Vacation Rentals & Apartments in Oak Bluffs

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1,289 apartments

    17

    Cozy MV Cottage with Charming Romantic Gardens

    Martha's Vineyard / Oak Bluffs

    Oak Bluffs house

    2 3 2 nights min

    • 2 bedrooms
    • sleeps 3
    • 2 nights min
    • Child Friendly
    • Car not necessary

    Price per night from

    $602

    Price per night from

    $602

    (1) Excellent 

      25

      WATERFRONT HOME WITH PRIVATE BEACH

      Martha's Vineyard / Oak Bluffs

      Oak Bluffs house

      7 12 min stay varies

      • 7 bedrooms
      • sleeps 12
      • min stay varies
      • Ask about children
      “A memorable week at the Vineyard” We had a most enjoyable week - very comfortable accommodation. Everything went smoothly for our son's wedding, even the weather was kind!
      …see more

      Price per night from

      $1,000

      Price per night from

      $1,000

        0

        Cozy townhouse w/ shared pool, tennis & great location close to the beach!

        Martha's Vineyard / Oak Bluffs

        Oak Bluffs house

        2 6 min stay varies

        • 2 bedrooms
        • sleeps 6
        • min stay varies
        • Swimming pool
        • Child Friendly
        • Car not necessary

        Price per night from

        $161

        Responds fast!
        avg. 37 minutes

        Price per night from

        $161

        (2) Excellent 

          47

          Charming house with lots of entertainment and gourmet kitchen!

          Martha's Vineyard / Oak Bluffs

          Oak Bluffs house

          3 6 min stay varies

          • 3 bedrooms
          • sleeps 6
          • min stay varies
          • Child Friendly
          • Car not necessary
          • Air conditioning

          Price per night from

          $182

          Responds fast!
          avg. 37 minutes

          Price per night from

          $182

            15

            Adorable Cottage Walking Distance to Town and Beach

            Martha's Vineyard / Oak Bluffs

            Oak Bluffs house

            4 7 min stay varies

            • 4 bedrooms
            • sleeps 7
            • min stay varies
            • Ask about children

            Price per night from

            $214

            Price per night from

            $214

              0

              Dog-friendly condo with shared pool & tennis courts - golf and beach nearby!

              Martha's Vineyard / Oak Bluffs

              Oak Bluffs house

              2 6 min stay varies

              • 2 bedrooms
              • sleeps 6
              • min stay varies
              • Swimming pool
              • Child Friendly
              • Car not necessary

              Price per night from

              $161

              Responds fast!
              avg. 1 hour 8 minutes

              Price per night from

              $161

              (69) Excellent 

                20

                In-Town Historic Property on Martha's Vineyard

                Martha's Vineyard / Oak Bluffs

                Oak Bluffs apartment

                2 5 min stay varies

                • 2 bedrooms
                • sleeps 5
                • min stay varies
                • Beach / lakeside relaxation
                • Nearest beach 0.2 mi
                • Child Friendly
                “One of Oak Bluffs best kept secrets!” My family and I have been vineyarders for decades, and have been accustomed to rental property's away from the busy streets of downtown Oak Bluffs. Needless, to say we weren't optomistic about what to expect. Howe
                …see more

                Price per night from

                $177

                Responds fast!
                avg. 2 hours 39 minutes

                Price per night from

                $177

                  27

                  CLARO - New Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch

                  Martha's Vineyard / Oak Bluffs

                  Oak Bluffs house

                  3 7 7 nights min

                  • 3 bedrooms
                  • sleeps 7
                  • 7 nights min
                  • Ask about children
                  • Air conditioning

                  Price per night from

                  $257

                  Price per night from

                  $257

                  (8) Very Good 

                  Certificate of Excellence

                    18

                    Oak Bluffs Contemporary Summer Home

                    Martha's Vineyard / Oak Bluffs

                    Oak Bluffs house

                    3 6 7 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 7 nights min
                    • Beach / lakeside relaxation
                    • Child Friendly

                    Certificate of Excellence

                    Price per night from

                    $276

                    Responds fast!
                    avg. 3 hours 51 minutes

                    Price per night from

                    $276

                      45

                      Charming cottage with deck and playroom one mile from beach

                      Martha's Vineyard / Oak Bluffs

                      Oak Bluffs house

                      4 8 2 nights min

                      • 4 bedrooms
                      • sleeps 8
                      • 2 nights min
                      • Child Friendly
                      • Car not necessary
                      • Air conditioning

                      Price per night from

                      $162

                      Responds fast!
                      avg. 1 hour 8 minutes

                      Price per night from

                      $162

                        10

                        COZY,CUTE COTTAGE NEAR TOWN & BEACH.

