Holiday 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 favourite
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.
Apartment in Westmoorings
4.86 out of 5 average rating, 64 reviews

Westmoorings. Pool /security 2 rm - 1 bed/bthrm

A home away from home in this sought after residential area of Bayshore, Westmoorings Trinidad. This charming and cozy 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 hr security/free parking space and visitor spaces. Sofa bed for 3rd guest strictly on request.

Guest favourite
Home in Goodwood Park Extension
4.93 out of 5 average rating, 28 reviews

Luxurious Oasis 3Br. Villa with Private Pool

Luxurious villa with private pool and beautifully sculpted gardens, offering privacy and relaxed elegance. The master bedroom and spacious living room both open directly onto the pool deck, perfect for seamless indoor-outdoor living. Fully air-conditioned, modern 3-bedroom home is exceptionally spacious and includes parking for up to four cars. Ideally located on Trinidad’s Gold Coast Minutes from The Falls Mall, supermarkets, pharmacy, and walking distance to Park & Trinidad Yacht Club.

Guest favourite
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.
Apartment in Port of Spain
4.98 out of 5 average rating, 141 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 .

Superhost
Apartment in Port of Spain
4.85 out of 5 average rating, 67 reviews

Deluxe 2BR Condo • Elegant • Homey • Amazing Views

✨ About This Space ✨ Recharge, reflect, and stay productive in this classic executive 2-bedroom, 2- bath condo located in POS at One Woodbrook Place. Perfectly suited for business travelers, executives, consultants, couples, friends and family. This well-appointed space offers the ideal balance of privacy, luxury, convenience and location. Just steps away from top restaurants, entertainment and key business hubs, this home away from home is your space for productivity and relaxation.

Superhost
A private pool is framed by a wooden deck and lush greenery, creating a calm outdoor space. The surrounding building features large windows that allow light to filter in, with carefully arranged plants adding a touch of color to the environment.
Flat in Port of Spain
4.88 out of 5 average rating, 109 reviews

Carnival safe 1BR, pool, kitchen, in St. Anns

Located in an attractive and safe neighborhood our 1 bed self contained apartment features 1 queen bed, ample closet space along with a spacious living, dining and kitchen area for your comfort. Fast wifi, SmarTV with Netflix signed in, BBC, YouTube apps. The kitchen is fully equipped with utensils, small appliances, washer & dryer so everything you need is in one place. Outdoor garden and pool area to enjoy. Easy access to Port Of Spain, the Savannah, restaurants, grocery and shops.

Top guest favourite
A bright living area features a green sofa and a dark leather couch, complemented by a glass coffee table. Large sliding doors open to a balcony with outdoor seating, offering views of the mountains. Artistic decor adorns the walls, enhancing the space.
Flat in Port of Spain
5.0 out of 5 average rating, 39 reviews

Beautiful and Spacious One Woodbrook Place Apt

Beautiful and spacious apartment in One Woodbrook Place, the best located upscale residence in Trinidad & Tobago. Quiet and secure, yet steps away from restaurants, bars, clubs and main entertainment areas, some within the complex. A short walk to the Queen’s Park Savannah, the heartbeat of Port of Spain, as well as offices of multinational companies, embassies and private medical facilities.

Guest favourite
Home in Goodwood Park
4.93 out of 5 average rating, 28 reviews

Goodwood Skyline Manor

Escape to Goodwood Skyline Manor, your serene sanctuary above Port of Spain. This spacious hilltop retreat features a luxurious hot tub, a massive pool, and breathtaking panoramic views of the city. Perfect for relaxing or entertaining, the home offers peace, privacy, and plenty of room to unwind. Enjoy stunning sunsets, cool breezes, and total tranquility in this quiet, exclusive getaway.

Superhost
Apartment in Port of Spain
4.87 out of 5 average rating, 23 reviews

Luxurious 2-Bed Condo near Beach (With Pool)

Kick back and relax in this calm, stylish apartment. - Self Check-In ✅ - Gated Compound with dedicated parking 🔐 - 5 minutes away from Massy Supermarket, Superharm (pharmacy), Starlite (pharmacy) and Box Park (food hub) 👌🏾 - 25 minutes from Maracas Bay 🏝️ - 15 minutes from Ariapita Avenue 🍱 Perfect for travelers or business professionals.

Guest favourite
Flat in Carenage
4.86 out of 5 average rating, 14 reviews

Luxury 3 BR, Ocean view, Pool, 10 mins from POS

Experience the perfect blend of luxury and tranquility at Avaya, a bright and breezy island-inspired apartment in Glencoe, Trinidad and Tobago. Enjoy spacious accommodations with three bedrooms, a refreshing swimming pool, and modern amenities. Perfect for events, this apartment offers a serene escape with easy access to local attractions.

Top guest favourite
A serene pool area is surrounded by lush greenery, featuring a stone wall and a gentle waterfall. Comfortable lounge chairs are positioned nearby, enhancing the tropical ambiance. The garden's vibrant plants contribute to a peaceful retreat, inviting relaxation in the outdoor space.
Guest suite in Port of Spain
4.91 out of 5 average rating, 132 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.

Guest favourite
A view of lush green trees and landscaped areas is presented, alongside urban structures and distant mountains under a clear blue sky. The scene captures an inviting balance of nature and modern architecture, enhancing the tranquil atmosphere of the surrounding area.
Flat in Port of Spain
4.89 out of 5 average rating, 46 reviews

One Woodbrook Place

Welcome to our chic 3-bedroom apartment in the city's most coveted area! Spacious and offering stunning views, it's an urban oasis. On-site perks include restaurants, bars, a gym, a bank, and even a night club. Ideal for a luxurious and convenient stay. Your urban escape awaits!

Guest favourite
A spacious studio room displays a cozy seating area with a dark blue chair and a floral-patterned sofa. Two single beds are positioned along one side, complemented by a large window dressed with bright yellow drapes, allowing ample natural light. A television stands on a wooden console.
Flat in Gaspar Grande
4.72 out of 5 average rating, 71 reviews

Gasparee island Studio

You will love this bright, clean, spacious apartment which has its own private patio perfect for outdoor dining while you take in the amazing views of the Gulf. This beautiful island retreat is the perfect place to Rest and Recharge.

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