Windward Rentals

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2,313 Houses

(3) Excellent 

    8

    BelAmour, Luxury and Romantic Designer Villa for 2

    Windward / Pointe Milou

    Pointe Milou villa

    1 2 5 nights min

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

    Price per night from

    $1,114

    Price per night from

    $1,114

      20

      La Plage

      Windward / Lorient

      Lorient villa

      7 14 7 nights min

      • 7 bedrooms
      • sleeps 14
      • 7 nights min
      • Child Friendly
      • Air conditioning
      • Private garden

      Price per night from

      $8,874

      Responds fast!
      avg. 3 hours 52 minutes

      Price per night from

      $8,874

        18

        Villa Tranquille

        Windward / Vitet

        Vitet villa

        3 6 7 nights min

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

        Price per night from

        $824

        Responds fast!
        avg. 3 hours 52 minutes

        Price per night from

        $824

        Great rentals within 20 miles that match your search

        Distance approx 18.67 km from Windward

          21

          Luxury studio 1 Sea view Orient bay

          Saint-Martin / Orient Bay

          Orient Bay studio

          Studio 4 4 nights min

          • Studio
          • sleeps 4
          • 4 nights min
          • Child Friendly

          Price per night from

          $95

          Price per night from

          $95

          Distance approx 15.85 km from Windward

          (4) Excellent 

            21

            Sint Maarten Utopian Retreat

            Sint Maarten / Philipsburg

            Philipsburg villa

            2 4 7 nights min

            • 2 bedrooms
            • sleeps 4
            • 7 nights min
            • Beach / lakeside relaxation
            • Nearest beach 0.5 mi
            • Swimming pool

            Price per night from

            $287

            Price per night from

            $287

            Distance approx 1.38 km from Windward Show on Map

              35

              Villa Bellevue St. Bart

              St. Barthelemy / Gustavia

              Gustavia house

              5 10 7 nights min

              • 5 bedrooms
              • sleeps 10
              • 7 nights min
              • Nearest beach 2 mi
              • Child Friendly

              Price per night from

              $1,473

              Price per night from

              $1,473

              Distance approx 18.6 km from Windward

              (1) Excellent 

                18

                Orient beach Premium view Frontsea Studio

                Saint-Martin / Orient Bay

                Orient Bay studio

                Studio 4 7 nights min

                • Studio
                • sleeps 4
                • 7 nights min
                • Beach / lakeside relaxation
                • Swimming pool
                • Child Friendly

                Price per night from

                $100

                Price per night from

                $100

                Distance approx 16.01 km from Windward

                (1) Excellent 

                  15

                  Lux apart in westin dawn beach club

                  Sint Maarten / Oyster Pond

                  Oyster Pond apartment

                  3 8 7 nights min

                  • 3 bedrooms
                  • sleeps 8
                  • 7 nights min
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $573

                  Price per night from

                  $573

                  Distance approx 16.81 km from Windward

                    14

                    3BED/ 2BA Ocean View Spacious Condo

                    Sint Maarten / Philipsburg

                    Philipsburg apartment

                    3 8 6 nights min

                    • 3 bedrooms
                    • sleeps 8
                    • 6 nights min
                    • Child Friendly

                    Price per night from

                    $343

                    Price per night from

                    $343

                    Distance approx 17.83 km from Windward

                    (20) Excellent 

                      36

                      Côté Chic, 2BR- gorgeous beach house 1line ocean front-

                      Saint-Martin / Orient Bay

                      Orient Bay house

                      2 5 min stay varies

                      • 2 bedrooms
                      • sleeps 5
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Nearest beach 0 mi
                      • Swimming pool
                      “Amazing second honeymoon” My wife Italia and I found "Cote Chic" on Flipkey. We contacted Moune and she said the unit was in the process of being renovated but would be available for rent. We would be the first guests. When we arrived Moune and her
                      …see more

                      Price per night from

                      $280

                      Price per night from

                      $280

                      Distance approx 1.44 km from Windward

                      (2) Excellent 

                        24

                        One Bedroom Brand New Villa With Private Pool !!

