Vacation Rentals By Owner In Oak Bluffs, MA

This beautiful 3 bedroom home is located in a quiet area on Martha’s Vineyard by Lagoon Pond. When you walk inside, you will be delighted by the beach stone fireplace and the comforting ambience. It presents gorgeous “costa esmeralda” granite counter tops with solid cherry cabinets, stainless steel appliances, and a kitchen which integrates to the dining area that sits 8 people. From there, the french doors invite you to a relaxing patio surrounded by artisan landscaping. The patio, complete with cobblestones, also has a grill and it is a fun place for a family BBQ. An outdoor shower is a great way to rinse off after a swim in the Lagoon. The master bedroom is located on the first floor and features a walk-in closet and a bathroom with calcutta gold marble, his and her sinks, a rain shower, and a cast iron herring bone tub. The den has a comfy couch and a flat screen TV mounted on the wall, which is perfect for movie night. On the second floor of the house, you can find two decorated guest bedrooms next to a full bathroom. The house boasts a finished lower level with a flat screen TV, soft leather seats, a laundry room and a full bathroom adjacent to a relaxing area. If you and your loved ones want to rent a canoe or kayak, you are just a 10 minute walk away from Lagoon Pond with access to a public beach and a bike path. The location of the home is very convenient, it is just a 5 minute ride to the heart of Oak Bluffs, a family-friendly town. A spacious driveway that borders the home can fit up to 3 cars. Long-term rentals are welcome! Please book your ferry in advance. Central AC and central heating are two great features. Surrounded by hedges for privacy and friendly neighbors, you are able to enjoy a well-earned vacation. This home is a safe haven that will provide you with a great place for rest and rejuvenation, as well as memories that will last a lifetime. brbrWe adhere to the customs for home rentals on the Vineyard, which do not include linens (sheets, pillowcases, towels, or beach towels) as a part of the rental experience. Please arrange to bring your own linens or visit http://takemmylinenrental.com to place an order for your linen rental. br1st Fl King Master, 2nd Fl Queen, 2nd Fl 2 Doublebrbr

The Island Collection MV: Experience a Luxury Getaway by the Lagoon

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1085.89

Nestled in the charming town of East Chop, this 3-bedroom vacation home offers the perfect escape for your next getaway. As you arrive, you'll be greeted by the cozy porch, inviting you to sit back, relax, and soak in the peaceful surroundings. brbrInside, you'll find a fully stocked kitchen, complete with a stove, oven, refrigerator, and all the necessary appliances to whip up delicious meals. Gather around the dining table and enjoy quality time with your loved ones. When it's time to unwind, retreat to the comfortable living room and catch up on your favorite shows on the smart TV with satellite/cable channels.brbrJust a short 16-minute walk away, you can explore the vibrant Oak Bluffs Harbor, or hop in the car for a 3-minute drive to the Oak Bluffs Ferry Terminal and Oak Bluffs Town Beach. Enjoy the convenience of having a washing machine and dryer, as well as free WiFi, to make your stay even more comfortable.brbrWhether you're looking to relax on the beach, enjoy outdoor activities, or simply spend quality time with family and friends, this vacation home has everything you need for an unforgettable getaway.

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$649.61

Tucked away in the charming town of Oak Bluffs, this delightful two-story house is the perfect retreat for a beach getaway. Just a short distance from the ocean, this cozy cottage offers a serene escape with a furnished wraparound deck where you can relax and enjoy the fresh sea breezebrbr-- THE PROPERTY --brbrC0480042210brbrStep inside to find a full, open-concept kitchen equipped, perfect for preparing delicious meals during your stay. The living area features matching sofas, creating a welcoming space to unwind after a day of exploring the beach. brbrWith amenities like Internet access, cable TV, and a washer/dryer for your convenience, this home ensures a comfortable stay for you and your family. The partial AC keeps you cool on warmer days, while the gas grill on the deck is ideal for summer cookouts.brbrWhether you're lounging on the deck, grilling on the patio, or exploring the nearby beach, this house offers a peaceful retreat for your vacation.brbr-- THE LOCATION --brbrbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- Linens and towels are not provided at the property. It is recommended that you supply your own or rent them from a linen company on the island

