Vacation rentals in Enterprise

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Top-rated vacation rentals in Enterprise

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

The living area is adorned with lush greenery and features a comfortable sectional sofa. A glass coffee table rests on a light rug, while large sliding doors provide an unobstructed view of the ocean and allow natural light to fill the space.

Vacation home in Port of Spain

4.88 out of 5 average rating, 128 reviews

Jungle Oasis: Sea&City Views with Ruby Sunsets

AbriannaRating, 5 stars1 week ago

Jungle Oasis is a beautiful and relaxing escape tucked away in nature. The surroundings were peaceful and the space was clean, cozy, and well thought out. It was the perfect place to unwind and recharge. The host was helpful and made sure everything went smoothly during our stay. I’d definitely recommend this spot to anyone visiting Trinidad!

Guest favorite

The salt-water pool is illuminated by soft purple lighting, creating a calming effect at night. Surrounding the pool, the stone deck features seating areas and lush tropical plants, enhancing the serene atmosphere of the outdoor space.

Guesthouse in Saint Joseph

4.84 out of 5 average rating, 97 reviews

Vista Stays ... The Cottage

AngelRating, 5 stars2 months ago

Anthony home was an amazing stay. The view alone just over looking the mountain views the pretty trees. He has beautiful fish in his backyard. The night time is even more stunning. Jump in the hot tub and just have a up to the sky and see the stars. He was so accommodating. Whenever you need him he is there to assist you in whatever needed to be done. Highly recommend a stay here. Nice and low and the mountains have some privacy.

Superhost

The illuminated private pool and spa create a serene ambiance at night. Soft blue lighting reflects off the water's surface, enhancing the tranquil atmosphere. A gazebo is visible in the background, providing a shaded area for relaxation.

Home in Las Lomas #2

4.87 out of 5 average rating, 192 reviews

Nature Getaway Resort with private pool

TanishaRating, 5 stars1 month ago

What a great staycation. The property had, pool, pool table, basketball, badminton outside kitchen, lots of seating areas and hammocks. The place was clean and we felt very comfortable and secure. The host was also great. Will difinitely recommend.

Superhost

Apartment in Couva

4.83 out of 5 average rating, 36 reviews

Simple Serenity

KarenRating, 5 stars1 week ago

The place was clean , surrounding well kept Hot water was great, laundry accessible. The grounds are will manicured. But hard to find at first. The street entrance looks a bit unwelcome but place looks great on e you go down the road. I would stay again. Great price!

Superhost

A well-equipped kitchen features grey cabinetry and a polished countertop. Basic appliances, including a kettle and microwave, are visible. A window covered with a light curtain allows natural light, while utensils are organized neatly on the countertop, creating a functional cooking space.

Condo in Saint Helena

4.55 out of 5 average rating, 11 reviews

El Carmen Apt, 6 mins from Airport (downstairs #4)

ChristinaRating, 5 stars1 month ago

We absolutely enjoyed our stay! The house was amazing, comfortable, tvs and ac work great. Nice kitchen and shower and comfortable bed. Felt very safe and relaxing. The host was amazing and very responsive and helpful. Will definitely book here again and highly recommend

Superhost

An inviting outdoor space features a curvy swimming pool surrounded by modern lounge chairs on a grassy area. A shaded dining area with a table and chairs complements the setting, providing a perfect spot for relaxation under the blue sky.

Apartment in Port of Spain

4.79 out of 5 average rating, 28 reviews

Maraval 2BD With Pool and Mountain View | Gated

KeyshannaRating, 5 stars1 week ago

My friends and I stayed at George Anthony’s place for four days on our 2025 girls trip from April 12 to April 16. It was an amazing time the apartment feels just like home. It’s beautiful. The amenities are accurate. The view is amazing and I love the pool. We had an amazing time just enjoying ourselves there and even though it’s a shared pool, it was a great time. Everyone had a chance to use the pool even when there were people there? Everyone was respectful and friendly in the compound very nice location. I would recommend to anyone. There are a lot of food places, grocery stores and pharmacy close by just as mention. I car is needed or a personal taxi if you want to go around and do activities but the location was so central that things to do were about 20 mins out in the day. I will definitely stay there again in future trips to Trinidad.

Top guest favorite

A spacious outdoor pool is located in a well-kept area, surrounded by palm trees and planters. Stunning mountain views are visible in the background, complemented by blue skies and fluffy clouds. A paved deck with lounge areas enhances the inviting atmosphere.

Condo in Port of Spain

5 out of 5 average rating, 22 reviews

City Scape Vacation property! (OWP)

LizRating, 5 stars2 weeks ago

This is a quiet unit and the balcony view of the hills is amazing! At night, the hills light up like a Christmas tree and that light breeze makes me want to stay out there and relax. Sam responded to my questions immediately. He is approachable and respectful. For example, the unit was a little too cold for me (20 degrees C) but Sam immediately adjusted it to 23 for my comfort when I asked. Everything is close by and I could walk to the pharmacy store when I needed water and a few things that I forgot to pack for my trip (it open late). This is a clean place, easy to access and the parking is easy, well light and has lots of security people around. The front-desk people, and restaurant people downstairs, everyone, are all super friendly. I highly recommend this unit!

