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Caribbean Cottage Rentals(699)

699 Results
Book it Now!
4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
    (17)
    Book it Now!
    3 - 7 night minimum stay
    • 1 BR,
    • 1 BA,
    • Sleeps 2
      (15)
      Book it Now!
      5 night minimum stay
      • 2 BR,
      • 1 BA,
      • Sleeps 4
        (9)
        7 night minimum stay
        • 1 BR,
        • 1 BA,
        • Sleeps 2
          (31)
          Book it Now!
          4 night minimum stay
          • 1 BR,
          • 1 BA,
          • Sleeps 4
            (7)
            3 night minimum stay
            • 1 BR,
            • 1 BA,
            • Sleeps 3
              (39)
              Book it Now!
              4 - 6 night minimum stay
              • 1 BR,
              • 1 BA,
              • Sleeps 2
                (10)
                Book it Now!
                4 night minimum stay
                • 2 BR,
                • 1 BA,
                • Sleeps 5
                  (27)
                  7 night minimum stay
                  • 1 BR,
                  • 1 BA,
                  • Sleeps 2
                    (39)
                    5 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 5
                      (30)
                      4 night minimum stay
                      • 1 BR,
                      • 1 BA,
                      • Sleeps 2
                        (34)
                        2 night minimum stay
                        • 2 BR,
                        • 2 BA,
                        • Sleeps 8
                          (4)
                          3 night minimum stay
                          • 1 BR,
                          • 1 BA,
                          • Sleeps 4
                            (9)
                            5 night minimum stay
                            • 1 BR,
                            • 1 BA,
                            • Sleeps 2
                              (33)
                              7 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 2
                                (17)
                                2 - 3 night minimum stay
                                • 1 BR,
                                • 1 BA,
                                • Sleeps 4
                                  (10)
                                  $3,100 - $4,600
                                  per week
                                  7 night minimum stay
                                  • 1 BR,
                                  • 1 BA,
                                  • Sleeps 2
                                    7 night minimum stay
                                    • 1 BR,
                                    • 1 BA,
                                    • Sleeps 2
                                      $3,700 - $6,150
                                      per week
                                      7 night minimum stay
                                      • 1 BR,
                                      • 1 BA,
                                      • 1 HF BA,
                                      • Sleeps 2
                                        3 night minimum stay
                                        • 2 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                          (26)
                                          7 night minimum stay
                                          • 1 BR,
                                          • 1 BA,
                                          • Sleeps 2
                                            2 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 10
                                              (14)
                                              3 - 7 night minimum stay
                                              • 2 BR,
                                              • 1 BA,
                                              • Sleeps 4
                                                (14)
                                                7 night minimum stay
                                                • 2 BR,
                                                • 2 BA,
                                                • Sleeps 4
                                                  (28)
                                                  3 - 7 night minimum stay
                                                  • 1 BR,
                                                  • 1 BA,
                                                  • Sleeps 2
                                                    (8)
                                                    4 - 7 night minimum stay
                                                    • 2 BR,
                                                    • 1 BA,
                                                    • Sleeps 4
                                                      (6)
                                                       

                                                      Recent Caribbean Reviews

                                                      Felt perfectly at home! Spectacular view!

                                                      5 of 5
                                                      We reserved the home for ten days for myself and my husband and our 14 year old son. The setup of the home with the sleeping areas separated was such that we could be together as a family but could also feel that we had our own private space. Our son used the pull out couch in the large air conditioned living room and loved that he had the big flat screen in his room lol. We loved the breeze and the exquisite view from the patio and my personal favorite space was the window seat in the dining room...just needed a few more pillows as a back rest to be the perfect reading spot. But that was a problem easily solved! We played some of the games provided at the big dining room table and even had our family over for snacks and to watch a movie. They live in Bermuda and were impressed with our view! The house is within walking distance to town and was about 5 mins from our family. Several good restaurants close by: Art Mels (great fries, huge fish sandwich and not so expensive), Chinese takeout, Tavern by the Sea (great pizza and salad). The airport, Fort St Catherine and a beach are close by and plenty of places to catch the buses that run constantly. Can't ask for a better location. Faith is excellent to work with and has really set this home up with everything that you might need: wifi, a prepaid cell, plus beach items, towels, snorkel gear, umbrella...located just a few steps down the inside stairs to the fully equipped modern laundry area. Also, an abundance of dishes, pots, pans etc that you need if you desire to have or cook meals at home. Loved the gas stove and convection oven and my husband made great use of the Tassimo coffee maker each morning. Coffee and teas provided! The pictures are accurate and show the house as comfortable, but I think the home is more up to date and modern feeling than the pics convey...especially the bathroom. The tile and cabinets are beautiful! The king size bed in the large bedroom was extremely comfortable and we slept just as good as in our bed at home. Extra large closet and great air conditioning in this space. A small TV would be nice for laying in bed, but we just used our Ipad since the home has wifi. I love to be on vacation and yet feel as comfortable and relaxed as if I were in my on home and this place fit that desire perfectly! We would definitely stay here again when we come to visit. We have already recommended the house for our friends. Thanks Faith for a wonderful home!!
                                                      • Submitted: Aug 11, 2014
                                                      • Stayed: Jul 2014

                                                      Highly recommend!

                                                      5 of 5
                                                      We totally agree with previous reviews and would highly recommend this cottage. Everything is comfortable and clean. Unlike some beach places there isn’t sand everywhere so the cottage really stays clean and there aren’t issues with slow drains that you sometimes find in beach houses. The location is perfect. You are close to a lot of stuff but the cottage is quiet and secluded. We went to a different beach every day, many of which have great snorkeling right when you enter the water. Between Chad’s recommendations and information in the guest book there are many great suggestions. We like a lot of quiet where we are staying and were able to come back in the afternoon and relax and hear nothing but the ocean. We had a perfect honeymoon.
                                                      • Submitted: Aug 2, 2014
                                                      • Stayed: Jul 2014

                                                      Amazing little villa on the hill

                                                      5 of 5
                                                      This was our second time to windwardside Guest cottage and we had another amazing experience. The view, the hot tub, the island, everything was great. Susan, Diane, and Margaret were fabulous with everything. Hope to be back again soon! Emily and Zack
                                                      • Submitted: Jul 30, 2014
                                                      • Stayed: Jul 2014