Top 11 Villas With Pool In Tobago - Updated 2024

| 5 min read

Christopher Columbus saw Tobago for the first time and named it “Belaforme.” It seemed beautiful from a distance, he thought. The shape of the island recalled a snail, a giant snake, and a fat cigar. Tobago is one of the two main islands in the country of Trinidad and Tobago in the West Indies, the closest of the Caribbean chain to South America. Tobago is much smaller, and the perfect place to hang a hammock between trees and drink something cool and refreshing. Leave Trinidad’s busy streets and head for Tobago’s rainforest reserves, exquisite bays, and welcoming villages. Fortunately for you, there are many accommodation options here. In particular, vacation rentals with pools in Tobago are abundant, and some of these rentals are fancy villas. If you’d like to stay in one, check out this list of the top villas with pool in Tobago.

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on May 21, 2024.

1. Idyllic villa nestled in the hills (from USD 248)

Whisk yourself and your loved ones away to paradise and book this idyllic villa in Tobago. This 3,000-square-foot (278.71 square-meter) property is situated in the hills above the Mount Irvine golf course, so you can enjoy stunning panoramic views of the hills, valleys, and ocean. You’re also close to some of Tobago’s best beaches, so feel free to sunbathe on the sandy shores and surf along the waves whenever you want.

This property is also beautifully furnished. The four beds can sleep seven people, and the kitchen has everything you need to prepare gourmet meals like a professional chef. For entertainment, you can stream movies on the smart television or play games with your companions.

Outside, you can find a kidney-shaped pool, perfect for a refreshing swim. There’s also a lush garden with flowers, butterflies, and seasonal fruits, such as avocados, oranges, and mangoes.

Stayed at this property?
Prospect, Tobago, Trinidad and Tobago
7.18 km (4.5 mi) from Xanda Tours & Rentals
villa 6 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
on a more practical level some bathroom updates and new kitchen cutlery and pots would be nice
the house is well decorated and well equipped especially in the kitchen which had everything we needed
pool was clean villa was nice and very airy
the villa was beautiful clean and with a view
the villa itself is airy spacious clean comfortable and details well thought out
the staff was very accommodating and helpful
the management team was excellent and responsive
keston was wonderful and so helpful
well equipped for all our needs lovely staff
the owners also provide all the basics in the kitchen which is very helpful
beaches are close by or a short drive beautiful
Read more reviews

2. Lovely villa in an exclusive gated community (from USD 338)

At 2,000 square feet (185.81 square feet), this lovely villa is spacious enough for large groups. With 5 beds, it can sleep a maximum of 10 people. Its kitchen is gorgeous and equipped with all the essential appliances and utensils, so you can prepare meals like a seasoned chef. Plasma television and WiFi access are provided as well for entertainment.

When the weather gets too hot, cool down by diving into the pool. You can also travel to several beaches if you prefer the ocean. Other attractions worth visiting here include Gulf City Mall, The Kimme Museum Institute, and Fort Milford.

Stayed at this property?
Canaan, Tobago, Trinidad and Tobago
3.37 km (2.1 mi) from Xanda Tours & Rentals
Wheelchair accessible Visual Aid: Braille
villa 10 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
the manager was very helpful
our host was a very pleasant and welcoming lady who responded efficiently whenever we needed any assistance
merle is excellent and very responsive and the property itself is lovely
house was in the perfect location for a weekend getaway and was in excellent condition
i would say it is a comfortable place to stay and a great neighborhood for kids
Read more reviews

3. Private oasis with saltwater pool (from USD 500)

This thoughtfully decorated suite in Tobago redefines Caribbean hospitality and luxury. Despite the many comforts of this luxury villa in Tobago, you’d want to spend a lot of time by the pool or savor wonderful sensations in the multi-level saltwater pool. The high-end facilities give justice to the name Nirvana, especially when you can arrange the services of a personal chef and have groceries brought to you. The luxury villa’s yard is equipped for a game of lawn croquet, and you can take quiet walks in the back garden. This exceptional Airbnb villa in Tobago is furnished for eight guests.