Charming 3BR Cottage Near the Beach w/ Deck

Oak Bluffs, Massachusetts, United States

Bed

1

Bath

6

Sleeps

$3839.9

WELCOME TO PARADISE!!! we sanitize!!!!! We have implemented a system so you are able to check in and out without any person to person contact. brbrThis beautiful Estate is located in Prestigious Fresh Pond Estates. It sits tucked away in the woods off the main roads, Plenty of privacy in a quiet neighborhood. Yet has easy access to beaches, bike paths and town, Fresh water pond in your back yard. (3 two person kayaks available plus 2 single kayaks for your use, with life jackets). Fresh water swimming offers calm waters which makes it great for the kids.brbrWe sanitize the entire place in-between each tenant. We wash all comforters each time someone new comes in, we bleach all surfaces and alcohol all door handles, toilet, air out the place for a period of time.brbrJust 2 miles from the HEART of Oak Bluffs & Circuit Avenue activities. brOak Bluffs center offers, restaurants, movies, the nation's first carousel, shopping, and more beaches. brJust 500 feet from bike path, This property is centrally located a 5 minute drive to Edgartown or Vineyard Haven. brNo need to bring anything, high chair, toys, video games, books, DVD collection, beach toys, towels, house is fully equipped. Crib upon request..brLots of extras available on this wonderful property Amenities include Air Conditioning, Wifi, 11 TVs & 2 Laundry Facilities. The large, modern windows accentuate the views. 1 of the 2 kitchens is commercial with Thermadore appliances in the main kitchen, Great Location for visitors with or without a vehicle. Public Transportation close by.Tour the beautiful island of Martha's Vineyard. Stay in comfort. Shops, restaurants & galleries are a short drive away. Ideal Retreat for Groups and friends traveling together.brHome is located just 100 yards from the pond which is a wonderful spot to enjoy a beautiful sunset or sunrise or your morning coffee. The house is bright and airy with an open floor plan and cathedral ceilings. The well equipped kitchens have everything needed . This exceptional property has a park-like setting with wildlife and gardens , apple trees, raspberries, grapes,- excellent for walking, biking, running and water sports. Take the nearby bike path to many Vineyard towns and beaches. A vacation to remember!brbrSalt water pool can be heated for a small fee, but usually warm enough from the sun in general.... 6 person Therma Spa heated Jacuzzi is a favorite hang out spot in this gorgeous yard, Sit at the TIKI bar and enjoy a cold beverage from the outdoor kitchen. Sit under the pergola and enjoy the outdoor fire place on cool nights..Spacious Seating for 40 in the back yard and 70 ft deck… 2 out door showers helps remove all the sand from the beach..brThe back yard is your own special oasis.brbrHistory of Oak Bluffs: Oak Bluffs is the quintessential old fashioned summer resort. Lively & upbeat, Circuit Avenue offers galleries, retail shops - clothing, crafts & jewelry, a variety of casual & upscale restaurants, ice cream parlors, pubs w/music, bicycle rentals, lodging & a harbor w/cafes & water-sports available. Ocean Park faces the water & is home to summer concerts & events. The gingerbread cottages dating back to the 1800s in the campgrounds surround the open air Tabernacle which offers services, community sings, art shows, high profile professional performing artists & political forums. Union Chapel bustles w/activity. Dancers, authors, artists. Just a mile from the property is Farm Neck is a world class 18 hole golf course frequented by presidents, visitors & locals alike. Music & Aromas fill the air. Walk to the Beach on Nantucket Sound. Walk to everything in town. Island ferries come into the harbor on a seasonal basis. Buses are available to all island towns. Plenty of street parkingbrbrThe island truly offers something for everyone and a vacation experience that won't soon be forgotten.brbrThis house is located on 2 acre ‘s of beautifully landscaped grounds with lots of trees. brJust a two minute walk to a pond and, a one minute ride to the bike trail, and 2 mile's to town. WIFI included and as well as 11 Smart TVsbr. Farm Neck Golf Course and the OB Library nearby. You'll never want to leave!brWe welcome you to our tastefully decorated home with all the charm and amenities that is all “Vineyard.” With all new appliances and furniture and hard wood floors, the house has a family-friendly open floor plan. With 5 bedrooms, All with a new Comfy mattresses , the house comfortably sleeps 12 /adults.brThis meticulously maintained charming home offers a great atmosphere with all the amenities for a perfect vacation. Quiet, end of the road location yet really close to town. Wooded backyard with lots of beautiful landscaping as a bonusbrChildren's toys for all ages, board games, pool floats, life jackets all help you have the best vacation. Owners are in a 2 bedroom sound proof apartment on the same 2 acre property… We give you all your privacy but make our selves available if needed.brbr Master bedroom has a sitting room and a fire place along with a private bathroom….brAnother thing that makes this beautiful 5 bedroom house unique , Included in the house is an additional separate living quarters that is fully private with a full kitchen , laundry room, and living room with 2 bedrooms that your able to shut off from the main living quarters with a pocket door so that 2 families could actually live totally separate from each other or leave it open for everyone to share.brbrSo many extras on this exquisite property…It has 5 bedrooms and 4 bathrooms, 2 washers and 2 dryers, 2 stoves and 2 refrigerators. Large kitchen, Dining room that seats 12 plus a breakfast table that abuts a slider with a 70ft deck..brbrAs stated earlier Nestled within a lovely private neighborhood in Oak Bluffs, this beautiful contemporary home unfolds with style and comfortably for all ages. Boasting five bedrooms and four bathrooms. The residence welcomes you with multiple shared living spaces for gatherings of family and friends. The 1st floor open floor plan exudes an inviting atmosphere with its bright eat-in kitchen bar, dining room for 12 and great room living area with gorgeous natural light from the south facing windows that connect to the expansive back deck. A highlight of the main floor design is the spacious primary suite with glass sliders that connect to back deck. In addition to the living room, Entertaining and summer living is enhanced by the expansive back deck with ample comfortable outdoor furnishings offering a very private space to relax and unwind and dine al fresco. There is 2 outdoor showers for added convenience when you return home from the beach. Every bedroom has its own TV in addition to the large Tv’s in the 1st floor great room and exercise room. The thoughtful design ensures a harmonious flow between each living space; creating an environment that effortlessly accommodates everyone. The heated saltwater pool is its own oasis…Just steps away is walking and biking trails, along with the island world renowned golf course, Farm Neck. Convenience abounds from this fantastic location just minutes to downtown Oak Bluffs to enjoy the eateries, shops, and beautiful island beaches that draw vacationers back every year!

Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1393.96

This Oak Bluffs home boasts 3 inviting bedrooms and a cozy loft, including 2 king beds, 2 full beds and a queen sofa bed. With 4 bathrooms equipped with amenities like a hair dryer and shower, guests will feel right at home. The pleasant living room space also provides a cozy soft bed, an excellent spot to unwind after a day of exploring. With speakers on every level ask Alexa a question or play your favorite tune. This is a stylish modern NEW CONSTRUCTION home. A 3 minute drive or a leisurely 10 minute walk to town. And a 20 min walk to Inkwell beach. This home is my home. Make it your home during your stay. Book now and enjoy everything this brand new house has to offer.

Charming 3-bedroom w/loft.New Construction home with AC,WiFi. Short walk to town

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1089.08

Recently built, this spectacular 3 Bedroom carriage house is located on 3/4 acre estate on beautiful East Chop Drive. The interior is finished with top of the line decor, including a beautifully decorated living room, bedrooms, and open-living professional kitchen with granite counter tops and island. Other amenities include a dishwasher, trash compactor, air conditioner, ceiling fans in each room, walk-in shower, and large capacity washer and dryer in the garage below. brbrThe Master Bedroom has 1 king bed, and the second bedroom has 1 queen bed. The pull out sofa is also queen size. All rooms have Smart TVs and Bluos sound systems to listen to your favorite music, and there are USB charging outlets throughout the house. Walnut hardwood flooring with oriental rugs. brbrThe first level Queen Bedroom, walk in shower, air conditioning, smart TV, closet. Own entrance from driveway. No stairs to enter, just one step up.brbrThe outdoor deck is furnished with Lloyd Flanders furniture and overlooks beautiful landscaped grounds. The home is just minutes to Jetty Beach and downtown Oak Bluffs where you will find many attractions, great restaurants and wonderful local shops. There is a private entrance to the Carriage House on West Ave.brbrWe think the greatest asset of staying in our carriage house is the privacy and serenity. Sitting on the deck overlooking the beautiful grounds, taking in the fresh ocean air. The best part is walking out the door, through the landscaped yard and ending up on the ''Chop'' where you will take in the East Chop Light House and beautiful Nantucket Sound. Besides being located on East Chop Drive, you can easily walk to the local beach, downtown Oak Bluffs where you will find great restaurants like the Red Cat, The Chowder Company (which, by the way, has the best chowder ever), Lookout Tavern, Nancy's, Biscuits to name a few. Also, many boating excursions, fishing, pirate ship, ferry to Nantucket, the oldest carousell in the U.S., Mopeds and renting a car to cruise around the island. Fun shopping for clothes, tee shirts, beautiful island made items, etc. East Chop is the perfect spot for when you want to get away for relaxation and peaceful surroundings and only be minutes away from downtown from the hustle and bustle of downtown Oak Bluffs' nightlife; The Ritz is a must see where local musicians play 2x a night with no cover before 10:00.

