Vacation Rentals & Villas in Simpson Bay

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1,838 villas

(2) Excellent 

    16

    Sapphire Ruby Suite - Unforgettable Getaway!

    Sint Maarten / Simpson Bay

    Simpson Bay condo

    1 4 3 nights min

    • 1 bedroom
    • sleeps 4
    • 3 nights min
    • Beach / lakeside relaxation
    • Child Friendly

    Price per night from

    $212

    Price per night from

    $212

    (4) Excellent 

      10

      2BR-Oceanfront-Royal Palm

      Simpson Bay / Simpson Bay Beach

      Simpson Bay condo

      2 6 5 nights min

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

      Price per night from

      $401

      Price per night from

      $401

        47

        TARA... Affordable oceanfront villa, walk to beach

        Sint Maarten / Simpson Bay

        Simpson Bay villa

        5 10 min stay varies

        • 5 bedrooms
        • sleeps 10
        • min stay varies
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Price per night from

        $843

        Price per night from

        $843

        (1) Excellent 

          15

          BEACHFRONTBLISS

          Sint Maarten / Simpson Bay

          Simpson Bay apartment

          2 4 3 nights min

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

          Price per night from

          $344

          Price per night from

          $344

          (30) Excellent 

          Certificate of Excellence

            22

            Carisma on the beach

            Sint Maarten / Simpson Bay

            Simpson Bay villa

            2 4 min stay varies

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

            Certificate of Excellence

            Price per night from

            $229

            Responds fast!
            avg. 1 hour 45 minutes

            Price per night from

            $229

            (2) Excellent 

              15

              The Sapphire: Pearl Suite - Peace of mind!

              Sint Maarten / Simpson Bay

              Simpson Bay condo

              1 4 3 nights min

              • 1 bedroom
              • sleeps 4
              • 3 nights min
              • Child Friendly

              Price per night from

              $197

              Price per night from

              $197

              (5) Excellent 

                26

                Le Papillon - Modern Luxurious Beachfront Unit, extra clean, stunning view

                Simpson Bay / Simpson Bay Beach

                Simpson Bay apartment

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Beach / lakeside relaxation
                • Nearest beach 0.01 mi
                • Child Friendly

                Price per night from

                $341

                Responds fast!
                avg. 1 hour 55 minutes

                Price per night from

                $341

                (1) Excellent 

                  17

                  Unrivaled Luxury Villa with beach access

                  Sint Maarten / Simpson Bay

                  Simpson Bay house

                  5 10 min stay varies

                  • 5 bedrooms
                  • sleeps 10
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 0.7 mi
                  • Swimming pool

                  Price per night from

                  $739

                  Price per night from

                  $739

                  (29) Excellent 

                    14

                    Blue Pelican Luxury Villas - Featured on HGTV!!!!!

                    Sint Maarten / Simpson Bay

                    Simpson Bay apartment

                    1 2 3 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 3 nights min
                    • Beach / lakeside relaxation
                    • Nearest beach 0 mi
                    • Swimming pool
                    “Excellent place to stay.” The pre-trip information was perfect and the welcome "meet and greet" was perfect and thorough too. We stayed in Villa #2. Essentially, you couldn't wish for more on the inside - serious attention has been paid to detail and

                    Price per night from

                    $194

                    Responds fast!
                    avg. 1 hour 39 minutes

                    Price per night from

                    $194

                    (8) Excellent 

                      34

                      Le Papillon Penthouse - NOW 20% DISCOUNT for all low season reservations!

                      Sint Maarten / Simpson Bay

                      Simpson Bay apartment

                      3 8 min stay varies

                      • 3 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Nearest beach 0.01 mi
                      • Child Friendly

                      Price per night from

                      $547

                      Responds fast!
                      avg. 1 hour 55 minutes

                      Price per night from

                      $547

                      (1) Excellent 

                        14

                        1 Bed Luxury Condo

                        Sint Maarten / Simpson Bay

                        Simpson Bay condo

                        1 2 4 nights min

                        • 1 bedroom
                        • sleeps 2
                        • 4 nights min

                        Price per night from

                        $172

                        Price per night from

                        $172

                        (4) Very Good 

                          12

                          PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW

                          Simpson Bay / Simpson Bay Beach

                          Simpson Bay apartment

                          1 2 4 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 4 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 0.8 mi
                          • Air conditioning