Superhost

The kitchen features wooden cabinetry with glass panels and a marbled countertop. A stainless-steel sink is located next to a dish drying rack. A microwave and paper towel holder are also present, contributing to a functional workspace.

Home in Diego Martin

4.77 out of 5 average rating, 26 reviews

Cozy Diamond Vale Villa

CherylRating, 5 stars1 month ago

I love Antea's home, it was very welcoming. We had fruits, coffee, water and other knick knacks ass a welcome treat. Her home was clean, questions were answered immediately and we had total privacy even though te host lives next door. I will definitely will stay again, if available.

Guest favorite

The image captures a serene waterfront view with calm turquoise waters. Rocky formations extend into the water, framed by lush green foliage. A circular patio area with a table and umbrella is visible, providing a peaceful spot for relaxation or dining, with boats seen in the distance.

Apartment in Gaspar Grande

4.71 out of 5 average rating, 63 reviews

Gasparee island Studio

AudreyRating, 5 stars1 month ago

Our stay at Rosemary's place was super peaceful and relaxing, just what we needed. We appreciated having all the necessary equipment available to make our stay comfortable. Rosemary & her brother Nigel are gems and super reactive to all demands.

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What guests are saying

Modern BonAir Oasis, Trinidad

4.89 out of 5 average rating, 9 reviews3 months ago

This home is located in a very nice area. The location is great so much close by and best of all.. the airport is only 10 mins away.All the amenities were provided, a lot of safety measures in place and my adult kids all loved the home. Cozy, comfy and well cared for home.

Home in Arouca

What guests are saying

VClose to POS Home away from H :Peaceful 2BR Apt

4.87 out of 5 average rating, 15 reviews1 month ago

We’re very grateful to Simi and Clytus for all of their great help in making our stay comfortable and enjoyable. They had everything we needed ready for us including some local treats and food so we had time to settle in and get our bearings. After our outings it was so nice to come “home” to comfort. Simi went out of her way to ensure we had everything we needed. Her recommendations for places to visit and eat were very helpful. Thanks again!!

Condo in Petit Valley

What guests are saying

Carnival Dream Stunning QPS

5 out of 5 average rating, 17 reviews3 weeks ago

This was one of the best bnb’s I have been to. The place was clean and well put together it made me feel like I was a home .The location is private and the security is amazing . Our host was very friendly and patient and understanding i would definitely recommend this to everybody . This was a definite 10/10 experience.

Apartment in Port of Spain

What guests are saying

Peaceful 3BR Luxury Villa -Pool & Modern Amenities

5 out of 5 average rating, 15 reviews6 days ago

Our stay at this Airbnb was truly unforgettable. Tucked away like a secret gem, this beautiful home felt like a hidden oasis — peaceful, lush, and full of charm. My family had a wonderful time relaxing, exploring, and simply enjoying the serene atmosphere. The home itself was stunning — spacious, tastefully decorated, and incredibly comfortable. Every detail felt thoughtful and inviting. But what truly made our stay exceptional were the hosts. They were so warm, welcoming, and accommodating from start to finish. It felt less like renting a place and more like staying with extended family. If you're looking for a tranquil escape with top-notch hospitality in Maraval, this is it. We can't wait to return!

Villa in D'Abadie

What guests are saying

Lovely 3 bedroom Condo Trincity East Gates

4.7 out of 5 average rating, 23 reviews3 months ago

Very easy check in and out process with the instructions provided. Host was also very responsive. The condo is very spacious and comfortable with accurate description following the listing. Surrounding area is very safe and secured with lots of near by restaurants. Would definitely stay here again!

Condo in Arouca

What guests are saying

Cozy Bed & Breakfast Private Room

4.96 out of 5 average rating, 24 reviews6 months ago

I was pleasantly surprised. Being that it was my first time staying at an Air B&B, everything was to my liking. It was clean, cozy and quiet . A place for relaxation 🙂. Wend is a very nice person, warm and inviting. Definitely a rare find. Will be back for sure.

Apartment in Lower Santa Cruz, San Juan,

What guests are saying

petit trou | Bayshore | Seaview 2 bedroom apt

4.82 out of 5 average rating, 33 reviews3 months ago

My stay at Michael's place exceeded all expectations.....Michael ALWAYS responded to whatever questions /requests I had. The accommodations were extremely neat...and well layed out. I definitely plan to do business with Michael for my next visit to Trinidad.......I recommend his place 100%............

Apartment in Diego Martin Regional Corporation

What guests are saying

Angelene's place - Oui Papa!