Cottage

Beautiful Carriage House on the Chop

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1882.15

About this spacebrFirst floor has AC and hosts windowed living, dining, work space, kitchen and garden bedroom that sleeps 2 and has AC, a private bath and patio.brbrThree 2nd floor bedrooms sleep 6 - each with AC, private bath & balcony.brbr3rd floor sleeps 4 - with AC, living, kitchen, bath & balcony connected to exterior staircase & breezewaybrbrThe large veranda has a gas barbecue, dining & seating area overlooking manicured groundsbrbrLandscaped yard, picnic area, fire pit, hammock, swings & outdoor showerbrThe spacebrThe home is located a true walking distance to Oak Bluffs Harbor, Beaches, Circuit Avenue Shopping & Dinning, the popular Gingerbread Cottages Community, Historic Ocean Park and steps away from many of the highlight properties on the African-American Heritage Trail of Martha’s Vineyard.brbrThis property is a former bed & breakfast and as such is capable of host multiple small groups of guests and families with independent rooms for sleeping and bathingbrbrGuests will notice the mix of African-American and north-Atlantic history and culture that influences much of the art and artifacts within the home.brGuest accessbrGuests will have access to the entire home except for specific storage areas:brbr* Curtained-off section in basement used for storagebr* Small locked tool shed on the far end of front lawn used for yard equipmentbr* Separate locked garages on the far back-end of property used for equipment storagebrbrApart from this, there are also two cabinets on the first floor (one in the kitchen and one in the dining room) with small locks on them. They contain the extra linens and supplies for the cleaning crew and are not to be accessed by guests.brOther things to notebrAir Conditioning: There are independent AC units in all of the 2nd floor bedrooms as well as on the 3rd and 1st floor of the house and in the garden apartmentbrbrTV/Cable: There is cable TV available in each of the bedrooms as well as in the 1st floor living room (any movie orders will be deducted from the security deposit)brbrAlarms: Guests should not operate the alarm system in the house

Oak Bluff's Victorian Walk to Town & Beaches

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Select Dates for Price

**Ferry reservations available at request for 7/3-7/10 and 7/24-7/31** Seaside serenity awaits you at this Oak Bluffs retreat! Immerse yourself in the charms of island life while staying at this welcoming classic cape. Full of natural light, this home is located in a peaceful neighborhood just a short bike ride or drive from downtown Oak Bluffs, and with easy access to several beautiful beaches and other vineyard towns.brThis secluded home offers a well-stocked kitchen, generous deck space with firepit and grill, and a tranquil screened-in porch, creating the perfect setting for an effortlessly enjoyable stay.brbrEnter into a relaxing living room that flows into a warm and bright dining area and kitchen. brThree generous sliding glass doors connect the living room and kitchen to a charming screened in porch and a large deck perfect for evening grilling or enjoying your morning coffee. brThe downstairs is completed with a full bath and a bedroom with queen size bed and large closet. Upstairs is a full bath and two bedrooms. One with a king sized bed, dresser, large closet and desk. The other upstairs room has a double bed, twin bunk bed, dresser and closet.brAll bedrooms as well as the living room have AC units.brA washer and dryer are located in the basement. Beach chairs, beach toys, boogie boards and kayaks are available for your enjoyment as well. brLast but not least there is an outdoor shower to wash away a long day at the beach.brbr***** Checkin is 3:30pm and checkout is 10:00am*****

Sunny 3 bedroom cape with large deck, porch and kayaks. Pet friendly.

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$873.51

Newly renovated three-level home with three bedrooms and two bathrooms within walking distance to the heart of Downtown Oak Bluffs and beaches. This location allows you to be at the center of activity, from Fourth of July fireworks to Illumination but a quick escape into the quiet neighborhood of The Highlands. Walking distance from Oak Bluffs Town Beach (Inkwell) and ferry station. A bright, spacious, fully renovated, and well-appointed must-see home that you won’t want to leave. Comfortable living spaces for six people to relax and socialize. Open kitchen with new appliances and all the cooking tools necessary to whip up a pot of chowda or to have guests over to enjoy a lobster bake. Beautiful front porch with a view of the Harbor and lake or a great place to listen to the morning chirping of birds. Two Bedrooms on the second floor- one with a comfortable Queen bed and the other with two twin beds. Master bedroom with bathroom with a peak of the Harbor.brbrShared parking.brbrSPEND SOME TIME EXPLORING OUR HOMES FOR YOUR NEXT VACATIONbrbrVeriCasa Properties invites you and your family to relax and enjoy beautiful, peaceful scenery in the mountains or blue invigorating ocean waters to enjoying an exhilarating football game in a college town. VeriCasa has everything in between for you and your family to find a vacation anytime.brbrOur Staff is ready to assist you in finding your luxury dream vacation or experience.brwebsite: vericasa.properties

Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1108.69

Turnover days are Saturday to Saturday Experience the ultimate in luxury and relaxation in the exclusive Eastville area of Oak Bluffs! This stunning custom contemporary log home offers the perfect blend of style and comfort, featuring a spacious 1300sq-ft private back deck for soaking up the sun or enjoying a meal on the large BBQ Grill or cast Iron pizza oven for a truly unique dining experience. brInside, you'll find four spacious bedrooms, each with ample closet space. Two bathrooms, including a master bathroom with a jetted tub, shower, sink and make-up table. brThe stylishly remodeled kitchen boasts high-end stainless steel appliances, a large hammered copper farmhouse sink, and plenty of seating for casual dining. The living room features a cozy leather reclining couch and love seat, as well as two power reclining chairs, perfect for unwinding after a day in the sun.brAdditional amenities include a covered front porch with a romantic log swing and Adirondack chairs, an outdoor shower complete with hot water. The side deck has an ocean view that can be enjoyed sitting at the bar hight table with umbrella, the perfect spot to enjoy your morning coffee or a nightcap. brthere is a laundry room with a large capacity HE washer and dryer. (We provide laundry detergent)brMake this vacation home your own and create memories that will last a lifetime!brTurn over days are Saturday to Saturday,brensuring a stress-free vacation experience.brbrbrC0235312210

Indulge in the ultimate vacation experience at this exquisite custom log home.

Oak Bluffs, Massachusetts, United States

Bed

2

Bath

Sleeps

$1214.99

Historic Oak Bluffs Cottage – Porch with ViewbrbrStep into the charm of a bygone era at this classic Oak Bluffs home, filled with antiques, Persian rugs, and vintage character. From the front porch, you can take in views of the pier while rocking in the chairs, enjoying the same simple pleasures that have made this neighborhood a beloved summer destination for generations.brbrThis is not a modern, luxury home—it’s a historic Vineyard cottage, complete with creaky floors, unique décor, and plenty of personality. It’s the perfect setting for families and groups who want a comfortable, lived-in space with history at its heart.brbrInside the home you’ll find:brbrSpacious living areas decorated with antique furnishings, including a red velvet camel-back sofa, pink chesterfield, striped chairs, and a striped settee.brbrAir conditioning in most rooms to help keep things cool during summer days.brbrDining options with a six-seat dining table and a two-seat dinette in the kitchen.brbrFull kitchen with a stainless steel stove, refrigerator, dishwasher, and all the essentials.brbrFamily room with two couches and a brand-new 50 TV for downtime.brbrBedrooms (all with new mattresses):brbrPrimary suite: King bed, hardwood floors, dresser, wicker sofa, and a private balcony.brbrSecond bedroom: Queen bed with a rocking chair and Persian rug.brbrTwo additional bedrooms: Each with two twin beds—great for kids or extra guests.brbrTwo full bathrooms plus an outdoor shower.brbrExtras for your stay:brbrWasher and dryerbrbrFree WiFi and cable TVbrbrFour beach chairsbrbrGas grill on the back deckbrbrLocation highlights:brbr5 minutes to Inkwell Beach and the Steamship Authority DockbrbrHalf a mile to the Flying Horses CarouselbrbrClose to parks, shops, and plenty of local attractionsbrbrThis stately, antique-filled home offers the true Oak Bluffs experience—comfortable, welcoming, and full of character. If you’re looking for a unique stay that blends history with family-friendly amenities, this is the place.

