Vacation Rentals with Pool in Trinidad and Tobago

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Filtering by: Swimming pool

139 vacation rentals

(19) Excellent 

    56

    Eagle's Base Villa

    Tobago / Prospect

    Prospect villa

    7 22 3 nights min

    • 7 bedrooms
    • sleeps 22
    • 3 nights min
    • Nearest beach 3 mi
    • Swimming pool
    • Child Friendly

    Price per night from

    $600

    Price per night from

    $600

    (3) Excellent 

      7

      Atlantis cove: beautiful Cottage above the Ocean

      Tobago / Scarborough

      Scarborough cottage

      1 3 2 nights min

      • 1 bedroom
      • sleeps 3
      • 2 nights min
      • Beach / lakeside relaxation
      • Swimming pool
      • Child Friendly

      Price per night from

      $115

      Responds fast!
      avg. 1 hour 41 minutes

      Price per night from

      $115

      (7) Very Good 

        18

        Large villa with 50ft pool in Samaan Grove Tobago

        Tobago / Canaan

        Canaan house

        3 6 3 nights min

        • 3 bedrooms
        • sleeps 6
        • 3 nights min
        • Beach / lakeside relaxation
        • Swimming pool
        • Child Friendly
        “beautiful, well maintained villa with all the comforts” We thoroughly enjoyed our stay here, it had all the amenities promised and even more. We did not feel cramped like some other vacation homes. The Bedrooms were spacious although we spend most of

        Price per night from

        $573

        Price per night from

        $573

        (10) Very Good 

          26

          Tobago three bedroom Villa with panoramic seaview, close to airport and town.

          Tobago / Prospect

          Prospect villa

          3 8 min stay varies

          • 3 bedrooms
          • sleeps 8
          • min stay varies
          • Nearest beach 0.8 mi
          • Swimming pool
          • Child Friendly
          “would stay here again!” We very much enjoyed our stay at this villa. The owner was easy to deal with, very pleasant and efficient with communication. The villa itself is in a great location, with good amenities close by. The local bar is a great pla

          Price per night from

          $241

          Responds fast!
          avg. 2 hours 13 minutes

          Price per night from

          $241

          (24) Excellent 

            16

            The Marion Villa

            Tobago / Bacolet Bay

            Bacolet Bay villa

            3 6 3 nights min

            • 3 bedrooms
            • sleeps 6
            • 3 nights min
            • Beach / lakeside relaxation
            • Swimming pool
            • Suitable for children age 5+

            Price per night from

            $400

            Price per night from

            $400

            (1) Excellent 

              26

              Luxury Villa with Pool, Hot Tub, Steam Room & Steps down to Surf of Mt Irvine

              Tobago / Mount Irvine

              Mount Irvine villa

              4 8 4 nights min

              • 4 bedrooms
              • sleeps 8
              • 4 nights min
              • Nearest beach 0.6 mi
              • Swimming pool
              • Child Friendly

              Price per night from

              $401

              Price per night from

              $401

                12

                Macaw

                Tobago / Canaan

                Canaan villa

                4 12 min stay varies

                • 4 bedrooms
                • sleeps 12
                • min stay varies
                • Swimming pool
                • Child Friendly
                • Air conditioning

                Price per night from

                $456

                Price per night from

                $456

                (9) Very Good 

                  10

                  Kilgwyn Bay Getaway

                  Tobago / Bon Accord

                  Bon Accord townhouse

                  2 5 2 nights min

                  • 2 bedrooms
                  • sleeps 5
                  • 2 nights min
                  • Beach / lakeside relaxation
                  • Nearest beach 2 mi
                  • Swimming pool

                  Price per night from

                  $183

                  Price per night from

                  $183

                    18

                    Honey P's Villa

                    Trinidad and Tobago / Santa Cruz

                    Santa Cruz villa

                    1 2 1 night min

                    • 1 bedroom
                    • sleeps 2
                    • 1 night min
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $92

