Home Vacation Rentals By Owner In Oak Bluffs, MA

Showing 60 Of 308 Vacation Rentals
Slider Thumb

$1340.26

/ Nightly
Private Vacation Home

Charming 3BR Vineyard Retreat, Lg Deck w/ Kitchen, Near Beach, Town Ctr & Ferry

Oak Bluffs, Massachusetts, United States

Welcome to RoBree Farm – Your Martha’s Vineyard Retreat in the Heart of Oak BluffsbrbrEscape to the serenity and magic of Martha’s Vineyard at RoBree Farm, a charming 3-bedroom, 2-bathroom home perfectly located between the island’s two bustling hubs—Vineyard Haven and Oak Bluffs. Whether you're seeking a peaceful retreat, a family getaway, or a memorable beach vacation with friends, this beautifully maintained property offers the ideal setting for your island escape.brbrThe Perfect Vineyard Stay Starts HerebrbrAs you arrive, you’ll immediately feel welcomed by the calm, coastal atmosphere and lush landscaping of RoBree Farm. Thoughtfully furnished and designed for comfort, our home is filled with everything you need to unwind, entertain, and make memories.brbr Comfortable Accommodations for Up to 8 Guestsbr3 Spacious Bedrooms – Each bedroom is outfitted with a plush queen-sized bed, fresh linens, and cozy furnishings to ensure a restful night’s sleep after days filled with adventure.brbrAdditional Sleeping Space – The living room features a queen-sized sofa bed and a futon, perfect for kids or extra guests.brbr2 Full Bathrooms – Modern, clean, and convenient with walk-in showers, hair dryers, and hotel-style essentials to make getting ready a breeze.brbr Indoor Living SpacesbrGather in the inviting living room with comfortable seating, a large flat-screen TV, and high-speed WiFi—ideal for movie nights, catching up on emails, or simply relaxing. The home has flat-screen TVs in every bedroom as well, so everyone can enjoy their favorite shows in privacy.brbrThe fully equipped kitchen features everything you need to cook up a meal with local ingredients from nearby markets, including cookware, dishes, utensils, and modern appliances. Prefer to grill Head outdoors to the deck!brbr Outdoor Living at Its BestbrThis home is built for enjoying the outdoors. Step onto the expansive back deck, where you’ll find:brbrA full outdoor kitchen with a gas grill—perfect for summer BBQsbrbrAmple outdoor seating and dining areasbrbrA beautifully manicured yard, great for lawn games, morning yoga, or soaking up the sunbrbrA refreshing outdoor shower, perfect after a beach daybrbrOnsite parking for 4–5 vehicles—a rare convenience on the island!brbr Prime Location – Close to It AllbrbrRoBree Farm is situated in a quiet residential area with easy access to:brbrVineyard Haven (1.5 miles) – Ferries, shops, dining, and cultural attractionsbrbrOak Bluffs Center (1 mile) – Restaurants, nightlife, gingerbread cottages, the Flying Horses Carousel, and morebrbrEastville Beach (0.7 miles) – Known for spectacular sunsets, soft sand, and views of the East Chop LighthousebrbrMartha’s Vineyard Hospital – Just minutes away for peace of mind during your staybrbrWhether you want to bike the island’s scenic trails, catch a ferry for a day trip, stroll to the beach, or explore local boutiques and galleries, our location makes it all easy and accessible.brbrThoughtful Amenities for a Seamless StaybrWe’ve outfitted our home with all the details that make your stay effortless:brbrAir conditioning throughoutbrbrHigh-speed WiFibrbrHot water on demandbrbrFlat-screen TVs in the living room and all bedroomsbrbrPortable washer for laundry conveniencebrbrBeach chairs and towelsbrbrHair dryers, linens, and bath towels providedbrbrCome Experience Vineyard CharmbrWhether you're sipping coffee on the deck, grilling dinner under the stars, or taking a sunset stroll along Eastville Beach, RoBree Farm provides the perfect home base for creating unforgettable Vineyard memories.brbrFrom family reunions and romantic getaways to friend trips and solo retreats, our home is ready to welcome you with comfort, style, and a touch of island magic.brbrBook your Martha’s Vineyard escape today at RoBree Farm. We can’t wait to host you!
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(151)

$312.76

/ Nightly
Cottage

Make Lasting Memories In This Adorable Vineyard Cottage!