                        Martha's Vineyard / Oak Bluffs

                        Oak Bluffs house

                        2 4 min stay varies

                        • 2 bedrooms
                        • sleeps 4
                        • min stay varies
                        • Ask about children
                        • Air conditioning

                        Price per night from

                        $129

                        Price per night from

                        $129

                          17

                          ALLER - Oak Bluffs 4 Bedroom Home, Walk to Town and Beach!

                          Martha's Vineyard / Oak Bluffs

                          Oak Bluffs house

                          4 8 7 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 7 nights min
                          • Ask about children
                          • Air conditioning

                          Price per night from

                          $386

                          Price per night from

                          $386

                            3

                            Lovely townhouse w/ private deck, shared pool & tennis - walk to the beach!

                            Martha's Vineyard / Oak Bluffs

                            Oak Bluffs house

                            2 6 min stay varies

                            • 2 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Swimming pool
                            • Child Friendly
                            • Car not necessary

                            Price per night from

                            $203

                            Responds fast!
                            avg. 37 minutes

                            Price per night from

                            $203

                            (1) Excellent 

                              19

                              Newly Renovated with Fabulous ocean views

                              Martha's Vineyard / Oak Bluffs

                              Oak Bluffs cottage

                              4 10 7 nights min

                              • 4 bedrooms
                              • sleeps 10
                              • 7 nights min
                              • Beach / lakeside relaxation
                              • Nearest beach 1 mi
                              • Child Friendly

                              Price per night from

                              $1,025

                              Price per night from

                              $1,025

                                15

                                GOLLB - Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

                                Martha's Vineyard / Oak Bluffs

                                Oak Bluffs house

                                3 4 7 nights min

                                • 3 bedrooms
                                • sleeps 4
                                • 7 nights min
                                • Ask about children
                                • Air conditioning

                                Price per night from

                                $207

                                Price per night from

                                $207

                                  1

                                  Coastal getaway w/ shared outdoor pool & 3 tennis courts - 1/2 mile to the beach

                                  Martha's Vineyard / Oak Bluffs

                                  Oak Bluffs house

                                  1 6 min stay varies

                                  • 1 bedroom
                                  • sleeps 6
                                  • min stay varies
                                  • Swimming pool
                                  • Child Friendly
                                  • Car not necessary

                                  Price per night from

                                  $155

                                  Responds fast!
                                  avg. 37 minutes

                                  Price per night from

                                  $155

                                    0

                                    Cozy condo with shared pool & tennis courts, close to golfing & the beach!

                                    Martha's Vineyard / Oak Bluffs

                                    Oak Bluffs house

                                    1 6 min stay varies

                                    • 1 bedroom
                                    • sleeps 6
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Car not necessary

                                    Price per night from

                                    $144

                                    Responds fast!
                                    avg. 1 hour 25 minutes

                                    Price per night from

                                    $144

                                      24

                                      Spacious Oak Bluffs Condo - Steps to Inkwell Beach

                                      Martha's Vineyard / Oak Bluffs

                                      Oak Bluffs apartment

                                      3 4 min stay varies

                                      • 3 bedrooms
                                      • sleeps 4
                                      • min stay varies
                                      • Child Friendly

                                      Price per night from

                                      $315

                                      Responds fast!
                                      avg. 9 minutes

                                      Price per night from

                                      $315

                                        13

                                        TOTHG - Adorable Updated Vineyard Cottage, Lovely Landscaped Yard, Central A/C,

                                        Martha's Vineyard / Oak Bluffs

                                        Oak Bluffs house

                                        3 5 7 nights min

                                        • 3 bedrooms
                                        • sleeps 5
                                        • 7 nights min
                                        • Ask about children
                                        • Air conditioning

                                        Price per night from

                                        $286

                                        Price per night from

                                        $286

                                          10

                                          BEAUTIFUL SECLUDED ESCAPE WITH CENTRAL A/C

                                          Martha's Vineyard / Oak Bluffs

                                          Oak Bluffs house

                                          4 8 7 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 7 nights min
                                          • Child Friendly

                                          Price per night from

                                          $716

                                          Price per night from

                                          $716

                                            48

                                            KEEFJ - Historic Waterfront Home Located just 1 Mile from Oak Bluffs Center, Pri

                                            Martha's Vineyard / Oak Bluffs

                                            Oak Bluffs house

                                            7 12 7 nights min

                                            • 7 bedrooms
                                            • sleeps 12
                                            • 7 nights min
                                            • Ask about children

                                            Price per night from

                                            $3,193

                                            Price per night from

                                            $3,193

                                            (1) Excellent 

                                              12

                                              “Gingerbread House”, water views, large porch!