Stayed at this property?
Tobago, Trinidad & Tobago
8.47 km (5.3 mi) from Xanda Tours & Rentals
72 reviews   Superhost Wifi Available
Entire villa 5 Beds 10 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 10

Top guest reviews
it is spacious clean and well equipped
the kitchen is spotlessly clean spacious and very well equipped
the pool area is clean and perfect for sunbathing
ally’s place was really chic modern and clean
the owners and staff were extremely responsive friendly and helpful throughout my stay
both the the host (ally) and the attendant (erla) were great and super attentive
the most fabulous villa i have stayed in tobago friendliest most attentive host and staff
the villa attendant was extremely friendly and kind which made for a memorable experience overall
ally and sophia were excellent hosts always there for any question and very attentive
plus it's close to a couple of great beaches
Read more reviews

4. Well-kept villa with private pool (from USD 240)

Canaan is a small village, but you don’t go there for shopping or fine dining. There is a villa in Canaan that is big enough for eight guests and comes with a private pool. The poolside and verandah together make up an open, airy space for barbecues or lazy afternoons lounging in chairs and hammocks. Count on the breeze and the peaceful community of Samaan Grove for a relaxing stay in Tobago. Air-conditioned bedrooms to counter the tropical heat and humidity should keep you comfortable after a long day of sun and surf at Pigeon Point and Store Bay.

Stayed at this property?
Canaan, Tobago, Tobago, Trinidad & Tobago
3.02 km (1.9 mi) from Xanda Tours & Rentals
71 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 4 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the entire space is nicely appointed and has much more room than depicted in the images
the villa was great the place is relaxing picturesque and had all of the ammenties for a comfortable stay
the place was clean the pool was clean and safe
clean and more than comfortable
everything was clean and nice and had everything you might think of
samsara villa is a very clean well kept villa
place was very clean and secured
marleis was a great host
the host was very hospitable as well as the manager thank you for everything
great host villa as pictured in a safe lovely environment
the area is safe staff and residents in the community were kind
prompt responses and very friendly
marleis' place is a great location to stay
i would recommend visitors stay at marleis'place
Read more reviews

5. Breezy retreat with a vast swimming pool (from USD 390)

A villa located in Sugar Hill in Mt. Irvine is a spacious and well-equipped Airbnb that keeps cool year-round. See the surrounding trees swaying in the breeze. The open plan layout and rambling rooms offer adequate space for as many as ten guests. The outdoor swimming pool is equally generous with space, and there are places around the poolside to lounge. The second-level verandah is the best place to watch the sunset and Buccoo Reef. A golf resort and a favored beach are a short drive away.

Stayed at this property?
Mt. Irvine, Tobago, Trinidad & Tobago
5.29 km (3.3 mi) from Xanda Tours & Rentals
68 reviews   Superhost Wifi Available
ENTIRE HOME 7 Beds 10 Guests 5 Bedrooms 5 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
very spacious property with all the necessary amenities for a comfortable stay
pool was absolutely amazing with breathtaking views
i loved the fresh flowers on the tables and that each room had its own name/theme
the house pool and the grounds were clean and well maintained
the accommodation was very clean and there was plenty of space for everyone
the villa was clean and near tourist attractions
the host is equally great
highly recommend this place and host
this is not my first stay at joie de vivre because the house and the host are both great
housekeeper yvette was very hospitable and friendly
beautiful house with a fabulous location
it is close to the capital and local attractions yet quiet and peaceful
Read more reviews

6. Secure getaway with child-friendly pool (from USD 320)

Head straight to this self-catering Airbnb and you’ll find out soon enough why it’s the perfect vacation home for a family of 10. Settle into comfortable surroundings, and sink into clean and plush covers. You can stock up on supplies and cook meals during your stay. The sparkling waters of the private pool will make you want to take a dip. Lounging on the covered patio after a swim should keep the tropical heat at bay. Villa 83 is a place where you can relax and feel secure so make the most out of it.