                          Price per night from

                          $136

                          Price per night from

                          $136

                            29

                            COCO BEACH CLUB #5.... step out the door on to the soft white powdery sand of S

                            Sint Maarten / Simpson Bay

                            Simpson Bay apartment

                            2 4 min stay varies

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

                            Price per night from

                            $414

                            Price per night from

                            $414

                            (3) Very Good 

                              32

                              Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI

                              Sint Maarten / Simpson Bay

                              Simpson Bay apartment

                              1 4 min stay varies

                              • 1 bedroom
                              • sleeps 4
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $165

                              Responds fast!
                              avg. 1 hour 8 minutes

                              Price per night from

                              $165

                              (1) Excellent 

                                18

                                The Sapphire: Aquamarine Suite- Breathtaking views!

                                Sint Maarten / Simpson Bay

                                Simpson Bay condo

                                1 4 3 nights min

                                • 1 bedroom
                                • sleeps 4
                                • 3 nights min
                                • Nearest beach 1 mi
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $212

                                Price per night from

                                $212

                                  37

                                  BEAU RIVAGE... Comfortable home on Burgeoux Bay beach, walk to Maho or Simpson B

                                  Sint Maarten / Simpson Bay

                                  Simpson Bay villa

                                  3 8 min stay varies

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

                                  Price per night from

                                  $857

                                  Price per night from

                                  $857

                                    33

                                    Steps to Caribbean, pool and 2 mile-long beach

                                    Sint Maarten / Simpson Bay

                                    Simpson Bay apartment

                                    1 2 7 nights min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 7 nights min
                                    • Beach / lakeside relaxation
                                    • Swimming pool
                                    • Car not necessary

                                    Price per night from

                                    $258

                                    Price per night from

                                    $258

                                      25

                                      Villa Sunshine

                                      Sint Maarten / Simpson Bay

                                      Simpson Bay villa

                                      5 12 5 nights min

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

                                      Price per night from

                                      $1,088

                                      Responds fast!
                                      avg. 3 hours 21 minutes

                                      Price per night from

                                      $1,088

                                        13

                                        SAPPHIRE... A casual, comfortable villa with ocean views in Pelican Key!

                                        Sint Maarten / Simpson Bay

                                        Simpson Bay villa

                                        3 6 min stay varies

                                        • 3 bedrooms
                                        • sleeps 6
                                        • min stay varies
                                        • Swimming pool
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $571

                                        Price per night from

                                        $571

                                        (1) Excellent 

                                          11

                                          Studio in Pelican Key Paradise

                                          Sint Maarten / Simpson Bay

                                          Simpson Bay apartment

                                          2 3 nights min

                                          • sleeps 2
                                          • 3 nights min
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Ask about children

                                          Price per night from

                                          $172

                                          Price per night from

                                          $172

                                          (1) Excellent 

                                            46

                                            CARIBBEAN BLUE... 5BR beachfront home in Pelican Key

                                            Sint Maarten / Simpson Bay

                                            Simpson Bay villa

                                            5 10 min stay varies

                                            • 5 bedrooms
                                            • sleeps 10
                                            • min stay varies
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $1,271

                                            Price per night from

                                            $1,271

                                            (5) Excellent 

                                              16

                                              Beachfront gated Condo directly on Simpson Bay

                                              Sint Maarten / Simpson Bay

                                              Simpson Bay apartment

                                              2 5 5 nights min

                                              • 2 bedrooms
                                              • sleeps 5
                                              • 5 nights min
                                              • Beach / lakeside relaxation
                                              • Swimming pool
                                              • Child Friendly
                                              “Right on the beach. Best location on Simpson Beach” On our 7th trip to St. Maarten, my husband and I decided to break free from the typical hotel experience, we booked a week at this condo on Simpson Bay Beach... and I'm so glad we did! The condo itse

                                              Price per night from

                                              $287

                                              Responds fast!
                                              avg. 2 hours 17 minutes

                                              Price per night from

                                              $287

                                                25

                                                LA CASITA...charming, comfortable oceanfront villa in Beacon Hill, St Maarten

                                                Sint Maarten / Simpson Bay

                                                Simpson Bay villa

                                                3 6 min stay varies

                                                • 3 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Swimming pool
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $543