                                              Martha's Vineyard / Oak Bluffs

                                              Oak Bluffs cottage

                                              4 8 6 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 6 nights min
                                              • Child Friendly
                                              • Car not necessary

                                              Price per night from

                                              $456

                                              Price per night from

                                              $456

                                                29

                                                ARMSA - Cozy Newly updated Seashore Cottage, East Chop Highlands Area, Farmers

                                                Martha's Vineyard / Oak Bluffs

                                                Oak Bluffs house

                                                3 6 7 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 7 nights min
                                                • Ask about children
                                                • Air conditioning

                                                Price per night from

                                                $286

                                                Price per night from

                                                $286

                                                  64

                                                  Tranquil, quiet home w/ private deck - walk to beaches and downtown Oak Bluffs!

                                                  Martha's Vineyard / Oak Bluffs

                                                  Oak Bluffs house

                                                  2 4 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • min stay varies
                                                  • Child Friendly
                                                  • Car not necessary
                                                  • Air conditioning

                                                  Price per night from

                                                  $232

                                                  Responds fast!
                                                  avg. 37 minutes

                                                  Price per night from

                                                  $232

                                                    22

                                                    BURBR - Perfect Retreat for Large Families, 1.5 miles Oak Bluffs Town Center

                                                    Martha's Vineyard / Oak Bluffs

                                                    Oak Bluffs house

                                                    6 13 7 nights min

                                                    • 6 bedrooms
                                                    • sleeps 13
                                                    • 7 nights min
                                                    • Ask about children
                                                    • Air conditioning

                                                    Price per night from

                                                    $354

                                                    Price per night from

                                                    $354

                                                      34

                                                      LIJOY - Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, B

                                                      Martha's Vineyard / Oak Bluffs

                                                      Oak Bluffs house

                                                      4 8 7 nights min

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • 7 nights min
                                                      • Ask about children
                                                      • Air conditioning

                                                      Price per night from

                                                      $357

                                                      Price per night from

                                                      $357

                                                        26

                                                        Solera Victorian charm, ocean view, steps to beach

                                                        Martha's Vineyard / Oak Bluffs

                                                        Oak Bluffs cottage

                                                        4 9 7 nights min

                                                        • 4 bedrooms
                                                        • sleeps 9
                                                        • 7 nights min
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 0.1 mi
                                                        • Child Friendly

                                                        Price per night from

                                                        $1,058

                                                        Price per night from

                                                        $1,058

                                                          0

                                                          Superb townhouse close to golfing & the beach - deck, tennis, & shared pool

                                                          Martha's Vineyard / Oak Bluffs

                                                          Oak Bluffs house

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $161

                                                          Responds fast!
                                                          avg. 37 minutes

                                                          Price per night from

                                                          $161

                                                            13

                                                            Charming Oak Bluffs Cottage

                                                            Martha's Vineyard / Oak Bluffs

                                                            Oak Bluffs house

                                                            2 6 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • min stay varies
                                                            • Ask about children
                                                            • Air conditioning

                                                            Price per night from

                                                            $257

                                                            Price per night from

                                                            $257

                                                              17

                                                              OCALC - Adorable Campground Cottage, Overlooks Park , Walk to Town and Ink Well

                                                              Martha's Vineyard / Oak Bluffs

                                                              Oak Bluffs house

                                                              2 4 7 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 7 nights min
                                                              • Ask about children
                                                              • Air conditioning

                                                              Price per night from

                                                              $357

                                                              Price per night from

                                                              $357

                                                                20

                                                                QUINTESSENTIAL VINEYARD SUMMER HOME

                                                                Martha's Vineyard / Oak Bluffs

                                                                Oak Bluffs house

                                                                6 12 min stay varies

                                                                • 6 bedrooms
                                                                • sleeps 12
                                                                • min stay varies
                                                                • Ask about children

                                                                Price per night from

                                                                $500

                                                                Price per night from

                                                                $500

                                                                  13

                                                                  DOHEM - East Chop Seaside Cottage, Large Porch, WiFi, Spectacular Views

                                                                  Martha's Vineyard / Oak Bluffs

                                                                  Oak Bluffs house

                                                                  3 6 7 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 6
                                                                  • 7 nights min
                                                                  • Ask about children

                                                                  Price per night from

                                                                  $529

                                                                  Price per night from

                                                                  $529

                                                                    20

                                                                    BRANF - Exquistie Contemporary Home in Fresh Pond Estates, Screened Porch, ****

                                                                    Martha's Vineyard / Oak Bluffs

                                                                    Oak Bluffs house

                                                                    4 8 7 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 8
                                                                    • 7 nights min
                                                                    • Ask about children
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $500

