Home Vacation Rentals By Owner In Oak Bluffs, MA

Showing 200 Of 308 Vacation Rentals
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Exceptional(42)

$1089.08

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Private Vacation Home

OB Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.

Oak Bluffs, Massachusetts, United States

Best of everything: We are located on the back side of Farm Pond, which overlooks Harthaven, Nantucket Sound, and Chappaquiddick beyond. Window air-conditioners in each room. House is quiet and private, but an easy walk to playgrounds, town, beach, fishing, shopping, bowling, bike paths. OB Arts district is nearby, as is a deli/ wine store, and great soul food restaurant.brbrHead out the door to bike paths and hiking trails, or paddle to great fishing across the pond. brbrHuge wrap-around porch/deck, big yard, hammock, use of canoe/kayak (row across the pond to the beach and a great fishing spot). Four bedrooms, all with water views, great mattresses and bedding, high cathedral ceilings. Nice napping spot in downstairs double daybed cubby; basement playroom is rustic but has painted floors and walls and enclosed ceiling with a pullout queen bed and dance floor/lights. Great place for teenagers to hang out. brbrHouse is a beachy cottage with painted wood floors, beaded board walls and ceiling rafters but also has all modern conveniences: w/d, kitchen with brand new KitchenAid gas range and lots of counter space. Two full baths plus huge outdoor shower. Nice big laundry/mud room for storing stuff out of the way.brbrKeywords: House, Cottage, Beachy, Private, Near town, dog-friendly, roomy, Islandy, waterfront, near beach, playroom, office, views, fireplace, big yard, near bike paths, woods, classic Vineyard, history, cozy, year-round, well-insulated, great beds.
Bed 4

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Bath 2

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Sleep 8

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Exceptional(94)

$1005.3

/ Nightly
Private Vacation Home

Multiple Ensuites, Central Air, Perfect Location

Oak Bluffs, Massachusetts, United States

Spacious ~2,200 sq. ft. home featuring 4 bedrooms and 3.5 bathrooms. Three bedrooms on the second floor include en-suite baths, plus a first-floor bedroom and powder room.brbrConveniently located:br0.75 miles to Oak Bluffs Center (15-minute walk)br1.2 miles to Inkwell Beachbr1.5 miles to Farm Neck Golf ClubbrbrHighlights:brbrCentral air conditioningbrBose smart speakers & WiFibr65 Smart TV (living room), 50 TV (primary bedroom)brHotel-quality linens, bath & beach towels includedbrOn-demand hot water + 3 full bathsbrScreened-in porch with ceiling fansbrOutdoor shower with privacy enclosurebrGas grill, yard games, beach chairs, toys & coolerbrLarge indoor dining table (seats 10) + outdoor picnic table (seats 10)brLevel 2 EV outlet (220v; bring your own cord)brSecond-floor washer/dryerbrHardwood floors throughoutbrbrFirst FloorbrOpen-concept kitchen, dining, and living area; ideal for gathering. The kitchen features a large island, quartz countertops, and stainless appliances, with seating for 10 at the table plus 4 at the island.brbrThe living room includes a large sectional and 65 Smart TV. Also on this level:brbrQueen bedroombrPowder roombrScreened porch with rocking chairsbrPatio with grill and backyard diningbrbrSecond FloorbrThree bedrooms, all with en-suite bathrooms, plus washer/dryer and linen closet:brbrPrimary Suite 1: Queen bed, private balcony, large bath with double sinks, walk-in shower, and clawfoot tubbrPrimary Suite 2: Queen bed, private bath (shower/tub combo)brBedroom 3: Three Twin XL beds, private bath with walk-in shower (also accessible from hallway)brbrBedrooms SummarybrbrPrimary Suite 1 (2nd floor): Queen, en-suite, private balconybrPrimary Suite 2 (2nd floor): Queen, en-suitebrBedroom 3 (2nd floor): 3 Twin XLs, en-suitebrBedroom 4 (1st floor): QueenbrbrAdditional NotesbrGuests have access to the entire home except the primary bedroom closet (ample storage provided elsewhere).brbrBooking Safety: This home is only listed on VRBO/HomeAway. We do not request wire transfers or direct payments; please book through VRBO for security.
Bed 4

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Bath 3

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Sleep 8

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Exceptional(37)

$343.59

/ Nightly
Private Vacation Home

Updated Oak Bluffs home! Close to everything! Walk to town!

