
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.
4.86 out of 5 average rating, 65 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.
4.82 out of 5 average rating, 33 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 .
4.98 out of 5 average rating, 144 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.
4.85 out of 5 average rating, 74 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.
4.87 out of 5 average rating, 111 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.
4.95 out of 5 average rating, 43 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.
4.9 out of 5 average rating, 31 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.
4.9 out of 5 average rating, 31 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.
4.91 out of 5 average rating, 132 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.
4.72 out of 5 average rating, 71 reviews
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
4.83 out of 5 average rating, 18 reviews
One Living OWP
Our Place is centrally located in the heart of all the activities in Port of Spain, the Capital of Trinidad and Tobago.
4.79 out of 5 average rating, 14 reviewsPopular amenities for Diego Martin rentals with a pool
House rentals with a pool

Luxury Westmoorings Family Villa with Pool
5.0 out of 5 average rating, 8 reviews
Villa Buena Vida, Westmoorings, Diego Martin
4.63 out of 5 average rating, 8 reviews
Pandora's Zen
5.0 out of 5 average rating, 15 reviews
Oasis in Port of Spain with private pool
4.71 out of 5 average rating, 41 reviews
Breathtaking views
4.88 out of 5 average rating, 17 reviews
Kasanya Suites
4.83 out of 5 average rating, 59 reviews
Ankara Hill
4.92 out of 5 average rating, 13 reviews
Stylish 3 Bdr close to Port of Spain
4.86 out of 5 average rating, 14 reviewsApartment rentals with a pool

*Spec VClose to POS:Peaceful 2BR Apt
4.9 out of 5 average rating, 29 reviews
City Scape Vacation property! (OWP)
4.98 out of 5 average rating, 45 reviews
*Luxurious Condo in One Woodbrook!* PoS *Carnival*
4.98 out of 5 average rating, 49 reviews
Luxury Condo with Amenities on the Sea
4.85 out of 5 average rating, 82 reviews
Spacious 3 bedroom condo in the heart of it all
4.85 out of 5 average rating, 55 reviews
West Hills Condo Petit Valley Pool 24hr Security
5.0 out of 5 average rating, 6 reviews
Opal Suite #1
4.89 out of 5 average rating, 9 reviews
Stacy's Place Apartment #4
4.86 out of 5 average rating, 7 reviewsOther holiday rentals with a pool

One Woodbrook Place
4.87 out of 5 average rating, 47 reviews
One Woodbrook Place
4.86 out of 5 average rating, 90 reviews
Beautiful and Spacious One Woodbrook Place Apt
5.0 out of 5 average rating, 40 reviews
One Great Place to Stay
4.9 out of 5 average rating, 60 reviews
Upscale 2-beds, 2 baths oasis
5.0 out of 5 average rating, 10 reviews
Le Lux Royale
4.64 out of 5 average rating, 14 reviews
Enchanted Garden Oasis - OWP
4.94 out of 5 average rating, 17 reviews
Luxury 1-Bd Apt Woodbrook
5.0 out of 5 average rating, 7 reviewsDestinations to explore
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- Rentals with pools Trinidad and Tobago





