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 April 09, 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.
Top guest reviews
Amenities & Room:
on a more practical level some bathroom updates and new kitchen cutlery and pots would be nicethe house is well decorated and well equipped especially in the kitchen which had everything we neededCleanliness:
pool was clean villa was nice and very airythe villa was beautiful clean and with a viewthe villa itself is airy spacious clean comfortable and details well thought outHost:
the staff was very accommodating and helpfulthe management team was excellent and responsivekeston was wonderful and so helpfulwell equipped for all our needs lovely staffthe owners also provide all the basics in the kitchen which is very helpfulRead more reviewsLocation:
beaches are close by or a short drive beautiful
2. Lovely villa in an exclusive gated community (from USD 319)
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.
Top guest reviews
Host:
the manager was very helpfulour host was a very pleasant and welcoming lady who responded efficiently whenever we needed any assistancemerle is excellent and very responsive and the property itself is lovelyRead more reviewsLocation:
house was in the perfect location for a weekend getaway and was in excellent conditioni would say it is a comfortable place to stay and a great neighborhood for kids
3. Private oasis with saltwater pool (from USD 486)
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.
Top guest reviews
Cleanliness:
it is spacious clean and well equippedthe kitchen is spotlessly clean spacious and very well equippedthe pool area is clean and perfect for sunbathingally’s place was really chic modern and cleanHost:
the owners and staff were extremely responsive friendly and helpful throughout my stayboth the the host (ally) and the attendant (erla) were great and super attentivethe most fabulous villa i have stayed in tobago friendliest most attentive host and staffthe villa attendant was extremely friendly and kind which made for a memorable experience overallally and sophia were excellent hosts always there for any question and very attentiveRead more reviewsLocation:
plus it's close to a couple of great beaches
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.
Top guest reviews
Amenities & Room:
the entire space is nicely appointed and has much more room than depicted in the imagesthe villa was great the place is relaxing picturesque and had all of the ammenties for a comfortable stayCleanliness:
the place was clean the pool was clean and safeclean and more than comfortableeverything was clean and nice and had everything you might think ofsamsara villa is a very clean well kept villaplace was very clean and securedHost:
marleis was a great hostthe host was very hospitable as well as the manager thank you for everythinggreat host villa as pictured in a safe lovely environmentthe area is safe staff and residents in the community were kindprompt responses and very friendlyRead more reviewsLocation:
marleis' place is a great location to stayi would recommend visitors stay at marleis'place
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.
Top guest reviews
Amenities & Room:
very spacious property with all the necessary amenities for a comfortable staypool was absolutely amazing with breathtaking viewsi loved the fresh flowers on the tables and that each room had its own name/themeCleanliness:
the house pool and the grounds were clean and well maintainedthe accommodation was very clean and there was plenty of space for everyonethe villa was clean and near tourist attractionsHost:
the host is equally greathighly recommend this place and hostthis is not my first stay at joie de vivre because the house and the host are both greathousekeeper yvette was very hospitable and friendlyRead more reviewsLocation:
beautiful house with a fabulous locationit is close to the capital and local attractions yet quiet and peaceful
6. Secure getaway with child-friendly pool (from USD 363)
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.
Top guest reviews
Amenities & Room:
the air conditioning worked amazingly wellbeautiful facility with great amenitiesbeautiful villa with a lovely pool and outside entertaining areavilla 83 is a wonderfully situated stay; exceedingly comfortable well-designed and infinitely relaxinghaving the pool was amazing our children utilized it every dayCleanliness:
clean modern and with beautifulfurnishingsthe villa is beautifully decorated with comfortable beds and clean linensremarkably clean spacious and carries all the necessary amenitiesthe villa itself has all the necessities you could want well kept and very cleanHost:
the hosts were very pleasant and accommodatingthe host made our stay extra specialthey were also very responsive and quick to answer any questions i hadfarley was also very responsive and accommodating; and i will definitely be backwhat a wonderful experience - the 2 ladies that greeted us were friendly and helpfulRead more reviewsLocation:
it was safe super comfortable and well located would definitely stay here againgreat location even better servicetruly a gem beautiful space convenient location and gracious hostsgreat location and awesome amenitieseverything was perfect the location very safe spot the pool is amazing the house was sparkling clean
7. Western Tobago villa with heated pool (from USD 121)
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.
Top guest reviews
Amenities & Room:
the property would benefit from an outside ceiling fan as it's very hot when there is no breezeexcellent facility with all the mod consthe kitchen has every conceivable appliance that you could possibly want together with excellent pots and pansthe heated pool is fantastic and we thoroughly enjoyed this featurethe villa is extremely well maintained including the private pool and is well equipped for self-cateringCleanliness:
the villa was clean and very comfortablethe place is clean secure and very very comfortablevery spacious and clean with everything you need providedhassle free booking clean and comfortablecomfortable clean and everything you would want in a rental property that makes you feel like you’re at homeHost:
a car is required and the owners are more than happy to help organise car hirenigel is an excellent host always available to contact before and during our stayit was a very relaxing and the owner made things easier locating a car for us to move aroundthe owner was always responsive and accurate in providing the best informationnigel was very helpful with everything and helped in hiring a car and transfersRead more reviewsLocation:
property is well presented in an ideal peaceful locationthe property and the location is indeed fantasticthe villa is also close to grocery stores within an easy drivewhat a great location really lovely villa very very relaxinglocation is excellent with several security guards along the way
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.
Top guest reviews
Amenities & Room:
the villa is very well appointed and designed and has all the requirements for a very comfortable staynice and relaxing to sit in the pool on those hot daysthe infinity pool is an absolute delightthe outdoor shower was spacious and delightful to bathe in on warm sunny morningsCleanliness:
the place was very clean and well taken care ofHost:
marlon was a perfect host and kept things running smoothlyeveryone was so helpful once you called your got a responsethe physical space created by the builders/owners is magnificentshe was always prompt in getting back to me friendly courteous thoughtful and knowledgableRead more reviewsLocation:
for us it was the perfect distance from town--we love to walki will recommend walking with a few major utensils fry pan can opener etc
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.
Top guest reviews
Amenities & Room:
what i liked most about the place was above the kitchen had a gorgeous view of the skyi enjoyed the comfort of the villa the furniture was comfortable and was well equippedCleanliness:
it was clean comfortable and well equippedit was clean well kept and the kitchen was well equippedthe villa was spacious clean and fully equippedHost:
owner and manager was super helpfulthe resort security staff were all helpful and courteousthe grounds were well maintained and we met so many staff members happy to engage in conversationthe people of tobago i find so kind and friendlythe villa owners are warm and accommodating and really try to pleaseRead more reviewsLocation:
i enjoyed also the one so close at canoe resorti also liked that i can walk in the evenings around the golf course
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.
Scarborough, Western Tobago, TT
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.
12.23 km (7.6 mi) from Xanda Tours & RentalsSuperhost
Accommodates: 8
Top guest reviews
Host:
the staff is very accommodating and efficientthe staff led by the amazing rena are just wonderfulRead more reviewsLocation:
if you are looking for a family vacation it’s the perfect locationwalk and safe the water is clear and warmgreat villa with a lovely charm to it location is perfect
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.
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