                                                                    Price per night from

                                                                    $500

                                                                      40

                                                                      SMEDM - Retreat to this Lovely Vacation Home with Main and Guest House, Central

                                                                      Martha's Vineyard / Oak Bluffs

                                                                      Oak Bluffs house

                                                                      7 10 7 nights min

                                                                      • 7 bedrooms
                                                                      • sleeps 10
                                                                      • 7 nights min
                                                                      • Ask about children
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $500

                                                                      Price per night from

                                                                      $500

                                                                      (1) Very Good 

                                                                        24

                                                                        Lovely Oak Bluffs home one mile from town and beach

                                                                        Martha's Vineyard / Oak Bluffs

                                                                        Oak Bluffs house

                                                                        3 9 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 9
                                                                        • min stay varies
                                                                        • Ask about children

                                                                        Price per night from

                                                                        $143

                                                                        Price per night from

                                                                        $143

                                                                          30

                                                                          Wonderful Contempory Home in Meadow View Farms

                                                                          Martha's Vineyard / Oak Bluffs

                                                                          Oak Bluffs house

                                                                          4 8 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Ask about children
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $400

                                                                          Price per night from

                                                                          $400

                                                                            33

                                                                            GOLDF - Outstanding Summer Home with Pool, Screened Porch, and Patio Area, Assoc

                                                                            Martha's Vineyard / Oak Bluffs

                                                                            Oak Bluffs house

                                                                            5 10 7 nights min

                                                                            • 5 bedrooms
                                                                            • sleeps 10
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Ask about children
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $700

                                                                            Price per night from

                                                                            $700

                                                                              15

                                                                              LECAY - Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bed

                                                                              Martha's Vineyard / Oak Bluffs

                                                                              Oak Bluffs house

                                                                              4 8 7 nights min

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • 7 nights min
                                                                              • Ask about children
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $429

                                                                              Price per night from

                                                                              $429

                                                                              About Oak Bluffs

                                                                              The town of Oak Bluffs lies on the island of Martha’s Vineyard and is a popular tourist destination during the summer months, home to the largest marina on the island. Choose from over 900 Oak Bluffs vacation rentals and find your dream accommodation with FlipKey.

                                                                              About Oak Bluffs

                                                                              The pretty Gingerbread Cottages here have appealed to vacationers for over 100 years, and it’s easy to see why this quaint and charming town remains such a popular destination. With ferries arriving at the harbor from the mainland several times a day, families and couples come to Oak Bluffs for a relaxing break.

                                                                              Beautiful beaches, rich history to explore and plenty of outdoor activities like golfing, fishing and hiking ensure that Oak Bluffs has everything you need for a great vacation. While you’re here, dine on delights such as fried seafood, blackened catfish and jambalaya. Wash it all down with a beer or root beer from the Offshore Ale Company, the island’s only brewery.

                                                                              With around 203 sunny days a year, summer is definitely the warmest time to visit the town, but Oak Bluffs is just as beautiful during the Fall. Average summer temperatures are around 78 degrees Fahrenheit.

                                                                              What to do

                                                                              The beaches here are simply stunning, whether you head for Oak Bluffs Town Beach or relax on Joseph A. Sylvia State Beach. With two miles of golden sands, the calm waters and views of Cape Cod ensure this is a popular family spot that’s also good for windsurfing.

                                                                              The marina here is a great spot for drinks and dining, with events like the Harbor Festival held here during the summer months. You’ll find the majority of stores, bars and restaurants on Circuit Avenue.

                                                                              Don’t miss the chance to see the Flying Horses Carousel, the oldest operating carousel in the US, with hand-carved horses created in 1876.

                                                                              There are plenty of outdoor activities here, too, with family fishing expeditions leaving from Oak Bluffs Dock and Farm Neck Golf Course with its 18-hole championship course and driving range. Pecoy Point Preserve is also nearby, with 14 acres of trails.

                                                                              Top Oak Bluffs travel tips

                                                                              Ferries arrive at the harbor from the mainland from five different destinations in Massachusetts: Falmouth, North Kingstown, Woods Hole, New Bedford and Hyannis.

                                                                              The best way to explore this compact town is definitely on foot, but there is a bus service, or you can rent a bike or moped in the town center. There’s also a free pedicab service, with any tips and donations going to charity.

                                                                              Beautiful beaches, family-friendly restaurants and outdoor activities continue to draw visitors to Oak Bluffs year after year.

                                                                              Why not book a vacation rental with ocean views on FlipKey today and come find out what Oak Bluffs has to offer?