Home Vacation Rentals By Owner In Oak Bluffs, MA

Showing 40 Of 308 Vacation Rentals
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Exceptional(1)

$1520.89

/ Nightly
Apartment

Modern Apt Near Martha's Vineyard Beaches!

Oak Bluffs, Massachusetts, United States

Whether you’re embarking on a couple’s weekend retreat or an upscale beach adventure with friends, this Oak Bluff vacation rental has what you need for an enjoyable stay! The 2-bedroom, 1-bathroom apartment boasts a full kitchen, a Smart TV, an electric fireplace, a washer/dryer set, and more. Hop on one of the home’s 2 bikes and cruise down to Inkwell Beach or explore the shops and cafes on Circuit Avenue. However you spend your time, this stylish getaway will make you feel right at home.brbr-- THE PROPERTY --brbrMassTaxConnect ID # C0370922210 | Bicycles Provided | Gas Grill | Outdoor ShowerbrbrBedroom 1: Queen Bed | Bedroom 2: Queen BedbrbrOUTDOOR LIVING: Gravel outdoor area, dining table w/ chairsbrINDOOR LIVING: Smart TV, books, dining table, electric fireplace, natural lightbrKITCHEN: Dishwasher, stove/oven, Keurig coffee maker, cooking utensils, pots & pans, toaster, microwave, spices, dishware & flatwarebrGENERAL: Free WiFi, ceiling fans, central A/C & heat, complimentary toiletries, towels/linens, washer/dryer, hair dryerbrFAQ: 1 step to enter, flight of interior stairs required, homeowner on-site (separate unit)brPARKING: Driveway (2 vehicles)brbr-- THE LOCATION --brbrBEACHES: Inkwell Beach (3 miles), Lighthouse Beach (5 miles), Joseph Sylvia State Beach (6 miles), Norton Point Beach (7 miles)brGET OUTSIDE: Manuel F. Correllus State Forest (2 miles), Vineyard Golf Club (4 miles), Edgartown Bicycles (4 miles), Long Point Wildlife Refuge (6 miles), Mytoi Japanese Garden (8 miles)brTHINGS TO SEE + DO: Circuit Avenue (3 miles), Martha’s Vineyard Museum (4 miles), East Chop Lighthouse (4 miles)brAIRPORTS: Martha's Vineyard Airport (5 miles), Boston Logan International Airport (89 miles)brbr-- 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 smoking br- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property requires 1 step to enter and an additional interior flight of stairs to access the unitbr- NOTE: The homeowner lives on-site, in a separate unit with a separate entrance, and may be present during your stay
Bed 2

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Bath 1

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Sleep 4

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Exceptional(4)

$3015.9

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Private Vacation Home

Grand Coastal-Style Estate In The Preserve

Oak Bluffs, Massachusetts, United States

POINT B EXCLUSIVE - This recently built luxury home features three floors of deluxe indoor living space, with nicely integrated outdoor space as well. The interior architecture and design was overseen by noted Vineyard architect Chuck Sullivan. The first floor features a modern layout with an open Great Room with Living, Dining, and Kitchen Areas, framed by walls of glass windows and doors that open to the outdoor spaces.brbrThe Living Area, with fireplace and media center, anchor one end of the space, while the Chef's Kitchen anchors the other end, and the Dining Area sits in the middle. The fully equipped Kitchen has a large center prep island/breakfast bar, marble counters, commercial Thermador stainless appliances, and a pantry. French doors open from the Living Area to a deluxe screened porch with outdoor Living and Dining Areas. There is a wood-burning fireplace and media center as well.brbrJust off the dramatic entryway with floating stairway, there is a formal Sitting Room with brick fireplace, built-ins, and a large bowed window. All five Bedrooms have deluxe en suite baths. The Primary Bedroom and three of the other Bedrooms are upstairs on the second floor. The Primary Bedroom and Suite #2 open to private covered porches that overlook the backyard and surrounding woodlands. Suites #3 and #4 face the front yard and open to smaller decks. The fifth-bedroom suite has its own private stairway from the first floor. It sits above the garage.brbrThe entire open third floor, houses a deluxe TV/Lounge space, with media center, sofa seating, and chairs. There is a built-in Kitchenette with under under-counter beverage refrigerator, microwave, and sink. French doors open to a covered porch with backyard and woodland views, and there is a full bath with shower as well. There is a multi-zone Sonos sound system feeding the first and third floors, the Primary Bedroom, and the screened porch.brbrThe 20 by 40-foot heated gunite pool and 9 by 9-foot hot tub anchor the outdoor living space. There is a large bluestone patio with multiple entertaining areas, including an outdoor living area with sofa and chairs, a dining area, and sun lounging areas. The grounds are professionally landscaped throughout, and the overall estate is surrounded by woodlands.brbrThe bike path is at the end of the road, and the central location of The Preserve makes it convenient to Vineyard Haven, Oak Bluffs, Edgartown, and of course, nearby Farm Neck Golf Club.brbrPOOL NOTE: Pool is heated to 81 degrees and included in the rent for July and August. There is an additional pool heating surcharge at other times, if the pool is open. Please inquire. brbrSECURITY CAMERA: For safety and security reasons, an exterior security camera is in operation and is located at the front of the home.
Bed 5