OAK BLUFFS, Massachusetts, United States

This home was updated in 2023! Beautiful detached 2 bedroom within walking distance to the center of Oak Bluffs. The exterior includes a large wrap around deck, terrific screened in porch, 2 car parking pad and a private outdoor shower. It offers a fully renovated kitchen with tiled granite counters, new flooring, gas stove/oven, stacked washer/dryer (HE detergent only!) and a small eat-in area. New full bath with a full sized bathtub and tiled tub surround. Living room with original refinished pine floors, new sofa with queen memory foam pull out, flat screen app compatible tv, dvd player with dvd's and small sitting area. The 2nd floor offers two bedrooms both having places to hang clothes per tenants feedback requests. The 1st bedroom has a vaulted ceiling, new king Casper hybrid bed, dresser, flat screen app compatible tv. The 2nd bedroom has a single bed with 2nd pull out trundle style single bed, flat screen app compatible tv and dresser. brbrRegardless of updates this is still a smaller old classic Marthas Vineyard home. It is also our home. If you want something brand new or perfect I suggest a hotel. If you want something close to town, well cared for, comfortable and a true Marthas Vineyard experience this is the place for you! We have many repeat guests who love it as much as we do. Please consider the stairs to the upper level are original and a bit steep. Also the ceiling heights in some areas are lower than new construction. I am 6'1 and have no issues (Low spots are living room 6'8 12, small bedroom and hallway 6'6 and sloped ceiling at bath sink 6'6). Also both bedrooms only have 1 window with AC units. They can be run on AC for cooling or fan to allow outside air into these rooms. brbrOak Bluffs: The Town of Oak Bluffs is a resort town on the northeast shore of the island of Martha's Vineyard, Massachusetts. Oak Bluffs is home to many historical and nationally recognized landmarks including the Flying Horses Carousel which is the nation's oldest operating platform carousel. Oak Bluffs operates the largest marina on Martha's Vineyard, which not only has the most slips, but is situated in the midst of the historic gingerbread campgrounds, and offers easy access to the rest of the Island. 'OB', as it is sometimes referred to, also is home to several beautiful public beaches, a teaming shore of wildlife, fish and shellfish, fabulous public parks, a golf course and even a microbrewery. Today, an active downtown is complete with exciting restaurants, charming inns, shops, and galleries, a variety of specialty food shops, movie theaters, and places to enjoy live entertainment and dancing. Oak Bluffs has a new fishing pier that was completed for the 2014 season and the new seawall and boardwalk from the ferry to the marina opened in 2016. There is also a bowling alley/entertainment center and a brand new walking path around Sunset Lake. Circuit Avenue improvements completed in 2024 with new wider sidewalks, park and upgrades. brbrCleaning: Our cleaners are still practicing Covid protocols and fully sterilizing the home. brbrLaundry/Linens: Linens are not provided. Each bed has a protective cover, pillow with protective cover and blanket. There are linen services that can service the property. They can deliver and pick up linens to the home if needed. There is Takemmy Linen Rental and Marthas Linen Rental. Takemmy does not have blankets so use Marthas if you also need blankets. The linens we recommend are:br(King bedroom)- A king sheet/bedroom set, blanket, two king pillows and two standard pillow cases.br(Single bedroom)- A single sheet/bedroom set, blanket and one standard pillow case plus a second single sheet/bedroom set, blanket and one standard pillow case if using the trundle bed.br(Sofa bed)- A queen sheet/bedroom set, blanket and one standard pillow case if using the sofa bed.br(Other)- Towels, wash cloths and maybe beach towels/blanket.brbrCall Jim with questions at 443-271-0926.
Bed 2

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Bath 1

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Sleep 5

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Exceptional(59)

