Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Homes
Townhomes
Villas
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Cottages
Estates
Farmhouses
Hotels
Lodges
Studios
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Simpson Bay Vacation Rentals with Air Conditioning(61)

61 Results
Book it Now!
2 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
    (30)
    Book it Now!
    2 - 7 night minimum stay
    • 2 BR,
    • 2 BA,
    • Sleeps 4
      (13)
      Book it Now!
      5 - 7 night minimum stay
      • 2 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 4
        (12)
        7 night minimum stay
        • 2 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 4
          (16)
          Book it Now!
          5 - 14 night minimum stay
          • 2 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 4
            2 Reviews
            5 - 10 night minimum stay
            • 1 BR,
            • 1 BA,
            • 1 HF BA,
            • Sleeps 2
              (16)
              1 - 4 night minimum stay
              • 1 BR,
              • 1 BA,
              • Sleeps 4
                (5)
                5 - 14 night minimum stay
                • 6 BR,
                • 6 BA,
                • 1 HF BA,
                • Sleeps 12
                  7 night minimum stay
                  • 6 BR,
                  • 5 BA,
                  • Sleeps 12
                    (4)
                    5 - 7 night minimum stay
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 4
                      (3)
                      4 - 7 night minimum stay
                      • 3 BR,
                      • 3 BA,
                      • 1 HF BA,
                      • Sleeps 6
                        1 Review
                        5 night minimum stay
                        • 1 BR,
                        • 2 BA,
                        • Sleeps 2
                          (6)
                          3 - 7 night minimum stay
                          • 1 BR,
                          • 1 BA,
                          • 1 HF BA,
                          • Sleeps 4
                            5 night minimum stay
                            • 2 BR,
                            • 2 BA,
                            • Sleeps 5
                              (5)
                              5 - 7 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • 1 HF BA,
                              • Sleeps 3
                                4 - 7 night minimum stay
                                • 2 BR,
                                • 2 BA,
                                • 1 HF BA,
                                • Sleeps 4
                                  1 Review
                                  5 night minimum stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 5
                                    (9)
                                    4 - 7 night minimum stay
                                    • 1 BR,
                                    • 1 BA,
                                    • Sleeps 3
                                      (8)
                                      4 - 7 night minimum stay
                                      • 2 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                        (21)
                                        5 - 10 night minimum stay
                                        • 2 BR,
                                        • 3 BA,
                                        • 1 HF BA,
                                        • Sleeps 4
                                          2 Reviews
                                          4 - 6 night minimum stay
                                          • 1 BR,
                                          • 1 BA,
                                          • Sleeps 4
                                            (5)
                                            • 4 BR,
                                            • 5 BA,
                                            • Sleeps 12
                                              (33)
                                              5 - 14 night minimum stay
                                              • 2 BR,
                                              • 2 BA,
                                              • 1 HF BA,
                                              • Sleeps 4
                                                5 - 14 night minimum stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 6
                                                  5 - 14 night minimum stay
                                                  • 3 BR,
                                                  • 3 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 6
                                                    5 - 14 night minimum stay
                                                    • 1 BR,
                                                    • 1 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 2
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 4
                                                        (8)
                                                        7 night minimum stay
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • Sleeps 4
                                                          (10)
                                                          5 - 14 night minimum stay
                                                          • 2 BR,
                                                          • 2 BA,
                                                          • Sleeps 4
                                                            5 night minimum stay
                                                            • 2 BR,
                                                            • 2 BA,
                                                            • Sleeps 5
                                                              Advertisement
                                                               

                                                              Recent Simpson Bay Reviews

                                                              Beautiful Villa! More than we expected

                                                              5 of 5
                                                              My girlfriends and I (8 of us) decided on Rick's Seaside Retreat for our girls vacation. This place did not disappoint, the Jacuzzi tubs were just what we needed after a day of sightseeing. The rooms were spacious and beautiful, the kitchen had everything we needed to make a meal. The only thing negative I could say was the gas took longer than what I'm used to with electric. The villa's view I feel is second to none, and I can't think of a better place to have spent my birthday. Jenny was a jewel and we were thankful for her insights and suggestions. Rick, you and Marie have a beautiful home and I thank you for allowing us to experience a bit of paradise.
                                                              • Submitted: Sep 7, 2014
                                                              • Stayed: Aug 2014

                                                              Amazing and than........

                                                              5 of 5
                                                              All you see is all you will found.It is a real luxurious beach penthouse,wide comfortable and functionale. Well located in a quiet area close to all you need. Simona is special person that help you in every situation. We miss that so much. Well-recommended
                                                              • Submitted: Aug 23, 2014
                                                              • Stayed: Jul 2014

                                                              Fantastic Condo

                                                              5 of 5
                                                              My wife, two daughters (ages 23,21) and I stayed here for a week from May 29th, 2013 - June 5th, 2013. We found this place to be absolutely fantastic. The pictures in this listing are accurate - in fact it looks better in person. This is 1 of only 2 condos in the complex that are on two floors. Condo is located in Simpson Bay, which we found to be ideally located to get to everything. Grocery is nearby. So are great restaurants such as Jimbo's, Crave (#1 on Tripadvisor as of this writing), SkipJacks, Izi, Toppers, Lee's Roadside grill. We ran out of time, but we could have easily walked on the beach down to Karakters, or Mary's Boon. You just can't beat waking up in the morning in the master suite and looking out at the clear blue waters. The pool was very nice too! Our contact for this condo, Amanda, was very helpful in suggesting things to do, and was quick to respond to questions. I highly recommend this condo.
                                                              • Submitted: Jul 11, 2013
                                                              • Stayed: May 2013