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Bath 7

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Sleep 12

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$1061.15

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Private Vacation Home

Beautiful 4 BR/4 BA Modern Victorian: The Mack on Winemack

Oak Bluffs, Massachusetts, United States

This beautiful Victorian home has all the charm of a true Martha’s Vineyard Gingerbread cottage combined with all of the space and amenities of a large modern home. Built in 1999 and redesigned in 2020, this home has 2,400 sf of living space with 4 bedrooms and 4 bathrooms.brbrWe are just one mile from downtown Oak Bluffs, the harbor and beaches. The home is located at the very end of a quiet dead end street, offering a large well-landscaped yard that backs to beautiful trees and walking paths.brbrA wrap-around porch with mahogany wood floors offers plenty of seating areas to enjoy the day and includes a sunroom to enjoy your morning coffee and breakfast. A grill and round fire-pit await you in a spacious back yard.brbrFirst FloorbrbrThe first floor has a spacious living room accented with mahogany wood pillars, stylish furniture and a 60in. SMART TV. Sunroom with Queen sofabed. There is a well-appointed kitchen with a separate dining room, and counter with seating. There is also a comfortable den in the back of the house for lounging, gaming, or taking a quick Zoom meeting. The first floor also has a full bath and laundry. There are three a/c window units on the first floor (living room, hallway, dining room).brbrSecond FloorbrbrWalk up the stairs to the spacious Primary Bedroom with a comfortable balcony and Flat screen SmartTV with cable. There are 2 additional bedrooms along with 2 full bathrooms located off the main hallway. Each room is equipped with a new, efficient a/c unit and Smart TVs.brbrBasementbrbrFull basement suite with full bathroom is the large 2nd Primary master bedroom with King bed (that can convert into two twins), sofa and SMART TV. Basement also has a cute children’s play area separate from the bedroom suite.brbrBath House CottagebrbrThe unique bath house cottage is a great place to shower coming from the beach (with a full bath) - and even has a TV and seating to get away for some quiet time.brbrBedroomsbrbrMaster (2nd Floor), King Bed, Smart TV with cable, BalconybrbrSecond Bedroom (2nd Floor), Queen Bed, SMART TVbrThird Bedroom (2nd Floor), Twin Beds, SMART TVbrbrSecond Master (Basement), King Bed with Full Bath, SMART TVbrbrWe are situated 1.5 miles from the Vineyard Haven Steamship Authority Terminal and 1 mile from the Oak Bluffs Steamship Authority Terminal, the Island Queen, and the Hyline Ferries.brbrNeed even more space and comfort There is an additional one bedroom apartment over the garage available as an addition to your rental (for an additional rental fee) or as its own rental. The apartment is on the property and has a completely separate entrance and parking. It may be owner or renter occupied during your stay but there is no connection to the main house and your complete privacy will be assured.
Bed 4

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Bath 3

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Sleep 10

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Exceptional(5)