Stayed at this property?
Trinidad & Tobago
2.87 km (1.8 mi) from Xanda Tours & Rentals
43 reviews   Superhost Wifi Available
Entire villa 5 Beds 10 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
the air conditioning worked amazingly well
beautiful facility with great amenities
beautiful villa with a lovely pool and outside entertaining area
villa 83 is a wonderfully situated stay; exceedingly comfortable well-designed and infinitely relaxing
having the pool was amazing our children utilized it every day
clean modern and with beautifulfurnishings
the villa is beautifully decorated with comfortable beds and clean linens
remarkably clean spacious and carries all the necessary amenities
the villa itself has all the necessities you could want well kept and very clean
the hosts were very pleasant and accommodating
the host made our stay extra special
they were also very responsive and quick to answer any questions i had
farley was also very responsive and accommodating; and i will definitely be back
what a wonderful experience - the 2 ladies that greeted us were friendly and helpful
it was safe super comfortable and well located would definitely stay here again
great location even better service
truly a gem beautiful space convenient location and gracious hosts
great location and awesome amenities
everything was perfect the location very safe spot the pool is amazing the house was sparkling clean
Read more reviews

7. Western Tobago villa with heated pool (from USD 120)

Imagine yourself spending hours on a sun deck of a lovely vacation home with the ocean nearby. If that’s how you want to spend the holidays, then book this cheap villa with a pool in Tobago. Aside from the sun deck and heated pool, the villa has a covered terrace that overlooks a tropical garden. Put the barbecue grill to good use and eat your meals on the villa’s adorable terrace. As soon as you’re ready to call it a day, the villa’s well-appointed bedrooms will surely give you the good night’s rest you deserve.

Stayed at this property?
Lowlands, Western Tobago, Trinidad and Tobago
7.23 km (4.5 mi) from Xanda Tours & Rentals
villa 4 Guests 2 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
the property would benefit from an outside ceiling fan as it's very hot when there is no breeze
excellent facility with all the mod cons
the kitchen has every conceivable appliance that you could possibly want together with excellent pots and pans
the heated pool is fantastic and we thoroughly enjoyed this feature
the villa is extremely well maintained including the private pool and is well equipped for self-catering
the villa was clean and very comfortable
the place is clean secure and very very comfortable
very spacious and clean with everything you need provided
hassle free booking clean and comfortable
comfortable clean and everything you would want in a rental property that makes you feel like you’re at home
a car is required and the owners are more than happy to help organise car hire
nigel is an excellent host always available to contact before and during our stay
it was a very relaxing and the owner made things easier locating a car for us to move around
the owner was always responsive and accurate in providing the best information
nigel was very helpful with everything and helped in hiring a car and transfers
property is well presented in an ideal peaceful location
the property and the location is indeed fantastic
the villa is also close to grocery stores within an easy drive
what a great location really lovely villa very very relaxing
location is excellent with several security guards along the way
Read more reviews

8. Lovely vacation home with hot tub (from USD 90)

A vacation in the Caribbean is all about gazing at sunsets on the horizon. Wake up to the sounds of the ocean. You will want to spend a lazy afternoon under the tropical sun. The beaches that make Tobago a tourist destination are a short drive away. You can stare at the sea while soothing your aching muscles in the hot tub or go swimming in the pool. This vacation home is available for four guests looking for a long-term booking.

