Vacation Rentals with Private Pool in Fort Bennett, Plymouth: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  Trinidad and Tobago

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  6.  Fort Bennett

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101 Best Vacation Rentals with Private Pool in Fort Bennett (Starting from $91)

Luxury 5-Bed Villa in Tobago The Big Yellow House
Luxury 5-Bed Villa in Tobago The Big Yellow House
Villa
Maryʼs Hill, Trinidad and Tobago
4.8k from Fort Bennett center

Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

4 Bedrooms10 Guests
8.0

Good

1 reviews

$343
Average price / night
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Mock Turtle is an Enchanting & Affordable Retreat!
Mock Turtle is an Enchanting & Affordable Retreat!
Villa
Black Rock, Trinidad and Tobago
0.8k from Fort Bennett center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$244
Average price / night
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Nirvana Tobago Luxury Villa with Saltwater Pool & Ocean View
Nirvana Tobago Luxury Villa with Saltwater Pool & Ocean View
Villa
Plymouth, WI, Trinidad and Tobago
0.9k from Fort Bennett center

AC, Balcony, Dryer, Extra Bed, Free Parking, Hot Tub, Housekeeping, Internet, Kitchen

4 Bedrooms9 Guests
9.4

Superb

13 reviews

$570
Average price / night
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Spacious 4-bedroom villa with en-suite baths, AC and WiFi in gorgeous Plymouth
Spacious 4-bedroom villa with en-suite baths, AC and WiFi in gorgeous Plymouth
Villa
Plymouth, Trinidad and Tobago
1.2k from Fort Bennett center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
6.0

Review score

1 reviews

$310
Average price / night
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Birdie's Nest holiday apartments are a gem, tucked away beside the beach.
Birdie's Nest holiday apartments are a gem, tucked away beside the beach.
Apartment
Black Rock, 00000, Trinidad and Tobago
1.2k from Fort Bennett center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, Outdoor Space

2 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$232
Average price / night
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Seaside 3-BR Apartment Style Villa Black Rock- Pride of Courland Tobago
Seaside 3-BR Apartment Style Villa Black Rock- Pride of Courland Tobago
Villa
Black Rock, Trinidad and Tobago
1.5k from Fort Bennett center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
8.0

Good

1 reviews

$334
Average price / night
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Birdie's Nest condo #2 with ocean view
Birdie's Nest condo #2 with ocean view
Apartment
Black Rock, 0000, Trinidad and Tobago
1.6k from Fort Bennett center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
10.0

Exceptional

12 reviews

$126
Average price / night
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Beachfront 2BR Family Apartment  Courland Bay, Saltwater Pool & Panoramic Views\n
Beachfront 2BR Family Apartment Courland Bay, Saltwater Pool & Panoramic Views\n
Apartment
Black Rock, 11702, Trinidad and Tobago
1.6k from Fort Bennett center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

7 reviews

$184
Average price / night
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 Family-Friendly Apartment - Beachfront Access/  Ocean Views /Salt Pool Access
Family-Friendly Apartment - Beachfront Access/ Ocean Views /Salt Pool Access
Apartment
Black Rock, 11702, Trinidad and Tobago
1.6k from Fort Bennett center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

13 reviews

$170
Average price / night
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Licorish by the Sea is splendidly set and secure!
Licorish by the Sea is splendidly set and secure!
House
Black Rock, Trinidad and Tobago
1.7k from Fort Bennett center

AC, Dryer, Internet, Laundry, Microwave, No Smoking, Outdoor Space, Patio, Pool

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$321
Average price / night
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Robbie's Place Tobago # 2 bedroom apartment
Robbie's Place Tobago # 2 bedroom apartment
Villa
Black Rock, Trinidad and Tobago
1.8k from Fort Bennett center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
New to Booking
$159
Average price / night
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Kapinjala With Jacuzzi, Infinity Pool And Panoramic Rain Forest and Sea Views
Kapinjala With Jacuzzi, Infinity Pool And Panoramic Rain Forest and Sea Views
Villa
Plymouth, Trinidad and Tobago
1.9k from Fort Bennett center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms8 Guests
9.2

Superb

12 reviews

$363
Average price / night
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Beautiful Caribbean Retreat
Beautiful Caribbean Retreat
Villa
Grafton, 901168, Trinidad and Tobago
2.0k from Fort Bennett center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Microwave

