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Enterprise Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Enterprise vacation rentals

A modern living room with a flat-screen TV on a wooden cabinet, a kitchen area with a refrigerator and a dining table, and a hallway leading to a door.

1. El Carmen Apartments

El Carmen Apartments
4.0 star property
St. Helena
9.8 out of 10, Exceptional, (7 reviews)
"v convenient for transit passengers no headaches no hassle no waist of time pickup drop will coust you only 20usd "
United States
DEEPIKA
$93 nightly
The price is $102
Oct 10 - Oct 11
Total with taxes and fees
El Carmen Apartments
A modern living room with a sectional sofa, a glass coffee table, and a sliding glass door with a geometric design.

2. Serene 1-bedroom apt with AC in charming Chaguanas

Serene 1-bedroom apt with AC in charming Chaguanas
Chaguanas
$150 nightly
The price is $157
Oct 10 - Oct 11
Total with taxes and fees
Serene 1-bedroom apt with AC in charming Chaguanas
A modern kitchen with granite countertops, white bar stools, wooden cabinets, and a built-in microwave.

3. 3-bedroom Home with Private Jacuzzi

3-bedroom Home with Private Jacuzzi
Chaguanas
10.0 out of 10, Exceptional, (1 review)
"Once the apartment was booked, communication with the host was almost immediate. Ms. Sue was kind and thoughtful throughout the entire process, checked up on us, and ensured we had all we needed. She was available at any time we needed her and was always pleasant; even after we departed, she contacted us to inquire about our safe arrival. The environment was quiet, safe, and peaceful. If you are looking to enjoy a nice quiet vacation without the noise, and is not far from all the major areas,...
United States
Casnel
$355 nightly
The price is $372
Oct 10 - Oct 11
Total with taxes and fees
3-bedroom Home with Private Jacuzzi
A bunk bed with a small table in the middle. The table has a stack of plates, a few cups, and a bottle of hand sanitizer.

4. Sunflower Apartments Trinidad

Sunflower Apartments Trinidad
3.0 star property
Couva
8.6 out of 10, Excellent, (12 reviews)
"I come here once a year I like the privacy and secure feeling I will continue to come here as long as it is available "
United States
Anonymous traveler
$101 nightly
The price is $101
Oct 10 - Oct 11
Total with taxes and fees
Sunflower Apartments Trinidad
A living room with a ceiling fan, a brown sofa, a dining table with chairs, and a TV mounted on the wall.

5. Cosy on the Avenue | Ariapita Ave | Port of Spain, Trinidad

Cosy on the Avenue | Ariapita Ave | Port of Spain, Trinidad
Woodbrook
10.0 out of 10, Exceptional, (1 review)
"If using hot water you just turn on a switch, otherwise host in fantastic in communicating with tenants."
United States
QUEENALICIA
$120 nightly
The price is $120
Nov 2 - Nov 3
Total with taxes and fees
Cosy on the Avenue | Ariapita Ave | Port of Spain, Trinidad
A modern living room with a flat-screen TV mounted on a wall, a black sofa, and a wooden entertainment unit with shelves.

6. Your Layover- 6 Mins to the Airport fully equipped for Short and Long Stays

Your Layover- 6 Mins to the Airport fully equipped for Short and Long Stays
Kelly Village
9.6 out of 10, Exceptional, (5 reviews)
"Excellent location and customer service."
United States
Preston
$95 nightly
The price is $95
Oct 13 - Oct 14
Total with taxes and fees
Your Layover- 6 Mins to the Airport fully equipped for Short and Long Stays
A neatly made bed with grey linens and a folded towel, a painting of palm trees at sunset on the wall, and a grey curtain.

7. The Layover - 6mins from the 🛫 great for layovers and long stays - Sleeps 1-4

The Layover - 6mins from the 🛫 great for layovers and long stays - Sleeps 1-4
Chin Chin Savanna Village
10.0 out of 10, Exceptional, (2 reviews)
"The place was very clean"
United States
Bryan
$95 nightly
The price is $95
Oct 13 - Oct 14
Total with taxes and fees
The Layover - 6mins from the 🛫 great for layovers and long stays - Sleeps 1-4
A compact kitchen with a stove, oven, and refrigerator. There is a dining area with a table and chairs. A television is mounted on the wall.

