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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  Trinidad and Tobago

  4.  Western Tobago
  5.  Plymouth
  6.  Fort Bennett

Refine your search

Price per night

Amenity Filter

Rating

239 Best Vacation Rentals with Pool in Fort Bennett (Starting from $75)

Starfish Tobago
Starfish Tobago
Resort
Scarborough, Trinidad and Tobago
0.8k from Fort Bennett center

Accommodations, Pools, Resorts, Parking, Romantic, 3-star, Lodgings, Beach, Jacuzzis

125 Bedrooms8 Guests
6.5

Good

351 reviews

$255
Average price / night
Check Availability
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
Check Availability
Birdie's Nest
Birdie's Nest
Apartment
Black Rock, Trinidad and Tobago
1.6k from Fort Bennett center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach

1 Bedroom2 Guests
8.9

Fabulous

9 reviews

$130
Average price / night
Check Availability
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
Check Availability
On the Beach
On the Beach
Apartment
Black Rock, Trinidad and Tobago
1.6k from Fort Bennett center

Parking, Security/Safety, Pool, Internet, Guest Services, Air Conditioner, Balcony/Terrace

1 Bedroom3 Guests
8.8

Fabulous

6 reviews

$113
Average price / night
Check Availability
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
Check Availability
Birdies Nest Upper 2 Bedroom Beach View
Birdies Nest Upper 2 Bedroom Beach View
Cabin
Black Rock, Trinidad and Tobago
1.6k from Fort Bennett center

Accommodations, Pools, Parking, Lodges, Lodgings, Places to stay, Family

1 Bedroom6 Guests
New to Booking
$204
Average price / night
Check Availability
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
Check Availability
Plantation Beach Villas
Plantation Beach Villas
Villa
Fort Bennett, Plymouth, Western Tobago, Trinidad and Tobago
2.3k from Fort Bennett center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

18 Bedrooms42 Guests
8.8

Fabulous

16 reviews

$536
Average price / night
Check Availability
Cabana 1 with private garden
Cabana 1 with private garden
Apartment
Plymouth, Trinidad and Tobago
1.4k from Fort Bennett center

Barbecue, Internet, Kitchen, Microwave, Outdoor Space, Patio, Pool, Toys, TV

1 Bedroom4 Guests
New to Booking
$114
Average price / night
Check Availability
La Jolie - Luxury Ocean View Villa
La Jolie - Luxury Ocean View Villa
Villa
Black Rock, Trinidad and Tobago
2.7k from Fort Bennett center

Luxury, Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings

4 Bedrooms8 Guests
8.9

Fabulous

40 reviews

$376
Average price / night
Check Availability
Cozy fully furnished apartment. Five walking distance from the beach.
Cozy fully furnished apartment. Five walking distance from the beach.
House
Black Rock, 00000, Trinidad and Tobago
1.5k from Fort Bennett center

AC, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, Outdoor Space, Pool

1 Bedroom1 Guest
New to Booking
$75
Average price / night
Check Availability
Villa Ananda Tobago
Villa Ananda Tobago
Villa
Trinidad and Tobago
3.2k from Fort Bennett center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

6 Bedrooms15 Guests
New to Booking
$1050
Average price / night
Check Availability
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
Check Availability
Reef Utopia Tobago
Reef Utopia Tobago
Villa
Mount Irvine, Trinidad and Tobago
3.3k from Fort Bennett center

Parking, Internet, Balcony/Terrace, Air Conditioner, Pool, Security/Safety, Child Friendly

1 Bedroom8 Guests
New to Booking
$334
Average price / night
Check Availability
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
Check Availability
Villas at Stonehaven
Villas at Stonehaven
Resort
Fort Bennett, Plymouth, Western Tobago, Trinidad and Tobago
3.7k from Fort Bennett center

Luxury, Accommodations, Pools, Resorts, Parking, 4-star, Lodgings, Places to stay, Family

14 Bedrooms19 Guests
9.7

Exceptional

16 reviews

$546
Average price / night
Check Availability
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
Check Availability
Tobago Hibiscus Golf Villas & Appartments
Tobago Hibiscus Golf Villas & Appartments
Apartment
Mount Irvine, Trinidad and Tobago
4.1k from Fort Bennett center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Pet-friendly, 4-star, Lodgings, Vacation rentals

10 Bedrooms32 Guests
8.9

Fabulous

104 reviews

$195
Average price / night
Check Availability
 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
Check Availability
Nature surrounded apartment w/pool and 5 minuets away from the beach!
Nature surrounded apartment w/pool and 5 minuets away from the beach!
Apartment
Plymouth, Tobago, Trinidad and Tobago
1.6k from Fort Bennett center

AC, Free Parking, Internet, Kitchen, Laundry, Microwave, Outdoor Space, Pool, TV

1 Bedroom3 Guests
New to Booking
$95
Average price / night
Check Availability
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
Check Availability
Beachfront 1 Bedroom Family Apartment on Courland Bay with Salt Water Pool.
Beachfront 1 Bedroom Family Apartment on Courland Bay with Salt Water Pool.
House
Black Rock, 11702, Trinidad and Tobago
1.7k from Fort Bennett center

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

1 Bedroom4 Guests
9.8

Exceptional

8 reviews

$126
Average price / night
Check Availability
Beach front, with infinity pool.
Beach front, with infinity pool.
Apartment
Black Rock, 0000, Trinidad and Tobago
1.7k from Fort Bennett center

AC, Dryer, Internet, Outdoor Space, Pool

1 Bedroom3 Guests
New to Booking
$108
Average price / night
Check Availability
Beachfront 1-Bedroom Apartment with Saltwater Pool Access on Great Courland Bay
Beachfront 1-Bedroom Apartment with Saltwater Pool Access on Great Courland Bay
Apartment
Black Rock, Trinidad and Tobago
1.8k from Fort Bennett center

AC, Barbecue, Dryer, Free Parking, Internet, Laundry, Microwave, Pool, TV

1 Bedroom2 Guests
New to Booking
$118
Average price / night
Check Availability
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
Check Availability
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
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 Pool in Fort Bennett.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Fort Bennett Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 239 verified vacation rentals with a pool in Fort Bennett. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Fort Bennett vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $75 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Fort Bennett offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Fort Bennett welcome pets. Currently, 11 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Fort Bennett often include additional outdoor features such as Pool, Balcony/Terrace, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Fort Bennett offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.