$1986.66

/ Nightly
Private Vacation Home

The Carousel House - Ocean Park - Featured in New York Times

Oak Bluffs, Massachusetts, United States

This house, built in 1865, was featured in the New York Times article on Oak Bluffs, 'The President Was Here (Grant, That Is).' The article described the unique Victorian homes on Ocean Avenue as 'the Fifth Avenue of Oak Bluffs.' Our house was featured in the article, and photographed in the New York Times online slide show. It is a unique Victorian home, wonderful for family gatherings. The location is ideal - it sits at the heart of Ocean Park, with the closest access to Circuit Avenue of any of the homes on the Park. brbrThe home has been completely renovated, including central air with two zones. Chef's kitchen with granite countertops and stainless appliances, a six burner commercial oven and a wine fridge. Bathroom sinks have marble tops. Four flat screen TVs. brbrThis house has unique charm and convenience. Walk to everything - you don't need a car. The child friendly beach is just across the road, where you can make sandcastles in the sand, or stroll along the boardwalk above the beach, and rest on a bench facing the water. Or stay at home, sit on the porch and gaze over Ocean Park with its iconic gazebo. Have your own private front seat to the concerts and fireworks in Ocean Park during the summer. brbrIt takes about 60 seconds to walk to Circuit Avenue and access the heart of Oak Bluffs: restaurants, quaint shops, art galleries, grocery store, wine and liquor store, hair salon, movies, ice cream parlors, churches, etc. Pick up the bike path from just in front of the house and ride around the island (bike rentals just a short stroll away). Visit the Flying Horses, the oldest carousel in America dating back to the 1800s, just a couple of short blocks away. Take a stroll to the harbor, and see the beautiful yachts docked there. Fly a kite in Ocean Park. brbrOn rainy days, walk just yards away to the movie house, or entertain the kids in the arcade on Circuit Avenue, a 90 second run in the rain! Or stay home and watch movies on the big TV in the living room, or play a board game of Monopoly or Scrabble. Or lose yourself in a book from our small library.brbrEntire downstairs has hard wired speaker system that you can connect to your phone or tablet, and play your own music.brbrBe sure to wake up early at least one day of your vacation to catch the breathtaking sunrise over Nantucket Sound, easily visible from the two master bedrooms!brbrFun Fact: The Emperor of Ocean Park, the New York Times best seller murder mystery, was written about this house. Read the book before you come, or on the porch while you are here, to relive this home's iconic history. We keep a couple of copies of the book in our bookcase for you to check out while you are with us.brbrKeywords: House
Bed 6

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Bath 3

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Sleep 12

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Exceptional(4)

$1524.71

/ Nightly
Private Vacation Home

**Vineyard Vacation Retreat** -3 BR

Oak Bluffs, Massachusetts, United States

Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.brbrThis delightful Cape Cod style residence in Oak Bluffs exudes warmth and charm through its inimitable French country, urban chic style. It has the added benefit of providing complete privacy by being situated at the end of a cul-de-sac opposite a wooded lot. brbrLIVING AREA brEntry to the house is via a large, sunny mudroom which leads into the open concept dining/kitchen/living space. Beautiful hardwood floors feature throughout the house. brEntertainment is provided in the living room by a 55’ Samsung Smart TV which streams many apps (e.g Netflix, HuluPlus, Amazon Prime) and a Blue Ray DVD player. These can be enjoyed on the comfortable couch and arm chairs surrounding the fire place. brYou can enjoy your evenings with a lot of different board games and books what we have in the house.brbrKITCHENbrThe kitchen has stainless steel appliances with all modern day amenities. There is everything you need - microwave, coffee maker, coffee grinder, blender and mixer. The dining area can accommodate 6 guests comfortably and has sliding doors to access the outdoor seating area.brbrMASTER BEDROOMbrKing size bedroom what is upstairs with a closet, a dresser and a cozy seating area. The house has a climate control with central AC.brThere is a bathroom upstairs.brbrBEDROOM #2brQueen bedroom what is upstairs with a closet, dresser and comfortable chair.brbrBEDROOM #3brBeyond the kitchen you will find a large bedroom comprising a queen bed, a quite reading nook with an armchair, and ample closet space. Next to the bedroom is a bathroom with a combined tub and shower, closet space and full laundry facilities. brbrOUTDOOR AREASbrThe back yard is extremely spacious and completely fenced in for privacy. The deck, which leads off the dining room, has a BBQ and an eating area. For your relaxation there are a number of double and single loungers dotted around the garden. There is also a hammock in which you can enjoy morning coffees, afternoon cocktails or whatever takes your fancy! Rinse off in the hot/cold outdoor shower from your beach activities. There is onsite parking for 2 cars. brbrThis is an ideal and charming vacation home with many amenities. It is close to all that Martha's Vineyard has to offer, yet it provides a welcome retreat from the hustle and bustle of the beaches and downtown Oak Bluffs which are just a couple of miles away.brThere is really no better place in which to relax and recharge your batteries so come and enjoy a slice of heaven in this home away from home.brbrWe do allow some pets which are allowed upon request.brbrPet policy: brOne pet maximum. No pets are allowed on the sofa, beds or on any of the furniture. You must bring your own dog bed as you are not allowed to use our blankets for them to sleep on. You must bring your own dog bowls. You must pick up all of your dog poop in the yard and do not let them pee in the house. Dogs must be supervised at all times and are not allowed to dig up the garden. brbrOur cleaners charge an additional 100$ pet fee. brbrAny damage to our home is your responsibility. If your dog does any damage to our home we will be going threw VRBO claims to immediately resolve the issues
Bed 3

