost

Home in Las Lomas #2

4.87 out of 5 average rating, 192 reviews

Nature Getaway Resort with private pool

Lovely 2 bedroom home plus loft with resort type amenities tucked away in the woods but just a 10 min drive from the airport. The house comes equipped with a full kitchen which includes - Gas burner stove/oven, double door refrigerator, dish washer, microwave and toaster oven. All utensils and cookware is included. There is a private pool (heated if required) with gazebo. There are four (4) hammocks for relaxing, kids play park with two slides and swings.

Guest favourite

Flat in Port of Spain

4.87 out of 5 average rating, 68 reviews

Short/Long term rental 2BD Gated-Pool-Netflix-A/C

Located in an attractive and safe neighborhood our modern 2 bed self contained space has 2 queen beds, ample closet space with a spacious living, dining and kitchen area for your comfort. SmarTV with Netflix signed in, YouTube & fast WIFI. The kitchen is fully equipped with stove top, utensils, small appliances, in unit washer & dryer. Outdoor garden and shared pool area to enjoy. Easy access to Port Of Spain, the Savannah, restaurants, grocery and shops.

Superhost

Flat in Port of Spain

4.68 out of 5 average rating, 19 reviews

Spacious 3 Bed Apartment | Pool | Maraval | Gated

Experience the perfect home away from home in Maraval, Trinidad! Nestled on Valleton Avenue, this charming 2-bedroom, 1-bathroom, fully equipped apartment offers a serene retreat with modern amenities and convenient proximity to nearby attractions. It is located within a minutes walk or drive away from restaurants, pharmacies, grocery stores, and shopping plazas and the Savannah.