Vacation rentals with a pool in San Juan

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Top-rated rentals with a pool in San Juan

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

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Guest favourite

Condo in Saint Augustine

4.89 out of 5 average rating, 56 reviews

What a feeling!!!

Emerald 304 is nestled in the safe, easy-going town of St. Augustine, about 20 minutes east of the capital city and 20 minutes west of the international airport. Within 3 minute's walk there's Starbucks and SuperPharm (think Walgreens, only better), a private hospital, Scotia Bank, Tunapuna market, UWI to the left and Sir Arthur Lewis Hall to the right, the Caribbean's best eye surgery and body sculpting, and a 10-minute drive will take you to Mount St Benedict Monastery, viewable from your room

Jun. 26 – Jul. 3

$152 CAD per night

Guest favourite

Place to stay in Port of Spain

4.93 out of 5 average rating, 44 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.

Oct. 25 – Nov. 1

$312 CAD per night

Guest favourite

Home in Petit Valley

4.92 out of 5 average rating, 24 reviews

Kasanya Suites

Forget your worries in this spacious and serene space. Relax by our beautiful pool and just get lost in our quiet scenic enviroment!Our home is a place where you and yours can come and enjoy time together in a clean and secure setting. Whether its playing on our pool table, bathing in the pool, playing table tennis,or relaxing in the hot tub, we have the perfect environment to just unwind and rejuvenate! If your stay is for business or pleasure you are sure to be comfortable at Kasanya Suites!

Aug. 3 – 10

$388 CAD per night

Guest favourite

Home in Chaguanas Borough Corporation

4.98 out of 5 average rating, 49 reviews

Cheerful 2-bedroom home with a private pool.

This exclusive location is conveniently situated near all amenities, simplifying your trip planning. Situated in a secure gated community in Chaguanas, Trinidad, it features a private backyard pool. Just a one-minute drive from the highway and a mere two-minute drive from the primary shopping districts of Heartland Plaza and Price Plaza and downtown Chaguanas. Moreover, it is just a 30-minute drive from the capital, Port of Spain, and only 20 minutes from the Piarco International Airport.

Aug. 8 – 15

$188 CAD per night

Guest favourite

Apartment in Port of Spain

4.94 out of 5 average rating, 89 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.

Aug. 27 – Sep. 3

$213 CAD per night

Guest favourite

Condo in Piarco

4.94 out of 5 average rating, 52 reviews

Modern Condo in 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.

Sep. 1 – 8

$214 CAD per night

Guest favourite

Guest suite in San Juan

4.92 out of 5 average rating, 111 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.

Oct. 11 – 18

$150 CAD per night

Guest favourite

Apartment in Port of Spain

5.0 out of 5 average rating, 9 reviews

Perfect location/ Pool - White Sand Apt

Welcome to “Sands of Time”, a secure compound with beautiful apartments. This apartment, which is named “White Sand” is perfect if you like a little bit of everything. Top-tier location. Comfortable living. Stylish and modern amenities. A place to retreat. You can choose to enjoy coffee on your private patio or lounge by the poolside. Also, if you are a nature lover, take advantage of the patio between 4:30 -5:30 pm as you see flocks of birds returning to their homes.

Dec. 18 – 25

$177 CAD per night

Guest favourite

Apartment in St Joseph

4.78 out of 5 average rating, 23 reviews

Vista Stays ... Garden View

Need to get away for that much needed staycation or from the hustle and bustle of everyday living. Look no further, this modern self contained space captures the tranquility and beauty of the rainforest and affords the conveniences that you are used to at home. 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.

Dec. 10 – 17

$133 CAD per night

Guest favourite

Vacation home in Port of Spain

5.0 out of 5 average rating, 28 reviews

Le Chalet

Located 25 minutes from the airport and nestled in the hills of Maracas valley, this cabin is just a 7 minute drive from the trail head of the highest waterfall in Trinidad at 300 feet and 3 minute drive from the hummingbird sanctuary. Also located nearby is the Ortinola estate where you can make your own chocolate and Horses Helping Humans that offer horseback riding. Please feel free to ask about airport transfers and additional tours of the island that we offer.

Aug. 6 – 13

$350 CAD per night

Superhost

Home in Las Lomas #2

4.86 out of 5 average rating, 175 reviews

Nature Getaway Resort with private pool

Lovely 2 bedroom home plus loft with resort type amenities tucked away in the woods but just a 10 min drive from the airport. The house comes equipped with a full kitchen which includes - Gas burner stove/oven, double door refrigerator, dish washer, microwave and toaster oven. All utensils and cookware is included. There is a private pool (heated if required) with gazebo. There are four (4) hammocks for relaxing, kids play park with two slides and swings.