Oak Bluffs, Massachusetts, United States

This quaint cottage, nestled in a quiet neighborhood of Oak Bluffs, is perfect for a romantic getaway, a special place to bring your favorite friends, or a wonderful spot to have a family vacation. Some guests also choose to have a solo retreat to read, write, explore, and re-center. Cottage visitors comment on the welcoming feeling they experience as soon as they walk in the door, and the sweet simplicity of this cozy abode.brbrThe Cottage sleeps 4 easily. There is a queen-sized futon on the ground level, and a king-sized sleeping loft. The living area has a comfy cozy futon, SmartTV, an activity/game drawer, and FREE WIFI. The kitchen contains a full-sized stove, microwave, fridge/freezer, and a Keurig machine - so bring your favorite k-cups! There is a washer/dryer for your use as well. There are plenty of towels and linens, so no need to bring your own. brbrAfter a full day of exploring, bike riding, shopping, or finding creative inspiration, enjoy a nice dinner or a bottle of wine on the attached deck. It's a perfect place for star gazing too! brbrThere’s plenty to do within walking distance, and a taxi or public transportation can get you to the other Vineyard towns, so a car is not necessary (but it’s nice to have). The Cottage is a mile from Oak Bluffs Center and the town beaches, so a 15 minute walk or a 5 minute bike ride will bring you to either.brbrCome make this lovely Cottage the heart of your own Vineyard experience!
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(5)

$1463.27

/ Nightly
Private Vacation Home

Modern Cottage Walk To Town & Beach

Oak Bluffs, Massachusetts, United States

Enjoy one of Oak Bluffs’ newest accommodations perched at the peak of the Highlands boasting just a 10 minute walk to town center and beaches. brbrThis home just completed a full (100%) renovation of its original 1900 build that has transformed everything from all rooms & living spaces along with associated appliances & fixtures, landscaping and outdoor amenities.brbrThis fully renovated property boasts all new accommodations including: brbrbrOUTDOORSbrbr- Wraparound porch with seating to enjoy views of the private yard or to observe passersby from the front of the housebrbr- Semicircular drive with private parking for 2 vehicles and access to a dedicated EV/Tesla chargerbrbr- Private patio with hot tub, lounge seating, outdoor dinning and grill areabrbr- Rear lawn with fire pit, space for games and fun brbr- Outdoor shower to use upon returning from the beach brbrbrFIRST FLOORbrbr- You will be greeted by an open 1st floor plan with living, kitchen and dining areasbrbr- Features include wood floors throughout, independent AC, wolf & sub-zero appliances, French doors opening to the porch and patio brbr- Rear of the home hosts a large pantry, mudroom rear-entry, half bath and complete laundry room brbrbrSECOND FLOORbrbr- Includes 3 bedrooms with raised vaulted ceilings and a bonus sunroom space, all with independent AC (mini splits) unitsbrbr- Two full baths with specialty features including a shared hall bath with spa-like wet room, Kohler fixtures and large soaker tubbrbr- Second bath is ensuite to the primary bedroom and has shower massage jets; and skylight windows adorn both bedroom & bathbrbr- Three balconies off of two bedrooms and the sunroom provide seating space and views over looking three different directions of the homebrbrbrSLEEPING ARRANGEMENTSbrbrIt will sleep up to 8 people. brbr- Primary bedroom has a queen (2)brbr- Second bedroom has a queen (2)brbr- Third bedroom has a queen bed (2)brbr- Sunroom can also sleep (2)brbrGuests can use all parts of the home except the basement and 2 hall closets on the second floor that are for cleaning crew supplies and owner storage.brbrbrbr
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(15)

$837.75

/ Nightly
Private Vacation Home

Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches

Oak Bluffs, Massachusetts, United States

Newly renovated three-level home with 3 bedrooms 2 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 6 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 rooftop deck 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 2 twin beds. Master bedroom with bathroom with a peak of the Harbor. brBackyard with picnic tables and a grill for those warm summer family cookouts. Shared parking.brbrbrbrSPEND SOME TIME EXPLORING OUR HOMES FOR YOUR NEXT VACATIONbrVeriCasa Properties invites you and your family to relax and enjoy beautiful, peaceful, scenery in the mountains or blue invigorating ocean waters to enjoy an exhilarating football game in a college town. VeriCasa has everything in between for you and your family to find a vacation any time of the year.brbrOur Staff is ready to assist you in finding your luxury dream vacation or experience.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(1)