5 Bedrooms10 Guests
10.0

Exceptional

27 reviews

$280
Average price / night
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Waterfall Villa - Pristine Condition With Splash Pool Near 4 White Sand Beaches
Waterfall Villa - Pristine Condition With Splash Pool Near 4 White Sand Beaches
Villa
Black Rock, Trinidad and Tobago
2.2k from Fort Bennett center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.2

Superb

13 reviews

$141
Average price / night
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Private Infinity Pool Overlooking the Ocean
Private Infinity Pool Overlooking the Ocean
Villa
Black Rock, 00000, Trinidad and Tobago
2.2k from Fort Bennett center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
New to Booking
$630
Average price / night
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Private Infinity Pool | Villa with an Ocean View!
Private Infinity Pool | Villa with an Ocean View!
Villa
Black Rock, 00000, Trinidad and Tobago
2.3k from Fort Bennett center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
New to Booking
$699
Average price / night
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Robbie's Place Tobago # 1 bedroom apartment
Robbie's Place Tobago # 1 bedroom apartment
Villa
Black Rock, Trinidad and Tobago
2.3k from Fort Bennett center

AC, Barbecue, Breakfast Available, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
9.4

Superb

3 reviews

$91
Average price / night
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Hibiscus - Holiday Home with the Caribbean Sea on its Doorstep!
Hibiscus - Holiday Home with the Caribbean Sea on its Doorstep!
Villa
Black Rock, N/A, Trinidad and Tobago
2.4k from Fort Bennett center

AC, Balcony, Dryer, Laundry, Microwave, No Smoking, Outdoor Space, Patio, Pool

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$528
Average price / night
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Mirage - Scenic Seaside Villa with 7 Spacious Bedrooms
Mirage - Scenic Seaside Villa with 7 Spacious Bedrooms
Villa
Black Rock, N/A, Trinidad and Tobago
2.4k from Fort Bennett center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen

7 Bedrooms16 Guests
9.0

Fabulous

4 reviews

$798
Average price / night
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\"Pellicano\" Tobago: your Personal Seaside Palace in the Caribbean
\"Pellicano\" Tobago: your Personal Seaside Palace in the Caribbean
Villa
Black Rock, N/A, Trinidad and Tobago
2.4k from Fort Bennett center

AC, Dryer, Free Parking, Hot Tub, Laundry, Microwave, No Smoking, Outdoor Space, Patio

5 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$749
Average price / night
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Luxury Villa | Private Infinity Pool + Free Wi-Fi
Luxury Villa | Private Infinity Pool + Free Wi-Fi
Villa
Black Rock, 00000, Trinidad and Tobago
2.5k from Fort Bennett center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms7 Guests
New to Booking
$1050
Average price / night
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Luxury Villa | Private Infinity Pool + Ocean View
Luxury Villa | Private Infinity Pool + Ocean View
Villa
Black Rock, 00000, Trinidad and Tobago
2.7k from Fort Bennett center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
New to Booking
$939
Average price / night
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Honeybee at Sanctuary Villas
Honeybee at Sanctuary Villas
Condo
Black Rock, 111111, Trinidad and Tobago
2.8k from Fort Bennett center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
8.0

Good

1 reviews

$149
Average price / night
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Victorian Style, Spacious Bungalow 4 bedroom Villa with swimming pool.
Victorian Style, Spacious Bungalow 4 bedroom Villa with swimming pool.
Villa
Tobago, Trinidad and Tobago
3.0k from Fort Bennett center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
9.4

Superb

3 reviews

$432
Average price / night
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Reef Utopia Tobago Private Beautiful Villa,3mins Walk to Beach,Great Pool,Garden
Reef Utopia Tobago Private Beautiful Villa,3mins Walk to Beach,Great Pool,Garden
Villa
Tobago, Trinidad and Tobago
3.3k from Fort Bennett center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$365
Average price / night
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Stunning Caribbean style villa set on a peaceful hillside surrounded by  nature
Stunning Caribbean style villa set on a peaceful hillside surrounded by nature
Villa
Prospect, 120110, Trinidad and Tobago
3.5k from Fort Bennett center

Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.8

Exceptional

68 reviews

$232
Average price / night
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Hawksbill House
Hawksbill House
Villa
Grafton Beach, Trinidad and Tobago
3.6k from Fort Bennett center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$299
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Fort Bennett.

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Fort Bennett Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 101 verified vacation rentals with a private pool in Fort Bennett. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Fort Bennett vary depending on the property size, location, and travel season. Rates typically start from around $91 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Fort Bennett also welcome pets. Currently, 4 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Fort Bennett often include additional features such as Private Pool, Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Fort Bennett include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.