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Bath 2

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Sleep 6

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Exceptional(21)

$726.05

/ Nightly
Private Vacation Home

Oak Bluffs Cutie Near Beach + Town Center! Ferry tix available for some dates!

Oak Bluffs, Massachusetts, United States

Enjoy both worlds - a peaceful atmosphere with many comfortable places to escape to read, nap or chat, near the heart of Oak Bluffs, close to a wide range of activities for all ages.brbrThe house is within easy walking distance to the village, harbor, beaches, waterfront parks and historic Victorian gingerbread cottages – but removed enough to provide quiet and light.brbrThe house has new sofas, appliances, a well equipped kitchen, and 4 social spaces - a living room, breezeway, loft + deck. brThis welcoming cottage is decorated in comfortable Vineyard style, with hand-hewn, antique and designer furnishings. brbrFerry tickets available for some dates - please inquire.brbrEven though on-site parking for five cars is available, cars are unnecessary. The house an excellent base to explore all that the island has to offer. Most Oak Bluffs attractions (Flying Horses carousel, trails, beach paths, Arts District, movie theater, restaurants, stores, tennis, basketball, beaches, Oak Bluffs Open Market and harbor) are within a fifteen minute walk; bicycles can be rented nearby; and the Island circulator stops at the Oak Bluffs Library, just a few doors away. (The library conveniently provides cultural events, computers, wi-fi and video rentals.) The house is within a 15 – 20 minute walk / 5 minute bike ride to ferries serving Hyannis, Woods Hole / Falmouth, Quonset Point RI, New Bedford and Manhattan. brbrThis is an ideal location for enjoying Oak Bluff’s traditions such as Illumination Night, the June and August Fireworks Celebrations, the Harbor Festival, Martha’s Vineyard Jazz Fest, the Wind Festival, Arts District Stroll and Portuguese Feast without worry over parking and other logistics. br
Bed 3

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Bath 3

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Sleep 8

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$2260.44

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Private Vacation Home

4-BR, Hot tub, Wifi, AC, Fire pit. No Pets.