                                                Price per night from

                                                $543

                                                (1) Excellent 

                                                  32

                                                  Barefoot Oceanfront Condo St Maarten

                                                  Simpson Bay / Simpson Bay Beach

                                                  Simpson Bay villa

                                                  2 6 4 nights min

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • 4 nights min
                                                  • Beach / lakeside relaxation
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $349

                                                  Price per night from

                                                  $349

                                                    9

                                                    Beautiful Studio in Pelican Key /Simpson Bay

                                                    Sint Maarten / Simpson Bay

                                                    Simpson Bay apartment

                                                    1 2 1 night min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 1 night min
                                                    • Beach / lakeside relaxation
                                                    • Swimming pool
                                                    • Air conditioning

                                                    Price per night from

                                                    $103

                                                    Price per night from

                                                    $103

                                                    (2) Excellent 

                                                      18

                                                      Anchorage Apartment

                                                      Simpson Bay / Simpson Bay Beach

                                                      Simpson Bay apartment

                                                      1 4 4 nights min

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • 4 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 2 mi
                                                      • Child Friendly

                                                      Price per night from

                                                      $171

                                                      Responds fast!
                                                      avg. 1 hour 1 minutes

                                                      Price per night from

                                                      $171

                                                      (2) Excellent 

                                                        20

                                                        2 BEDR townhouse overlooking OCEAN ST- MAARTEN

                                                        Sint Maarten / Simpson Bay

                                                        Simpson Bay house

                                                        2 4 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 7 nights min
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 2 mi
                                                        • Swimming pool
                                                        “Fabulous resort living with a tropical breeze!” A most wonderful place to enjoy all St Maarten has to offer! Beautiful, airy, spotless accommodations with a contemporary Carribean decor and all the amenities you need for a wondrous vacation! Centrally

                                                        Price per night from

                                                        $245

                                                        Price per night from

                                                        $245

                                                          9

                                                          Beachfront Condo

                                                          Simpson Bay / Simpson Bay Beach

                                                          Simpson Bay condo

                                                          2 4 5 nights min

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

                                                          Price per night from

                                                          $589

                                                          Price per night from

                                                          $589

                                                          (1) Excellent 

                                                            26

                                                            Vacation Villa at Simpson's bay and Marina

                                                            Simpson Bay / Simpson Bay Beach

                                                            Simpson Bay villa

                                                            1 4 7 nights min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 7 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 0.2 mi
                                                            • Swimming pool

                                                            Price per night from

                                                            $156

                                                            Responds fast!
                                                            avg. 2 hours 41 minutes

                                                            Price per night from

                                                            $156

                                                              25

                                                              MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate

                                                              Sint Maarten / Simpson Bay

                                                              Simpson Bay apartment

                                                              2 4 min stay varies

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

                                                              Price per night from

                                                              $329

                                                              Price per night from

                                                              $329

                                                                11

                                                                15 steps away from the beach

                                                                Sint Maarten / Simpson Bay

                                                                Simpson Bay apartment

                                                                1 4 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • 3 nights min
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Ask about pets

                                                                Price per night from

                                                                $148

                                                                Responds fast!
                                                                avg. 57 minutes

                                                                Price per night from

                                                                $148

                                                                  17

                                                                  Pearl on the Beach

                                                                  Simpson Bay / Simpson Bay Beach

                                                                  Simpson Bay condo

                                                                  2 4 5 nights min

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

                                                                  Price per night from

                                                                  $589

                                                                  Price per night from

                                                                  $589

                                                                    50

                                                                    BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key

                                                                    Sint Maarten / Simpson Bay

                                                                    Simpson Bay villa

                                                                    3 6 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $671

                                                                    Price per night from

                                                                    $671

                                                                    (1) Excellent 

                                                                      29

                                                                      SMART VILLA...Beachfront at Pelican Key

                                                                      Sint Maarten / Simpson Bay

                                                                      Simpson Bay villa

                                                                      3 6 min stay varies

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • min stay varies
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $429

