Vacation rentals with a pool in Diego Martin

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Top-rated rentals with a pool in Diego Martin

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.

Superhost

A spacious living area features a large sectional sofa, complemented by a wooden coffee table and decorative vase. Natural light filters through vertical blinds on the window, while a dining area with a round table and chairs is visible in the background, accented by greenery.

Condo in Petit Valley

4.86 out of 5 average rating, 93 reviews

Modern 3 Bedroom Condo In Private Community #8

Located in the scenic, safe, and private residential community of West Hills. This unit comes fully equipped for the modern day traveller with quality furnishings ensuring guest comfort. Upon arrival at the entrance you'll quickly notice the community conveniences of a coffee shop/cafe, a bodega and pharmacy. There are also onsite amenities such as a swimming pool, tennis courts, and kids playground. This community is gated and secured, with key card access and 24/7 on site security.

Top guest favorite

A modern living area features a plush sectional sofa with decorative pillows, oriented towards a sleek glass coffee table. A large flat-screen TV is mounted on a stylish accent wall, with calming blue lighting enhancing the contemporary design. An open layout is visible, leading to a well-appointed kitchen.

Condo in Piarco

4.95 out of 5 average rating, 147 reviews

The Pad Luxury, 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 favorite

A saltwater pool is surrounded by tropical plants and flowering shrubs. The pool deck features beige stone tiles, and a jacuzzi is located nearby. A modern cottage structure with large windows and a staircase can be seen in the background.

Guesthouse in Saint Joseph

4.84 out of 5 average rating, 101 reviews

Vista Stays ... The Cottage

Looking for a quiet and peaceful setting away from the hustle and bustle of everyday living, look no further. Our modern cottage is set in a rainforest environment with mountain views and tropical garden for relaxation. Rejuvenate in the refreshing salt water pool and jacuzzi. 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.

Guest favorite

A serene swimming pool features a clear blue surface, surrounded by a tiled deck. Lush greenery, including potted plants, enhances the inviting ambiance. The property’s entrance includes large French doors, allowing natural light to flow into the space.

Guest suite in San Juan

4.9 out of 5 average rating, 134 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 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.