Stayed at this property?
Scarborough, Tobago, Trinidad and Tobago
11.49 km (7.2 mi) from Xanda Tours & Rentals
villa 4 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
the villa is very well appointed and designed and has all the requirements for a very comfortable stay
nice and relaxing to sit in the pool on those hot days
the infinity pool is an absolute delight
the outdoor shower was spacious and delightful to bathe in on warm sunny mornings
the place was very clean and well taken care of
marlon was a perfect host and kept things running smoothly
everyone was so helpful once you called your got a response
the physical space created by the builders/owners is magnificent
she was always prompt in getting back to me friendly courteous thoughtful and knowledgable
for us it was the perfect distance from town--we love to walk
i will recommend walking with a few major utensils fry pan can opener etc
Read more reviews

9. Family lodging with pool near golf course (from USD 186)

The best kinds of vacation homes are the ones that offer familiar comfort and excellent amenities. This four-bedroom villa with a swimming pool in Tobago can accommodate eight people and has modern appliances and a deck. The outdoor space is furnished for family gatherings. There is a barbecue grill on the deck and a hot tub right beside the pool. This Tobago family villa is right next to a golf course so you can surely tee off in the Caribbean.

Stayed at this property?

6.45 km (4.1 mi) from Xanda Tours & Rentals
31 reviews   Wifi Available
villa 8 Guests 4 Bedrooms 6 Bathrooms

Accommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
what i liked most about the place was above the kitchen had a gorgeous view of the sky
i enjoyed the comfort of the villa the furniture was comfortable and was well equipped
it was clean comfortable and well equipped
it was clean well kept and the kitchen was well equipped
the villa was spacious clean and fully equipped
owner and manager was super helpful
the resort security staff were all helpful and courteous
the grounds were well maintained and we met so many staff members happy to engage in conversation
the people of tobago i find so kind and friendly
the villa owners are warm and accommodating and really try to please
i enjoyed also the one so close at canoe resort
i also liked that i can walk in the evenings around the golf course
Read more reviews

10. Exquisite hideout by the sea

If you’re partial to the blue-green shades of the Caribbean Sea, then book a Vrbo property on Bacolet called Emoyeni. This luxury villa brings you right to the edge of the effervescent waters. This property has four bedrooms for eight guests. The glass doors and balconies would appeal to you because they offer uninterrupted views. An infinity pool exclusive to guests could be the best place to observe the sea. You can also sit on the gazebo and contemplate the stunning vistas. Use its modern conveniences and marvel at the inspired architectural features. The house is adorned with a verdant courtyard and garden of local trees and flowering plants. Emoyeni Villa brings together the beauty of land and sea effortlessly.

Stayed at this property?
Scarborough, Western Tobago, TT
8 Guests 4 Bedrooms 4 Bathrooms

11. Beautiful villa for eight

Check out this sought-after Airbnb vacation home in Scarborough, the capital city of Tobago and home of the formidable 18th-century Fort King George. The striking Balinese inspiration is evident in the exterior. The sun deck is put to good use with the addition of a koi pond, hot tub, and swimming pool. While modern and furnished with all the convenience of a luxury hotel suite, you will want to bask in the relaxing interiors of the elegant wooden home. All you need to do is figure out where to go exploring for the day. Delicious meals and meticulous housekeeping are yours when you book this splendid Caribbean getaway for eight travelers.

Stayed at this property?

12.23 km (7.6 mi) from Xanda Tours & Rentals
23 reviews   Superhost Wifi Available
Entire villa 4 Beds 8 Guests 4 Bedrooms 6 Bathrooms

Accommodates: 8

Top guest reviews
the staff is very accommodating and efficient
the staff led by the amazing rena are just wonderful
if you are looking for a family vacation it’s the perfect location
walk and safe the water is clear and warm
great villa with a lovely charm to it location is perfect
Read more reviews

Go for an extraordinary holiday

Tobago dares you to go beyond the ordinary. If you’re looking for the best places to stay with a pool in Tobago, check out the rentals mentioned above. This holiday season, treat yourself to a luxurious vacation and book one of the properties above for a few days.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Deanna Kathrina, a pediatric physical therapist specializing in neurodevelopmental disability, serves as a teacher and advocate. As a lifelong learner, she enjoys the company of music and aspires...Read more

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