                        St. Barthelemy / Anse des Cayes

                        Anse des Cayes villa

                        1 2 min stay varies

                        • 1 bedroom
                        • sleeps 2
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Swimming pool
                        • Ask about children

                        Price per night from

                        $221

                        Price per night from

                        $221

                        Distance approx 17.75 km from Windward

                          28

                          Sunny Beach : charming condo beach front, behind Kontiki Beach

                          Saint-Martin / Orient Bay

                          Orient Bay condo

                          1 4 min stay varies

                          • 1 bedroom
                          • sleeps 4
                          • min stay varies
                          • Nearest beach 0 mi
                          • Swimming pool
                          • Child Friendly

                          Price per night from

                          $183

                          Responds fast!
                          avg. 3 hours 58 minutes

                          Price per night from

                          $183

                          Distance approx 17.85 km from Windward

                          (7) Very Good 

                            27

                            Soleil Blanc, gorgeous 2 bedrooms villa with private pool

                            Saint-Martin / Orient Bay

                            Orient Bay house

                            2 6 min stay varies

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

                            Price per night from

                            $280

                            Price per night from

                            $280

                            Distance approx 0.1 km from Windward

                              20

                              Villa Eden Island, 1 bedroom

                              St. Barthelemy / Gustavia

                              Gustavia villa

                              1 2 5 nights min

                              • 1 bedroom
                              • sleeps 2
                              • 5 nights min
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Ask about children

                              Price per night from

                              $655

                              Price per night from

                              $655

                              Distance approx 0.1 km from Windward Show on Map

                                16

                                Bellevue St. Barts

                                St. Barthelemy / St. Jean

                                St. Jean apartment

                                2 4 5 nights min

                                • 2 bedrooms
                                • sleeps 4
                                • 5 nights min

                                Price per night from

                                $630

                                Price per night from

                                $630

                                Distance approx 19.1 km from Windward

                                  7

                                  Furnished apartment, cozy and comfortable, a perfect vacation experience

                                  Sint Maarten / Cole Bay

                                  Cole Bay apartment

                                  1 3 7 nights min

                                  • 1 bedroom
                                  • sleeps 3
                                  • 7 nights min
                                  • Child Friendly

                                  Price per night from

                                  $97

                                  Price per night from

                                  $97

                                  Distance approx 17.13 km from Windward

                                    38

                                    Divi LIttle Bay Beach St Maarten Studio 1BA Suite

                                    Sint Maarten / Philipsburg

                                    Philipsburg apartment

                                    2 2 7 nights min

                                    • 2 bedrooms
                                    • sleeps 2
                                    • 7 nights min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 0 mi
                                    • Swimming pool

                                    Price per night from

                                    $196

                                    Responds fast!
                                    avg. 14 minutes

                                    Price per night from

                                    $196

                                    Distance approx 0.1 km from Windward

                                      23

                                      Luxury Villa in the Heart of Paradise - St. Jean

                                      St. Barthelemy / St. Jean

                                      St. Jean villa

                                      3 6 7 nights min

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

                                      Price per night from

                                      $1,339

                                      Price per night from

                                      $1,339

                                      Distance approx 18.04 km from Windward

                                      (9) Excellent 

                                        65

                                        WOW WOW WOW, STUNNING INSIDE AND OUT! VILLA LIBRE`

                                        Sint Maarten / Simpson Bay

                                        Simpson Bay villa

                                        3 7 min stay varies

                                        • 3 bedrooms
                                        • sleeps 7
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Swimming pool
                                        • Child Friendly
                                        “Incredible ! Definiately five star 5* Accomdations” This villa is incredible. It exceeded my expectations. It was immaculate. It is beautiful inside and out. All three of the bedrooms are very spacious with their own large, modern bathrooms.
                                        …see more