Historic Oak Bluffs Cottage – Porch with View

Oak Bluffs, Massachusetts, United States

Bed

2

Bath

Sleeps

$1344.87

Experience comfort and style in this newly completed 5-bedroom home just 1 mile from downtown OB. The home features fantastic outdoor spaces, including a large front Farmers Porch and an oversized Patio with a gas grill. Enjoy all the desired amenities, including an outdoor shower, an open kitchen layout, and a 75 Smart TV.brbrBoth walkable and bikeable to Oak Bluffs Center and Harbor you can easily explore the town's lively shops, restaurants, and local attractions.brbrThe spacebrbrWelcome to your dream getaway in beautiful Oak Bluffs, Martha’s Vineyard. Our spacious 5-bedroom residence is designed to accommodate up to 14 guests with comfort and style. The home features 9-foot ceilings, a spacious Farmers Porch with exposed beams, and an oversized Bluestone Patio for outdoor gatherings and more! Whether you’re here for a short escape or an extended stay, you’ll find everything you need to relax and create lasting memories.brbrSLEEPING ARRANGEMENTSbrbrThis spacious retreat offers 5 cozy bedrooms.brbr- Downstairs Master Bedroom: Located on the ground floor, this master bedroom features a Queen-sized bed and its own full ensuite bathroom, providing privacy and comfort.brbr- Upstairs Master Bedrooms (2): Both master bedrooms on the upper floor are equipped with King-sized beds and ensuite bathrooms, offering spacious and comfortable accommodations.brbr- Bunk Room: This bedroom is perfect for families or groups, featuring 2 bunk bed sets, each with full-sized lower bunks and twin-sized upper bunks. This room shares a Jack & Jill bathroom with another bedroom featuring a king-sized bed for added family convenience.brbr- Upstairs King-Sized Bedroom (1): the spacious bedroom features a king-sized bed and is connected to the bunk room by a shared Jack and Jill bathroom.brA Queen-sized pullout couch in the living room for additional sleeping space.brbrLIVING AREASbrbr- Main Living Room: Relax in style with plush seating, a 75 Smart TV, and an open-concept design that seamlessly connects the living area to the kitchen and dining space, making it ideal for gatherings.brbr- Second Living Room: Located on the opposite side of the house, this cozy area includes a queen pullout couch for additional sleeping arrangements. Adjacent to a mudroom with a side entrance, this space also features an office alcove, perfect for working from home or a quiet retreat.brbrFull-sized washer and dryers are conveniently located in the hall closet upstairs.brbrKITCHEN & DININGbrbr- Fully Equipped Kitchen: Enjoy a delightful cooking experience with high-end appliances, white countertops, sleek cabinets, a gas range, and a large refrigerator.brbr- Dining Area: The kitchen opens up to a spacious dining area anchored by a large farmhouse-style table, comfortably seating 8-10 guests, perfect for family meals or gatherings.brbr- Outdoor Dining: Step out to the large bluestone patio featuring an outdoor dining table that seats 8, a gas grill, and a cozy sitting area with a coffee table for alfresco dining and relaxation.brbrOUTDOOR AMENITIESbrbr- Farmer’s Porch: Enjoy your morning coffee or unwind in the evening on the spacious front porch with exposed beams, perfect for relaxation.brbr- Bluestone Patio: Located at the back of the home, this oversized patio is ideal for outdoor gatherings, featuring a gas grill and ample space for dining and lounging.brbr- Outdoor ShowerbrbrWhether you're seeking adventure or relaxation, our home offers the perfect base in Oak Bluffs for your Vineyard getaway. Enjoy a delightful, luxurious experience in this beautiful home! We look forward to welcoming you to your home away from home.brbrGuest accessbrThe whole house is yours!!brbrOther things to notebrThe lawn is fully grown in and we have landscaped the perimeter as well as the front porch area since taking these photos!

Vineyard Social-Spacious 5BR Home in Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$319.14

Welcome to The Suite at Leah’s Landing—a refined and elevated retreat tucked at the end of a quiet dead-end road, yet less than a mile from the heart of Oak Bluffs. For exclusive photos, video previews, and our curated island guide, follow us on IG and FB @leahslandingmvbrbrThis newly built space is just welcoming its first guests in Summer '26, so there are no reviews yet. You can check out our other listing and its great guest reviews for peace of mind!brbrTHE SPACEbrStep outside to your private stone patio with lounge seating, a gas fire pit, and an enclosed outdoor shower, perfect after a beach day. Beach gear is provided, including towels, chairs, and a cooler.brbrAdditional comforts include hotel-quality linens, fluffy towels, board games, and books for relaxed evenings in. We look forward to hosting you at this thoughtfully curated island retreat—peaceful, refined, and moments from everything Martha’s Vineyard has to offer.brbrGUEST ACCESSbrThe suite is a fully private, attached unit with separate entrances and no shared indoor spaces. A locked interior door fully separates the two units, ensuring complete privacy for both you and us. We live quietly in the main house year-round and are typically at work during the day. brbrOne parking space is included in the shared driveway. You’ll also enjoy your own private front and side entrances, patio area, gas grill, and outdoor shower.brbrWhile your space is entirely private, you may occasionally see or hear us in our backyard tending the gardens, using the grill, or passing through the shared driveway.brbrINTERACTION WITH GUESTSbrWe want your stay to feel easy, comfortable, and entirely your own. Prefer complete privacy We absolutely respect that. Up for a friendly chat about the island or looking for local recommendations We’re always happy to connect. We live right next door and are available if you need anything at all during your stay.brbrOTHER DETAILS TO NOTEbrThe home is thoughtfully maintained as a fragrance-free environment with fragrance-free and MI/MIC-free products throughout due to chemical sensitivities. We kindly ask that you refrain from using perfumes and outside cleaning or laundry supplies during your stay. brbrThe bedroom and bathroom are located on the second floor. brbrAll stays include complimentary professional housekeeping between guests, ensuring a consistently pristine, hotel-quality environment at every arrival.brbrThere is no smoking or vaping indoors, but you are welcome to smoke outside as long as the apartment windows are closed.brbrAdvance Steamship Authority reservations are required for bringing a car to the island, though the location is also highly walkable, bike-friendly, and serviced by public transportation.