Oak Bluffs, Massachusetts, United States

Located in a very quiet Oak Bluffs neighborhood, two miles from the Atlantic Ocean and Town Center. Get ready for a vacation house that every member of your family and friends will enjoy! This newly renovated home boasts plenty of room, 5 bedrooms, and 4.5 bathrooms situated on a private 1.2 acre parcel with a completely fenced in front and backyard. Beautiful Outdoor Shower with a private dry dressing area. Very feng shui.brbrThis home has been completely transformed with high-end finishes, and luxurious upgrades—perfect for unforgettable getaways!brbr 5 bedrooms, 4.5 baths + large outdoor showerbr Backyard stone fire pit & grill for cozy evenings outsidebr❄️ Central AC. Top floor has mini splitsbr Smart TV's & WiFi in every bedroom & living room brbrWith its prime location, luxurious amenities, and upcoming renovations, this home offers the ultimate Martha’s Vineyard experience!brbrEnjoy the backyard with the Private heated pool (May 15- September 10), hot tub and expansive bluestone patio with outdoor grill, dining tables, and gathering, lounging areas. Half basketball court in the front of the house.brbrStart a fire in the stone fire pit and create summer memories! Or if it's raining outside gather inside and play a game of Backgammon! Grill fresh fish on the masonry outdoor grill that requires no propane tanks- it gets propane from the house. brbrThe kitchen features granite counters, dishwasher, and 80 inch Hestan refrigerator. In the entry room there’s extra refrigerator/freezer & large table.brbrOur game room/fifth bedroom is every kids dream. They can enjoy the X-box One game system or Playstation 4 on a 65- inch TV. There are 3 twin beds down here plus 2 pullout sleepers. Plus half bath just outside the room.brbrPrivate tennis court just down the street! Farm Neck Golf Course across the street.brbrThere is plenty of parking at the house.brbrOther Details:brbr5 bedrooms, 4.5 bathroomsbrbr*Master Bedroom 1: King bed w/ private bath + bidetbr - attached there is a large walk-in bedroom with 2 Twin beds for overflow guests on second floorbr*Master Bedroom 2: King bed w/ private bath on top floorbr*Guest Bedroom 1: Queen bed w/ shared bath in hallway on second floorbr*Guest Bedroom 2: Queen bed w/ shared bath in hallway on second floorbr*Game room: 3 Twin beds, 2 pullout sofas, half bath, closet area on bottom floorbr*TV room: sofa with 65 inch TVbr*Living Room: Knoll Barcelona Daybed & 2 Swell chairs to relax inbr*Dining room: directly next to kitchen with large dining table for 10 & Banquette seating on 2 sidesbr*Entry room: Beautiful Mahogany doors for easy access from the driveway, New glass door leading to the backyard, large table and extra refrigerator for overflow food and drinksbr*Laundry room with new washer, dryer, and folding / hanging areabr*Expansive backyard with heated pool open 5/15 to 9/15, large bluestone patio, brand new Lynx grill, outdoor shower, multiple dining and lounging areas, fire pit, and grass areas. All fenced in!brbrAdditional Details:br*The house has 6 smart TV's. br*There is high speed wireless internet throughout the house. br*Linens and towels are supplied.br*Beach towels are available for your use.br*Kitchen is equipped with everything you need to cook and serve meals.br*Plenty of grill / BBQ tools.br*Please ask about our Stock Your Fridge service, so you can have all of your groceries ready upon arrival!brbrMartha's Vineyard is accessed via a Ferry Boat which you need to make a reservation for through The Steamship Authority if you wish to bring your own vehicle.brbrThere are many lovely shops with local clothing, arts and crafts, gifts, beach needs, ice cream & candy, and plenty more for all your shopping needs. There are incredible beaches, beautiful parks, a variety of water sports, high quality fishing and charter boats, terrific hiking and bike paths with access to bike rentals, really there is everything you could ever imagine for all of your outdoor fun! Delicious local markets and grocery stores for all of your grocery needs, fine wines, farmer markets, and pharmacies are all very close by! There are movie theaters, an arcade, and the oldest carousel in the United States: The Flying Horses!brbrIf there are any other questions please do not hesitate to ask us!
Bed 5

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Bath 4

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Sleep 12

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$4779.09

/ Nightly
Private Vacation Home

5-bedroom home, 2.5 mi to Oak Bluffs town, AC, heated pool, hot tub, fire pit

Oak Bluffs, Massachusetts, United States

**Luxury Vineyard Retreat | Heated Pool, Hot Tub & Fire Pit | Minutes to Oak Bluffs**brbrExperience the best of Martha’s Vineyard from this stunning 5-bedroom luxury retreat located just 2.5 miles from the heart of Oak Bluffs. Perfectly designed for families and groups, this beautifully appointed home combines upscale comfort, privacy, and resort-style outdoor living for an unforgettable island escape.brbrStep inside to discover spacious, light-filled interiors, stylish coastal décor, and multiple gathering spaces ideal for entertaining or relaxing after a day exploring the Vineyard. The fully equipped gourmet kitchen flows effortlessly into open living and dining areas, creating the perfect setting for memorable meals and celebrations.brbrOutdoors, the property transforms into your own private resort. Lounge beside the **heated pool**, unwind in the ** hot tub **, or gather around the **fire pit** for evenings under the stars. The expansive yard and outdoor seating areas provide the perfect setting for summer barbecues, morning coffee, or sunset cocktails.brbrLocated just minutes from the vibrant harbor, beaches, shops, and restaurants of Oak Bluffs, this home offers the ideal balance of tranquility and convenience.brbr**Property Highlights**brbr* 4 beautifully appointed bedrooms, plus 1 for kidsbr* 2.5 miles to downtown Oak Bluffsbr* Private **heated swimming pool**br* Relaxing **hot tub** spabr* Outdoor **fire pit** and lounge areabr* Spacious yard with outdoor seatingbr* Well appointed kitchen and open living spacesbr* Perfect for families, groups, and girls Summer getaways!!brbrWhether you're exploring Martha’s Vineyard’s beaches, biking through scenic island roads, or simply enjoying the luxury amenities at home, this exceptional property offers a truly elevated Vineyard vacation experience.
Bed 5

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Bath 4

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Sleep 13

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