Vacation rentals with a pool in Diego Martin Regional Corporation

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Top-rated rentals with a pool in Diego Martin Regional Corporation

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

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Guest favorite

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

4.93 out of 5 average rating, 113 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.

Superhost

A modern living area features a sleek sofa and a large television displaying a fireplace, creating a cozy feel. Potted plants are positioned on either side of the TV, adding a touch of greenery to the space. Soft lighting enhances the inviting ambiance.

Apartment in Port of Spain

Modern Luxury

Relax and recharge in this, modern apartment designed for families and couples. This condo features a shared pool, a private balcony with breathtaking views, and spacious, stylish interiors. Enjoy free Wi-Fi, free parking, and fully equipped kitchen. Whether you're planning a family getaway or a romantic retreat, this is the ideal space to unwind. Close to popular local attractions, restaurants, you’ll have everything you need for a memorable stay—peace, convenience, and beauty all in one.

Top guest favorite

An open-concept living area is highlighted by modern furnishings, featuring a large sectional sofa and a sleek entertainment unit. The adjoining kitchen boasts contemporary appliances and an island, with warm wooden flooring enhancing the spacious feel. Soft, natural light fills the space through recessed lighting.

Condo in Port of Spain

5 out of 5 average rating, 117 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 favorite

An outdoor pool area is visible, surrounded by well-kept landscaping and several lounge chairs. A multi-story condominium building stands adjacent, featuring large windows and balconies. The clear sky reflects on the pool's surface, creating a serene environment.

Apartment in Port of Spain

4.89 out of 5 average rating, 64 reviews

Exquisite 1BR • Modern • Vibrant • City View

✨ About This Space✨ Welcome to your private escape at One Woodbrook Place — a sleek, 1 bedroom, 1 bath apartment crafted for travelers who appreciate refined comfort, modern amenities and convenience. Step into a bright, thoughtfully designed space featuring an open-concept layout and amazing city views by day and dazzling lights by night. Whether you're a business traveler, consultant, digital nomad, or simply escaping for a relaxing getaway, this apartment is exactly what you need.

Superhost

A serene outdoor area is depicted, featuring a lush green lawn and a tranquil pool surrounded by palm trees. Gazebo structures with red roofs provide shaded seating, with the calm coastal waters visible in the background.

Condo in Port of Spain

4.86 out of 5 average rating, 72 reviews

Luxury Condo with Amenities on the Sea

Welcome to Luxury Condo with Amenities on the Sea-your tropical escape! This spacious 2BR/2BA condo features 1 king & 2 queen beds with 24/7 Security, Pool, Tennis Courts & Playground. Enjoy breathtaking bay and hillside, right on the seafront. This resort-style retreat has it all! Perfect for families or groups (up to 6 guests). CARNIVAL SPECIAL: 10-Night Package Stay close to the action! 10 nights | Up to 6 guests | USD 7,650 Book now and celebrate Carnival in comfort and style!

Guest favorite

An outdoor area features an infinity pool complemented by a jacuzzi, surrounded by well-maintained gardens. Lush green hills provide a scenic backdrop, and various tropical plants line the edges of the patio, creating a tranquil setting.

Apartment in Port of Spain

4.98 out of 5 average rating, 51 reviews

Cascade Mountain View Oasis

Situated 10 minutes from Port of Spain and nestled in Cascade in the Northern Mountain Range, lies the beautiful Cascade Mountain View Oasis. Experience a safe, peaceful haven for the ideal getaway. Equipped with an infinity pool and jacuzzi that overlooks the view of the mountains. 7 minutes from the historic Queens Park Savannah, home of our iconic carnival celebrations, 12 minutes’ drive from the popular Ariapita Avenue with its diverse array of restaurants, bars and night life.

Guest favorite

A tranquil pool area is surrounded by a spacious deck, featuring comfortable lounge chairs and a shaded dining space. Potted plants add greenery to the setting, while string lights subtly enhance the ambiance above the pool.

Apartment in Port of Spain

4.92 out of 5 average rating, 24 reviews

Prime location - River Sand Apt

You can't beat this location! If you love food, this apartment has over 30 food places within its vicinity. If you like to walk, then take a 20 mins stroll to the Savannah. If not a 7 min drive will do the trick. You can relax on our spacious pool deck or go for a swim! The Sands of Time compound is absolutely stunning. The building has charm with its steps and layered levels. Plus it is unique as it was designed by an Interior Designer who has done projects across the Caribbean.

Guest favorite

A private pool is surrounded by lush tropical vegetation, creating a tranquil retreat. A small table with a bottle and glasses is set nearby, inviting relaxation. Sunlight filters through the leaves, adding warmth to the serene outdoor space.

Villa in Diego Martin Regional Corporation

4.95 out of 5 average rating, 41 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 favorite

A large community pool reflects the surrounding greenery and blue sky. Apartment buildings are visible in the background, framed by landscaped gardens and trees, creating an inviting outdoor space for relaxation.

Apartment in Petit Valley

4.87 out of 5 average rating, 46 reviews

Cozy Condo near Port-of-Spain

The whole family will feel at home, enjoying easy access to everything from this centrally located comfortable abode in West Trinidad. This cozy 2-bed, 2 bath apartment is located in an upscale gated community with 24-hour security, large community pool, tennis courts and playground. The apartment includes a fully equipped kitchen with stainless steel appliances, pillow top mattresses and contemporary furniture throughout to provide ultimate comfort and relaxation.

Superhost

A clear blue swimming pool is framed by lush greenery and colorful flowering plants. Surrounding the pool, manicured grass adds to the serene environment. Steps lead into the water, providing easy access for guests to enjoy the inviting space.

Condo in Westmoorings

4.86 out of 5 average rating, 49 reviews

Westmoorings/Bayshore. Gated with pool 1 bed/bthrm

A home away from home in this sought after residential area of Bayshore, Westmoorings Trinidad. This charming and homey 1 bedroom ( Queen bed ) 1-bathroom, fully equipped apartment offers a serene tranquil gardens and pools to view from a private ground floor patio. It is 20 minutes walk to West Mall, Massy grocery and a short drive away from Savannah and much of the entertainment in Trinidad. 24 hour gated security with free parking space and visitor spaces.

Top guest favorite

A night view captures the scenic hills illuminated by countless city lights. The vibrant colors of the buildings contrast with the dark sky, while greenery from palm trees frames the image, creating a serene urban landscape.

Condo in Port of Spain

5 out of 5 average rating, 29 reviews

City Scape Vacation property! (OWP)

Enjoy a stylish experience at this centrally located in-demand, secure property! Experience T&T in the liveliest place on the island, with beautiful mountain views, access to the nicest beaches (Maracas, Las Quevas & more), pool, on site restaurants & bars, and easy access to the hottest entertainment and dining experience on the island Even home to some popular local celebs!”

Top guest favorite

A spacious pool area is surrounded by lush tropical plants and palm trees. The inviting pool features a hot tub nearby. Natural stone borders the pool, while a smooth patio provides a serene outdoor environment, enhancing the feeling of relaxation amidst the verdant garden.

Guest suite in Port of Spain

4.9 out of 5 average rating, 124 reviews

Tropical Haven - 2 bedroom apartment in Maraval

This spacious and tropical apartment has two bedrooms and two bathrooms, as well as a large open-plan kitchen and living room. There is also a luxurious pool in the lush garden. It is located in a quiet neighbourhood on the St. Andrews Golf Course in Moka and is only 20 minutes away from Maracas Beach or Port of Spain.