8. Stewart Suite Apt -Trincity, Airport, Full Apt

Stewart Suite Apt -Trincity, Airport, Full Apt
Trincity
9.6 out of 10, Exceptional, (8 reviews)
"The accommodation is clean and the hoste was very responsive and welcoming. "
France
Anonymous traveler
$92 nightly
The price is $92
Oct 10 - Oct 11
Total with taxes and fees
Stewart Suite Apt -Trincity, Airport, Full Apt
A pool area with a covered seating area, columns, and a tiled roof.

9. Emporis Resort

Emporis Resort
3.5 star property
Arouca
$179 nightly
The price is $196
Oct 10 - Oct 11
Total with taxes and fees
Emporis Resort
A building with a dark facade, a wooden door, and a window with shutters. There are two wall-mounted lights on either side of the window.

10. A modern tiny house, big on comfort, with an urban tiny living experience.

A modern tiny house, big on comfort, with an urban tiny living experience.
Chaguanas
9.4 out of 10, Exceptional, (6 reviews)
"Our stay was amazing and surprisingly comfortable and large for a tiny home. My family enjoyed all the amenities offered and the little touches that made it feel like home away from home. Highly recommended and looking forward to our next trip."
Canada
Sherryann P.
$127 nightly
The price is $127
Oct 26 - Oct 27
Total with taxes and fees
A modern tiny house, big on comfort, with an urban tiny living experience.
A bedroom with a bed, a television on a stand, a window with curtains, and a ceiling fan.

11. Port of Spain City Studio | Central Location | AC | WiFi | Trinidad

Port of Spain City Studio | Central Location | AC | WiFi | Trinidad
Downtown Port of Spain
$113 nightly
The price is $113
Nov 1 - Nov 2
Total with taxes and fees
Port of Spain City Studio | Central Location | AC | WiFi | Trinidad
A modern kitchen with grey cabinets, a stainless steel refrigerator, and a white countertop.

12. Charming 2-bedroom apartment with WiFi, AC in fabulous Tacarigua

Charming 2-bedroom apartment with WiFi, AC in fabulous Tacarigua
Tacarigua
9.0 out of 10, Wonderful, (2 reviews)
"Very nice place. Host was very accommodating with quick replies to all my queries. Unfortunately lots of barking dogs in the neighborhood which kept me up at night."
United States
Stephen S.
$121 nightly
The price is $121
Oct 29 - Oct 30
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in fabulous Tacarigua
Exterior detail

13. Charming Piarco Home With Garden View

Charming Piarco Home With Garden View
2.0 star property
Piarco
$117 nightly
The price is $117
Oct 12 - Oct 13
Total with taxes and fees
Charming Piarco Home With Garden View
A bedroom with a bed, a nightstand, a wall-mounted lamp, a ceiling fan, a chandelier, a wardrobe, and a painting of a sunset.

14. Stewart Hotel Apt - Trincity, Airport, Full Apt

Stewart Hotel Apt - Trincity, Airport, Full Apt
Trincity
9.4 out of 10, Exceptional, (3 reviews)
"Very Good & Pleasant Apt. In a Good Area too and the host and his wife is helpful and lovely. "
United States
Lindy-Ann
$92 nightly
The price is $96
Nov 6 - Nov 7
Total with taxes and fees
Stewart Hotel Apt - Trincity, Airport, Full Apt
A room with a washing machine, a small table, and a window with curtains.

15. Charming 1-bedroom house with AC, WiFi in peaceful St. Helena Village Piarco

Charming 1-bedroom house with AC, WiFi in peaceful St. Helena Village Piarco
St helena village piarco
$184 nightly
The price is $184
Oct 10 - Oct 11
Total with taxes and fees
Charming 1-bedroom house with AC, WiFi in peaceful St. Helena Village Piarco
A modern kitchen with stainless steel appliances, white cabinetry, and a gas stove.