                                                                      Price per night from

                                                                      $429

                                                                        26

                                                                        Contemporary penthouse at La Brisas

                                                                        Sint Maarten / Simpson Bay

                                                                        Simpson Bay apartment

                                                                        3 6 3 nights min

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

                                                                        Price per night from

                                                                        $500

                                                                        Price per night from

                                                                        $500

                                                                          20

                                                                          Villa Casa Carib, Luxuary 2 Bedroom/2 Bath on Simpson Bay Beach

                                                                          Sint Maarten / Simpson Bay

                                                                          Simpson Bay villa

                                                                          2 4 5 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • 5 nights min
                                                                          • Swimming pool
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $279

                                                                          Price per night from

                                                                          $279

                                                                          (2) Very Good 

                                                                            23

                                                                            CASA DE BELLA... Great location at a great price!!

                                                                            Sint Maarten / Simpson Bay

                                                                            Simpson Bay house

                                                                            3 6 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $400

                                                                            Price per night from

                                                                            $400

                                                                            (1) Excellent 

                                                                              30

                                                                              SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t

                                                                              Sint Maarten / Simpson Bay

                                                                              Simpson Bay villa

                                                                              3 8 min stay varies

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

                                                                              Price per night from

                                                                              $729

                                                                              Price per night from

                                                                              $729

                                                                              About Simpson Bay

                                                                              The beach at Simpson Bay is wide, and over a mile long—a stretch of glorious, uninterrupted sand. The blue waters of the Caribbean lap the shore, providing the perfect backdrop for a relaxing vacation.

                                                                              But it’s not all relaxation—the main streets of Simpson Bay are bustling hives of activity with bars, restaurants and stores. Why not start searching FlipKey for the perfect vacation rental and plan your perfect trip?

                                                                              About Simpson Bay, St. Maarten-St. Martin

                                                                              Many years ago, Simpson Bay was home to the fishermen of the island and their families. Now, it's a popular tourist destination, although the fishermen still ply their trade. The first inhabitants of Simpson Bay and the surrounding area were the Arawaks, from the Amazon basin.

                                                                              Named after St Martin of Tours, it first appeared on a map in 1516 as Sam Mtim. It was already a Spanish territory by then, though it wasn't a colony. The island has been in the hands of the Spanish, Dutch and French. Today, the island is shared by the Dutch and French whose cultures still influence life on the island.

                                                                              The cuisine on the island is international, but you can find some traditional food if you look hard enough. Ask a local for their recommendations to discover some authentic places to eat.

                                                                              Simpson Bay has a vibrant nightlife which contrasts with the peace you can find on Simpson Bay beach. You'll get the best of both worlds here!

                                                                              What to do in Simpson Bay, St. Maarten-St. Martin

                                                                              As Saint Maarten-St Martin is an island, water sports are very popular. Why not try some?

                                                                              If you're looking for a more calming vacation, swim in the clear blue waters, or relax on the beach.

                                                                              Try a Rhino Safari excursion on a Rhino Rider—an inflatable motorboat. Pilot your own craft and go snorkeling with a guide.

                                                                              Charter a yacht for a sunset cruise, or hire a 4x4 and go in a guided convoy to see the sights on both the French and Dutch side of the island. This tour will take you to Oyster Pond, Maho Beach and you'll have two hours to laze on Orient Beach.

                                                                              Traveling with the kids? If the beach is too hot for them, head to the Butterfly farm—it's a great day out.

                                                                              Happy Bay Beach is for nudists. If you're feeling adventurous, go there for an all-over tan.

                                                                              Top travel tips for St. Marteen-St. Martin

                                                                              It's best to rent a car on St. Maarten-St Martin as you'll have the freedom to explore the island in our own time. That being said, there are taxis and local buses if you don't want to bother.

                                                                              If you do drive, watch out for potholes! If you can find an all-terrain vehicle to rent, do. It'll definitely be worth it!

                                                                              You will probably find, on both the French and Dutch sides of the island, that a service charge is included in your restaurant bills. Of course, if the service was very good, you can leave an extra cash tip.

                                                                              There's plenty to do and see on St. Maarten-St. Martin, whichever side of the island you visit, the Dutch or French. Go around the island and see it all!

                                                                              For a wide choice of accommodation, search the rental properties available here on FlipKey and book your next trip. You won’t be disappointed!