Vacation Rentals with Pool in Tobago

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Filtering by: Swimming pool

127 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

    Responds fast!
    avg. 3 hours 54 minutes

    Price per night from

    $600

    (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

      (10) Very Good 

        25

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

        Tobago / Prospect

        Prospect villa

        3 8 3 nights min

        • 3 bedrooms
        • sleeps 8
        • 3 nights min
        • 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
        …see more

        Price per night from

        $241

        Responds fast!
        avg. 2 hours 4 minutes

        Price per night from

        $241

        (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
          …see more

          Price per night from

          $573

          Price per night from

          $573

          (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

            $184

            Price per night from

            $184

            (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 2 nights min

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

                Price per night from

                $516

                Price per night from

                $516

                (2) 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 43 minutes

                  Price per night from

                  $115

                  (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

                    $242

                    Price per night from

                    $242

                    (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
                      …see more

                      Price per night from

                      $152

                      Price per night from

                      $152

                      (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

                          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

                            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

                              $584

                              Price per night from

                              $584

                              (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

                                  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

                                  (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

                                    (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
                                      …see more

                                      Price per night from

                                      $200

                                      Price per night from

                                      $200

                                        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

                                        (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
                                          …see more

                                          Price per night from

                                          $418

                                          Price per night from

                                          $418

                                          (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

                                              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

                                              (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

                                                  14

                                                  Sunny Daze Villa

                                                  Tobago / Lowlands

                                                  Lowlands bungalow

                                                  2 6 1 night min

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

                                                  Price per night from

                                                  $344

                                                  Price per night from

                                                  $344

                                                  (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

                                                    $115

                                                    Responds fast!
                                                    avg. 1 hour 47 minutes

                                                    Price per night from

                                                    $115

                                                      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

                                                      (5) Excellent 

                                                        14

                                                        2BR Ocean Front Bungalow with pool, deck and wifi

                                                        Tobago / Riseland

                                                        Riseland cottage

                                                        2 4 3 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 3 nights min
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 2 mi
                                                        • Swimming pool

                                                        Price per night from

                                                        $344

                                                        Responds fast!
                                                        avg. 1 hour 45 minutes

                                                        Price per night from

                                                        $344

                                                        (5) Excellent 

                                                          23

                                                          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

                                                          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
                                                            …see more

                                                            Price per night from

                                                            $155

                                                            Responds fast!
                                                            avg. 2 hours 58 minutes

                                                            Price per night from

                                                            $155

                                                            (4) Very Good 

                                                              24

                                                              VOTED TOP 20 CONDE NAST CARIBBEAN VILLA - 74 STEPS TO BEACH - KIDS TRAVEL FREE

                                                              Tobago / Scarborough

                                                              Scarborough villa

                                                              4 8 5 nights min

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • 5 nights min
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Child Friendly

                                                              Price per night from

                                                              $1,002

                                                              Price per night from

                                                              $1,002

                                                              (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

                                                                $380

                                                                Price per night from

                                                                $380

                                                                (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
                                                                  …see more

                                                                  Price per night from

                                                                  $182

                                                                  Price per night from

                                                                  $182

                                                                    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

                                                                    (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

                                                                        9

                                                                        New Timbers

                                                                        Tobago / Bon Accord

                                                                        Bon Accord bungalow

                                                                        3 6 1 night min

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

                                                                        Price per night from

                                                                        $315

                                                                        Price per night from

                                                                        $315

                                                                          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 18 minutes

                                                                          Price per night from

                                                                          $264

                                                                          (21) Excellent 

                                                                            20

                                                                            Mahogany Ridge, Elegant comfort,Pool, Ocean Views.

                                                                            Tobago / Black Rock

                                                                            Black Rock villa

                                                                            4 8 3 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 3 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 0.5 mi
                                                                            • Swimming pool
                                                                            “A great place to relax and unwind” I took some of my students here for a yoga retreat and we all enjoyed it very much. Towards the end we just did not want to leave. Even now, back in cold Germany, we are still sitting on the beautiful verandah enjoyi
                                                                            …see more

                                                                            Price per night from

                                                                            $270

                                                                            Price per night from

                                                                            $270

                                                                              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

                                                                              $344

                                                                              Price per night from

                                                                              $344