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Simpson Bay Waterfront Vacation Rentals(25)

Affordable Luxury~On Simpson Bay~Direct Beach & Pool Access
    1 Bedrooms,
  • 1 Bathroom
  • , Sleeps 2
Book it Now!
5 - 7 night Minimum Stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
#168611
    (31)
    Simpson Bay Oceanfront w/ pool ~Private 2nd Fl ~Rent as 1 or 2 BR
      2 Bedrooms,
    • 2 Bathrooms
    • , Sleeps 4
    Book it Now!
    5 - 7 night Minimum Stay
    • 2 BR,
    • 2 BA,
    • Sleeps 4
    #329357
      (39)
      Bella Mare! Beach Front, Ground Floor & Luxurious
        2 Bedrooms,
      • 2 Bathrooms
      • , Sleeps 5
      • 2 BR,
      • 2 BA,
      • Sleeps 5
      #87855vb
        (42)
        Beach Front Ground Floor Luxury, 2 Bedroom Condo
          2 Bedrooms, Sleeps 5
        5 night Minimum Stay
        • 2 BR,
        • Sleeps 5
        #212403vb
          (7)
          BeachFront, Ground Floor....Luxury at it's Best
            1 Bedrooms,
          • 2 Bathrooms
          • , Sleeps 2
          • 1 BR,
          • 2 BA,
          • Sleeps 2
          #450377vb
            Beachfront Elegance W/ Private Jacuzzi Hot Tub On Deck
              2 Bedrooms,
            • 2 Bathrooms
            • , Sleeps 4
            • 2 BR,
            • 2 BA,
            • Sleeps 4
            #476090vb
              Casa Carib, Luxury 2 Bedroom / 2 Bath on Simpson Bay Beach
                2 Bedrooms,
              • 2 Bathrooms
              • , Sleeps 4
              • 2 BR,
              • 2 BA,
              • Sleeps 4
              #233071
                (7)
                Beachfront Bliss-2-bedroom condo on beautiful Simpson Bay
                  2 Bedrooms,
                • 2 Bathrooms
                • , Sleeps 4
                • 2 BR,
                • 2 BA,
                • Sleeps 4
                #184582
                  (5)
                  Beach Heaven at La Siesta-for the Vacation of Your Dreams!
                    2 Bedrooms, Sleeps 4
                  • 2 BR,
                  • Sleeps 4
                  #177475
                    The Penthouse at La Siesta - Newly Constructed 3BR/3BA Condo
                      3 Bedrooms,
                    • 3 Bathrooms
                    • , Sleeps 8
                    • 3 BR,
                    • 3 BA,
                    • Sleeps 8
                    #183724
                      (9)
                      Luxurious Beachfront 2 BR/ 2 Bath Caribbean Condo in 5-Star Resort
                        2 Bedrooms,
                      • 2 Bathrooms
                      • , Sleeps 4
                      7 night Minimum Stay
                      • 2 BR,
                      • 2 BA,
                      • Sleeps 4
                      #253570
                        (9)
                        New Luxury Condo ** Fine Furnishings
                          2 Bedrooms,
                        • 2 Bathrooms
                        • , Sleeps 4
                        • 2 BR,
                        • 2 BA,
                        • Sleeps 4
                        #385284
                          (22)
                          A spectacular well appointed ground floor unit with breathtaking views
                            2 Bedrooms,
                          • 2 Bathrooms
                          • , Sleeps 4
                          7 night Minimum Stay
                          • 2 BR,
                          • 2 BA,
                          • Sleeps 4
                          #146715
                            (10)
                            Luxury Beachfront 2 Bedroom Caribbean Condo in 5-Star Resort
                              2 Bedrooms,
                            • 2 Bathrooms
                            • , Sleeps 4
                            5 - 7 night Minimum Stay
                            • 2 BR,
                            • 2 BA,
                            • Sleeps 4
                            #232586
                              (5)
                              Luxurious Villa Vittoria ~ Private Beach. *Discounted rates available for summer
                                6 Bedrooms,
                              • 5 Bathrooms
                              • , Sleeps 12
                              7 night Minimum Stay
                              • 6 BR,
                              • 5 BA,
                              • Sleeps 12
                              #443987vb
                                1 Review
                                Condo le Bateau Simpson Bay Yacht Club
                                  1 Bedrooms,
                                • 2 Bathrooms
                                • , Sleeps 4
                                7 night Minimum Stay
                                • 1 BR,
                                • 2 BA,
                                • Sleeps 4
                                #954566a
                                  Coco Belle Beach Front Villa
                                    1 Bedrooms,
                                  • 1 Bathroom
                                  • , Sleeps 2
                                  5 - 7 night Minimum Stay
                                  • 1 BR,
                                  • 1 BA,
                                  • Sleeps 2
                                  #245562
                                    4 Reviews
                                    Charming studio for 2 in the heart of Simpson Bay
                                      1 Bedrooms,
                                    • 1 Bathroom
                                    • , Sleeps 2
                                    5 - 7 night Minimum Stay
                                    • 1 BR,
                                    • 1 BA,
                                    • Sleeps 2
                                    #3497731
                                      Simpson Bay Yacht Club Condo
                                        2 Bedrooms,
                                      • 1 Bathroom
                                      • 1 Half Bath
                                      • , Sleeps 6
                                      • 2 BR,
                                      • 1 BA,
                                      • 1 HF BA,
                                      • Sleeps 6
                                      #158182
                                        (3)
                                        Luxury Condo has private deck area with spectacular Yacht views
                                          1 Bedrooms,
                                        • 1 Bathroom
                                        • , Sleeps 4
                                        • 1 BR,
                                        • 1 BA,
                                        • Sleeps 4
                                        #357573
                                          5 More choices from HomeAway International Websites
                                          5 Star/flexible wks/fab water sports/BEACHFRONTRESORT.
                                            2 Bedrooms,
                                          • 2 Bathrooms
                                          • , Sleeps 8
                                          4 night Minimum Stay
                                          • 2 BR,
                                          • 2 BA,
                                          • Sleeps 8
                                          #188078vb
                                            (10)
                                            Sea View @ La Siesta, St. Maarten, N.a.
                                              2 Bedrooms,
                                            • 2 Bathrooms
                                            • , Sleeps 4
                                            • 2 BR,
                                            • 2 BA,
                                            • Sleeps 4
                                            #339989vb
                                              (5)
                                              Simpson Bay Resort & Marina: All Weeks, Best Prices! Beachfront resort
                                                Studio, Sleeps 6
                                              7 night Minimum Stay
                                              • Studio,
                                              • Sleeps 6
                                              #463855vb
                                                Fantastic View Beach Front Condo. Caribbean Sun
                                                  2 Bedrooms,
                                                • 2 Bathrooms
                                                • 1 Half Bath
                                                • , Sleeps 4
                                                • 2 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 4
                                                #88462vb
                                                  5 Reviews
                                                  Waterfront Villa with Pool/Deck. Special $100 Pp/Per Night.
                                                    4 Bedrooms, Sleeps 10
                                                  • 4 BR,
                                                  • Sleeps 10
                                                  #235470vb
                                                    (7)
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