                    Price per night from

                    $92

                    (27) Excellent 

                      33

                      Sundowner - Beautiful apartment with infinity pool

                      Tobago / Moriah

                      Moriah apartment

                      2 3 7 nights min

                      • 2 bedrooms
                      • sleeps 3
                      • 7 nights min
                      • Nearest beach 6 mi
                      • Swimming pool
                      • Ask about children
                      “Spectacular setting for a comfortable appartment with very welcoming,friendly hosts on site.” North west Tobago is a very special place if you value natural landscape, magnificent rainforest, blossoming trees,wildlife and few tourists. Beautiful remot

                      Price per night from

                      $149

                      Price per night from

                      $149

                      (1) Excellent 

                        18

                        Sunflower

                        Tobago / Canaan

                        Canaan villa

                        4 12 1 night min

                        • 4 bedrooms
                        • sleeps 12
                        • 1 night min
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $573

                        Price per night from

                        $573

                        (1) Excellent 

                          18

                          Side one side the

                          Tobago / Crown Point

                          Crown Point villa

                          4 8 3 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 3 nights min
                          • Swimming pool
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $596

                          Price per night from

                          $596

                          (8) Excellent 

                            12

                            Romantic Caribbean Get Away.

                            Tobago / Parlatuvier

                            Parlatuvier chalet

                            2 4 4 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 4 nights min
                            • Beach / lakeside relaxation
                            • Swimming pool
                            • Child Friendly

                            Price per night from

                            $155

                            Price per night from

                            $155

                              11

                              Home away from home

                              Trinidad and Tobago / St Augustine

                              St Augustine apartment

                              2 4 min stay varies

                              • 2 bedrooms
                              • sleeps 4
                              • min stay varies
                              • Nearest beach 30 mi
                              • Swimming pool
                              • Child Friendly

                              Price per night from

                              $172

                              Price per night from

                              $172

                              (9) Excellent 

                                16

                                Coasting Villa - Beautiful, Intimate, Waterfront

                                Trinidad and Tobago / Tobago

                                Tobago house

                                3 5 7 nights min

                                • 3 bedrooms
                                • sleeps 5
                                • 7 nights min
                                • Beach / lakeside relaxation
                                • Nearest beach 0 mi
                                • Swimming pool
                                “A gorgeous escape” Our group stayed at Coasting in March and couldn't have been happier with the accommodation. We were 4 adults and a 13 month old. The house and grounds are breath taking---think tropical flowers, a view to die for, birds galore, pat

                                Price per night from

                                $200

                                Price per night from

                                $200

                                (1) Excellent 

                                  32

                                  Beautiful 2 Bedroom Condo

                                  Trinidad / Piarco

                                  Piarco condo

                                  2 6 3 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 3 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $171

                                  Responds fast!
                                  avg. 51 minutes

                                  Price per night from

                                  $171

                                  (2) Very Good 

                                    13

                                    Cisantt

                                    Tobago / Canaan

                                    Canaan villa

                                    3 6 1 night min

                                    • 3 bedrooms
                                    • sleeps 6
                                    • 1 night min
                                    • Swimming pool
                                    • Ask about children
                                    • Air conditioning

                                    Price per night from

                                    $373

                                    Price per night from

                                    $373

                                    (1) Excellent 

                                      21

                                      Oceana: Luxurious 4BR/4BA private pool, 24hr guard gated community.

                                      Tobago / Canaan

                                      Canaan house

                                      4 12 2 nights min

                                      • 4 bedrooms
                                      • sleeps 12
                                      • 2 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $413

                                      Price per night from

                                      $413

                                      (3) Excellent 

                                        17

                                        Terrace Villa , Champ Fleur Heights

                                        Trinidad / Port of Spain

                                        Port of Spain apartment

                                        3 6 5 nights min

                                        • 3 bedrooms
                                        • sleeps 6
                                        • 5 nights min
                                        • Swimming pool
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $102

                                        Price per night from

                                        $102

                                          16

                                          Lagoona Villa

                                          Tobago / Bon Accord

                                          Bon Accord villa

                                          4 10 2 nights min

                                          • 4 bedrooms
                                          • sleeps 10
                                          • 2 nights min
                                          • Nearest beach 5 mi
                                          • Swimming pool
                                          • Child Friendly