$1163.55

/ Nightly
Private Vacation Home

Sengekontacket Contemporary With Water Views

Oak Bluffs, Massachusetts, United States

**JUNE SPECIAL: SAVE $500/WEEK OFF OPEN WEEKS 5/31 - 6/21 | NEW RATES PROGRAMMED IN **brPOINT B EXCLUSIVE - Tucked away in the desirable Waterview Farm enclave on Sengekontacket Pond, this newly outfitted Contemporary is wrapped around water views throughout much of the home, and enjoys private association beach and dock access on Senge, as well as miles of walking trails, conservation land and a location abutting Farm Neck Golf Course.brbrTRANSFERABLE FERRY TICKETS AVAILABLE: 8/23 - 8/30. Please Inquire about price and availability.brbrThe first floor features a Great Room with vaulted ceiling, beams, and open Living Area and Kitchen. The Living Area is framed by a two-story wall of glass windows and sliding doors that look out toward the water, and open to a large wraparound deck for outdoor lounging and entertaining. The Living Area has sofa and chair seating plus large screen TV.brbrA nicely-equipped Chef Kitchen anchors the other end of the Great Room. There is a large center island/breakfast bar with seating and prep sink. The Kitchen has stainless appliances, gas cooktop with separate ovens, plus stone counters. Just off the Kitchen is a formal Dining Area. It is framed by a wall of glass windows and door to the deck, and water views. There is a separate Service Bar area with sink and beverage refrigerator that also opens to the deck for easy outdoor entertaining.brbrThere is also a first-floor Primary Bedroom that occupies its own wing with deluxe en suite bath. An office and half bath round out the first floor. The other three Bedrooms are all upstairs. Bedroom #2 has vaulted ceiling, skylights, and its own private bath. The other two Bedrooms share a full bath. brbrThe fully finished Lower Level features a large Game Room/Lounge with pool table, foosball, sofa seating, large screen TV, and a Bar Area with sink and beverage refrigerator.brbrOutdoor entertaining centers around the large deck that overlooks Senge and Nantucket Sound in the distance. There is outdoor seating, grilling area, and lounging areas. Waterview Farm has its own small association beach, dock, and swimming on Sengekontacket. The water access is about a 5 or 10-minute walk away. There are calm swimming waters, and many people enjoy kayaking, paddleboarding, and similar water fun on Senge. There are two standup paddleboards at the association dock available for renter use.brbrFarm Neck Golf Course is nearby, as is the bike path, and State Beach (if you prefer a large public beach). The association also has a network of trails that run throughout the grounds. The property is very near the Landbank Pecoy Point Preserve with its trail that winds through 17 acres and ends of the pond shoreline.brbrNOTE: Point B can help you rent small watercraft for use in Sengekontacket Pond. Please inquire.brbrPETS: Pets considered, pending owner approval. Additional fee required for pets, please inquire.
Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps

Slider Thumb

$757.68

/ Nightly
Private Vacation Home

Modern Colonial Near The Lagoon

Oak Bluffs, Massachusetts, United States

**JULY HOT DEALS: SAVE 10% WEEKLY RATE 7/11 - 8/1 OR SHORTER STAYS ALSO AVAILABLE | BOOK BY PHONE ONLY**brPOINT B EXCLUSIVE - This recently built Modern Colonial has a stylish Vineyard vibe throughout, and is tucked away in a quiet neighborhood near The Sailing Camp and The Lagoon Pond.brbrThe first-floor features a light-filled, modern floor plan with open Living, Dining, and Kitchen Areas. The Living Area is centered around a stone fireplace with seating and large screen TV. It opens to the Dining and Kitchen Areas. The Dining Area is framed by two walls of glass windows and French doors that open out to a screened porch with an outdoor Living Area. Back inside, the Cook's Kitchen has stainless appliances, large center prep island/breakfast bar, and marble counters.brbrThe three Bedrooms are all upstairs. The Primary has its own private en suite bath, while the two other Bedrooms share a Full Bath. There is a fully finished lower level with a large TV/Family Room with sectional seating, large screen TV, plus a separate area with bar and table seating. There is also a full Bath.brbrIn addition to the screened porch, there is a large fenced backyard, plus fire pit with Adirondack chairs.brbrThe popular Sailing Camp is literally across the road — just a short stroll away. With its convenient location, downtown Oak Bluffs with its restaurants, shops and beaches is nearby, as is downtown Vineyard Haven.
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(4)

$1489.67

/ Nightly
Private Vacation Home

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs, Massachusetts, United States