                                        Price per night from

                                        $458

                                        Price per night from

                                        $458

                                        Distance approx 16.8 km from Windward

                                          6

                                          Large Time Share Rental

                                          Sint Maarten / Philipsburg

                                          Philipsburg condo

                                          3 8 7 nights min

                                          • 3 bedrooms
                                          • sleeps 8
                                          • 7 nights min
                                          • Child Friendly

                                          Price per night from

                                          $589

                                          Price per night from

                                          $589

                                          Distance approx 1.77 km from Windward Show on Map

                                            12

                                            The Fountain of La Cote Sauvage - Anse de Toiny

                                            St. Barthelemy / Toiny

                                            Toiny bungalow

                                            1 3 1 night min

                                            • 1 bedroom
                                            • sleeps 3
                                            • 1 night min
                                            • Child Friendly
                                            • Air conditioning
                                            • Pet Friendly

                                            Price per night from

                                            $781

                                            Price per night from

                                            $781

                                            Distance approx 16.14 km from Windward

                                              23

                                              Summerwinds Villa

                                              Sint Maarten / Oyster Pond

                                              Oyster Pond villa

                                              4 11 min stay varies

                                              • 4 bedrooms
                                              • sleeps 11
                                              • min stay varies
                                              • Swimming pool
                                              • Child Friendly
                                              • Car not necessary

                                              Price per night from

                                              $566

                                              Responds fast!
                                              avg. 3 hours 35 minutes

                                              Price per night from

                                              $566

                                              Distance approx 15.92 km from Windward

                                                11

                                                Dawn Beach Luxury Vacation Rental

                                                Sint Maarten / Philipsburg

                                                Philipsburg condo

                                                3 8 7 nights min

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

                                                Price per night from

                                                $409

                                                Price per night from

                                                $409

                                                Distance approx 19.59 km from Windward

                                                  14

                                                  JUNIOR SUITE SIMPSON BAY RESORT & MARINA 1BR 1BA 2pers

                                                  Sint Maarten / Simpson Bay

                                                  Simpson Bay apartment

                                                  1 2 7 nights min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Air conditioning

                                                  Price per night from

                                                  $115

                                                  Price per night from

                                                  $115

                                                  Distance approx 16 km from Windward

                                                    9

                                                    Caribbean Warmth 3 Bedroom 2 bath luxury condo

                                                    Sint Maarten / Oyster Pond

                                                    Oyster Pond condo

                                                    3 6 4 nights min

                                                    • 3 bedrooms
                                                    • sleeps 6
                                                    • 4 nights min
                                                    • Child Friendly

                                                    Price per night from

                                                    $247

                                                    Price per night from

                                                    $247

                                                    Distance approx 19.13 km from Windward

                                                      77

                                                      VILLA PINEL facing the Caribbean Sea and Pinel, pool, private beach

                                                      Saint-Martin / Cul de Sac

                                                      Cul de Sac villa

                                                      4 10 4 nights min

                                                      • 4 bedrooms
                                                      • sleeps 10
                                                      • 4 nights min
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $579

                                                      Price per night from

                                                      $579

                                                      Distance approx 1.44 km from Windward Show on Map

                                                      (3) Very Good 

                                                        6

                                                        AU COEUR CARAIBE ST BARTH COTTAGE DE CHARME CINDY

                                                        St. Barthelemy / St. Jean

                                                        St. Jean cottage

                                                        1 2 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • min stay varies

                                                        Price per night from

                                                        $246

                                                        Price per night from

                                                        $246

                                                        Distance approx 1.64 km from Windward Show on Map

                                                        (23) Excellent 

                                                          14

                                                          Villa Summer Breeze (Villaminou)

                                                          St. Barthelemy / Grand Cul-de-Sac

                                                          Grand Cul-de-Sac villa

                                                          4 8 7 nights min

                                                          • 4 bedrooms
                                                          • sleeps 8
                                                          • 7 nights min
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 0 mi
                                                          • Swimming pool