                                          Price per night from

                                          $264

                                          Responds fast!
                                          avg. 1 hour 30 minutes

                                          Price per night from

                                          $264

                                          (5) Very Good 

                                            10

                                            Villa Sweet Breeze

                                            Tobago / Prospect, Tobago

                                            Prospect, Tobago villa

                                            3 6 min stay varies

                                            • 3 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $238

                                            Price per night from

                                            $238

                                            (6) Very Good 

                                              18

                                              Crown Point 2BR Condo

                                              Tobago / Crown Point

                                              Crown Point condo

                                              2 4 2 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 2 nights min
                                              • Beach / lakeside relaxation
                                              • Swimming pool
                                              • Suitable for children age 5+

                                              Price per night from

                                              $184

                                              Responds fast!
                                              avg. 1 hour 47 minutes

                                              Price per night from

                                              $184

                                              (16) Excellent 

                                                14

                                                Villa Colibri: 3BR villa/pool/24 hr guard gated community/Tobago

                                                Tobago / Canaan

                                                Canaan villa

                                                3 8 2 nights min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 2 nights min
                                                • Beach / lakeside relaxation
                                                • Nearest beach 4 mi
                                                • Swimming pool
                                                “wonderful vacation retreat” My family stayed at the villa during February and we could not have been happier with our choice in selecting this location. It was immaculately maintained with numerous amenities. The villa has large open common areas with

                                                Price per night from

                                                $418

                                                Price per night from

                                                $418

                                                (1) Very Good 

                                                  21

                                                  CoCo Chalet in Caribbean - only missing the fireplace!

                                                  Tobago / Mount Irvine

                                                  Mount Irvine house

                                                  3 8 3 nights min

                                                  • 3 bedrooms
                                                  • sleeps 8
                                                  • 3 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $258

                                                  Price per night from

                                                  $258

                                                  (5) Very Good 

                                                    51

                                                    Hummingbird Villa

                                                    Tobago / Grafton

                                                    Grafton villa

                                                    4 8 1 night min

                                                    • 4 bedrooms
                                                    • sleeps 8
                                                    • 1 night min
                                                    • Nearest beach 1 mi
                                                    • Swimming pool
                                                    • Child Friendly

                                                    Price per night from

                                                    $378

                                                    Price per night from

                                                    $378

                                                    (1) Excellent 

                                                      59

                                                      Top O' Tobago

                                                      Tobago / Plymouth

                                                      Plymouth apartment

                                                      1 4 2 nights min

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • 2 nights min
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $138

                                                      Price per night from

                                                      $138

                                                        26

                                                        Hibiscus, Holiday Home with the Caribbean Sea on its Doorstep!

                                                        Tobago / Black Rock

                                                        Black Rock villa

                                                        5 10 min stay varies

                                                        • 5 bedrooms
                                                        • sleeps 10
                                                        • min stay varies
                                                        • Nearest beach 0 mi
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $630

                                                        Price per night from

                                                        $630

                                                          11

                                                          Cool-O Breeze-O

                                                          Tobago / Lambeau

                                                          Lambeau villa

                                                          3 6 1 night min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 1 night min
                                                          • Swimming pool
                                                          • Ask about children
                                                          • Air conditioning

                                                          Price per night from

                                                          $373

                                                          Price per night from

                                                          $373

                                                            20

                                                            Mango Tango - A Holiday Home with A truly Authentic and Exotic Heart!

                                                            Tobago / Black Rock

                                                            Black Rock villa

                                                            5 9 3 nights min

                                                            • 5 bedrooms
                                                            • sleeps 9
                                                            • 3 nights min
                                                            • Nearest beach 2 mi
                                                            • Swimming pool
                                                            • Child Friendly

                                                            Price per night from

                                                            $344

                                                            Price per night from

                                                            $344

                                                              6

                                                              Indigo 2 Bedroom Apartment

                                                              Tobago / Mount Irvine

                                                              Mount Irvine apartment

                                                              2 5 2 nights min

                                                              • 2 bedrooms
                                                              • sleeps 5
                                                              • 2 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $103

