Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Oak Bluffs Vacation Rentals with Online Booking(53)

53 Results
Book it Now!
1 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 15
    (7)
    Book it Now!
    4 - 5 night minimum stay
    • 3 BR,
    • 2 BA,
    • 1 HF BA,
    • Sleeps 6
      (3)
      Book it Now!
      7 night minimum stay
      • 5 BR,
      • 1 BA,
      • 1 HF BA,
      • Sleeps 9
        (5)
        Book it Now!
        3 - 7 night minimum stay
        • Studio,
        • 1 BA,
        • Sleeps 2
          Book it Now!
          2 - 7 night minimum stay
          • 5 BR,
          • 2 BA,
          • Sleeps 13
            (15)
            Book it Now!
            2 - 7 night minimum stay
            • 5 BR,
            • 1 BA,
            • 1 HF BA,
            • Sleeps 9
              (5)
              Book it Now!
              7 night minimum stay
              • 3 BR,
              • 3 BA,
              • Sleeps 8
                1 Review
                $275 - $425
                per night
                Book it Now!
                4 - 7 night minimum stay
                • 4 BR,
                • 3 BA,
                • Sleeps 9
                  1 Review
                  Book it Now!
                  • 4 BR,
                  • 4 BA,
                  • Sleeps 8
                    Book it Now!
                    2 - 7 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 5
                      (5)
                      Book it Now!
                      2 - 7 night minimum stay
                      • 2 BR,
                      • 2 BA,
                      • Sleeps 6
                        1 Review
                        $37 - $340
                        per night
                        Book it Now!
                        2 - 28 night minimum stay
                        • 2 BR,
                        • 1 BA,
                        • Sleeps 4
                          Book it Now!
                          2 night minimum stay
                          • 2 BR,
                          • 1 BA,
                          • 1 HF BA,
                          • Sleeps 7
                            Book it Now!
                            2 - 7 night minimum stay
                            • 4 BR,
                            • 4 BA,
                            • 1 HF BA,
                            • Sleeps 9
                              (6)
                              Book it Now!
                              2 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 2
                                1 Review
                                Book it Now!
                                3 - 7 night minimum stay
                                • 3 BR,
                                • 3 BA,
                                • Sleeps 12
                                  Book it Now!
                                  4 - 5 night minimum stay
                                  • 4 BR,
                                  • 2 BA,
                                  • 1 HF BA,
                                  • Sleeps 9
                                    2 Reviews
                                    Book it Now!
                                    2 - 7 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                      Book it Now!
                                      7 night minimum stay
                                      • 2 BR,
                                      • 1 BA,
                                      • 1 HF BA,
                                      • Sleeps 4
                                        Book it Now!
                                        2 - 7 night minimum stay
                                        • 3 BR,
                                        • 1 BA,
                                        • Sleeps 6
                                          (9)
                                          Book it Now!
                                          2 - 7 night minimum stay
                                          • 2 BR,
                                          • 1 BA,
                                          • Sleeps 4
                                            (7)
                                            Book it Now!
                                            1 - 7 night minimum stay
                                            • 1 BR,
                                            • 1 BA,
                                            • Sleeps 4
                                              (8)
                                              Book it Now!
                                              2 - 7 night minimum stay
                                              • Studio,
                                              • 1 BA,
                                              • Sleeps 4
                                                (7)
                                                Book it Now!
                                                3 - 7 night minimum stay
                                                • 5 BR,
                                                • 2 BA,
                                                • Sleeps 9
                                                  (5)
                                                  Book it Now!
                                                  3 - 7 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                    (4)
                                                    Book it Now!
                                                    3 - 7 night minimum stay
                                                    • 4 BR,
                                                    • 1 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 8
                                                      2 Reviews
                                                      Book it Now!
                                                      7 night minimum stay
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 5
                                                        (4)
                                                        Book it Now!
                                                        3 - 7 night minimum stay
                                                        • 3 BR,
                                                        • 1 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 6
                                                          (4)
                                                          Book it Now!
                                                          7 night minimum stay
                                                          • 4 BR,
                                                          • 2 BA,
                                                          • 2 HF BA,
                                                          • Sleeps 10
                                                            (3)
                                                            Book it Now!
                                                            7 night minimum stay
                                                            • 3 BR,
                                                            • 1 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 8
                                                              (4)
                                                              Advertisement
                                                               

                                                              Recent Oak Bluffs Reviews

                                                              Truly a home away from home!

                                                              5 of 5
                                                              My family has been staying at this wonderful house for (I believe) the past 5+ years! We look forward so much to going back to "our" place in Oak Bluffs, It has become so loved and familiar to us that we consider it our own! The big, comfortable, well decorated rooms, clean/updated bathrooms and kitchen, wonderful deck, roomy wrap-around deck for those (rare) times when the weather isn't great, the huge dining room table where 10+ of us can sit at once -- I could go on and on. It couldn't be more convenient to downtown Oak Bluffs, the ferry, bike paths, shopping, restaurants, the supermarket . . . all in walking distance. There are too many special memories to list - hours of fun, laughs, cooking, eating, flying kites, having wine and pie on the porch, sightseeing by bike, car, or bus, playing board games and cards in the evening. It's a couple of weeks none of us ever want to miss and getting there is like coming home. You won't be disappointed!
                                                              • Submitted: Sep 20, 2014
                                                              • Stayed: Sep 2014

                                                              Strong recommendation of modern, private MV home

                                                              5 of 5
                                                              We stayed at this property over the 2014 Labor Day weekend and would highly recommend it. It is a beautiful, modern home in a secluded but easy-to-access location. The home is well-equipped and nicely maintained. The owners made the reservation process simple and they are very accommodating. Their caretaker went above and beyond to help us out. The property is centrally located between villages with easy access to the airport and walking-distance access to bike and walking trails. It is a first-class property, and we look forward to returning.
                                                              • Submitted: Sep 18, 2014
                                                              • Stayed: Aug 2014

                                                              Perfect Vineyard Charm, Beautiful Lagoon View!!!

                                                              5 of 5
                                                              We just got back from two weeks at this lovely home. This was our second year at the home, and we hope to return again next year. Views are stunning, especially around dinner. We did not want to leave the house. We would recommend this home very highly. The owners are great...very responsive and easy to deal with.
                                                              • Submitted: Aug 10, 2014
                                                              • Stayed: Jul 2014