Sep. 16 – 23

$299 CAD per night

Guest favourite

Guest suite in Port of Spain

4.89 out of 5 average rating, 111 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.

May 15 – 22

$189 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for San Juan rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

Home in Tunapuna/Piarco Regional Corporation

5.0 out of 5 average rating, 7 reviews

Esther’s Retreat:

Aug. 26 – Sep. 2

$768 CAD per night

Guest favourite

Home in Tunapuna/Piarco Regional Corporation

4.83 out of 5 average rating, 12 reviews

Tunapuna/St Augustine: 3 Bed, 4 Bath, Pool, Garden

Sep. 25 – Oct. 2

$300 CAD per night

Home in San Juan

4.83 out of 5 average rating, 18 reviews

Modern Home 2 Bedrooms and Pool

Mar. 25 – Apr. 1

$297 CAD per night

Home in Port of Spain

4.72 out of 5 average rating, 18 reviews

Four bedroom oasis in town with private pool

Aug. 21 – 28

$239 CAD per night

Home in Port of Spain

5.0 out of 5 average rating, 5 reviews

Ankara Hill

Sep. 13 – 20

$456 CAD per night

Guest favourite

Home in Arima

4.89 out of 5 average rating, 9 reviews

The Relaxant

Mar. 28 – Apr. 4

$234 CAD per night

Home in Port of Spain

4.76 out of 5 average rating, 17 reviews

Westmoorings 4 Bed Home | With Pool | Gated

Sep. 18 – 25

$376 CAD per night

Home in Gaspar Grande

4.57 out of 5 average rating, 14 reviews

DDI Island home with pool and private jetty

Dec. 16 – 23

$517 CAD per night

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Condo rentals with a pool

Guest favourite

Condo in Westmoorings

4.86 out of 5 average rating, 28 reviews

Secure gated compound,pool,1bd 1bth. Bayshore Pos

Jul. 10 – 17

$142 CAD per night

Guest favourite

Condo in Port of Spain

4.88 out of 5 average rating, 32 reviews

Cozy 2BR condo in Woodbrook, Port-of-Spain

Sep. 14 – 21

$211 CAD per night

Guest favourite

Condo in D'Abadie

5.0 out of 5 average rating, 22 reviews

Piarco Area Luxury 3 bedroom condo with Pool

Oct. 2 – 9

$211 CAD per night

Superhost

Condo in Port of Spain

4.73 out of 5 average rating, 26 reviews

Woodbrook Place One LuXurious Apartments

Dec. 13 – 20

$398 CAD per night

Guest favourite

Condo in Port of Spain

5.0 out of 5 average rating, 16 reviews

*Luxurious Condo in Woodbrook! *

Jul. 29 – Aug. 5

$292 CAD per night

Guest favourite

Condo in Port of Spain

5.0 out of 5 average rating, 80 reviews

Contemporary Port of Spain Condo

Sep. 3 – 10

$279 CAD per night

Guest favourite

Condo in Port of Spain

4.93 out of 5 average rating, 27 reviews

Great 3 bedroom condo in the heart of it all

Jul. 15 – 22

$324 CAD per night

Guest favourite

Condo in Port of Spain

4.83 out of 5 average rating, 83 reviews

Tropical St James Trinidad Seaview 24/7 Gated Park

Oct. 10 – 17

$320 CAD per night

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Quick stats about vacation rentals with a pool in San Juan

Total rentals
20 properties
Local attractions
Aranguez Savannah, The City of Grand Bazaar, and Grand Bazaar Food Court
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
80 reviews
Nightly prices starting at
$69 CAD before taxes and fees

Vacation rentals with a pool in San Juan

Top-rated rentals with a pool in San Juan

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for San Juan rentals with a pool

House rentals with a pool

Home in Tunapuna/Piarco Regional Corporation

Home in Tunapuna/Piarco Regional Corporation

Home in San Juan

Home in Port of Spain

Home in Port of Spain

Home in Arima

Home in Port of Spain

Home in Gaspar Grande

Condo rentals with a pool

Condo in Westmoorings

Condo in Port of Spain

Condo in D'Abadie

Condo in Port of Spain

Condo in Port of Spain

Condo in Port of Spain

Condo in Port of Spain

Condo in Port of Spain

Quick stats about vacation rentals with a pool in San Juan

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

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