
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.

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.
ValueFamilyAir conditioning

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.
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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 .
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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.
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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!
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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.
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Elm's Secret Nest
Welcome to Your Cozy Home Away from Home! Escape to a relaxing haven where comfort meets convenience. Nestled in a prime location, our charming apartment is the perfect retreat for families, couples, or solo travelers. Why You’ll Love Staying Here: • Prime Location: Just minutes from popular malls, top-rated restaurants, and a well-stocked supermarket. *Complimentary coffee/ Tea *Complimentary local snacks *Netflix *Complimentary Toiletries
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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.
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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.
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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.
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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!
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Ocean View, 2 Br, Pool, 10 mins from POS
Tropical charm with ocean views. Relax in a spacious, sunlit setting that captures the warmth of the Caribbean. Perfect for a restful stay with the sound of birds nearby
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Popular amenities for Diego Martin rentals with a pool
House rentals with a pool

Stylish 3 Bdr close to Port of Spain
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Villa Buena Vida, Westmoorings, Diego Martin
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Hillcrest Apt, Cozy suite #1, Room #2 Family suite
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Oasis in Port of Spain with private pool
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Ankara Hill
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Luxury Westmoorings Family Villa with Pool
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Maraval Hilltop Views
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Pandora's Zen
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Apartment rentals with a pool

Opal Suite #1
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*Luxurious Condo in One Woodbrook!* PoS *Carnival*
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*Spec VClose to POS:Peaceful 2BR Apt
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Stacy's Place Apartment #4
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Cozy 2BR condo in Woodbrook, Port-of-Spain
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City Scape Vacation property! (OWP)
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2-bedroom condo overlooking sea
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West Hills Condo Petit Valley Pool 24hr Security
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Other holiday rentals with a pool

Luxury 1-Bd Apt Woodbrook
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Stylish Condo Escape – Peaceful, Secure & Central
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1*-bedroom Tranquil Retreat Maraval (Apt5)
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One Great Place to Stay
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Gasparee island Studio
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Luxurious/Relaxing Sands of Time - Beach Sand Apt
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Upscale 2-beds, 2 baths oasis
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One Living OWP
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