Apartment

NEW Luxe suite with outdoor shower & firepit - walk to town!

Oak Bluffs, Massachusetts, United States

1

Bed

1

Bath

Sleeps

$874.45

Enjoy the best of Oak Bluffs from this spacious 5-bedroom, 4.5-bath Martha’s Vineyard home. Located near downtown Oak Bluffs, beaches, restaurants, and the ferry, this home is perfect for families and groups looking for a relaxing island getaway.brbrThe house comfortably sleeps 8 and features 1 king bedroom, 3 queen bedrooms, and a twin room. Central AC, multiple living spaces, a fully equipped kitchen, and outdoor gathering areas make it easy to relax after a day at the beach or exploring the island.brbrWhether you’re walking into town for dinner, spending the day by the water, or enjoying a quiet evening at home, this Oak Bluffs retreat offers the perfect blend of comfort, space, and convenience.

Beautiful 5BR Oak Bluffs Home with AC -Walk to Beaches, Town & Ferry

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1771.24

This newly renovated, beautifully landscaped, air conditioned, spacious 3 level Cape Cod style home is situated on a quiet street in the Tower Ridge Community and located steps away from the Farm Neck Golf Club, a bike path, and walking/hiking trails. It is a short drive from the Oak Bluffs Ferry Terminal, bustling downtown Oak Bluffs with its many shops, restaurants, the iconic Flying carousel (the nation’s oldest platform carousel) and Inkwell Beach. Easy access to other island towns as well.brbrThe airy layout on the first floor is perfect for enjoying your friends and family. Love to cook Whether you are returning from a fishing trip (we have some favorites), grabbing some fresh seafood from Larsen's or farm produce from Morning Glory, the fully stocked gourmet kitchen has large cooking/prep stone counters, state of the art appliances and ample space for helpers. Take advantage of the island air and use the Weber gas grill for dining al fresco. The patio cart is stocked with dinnerware, utensils, tumblers, serving platters and bowls even citronella sticks. And for you lobster lovers, we have a lobster pot with tool kits and butcher paper. We hope you saved room for dessert, because we have a stocked Smores caddy complete with mini table top fire pits and telescopic fork skewers.brbrNeed some R&R The sun filled breakfast nook is perfect for early risers to enjoy your first cup of tea or coffee and just exhale... Or spend some time is the sunroom under the ceiling fan with one of the many coffee table books while listening to nature.brbrHeading to the beach No problem! You will find fresh beach towels in the basket in the laundry room and beach chairs in the storage bench by the deck. And, don't forget to grab one or two of the house coolers to stock your favorite snacks and beverages for your excursion. Need to wash off the beach before heading in the house The outdoor shower on the patio is heaven.brbrReady to turn in for the evening after a day of festivals, fairs and fun All second floor bedrooms have en suite bathrooms with an overhead & handheld shower system, great shower pressure and Cariloha Bamboo washcloths and towels. And, all beds are fitted w/ sleep innovations 4 memory foam mattress toppers along w/ mattress & pillow protectors and soft, breathable, cooling bed sheets for a restful slumber. Remember to check out the nights sky before retiring. It's magical.brbrThere are so many things to do on island including just unplugging and relaxing. We will be honored to host you for a few days to a few weeks and hope you love our home as much as we do.

An Oasis on Martha's Vineyard-A 4 Bedroom 4.5 Bath Home In Historical Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1286.06

Escape to a tranquil retreat at this 4-bedroom house in Oak Bluffs. With 2 full beds, 2 twin beds, and 2 king beds, this gorgeous property offers a tremendous amount of space for guests to relax and unwind. The 3 bathrooms are equipped with all the essentials you need, including a hairdryer and a refreshing shower. Whether you're looking to explore the area or simply enjoy a peaceful getaway, this vacation rental is the perfect choice for your next trip. We look forward to welcoming you to our place.