16. "Modern Comfort Near Airport & Shopping - The Cozy Condo"

"Modern Comfort Near Airport & Shopping - The Cozy Condo"
Arouca, Tunapuna/Piarco Regional Corporation
10.0 out of 10, Exceptional, (2 reviews)
"Great location approximately 10-15 minutes away from the airport. Close to Trincity mall with grocery. About a 30 minute drive to Port of Spain without traffic, considering all Carnival activities was in Port of Spain. The entire condo was very clean and tidy, which made our stay comfortable. The two areas of improvement in my humble opinion would be the directions received was not clear, it was challenging being a visitor to the country. But the instructions inside of the booklet at the condo I...
United States
seema p.
$119 nightly
The price is $129
Oct 11 - Oct 12
Total with taxes and fees
"Modern Comfort Near Airport & Shopping - The Cozy Condo"
A flat-screen TV on a wooden stand with a lamp beside it, displaying a home hub interface with various app icons.

17. Entire Cozy Luxe 3 BR/ 3 Bath House for Couples and Groups

Entire Cozy Luxe 3 BR/ 3 Bath House for Couples and Groups
Couva
10.0 out of 10, Exceptional, (1 review)
"This property was just as advertised. It was comfortable and inviting. Treston communicated with us to ensure we had everything we needed. If you do not have transport, you do have to walk out to get it, which we did not mind. Otherwise, the place did not disappoint at all. I would stay there again. Thank you Treston for your hospitality!"
United States
Ianna P.
$136 nightly
The price is $136
Oct 20 - Oct 21
Total with taxes and fees
Entire Cozy Luxe 3 BR/ 3 Bath House for Couples and Groups
A pool area with a view of a hill and a building in the background.

18. Flower Of Joy Wellness Villa

Flower Of Joy Wellness Villa
4.5 star property
St. Anns
5.0 out of 10, (2 reviews)
"Family of Nine Left Stranded Outside in the Dark An extremely distressing experience. I booked Flowers of Joy Wellness Villa through Hotels.com for nine family members, including my elderly mother and four children aged 7–14. The host called on check-in day and I confirmed arrival between 5–6 pm. Check-in was advertised until 9 pm. At 6:06 pm, I WhatsApped to say we were almost there; the message was delivered. We arrived at 6:20 pm, but repeated calls went unanswered. At 6:24 pm, I messaged...
United States
Bevil
$175 nightly
The price is $175
Oct 10 - Oct 11
Total with taxes and fees
Flower Of Joy Wellness Villa
A pool area with a view of a hill and a building in the background.

19. WINDCREST VILLA - Great view near Port of Spain

WINDCREST VILLA - Great view near Port of Spain
St. Anns
$116 nightly
The price is $116
Oct 10 - Oct 11
Total with taxes and fees
WINDCREST VILLA - Great view near Port of Spain
A bed with a grey sheet and pillows, a beige blanket, and a wooden nightstand.

20. Cozy Nook nestled in the Santa Cruz Valley. Queen sized bed Hot and cold shower

Cozy Nook nestled in the Santa Cruz Valley. Queen sized bed Hot and cold shower
Santa Cruz
$135 nightly
The price is $135
Oct 10 - Oct 11
Total with taxes and fees
Cozy Nook nestled in the Santa Cruz Valley. Queen sized bed Hot and cold shower
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Enterprise Hotel Reviews

Radisson Hotel Trinidad

Radisson Hotel Trinidad

10/10 Excellent
"Good breakfast friendly staff and clean room."
anthony 3-night trip
Posted 1 day ago
Radisson Hotel Trinidad

Find out more about Enterprise

Everything you need to know about Enterprise vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Enterprise vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Enterprise vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Enterprise vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Enterprise. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Enterprise in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $102 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Enterprise rentals

At Expedia, we put the best Enterprise vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Enterprise rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Enterprise vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Enterprise. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Enterprise?

Yes, we have vacation rentals near well known sights in Enterprise, or you can choose a more remote option if you want a relaxing place to stay.

What are some of the best vacation rentals that Enterprise has to offer?

Gulfview Townhouse With Pool and Jacuzzi: This vacation home rental outside of Enterprise offers an outdoor pool, a garden, and laundry facilities to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

What can I see and do in Enterprise?

Explore the area and family-friendly sights such as Emperor Valley Zoo, or get out into nature at a spot like Queen's Park Savanah. Trinidad and Tobago Civil Aviation Authority and Trincity Mall are a couple of places you'll find in the larger area.

What are vacation rentals like in Enterprise?

Vacation rentals are private accommodations you can stay in for a couple days or more in Enterprise. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips or small group gatherings.