4.82 out of 5 average rating, 22 reviews1 month ago

Ramona and Pradesh are great hosts! This is my second time staying here, and I will definitely be back. Pradesh met me at check-in. He showed me some update to the entertainment center, he also shared the local events calendar, and there is an outside shower for j’ouvert and beach days. There is also a great little grocery store across the street and a little breakfast & lunch restaurant right next door to that. This place is private and mostly quiet. So, it is the perfect place to relax after carnival events or partying on the avenue.

Home in San Juan

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Popular amenities for Enterprise vacation rentals

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Pool

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Air conditioning

Stay near Enterprise's top sights

Price Plaza17 locals recommend

MovieTowne - Chaguanas14 locals recommend

Ruby Tuesday6 locals recommend

Starbucks6 locals recommend

Woodford Cafe6 locals recommend

The Rise Restaurant6 locals recommend

Other great vacation rentals in Enterprise

Guest favorite

Villa in Diego Martin

4.94 out of 5 average rating, 89 reviews

Garden Oasis 2: Villa with Private Pool

RominaRating, 5 stars2 weeks ago

Lovely place, clean and comfortable. We were very comfortable and had a great stay.

A two-story cottage stands against a lush green landscape. The balcony features wooden railings and two chairs, offering a space to enjoy the surroundings. Each floor is equipped with large windows, and the ground level includes an open area with seating and a water tank visible in the background.

Cottage in Gaspar Grande

4.8 out of 5 average rating, 5 reviews

Serene 3-bedroom cottage with pool & ocean view!

JoseRating, 5 stars4 months ago

Our small group of friend's thoroughly enjoyed our weekend get away at Brend'a home. The space was exactly as advertised and ultimately facilitated a much needed city escape in a comfortable, clean, quite, and most importantly beautiful waterfront setting. Brenda herself was extremely helpful; attentively communicating clear check-in/check-out instructions as well as furnishing any additional items that we may have needed throughout our short stay. I highly recommend this stay to anyone travelling to T&T or locals craving a relaxing weekend in the water. We definitely look forward to staying there again in the near future.

A modern kitchen showcases sleek white cabinetry and stainless steel appliances. A central island with two black stools provides a space for casual dining. Natural light is filtered through a sheer curtain, illuminating the polished surfaces and contemporary light fixtures.

Apartment in Port of Spain

4.86 out of 5 average rating, 7 reviews

2 *bedroom Tranquil Retreat

JaneaveRating, 5 stars1 month ago

Koral went above and beyond to help me with everything. Very friendly and responsive. The surroundings were serene and peaceful and I felt very safe. Looking forward to my next stay.

The exterior of the villa features a unique architecture with a steep roof and multiple gables. A spacious terrace with outdoor seating is visible, alongside large windows that enhance natural light. Surrounding greenery creates a serene atmosphere.

Apartment in Cameron

4.95 out of 5 average rating, 20 reviews

Perico Villas (Modern Eco-Living)

AdolfoRating, 5 stars62 months ago

Beautiful place surrounded by amazing nature view. Natalie was a great cohost and made sure we had everything we needed in our rooms. Very quiet and peaceful area away from the city.

Villa in Tunapuna/Piarco Regional Corporation

5 out of 5 average rating, 4 reviews

Luxury Vacation Villa in Valsayn

AnthonyRating, 5 stars4 months ago

Let tell you all something I have stay in places all over the United States and internationally and hands down this is the absolute best it’s not just a villa it’s a mansion trust me stay here no words can describe how advanced the technology in his place is and no host can match his courtesy and attentiveness. He so polite. Will stay here again and again.

A walk-in shower is displayed with smooth, light-colored tiled walls. The rainfall showerhead and sleek faucet are mounted on one wall, with a tiled floor ensuring a minimalistic design. A glass door provides accessibility while maintaining an open feel.

Home in Arima

5 out of 5 average rating, 3 reviews

Chrislou’s

EugeneRating, 5 stars1 month ago

Christina and her husband’s place was one of my most memorable stays to date. She went above and beyond to ensure my friend and I were comfortable and had a fantastic experience. Her attentiveness, hospitality, responsiveness, and kindness made our stay truly special. I highly recommend this wonderful home and would definitely visit again! Thank you again🫶🏾

Guest favorite

A modern outdoor hot tub is set within a wooden deck, surrounded by a privacy wall. The clear water reflects natural light, creating a calming ambiance. The clean lines of the tub complement the sleek design of the surrounding area.

Home in Tacarigua

4.9 out of 5 average rating, 48 reviews

The Prestige

AqeelaRating, 5 stars3 months ago

Check in was great. Damien was at the location upon arrival. He gave clear instructions about the house. There was no need to contact him during the stay. The house looks exactly like the photos. The house and its amenities is definitely worth the price. I would stay here again and I would definitely recommend this place to anyone visiting.