MV Sea Glenn Flowers Pleasant 4-bedroom 3-bathroom house with AC in Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$763.62

Plan your escape to Martha's Vineyard! Conveniently located near downtown Oak Bluffs, this 2BD/2BA home provides easy access to beaches, bike paths, buses, festivals, concerts, fireworks, and all your favorite seasonal events. Venture out to relax on the beach, shop the stores, enjoy fresh seafood in nearby restaurants. Walking distance to Circuit Avenue, Ocean Park, the beach. After all your activities, rinse off in the outdoor shower and unwind in a space that’s fun, stylish, and welcoming.brbrThe spacebrC0464632210 | Stairs Required to Access | Outdoor Shower | Front Porch w/ Seating | Washer & DryerbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Living Room: Full Sleeper SofabrbrMAIN FEATURES: Smart TV w/ cable, dining table, board games, open floor planbrKITCHEN: Stove/oven, refrigerator, drip & French press coffee makers, dishware & flatware, microwave, cooking basics, spices, toaster oven, trash bags/paper towelsbrGENERAL: Free WiFi, central heating & A/C, linens/towels, hair dryer, keyless entrybrFAQ: 2 exterior security cameras (facing out), upper level not available for guest usebrACCESSIBILITY: 2-story home, exterior stairs required to enter, 1 bedroom & 1 bathroom on main levelbrPARKING: Driveway (2 vehicles)brbrGuest accessbrGuests will have access to the property via keyless entrybrbrOther things to notebr- No smoking or vaping inside (our family is sensitive)br- No pets allowed (our family is allergic)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 2-story home requires exterior stairs to enter. While all bedrooms and bathrooms are located on the main level, interior stairs are required to access the laundry in the basementbr- NOTE: The upper level of the home will be locked and is not available for guest usebr- NOTE: The property provides towels and linens. If you need any additional please order directly from Takemmy Linen Rental. They allow in-person pick-up (near the airport), or have a delivery servicebr- NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is located near the front door facing the front outdoor entry, and 1 camera is located near the side door facing the side outdoor entry. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion

Oak Bluffs home conveniently located.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1284.55

Year-round in-town Historical Famous Seashrimp Gingerbread House across from harbor/Nancy's all on the water restaurants. 3 Bedrooms 2.5 baths. Lovely ocean views of harbor from the rockers on porch. Fully Air Conditioned/Heated. This home is across the street to public beaches and harbor.One street over from Circuit Ave., shops and restaurants, Flying Horses (oldest carousel in the country). Walk to Steamship Authority dock or take fast ferry from across the street to Falmouth, Nantucket. Charter many boats across the street in harbor for fishing, sunset cruises etc. Onsite parking for 1 car in private driveway. This property is part of the Martha’s Vineyard Camp Meeting Association. Renters must observe quiet hours and all rules located on our website.

Famous Gingerbread House named Seashrimp across from Oak Bluffs Harbor

Oak Bluffs, Massachusetts, United States

Bed

2

Bath

6

Sleeps

$2602.61

Set back off a bluff with expansive views of Nantucket Sound and beyond to Chappy is this sophisticated waterfront home with a private beach on Nantucket Sound. Well-appointed, newly renovated 4-bedroom, 3-bath home exudes coastal elegance. It is thoughtfully furnished inside and out with pieces that make this waterfront home a comfortable spot for your Martha's Vineyard vacation. brbrPast guests have said, ''Truly magical. A special piece of paradise.'' The reverse style allows for the living area, kitchen, and primary suite to enjoy sweeping water views. Don't worry, there are still plenty of views from the first floor, which features 3 bedrooms, 2 newly renovated full baths, and access to the expansive decks. The outdoor spaces are as well-appointed as the indoor ones. brbrNew in 2025 – a bluestone patio with a gourmet outdoor kitchen with grill, pizza oven, beverage fridge, and ice maker. brbrPool coming in 2026!brbrThe upper and lower decks have outdoor sofas, tables, and chairs. In addition, there are cushioned lounge chairs and umbrellas along the beach and two wood-burning fire pits surrounded by Adirondack chairs. You can also enjoy kayaks and paddleboards that are available for use.brbrPart of a compound, you can rent this home alone or with the other house (https://www.vrbo.com/4935237).brbrAcross the street from the bike path and just 1.2 miles to Ocean Park, ferry, shopping, and more, you will soon learn what a special place on Martha's Vineyard you have landed on. Plus, you are only a 7-minute walk away from Nomans, which is a local favorite for live music and fun times.brbrTurnover Day is Saturday to Saturday through the beginning of August and then switches to Sunday to Sunday at the end of the summer. Long weekends and flexible turnover days in the off-season.

Luxury 4-Bedroom Property with Private Beach on Seaview Ave in Oak Bluffs

Oak Bluffs, Massachusetts, United States

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