                                                          Price per night from

                                                          $1,706

                                                          Price per night from

                                                          $1,706

                                                          Distance approx 1 km from Windward

                                                          (1) Excellent 

                                                            13

                                                            Villa Nevis

                                                            St. Barthelemy / Lurin

                                                            Lurin villa

                                                            2 6 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • min stay varies
                                                            • Nearest beach 1 mi
                                                            • Swimming pool
                                                            • Child Friendly

                                                            Price per night from

                                                            $557

                                                            Price per night from

                                                            $557

                                                            Distance approx 19.07 km from Windward

                                                            (1) Excellent 

                                                              21

                                                              THE ROCK 1 New Seaview Duplex Condo with Jacuzzi !

                                                              Saint-Martin / Orient Bay

                                                              Orient Bay apartment

                                                              2 4 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • min stay varies
                                                              • Nearest beach 1 mi
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $170

                                                              Price per night from

                                                              $170

                                                              Distance approx 2.38 km from Windward Show on Map

                                                                33

                                                                Villa Rose Lagoon

                                                                St. Barthelemy / Petit Cul de Sac

                                                                Petit Cul de Sac villa

                                                                5 10 min stay varies

                                                                • 5 bedrooms
                                                                • sleeps 10
                                                                • min stay varies
                                                                • Nearest beach 0.5 mi
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $1,301

                                                                Price per night from

                                                                $1,301

                                                                Distance approx 1.86 km from Windward

                                                                  21

                                                                  Villa Lenalee

                                                                  St. Barthelemy / Colombier

                                                                  Colombier villa

                                                                  4 8 7 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 7 nights min
                                                                  • Nearest beach 2 mi
                                                                  • Swimming pool
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $2,230

                                                                  Price per night from

                                                                  $2,230

                                                                  Distance approx 19.07 km from Windward

                                                                    23

                                                                    THE ROCK 2 New Seaview Duplex Condo with Jacuzzi !

                                                                    Saint-Martin / Orient Bay

                                                                    Orient Bay apartment

                                                                    2 4 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • min stay varies
                                                                    • Child Friendly
                                                                    • Ask about pets

                                                                    Price per night from

                                                                    $170

                                                                    Price per night from

                                                                    $170

                                                                    Distance approx 18.05 km from Windward

                                                                      6

                                                                      Duplex of 160 m2 and 4 bedrooms on Orient Bay beach

                                                                      Saint-Martin / Orient Bay

                                                                      Orient Bay apartment

                                                                      4 8 4 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • 4 nights min
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $456

                                                                      Price per night from

                                                                      $456

                                                                      Distance approx 1 km from Windward

                                                                        12

                                                                        Turtle Villa

                                                                        St. Barthelemy / Lurin

                                                                        Lurin villa

                                                                        2 6 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Nearest beach 2 mi
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $557

                                                                        Price per night from

                                                                        $557

                                                                        Distance approx 1.35 km from Windward

                                                                          22

                                                                          Charmante Case St Barth

                                                                          St. Barthelemy / Gustavia

                                                                          Gustavia house

                                                                          1 2 5 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • 5 nights min

                                                                          Price per night from

                                                                          $196

                                                                          Price per night from

                                                                          $196

                                                                          Distance approx 1.36 km from Windward

                                                                            32

                                                                            Spacious villa with swimming-pool

                                                                            St. Barthelemy / Gustavia

                                                                            Gustavia villa

                                                                            4 8 min stay varies

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 500 mi
                                                                            • Swimming pool

                                                                            Price per night from

                                                                            $1,261

                                                                            Responds fast!
                                                                            avg. 1 hour 10 minutes

                                                                            Price per night from

                                                                            $1,261

                                                                            Distance approx 1.24 km from Windward

                                                                            (1) Excellent 

                                                                              12

                                                                              Key Lime - 2 Bedroom Villa at

                                                                              St. Barthelemy / Anse des Cayes

                                                                              Anse des Cayes villa

                                                                              2 4 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $450

                                                                              Price per night from

                                                                              $450