Our amazing property is a perfect place to spend with family andbrfriends! The property is wonderful for everything from a memorablebrfamily vacation to a serene couples retreat. You and your guests willbrbegin to enjoy the feeling of privacy the minute you arrive. You can'tbrbeat the location of this home! It is conveniently located in OakbrBluffs, just minutes to all the Island's amenities - beaches, shops,brrestaurants, airport, and ferries. Also minutes away from the townbrcenters of Oak Bluffs, Vineyard Haven, and Egdartown! A short bikebrride or drive will land you at some of the island’s best parks,brbeaches, fishing, entertainment, shops, ferries, restaurants,brhistorical landmarks, art galleries and much more. The Island AlpacabrFarm is steps away from the property!brbrThis home can be rented individually or if you need more space, pleasebrview our other two listings. The three homes are just steps from onebrother: brbrhttps://www.vrbo.com/9397806habrhttps://www.vrbo.com/3855510habrbrThe home was completely updated in 2019, with an all new interior thatbris bright and fresh! It features an open floor plan, with a brightbrkitchen, all new appliances and new finishes. The kitchen opens tobrthe dining area that seats eight, and into the comfortable living room with fireplace. The dining area and living room space opens onto a large deck where the family can gather day or evening. A separate den/club room is just off the kitchen/dining area. It isbrcomplete with convertible card table for family fun! Also, on the first floor is a Master bedroom, full bathroom en-suite and a hallway powder room. The second floor features two large bedrooms, and two full bathrooms. The washer/dryer is in the unfinished basement. The lot is landscaped and private.brbrDetails:br3 bedrooms, and 3.5 bathrooms.br* Master Bedroom: King/en-suite bathroombr* Bedroom 2: Queen/en-suite bathroombr* Bedroom 3: Two Twins/adjoining bathroombr* Den/Club room.br* Large, furnished deck with access from dining/living rooms andbrMaster bedroom.br* Laundry in basement.br* Outdoor shower.brbrAdditional notes:br* Linens and towels are supplied.br* Beach towels are available for your use.br* Kitchen is equipped with everything you will need to cook and servebrmeals.brbrThe house is air conditioned and heated.brbrOn arrival you will receive a wifi password.brbrOur housekeepers come prior to check in, and after check-out. Abrcleaning fee in the amount of $500 will be added to all rentals. Also,breach approved guest over the maximum number of guests (6 max) willbrincur a $100 per night (per person) fee. For an additional fee thebrhousekeepers can come more frequently. Cost depends on your needs.brbrThe refundable security deposit is $500. This will be returned withinbr14 days of check out.brbrGuest is also required to get the Property Damage Protection policy for $79. Upon receipt of signed contract, Guest must go to www.propertydamageprotection.com and purchase the “Standard” plan for $79 which provides $3,000 in coverage.brbrOur house manager and caretaker will be your direct contactsbrthroughout your stay. They are happy to help with anything specificbryou need. If anything on site needs to be addressed our caretaker willbrhandle. Our caretaker will be there to greet you and your guests. Hebrwill give you a walk through of the home and answer any questions youbrmay have.brbrWe do NOT allow weddings or events of any kind to take place on thebrproperty.brbrNO pets allowed.brbrMartha's Vineyard has many charming shops with unique clothing, artsbrand crafts, eclectic gifts, gear, candy, and lots more for shoppers.brGreat parks, beaches, fishing and lots of terrific bike paths forbroutdoor fun. Local markets for groceries, fine wines, farmers markets,brand pharmacies are all close by. Movie theaters, arcade, and thebroldest carousel in the US, the Flying Horses, are all nearby. Charterbrboats, jet skiing, para-sailing, bikes and jeeps are available for thebradventurous. Oak Bluffs has a great library, arts district, andbrhistorical sites to visit too. Eat out everyday at a differentbrrestaurant, from fine dining to snack bars, or pick up some freshbrseafood to cook at home in the fully equipped gourmet kitchen. Watchbrbeautiful sunsets while enjoying a glass of wine on Oak Bluffs Harborbror while relaxing comfortably at home with friends and family.brGetting around the island is easy! Rental car, taxi, or bike... all easybrand convenient options. Also, Martha's Vineyard offers a comprehensivebrbus system that connects all towns, Edgartown, Oak Bluffs, VineyardbrHaven, Aquinnah, Chilmark, and West Tisbury. Frequency of servicebrvaries with the season, but buses run regularly year-round and are abrgreat cost-effective way to see the beauty of the Island. You can paybras you go, or purchase 1-day, 3-day, or 1-week bus passes on thebrbuses, at the Steamship Authority or at the Edgartown Visitors Center.brBuses may be boarded at stop or flagged en route in safe places forbryour convenience. All Vineyard Transit Authority (VTA) buses arebrhandicap accessible. Visit their website for current schedules, route maps, fares and additional information. VTA buses are all equippedbrwith bike racks, so you can take your bike with you on your morebrdistant excursions—bike and bus— it's a great way to go!
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(9)

$2680.8

/ Nightly
Private Vacation Home

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs, Massachusetts, United States

Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from a memorable family vacation to a serene couples retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive. You can't beat the location of this home! It is conveniently located in Oak Bluffs, just minutes to all the Island's amenities - beaches, shops, restaurants, airport, and ferries. Also minutes away from the town centers of Oak Bluffs, Vineyard Haven, and Egdartown! A short bike ride or drive will land you at some of the island’s best parks, beaches, fishing, entertainment, shops, ferries, restaurants, historical landmarks, art galleries and much more. The Island Alpaca Farm is steps away from the property!brbrThis home can be rented individually or if you need more space, please view our other two listings. The three homes are just steps from one other:brbrhttps://www.vrbo.com/7953697habrhttps://www.vrbo.com/3855510habrbrThe home was completely remodeled in 2019, with everything new and updated. It features a bright, gourmet kitchen that opens to a gorgeous dining area that seats eight. The dining area opens onto a large deck where the family can gather day or evening. The comfortable living room opens to the dining area. Also, on the first floor is a Master bedroom, full bathroom with a bench seat and storage. The second floor features two large bedrooms and a full bath. The washer/dryer is also on the second floor. The finished basement is where you will find a large family room, an amazing bathroom with walk in shower and bunkbeds. The lot is landscaped and private.brbrDetails:brbr3 bedrooms, 1 bunk room, and 3 bathrooms.brbr* Master Bedroom: King/adjoining bathroombr* Bedroom 2: Queen (bathroom in hallway)br* Bedroom 3: Two Twins (bathroom in hallway)br* Finished Basement: Bunks/adjoining bathroombr* Dining room with slider leading out to deckbr* Laundry br* Large deck with outdoor furniturebrbrbrAdditional notes:br* Linens and towels are supplied. br* Beach towels and chairs are available for your use.br* Kitchen is equipped with everything you will need to cook and serve meals.brbrThe house is air conditioned and heated.brbrOn arrival you will receive a wifi password.brbrOur housekeepers come prior to check in, and after check-out. A cleaning fee in the amount of $750 will be added to all rentals. Also, each approved guest over the maximum number of guests (10 max) will incur a $100 per night (per person) fee. For an additional fee the housekeepers can come more frequently. Cost depends on your needs.brbrThe refundable security deposit is $750. This will be returned within 14 days of check out.brbrGuest is also required to get the Property Damage Protection policy for $79. Upon receipt of signed contract, Guest must go to www.propertydamageprotection.com and purchase the “Standard” plan for $79 which provides $3,000 in coverage.brbrOur house manager and caretaker will be your direct contacts throughout your stay. They are happy to help with anything specific you need. If anything on site needs to be addressed our caretaker will handle. Our caretaker will be there to greet you and your guests. He will give you a walk through of the home and answer any questions you may have.brbrWe do NOT allow weddings or events of any kind to take place on the property.brbrNO pets allowed.brbrMartha's Vineyard has many charming shops with unique clothing, arts and crafts, eclectic gifts, gear, candy, and lots more for shoppers. Great parks, beaches, fishing and lots of terrific bike paths for outdoor fun. Local markets for groceries, fine wines, farmers markets, and pharmacies are all close by. Movie theaters, arcade, and the oldest carousel in the US, the Flying Horses, are all nearby. Charter boats, jet skiing, para-sailing, bikes and jeeps are available for the adventurous. Oak Bluffs has a great library, arts district, and historical sites to visit too. Eat out everyday at a different restaurant, from fine dining to snack bars, or pick up some fresh seafood to cook at home in the fully equipped gourmet kitchen. Watch beautiful sunsets while enjoying a glass of wine on Oak Bluffs Harbor or while relaxing comfortably at home with friends and family.brbrGetting around the island is easy! Rental car, taxi, or bike… all easy and convenient options. Also, Martha's Vineyard offers a comprehensive bus system that connects all towns, Edgartown, Oak Bluffs, Vineyard Haven, Aquinnah, Chilmark, and West Tisbury. Frequency of service varies with the season, but buses run regularly year-round and are a great cost-effective way to see the beauty of the Island. You can pay as you go, or purchase 1-day, 3-day, or 1-week bus passes on the buses, at the Steamship Authority or at the Edgartown Visitors Center. Buses may be boarded at stop or flagged en route in safe places for your convenience. All Vineyard Transit Authority (VTA) buses are handicap accessible. Visit their website for current schedules, route maps, fares and additional information. VTA buses are all equipped with bike racks, so you can take your bike with you on your more distant excursions—bike and bus— it's a great way to go!
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

Home Most popular vacation rentals in Oak Bluffs