                                                              Price per night from

                                                              $103

                                                                4

                                                                177 Sea Shell Villas

                                                                Tobago / Bon Accord

                                                                Bon Accord house

                                                                3 9 2 nights min

                                                                • 3 bedrooms
                                                                • sleeps 9
                                                                • 2 nights min
                                                                • Nearest beach 2 mi
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $298

                                                                Price per night from

                                                                $298

                                                                  14

                                                                  Atlantic

                                                                  Tobago / Lowlands

                                                                  Lowlands villa

                                                                  4 8 1 night min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 1 night min
                                                                  • Swimming pool
                                                                  • Ask about children
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $916

                                                                  Price per night from

                                                                  $916

                                                                  (4) Very Good 

                                                                    19

                                                                    Crown Point 1BR Condo

                                                                    Tobago / Crown Point

                                                                    Crown Point condo

                                                                    1 2 2 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 2 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 0.5 mi
                                                                    • Swimming pool

                                                                    Price per night from

                                                                    $114

                                                                    Responds fast!
                                                                    avg. 1 hour 47 minutes

                                                                    Price per night from

                                                                    $114

                                                                      27

                                                                      Luciana: Light & Airy 4-Bedroom Home with Windows for Walls

                                                                      Tobago / Mount Irvine

                                                                      Mount Irvine villa

                                                                      4 8 3 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • 3 nights min
                                                                      • Nearest beach 2 mi
                                                                      • Swimming pool
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $342

                                                                      Price per night from

                                                                      $342

                                                                      (5) Excellent 

                                                                        19

                                                                        Birdie's Nest Apt#2

                                                                        Tobago / Black Rock

                                                                        Black Rock apartment

                                                                        1 2 3 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 3 nights min
                                                                        • Nearest beach 0.1 mi
                                                                        • Swimming pool
                                                                        • Ask about children

                                                                        Price per night from

                                                                        $126

                                                                        Responds fast!
                                                                        avg. 3 hours 59 minutes

                                                                        Price per night from

                                                                        $126

                                                                        (19) Excellent 

                                                                          17

                                                                          OCEANVIEW APARTMENT (POOL & BEACH ACCESS) with WIFI - Casa Cassini Tobago

                                                                          Tobago / Scarborough

                                                                          Scarborough apartment

                                                                          1 2 3 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • 3 nights min
                                                                          • Nearest beach 0.1 mi
                                                                          • Swimming pool
                                                                          • Ask about children
                                                                          “Totally chilled” We absolutely loved our stay at Casa Cassini. Our last few vacations we stayed at all-inclusive resorts and we were looking for a change from the locked-in environment. I was a bit apprehensive about staying in a guest house situation

                                                                          Price per night from

                                                                          $155

                                                                          Responds fast!
                                                                          avg. 2 hours 53 minutes

                                                                          Price per night from

                                                                          $155

                                                                          (22) Excellent 

                                                                            16

                                                                            Flipkey'sTopVillaRental 4BED villa Nr..QUIET BEACH

                                                                            Tobago / Bacolet Bay

                                                                            Bacolet Bay villa

                                                                            4 7 5 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 7
                                                                            • 5 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            “Wonderful and Relaxing” We spent a week at Dolphin Villa and can't say enough good things about both the house and the owners, Kelvin and Marilyn. From the moment we reserved, and then arrived and were met at the airport, until we checked out, Kelvin

                                                                            Price per night from

                                                                            $287

                                                                            Price per night from

                                                                            $287

                                                                            (32) Excellent 

                                                                              29

                                                                              Mary's Hill Lodge, Tobago

                                                                              Trinidad and Tobago / Tobago

                                                                              Tobago house

                                                                              3 9 2 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 9
                                                                              • 2 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 2 mi
                                                                              • Swimming pool
                                                                              “A place for great family fun.” My sister and I took her six children all under the age of twelve and they had a blast. The pool was safe enough for the children since the deepest point was 5ft, they enjoyed all the board games and the beds were very c

                                                                              Price per night from

                                                                              $179

                                                                              Responds fast!
                                                                              avg. 3 hours 56 minutes

                                                                              Price per night from

                                                                              $179