$1304.64

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Private Vacation Home

Coastal Farmhouse With Connected Carriage House

Oak Bluffs, Massachusetts, United States

POINT B EXCLUSIVE - This newly built Farmhouse with Connected Carriage House features a modern coastal-style with nice indoor and outdoor living space, is conveniently located near downtown Oak Bluffs, but tucked away in a quieter neighborhood.brbrThe property features a four-bedroom Main House with a connected one-bedroom Carriage House suite with its own entrance. The first floor of the Main House features an open layout with Living, Dining and Kitchen Areas. The hip coastal-vibe has combinations of white and natural wood, with subtle use of blues, greys and some other subdued colors. The Living Area has fireplace, large screen TV, built-ins, plus sofa and chair seating.brbrThe Dining Area sits between the Living Area and Kitchen. It is framed by a sliding glass door that opens to the large back patio for outdoor dining. The Chef Kitchen has a center prep island/breakfast bar, stainless appliances, farmer's sink, and white quartz counters.brbrThe Primary Bedroom with deluxe en suite bath is also on the first floor. The other Bedrooms in the Main House are all upstairs. One has a private en suite bath, while the other two share a full bath. The second Primary Bedroom is located in the connected Carriage House, on the second floor above the Garage. It has a private entrance as well as a deluxe en suite bath, plus a Kitchenette with microwave and mini refrigerator.brbrThe house features great outdoor space, with a bi-level bluestone patio that has lounging, and dining areas, as well as an area with a custom stone fire pit. There is also a front wraparound farmer's porch for shaded seating. All of downtown Oak Bluffs, with its restaurants, shops, beaches, parks, and harborfront, is only a few blocks away.brbrBEDROOM CONFIGURATION NOTE: There is an option for Bedroom #3 or #4 to be made-up as two twin beds or one king-sized bed. Unless otherwise requested in advance of check-in, both bedrooms will be set up as two twins. Please inquire. brbrNOTE: There is a doorbell camera on the front door.
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Bath 4

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Sleep 10

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Exceptional(31)

$949.45

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Private Vacation Home

Beautiful MV Retreat - Central AC - Large Deck, Blue Stone Patio and Fire Pit

Oak Bluffs, Massachusetts, United States

Welcome to Martha's Vineyard! Many of our guests return year after year, drawn by our property’s prime location, cleanliness, modern updates, and tranquil atmosphere. We work hard to ensure that our home remains comfortable, fresh, and inviting, adding new touches each year to enhance your experience.brbrSurrounded by a forest on one side and a spacious meadow to the front, our property is designed for privacy, featuring a lush wall of arborvitaes that encloses the space. Here, you can truly enjoy your own oasis, adorned with classic New England hydrangeas that burst with color and provide countless photo opportunities. The front porch offers a relaxing spot to take in the park-like surroundings, enjoy views of the picturesque meadow, catch sunsets, or stargaze at night.brbrInside, the living area boasts an architecturally designed layout that maximizes the stunning views of the landscaped grounds, providing a bright and airy space for relaxation. The home is equipped with a central air conditioning and dehumidifying system, alongside a cozy wood-burning fireplace for those cooler evenings. The dining room comfortably seats six, with an expandable table for larger gatherings. The living room features a large Samsung SMART TV equipped with streaming options and a Bose sound system for an immersive viewing experience. Enjoy streaming music through the Bose radio system or play your favorite CDs. The fully stocked kitchen offers additional seating for three at the granite counter and includes high-end cookware, baking equipment, a coffee maker, a Keurig machine, Nespresso, microwave, and toaster oven. Each bedroom comes with its own flat-screen TV, and the basement includes a large TV, Xbox, and ping pong table for entertainment on rainy days.brbrStep outside to the back oasis, which features a spacious rear deck furnished with Pottery Barn teak furniture, including an extending dining table that accommodates everyone. The deck flows onto a blue stone patio, complete with a second teak dining table, comfortable seating, a Lynx professional grill, and an outdoor wood fire pit perfect for S'mores or simply relaxing. Adjacent to the deck is an enclosed hot/cold outdoor shower, ideal for rinsing off after a day at the beach or for everyday use.brbrCentrally located near Edgartown, Vineyard Haven, West Tisbury, Chilmark, and Oak Bluffs, our home is just a short drive from the town beaches, with Sailing Camp Park easily accessible by bike. Set on over half an acre of landscaped property in a beautiful, private neighborhood, the area features paved roads perfect for biking and is ideal for families, friends, or a romantic getaway. The community is exclusive to guests and offers a tranquil atmosphere. The bike path and bus route are conveniently close, making it easy to explore. Within walking distance, you'll find the State Park with jogging trails and exploration opportunities, the newly renovated Vineyard Family Tennis Center where you can rent court time, and the excellent YMCA offering daily or weekly passes for workouts, complete with a pool, babysitting services, and a teen center. Nearby, you'll also find an ice skating rink and skateboard park.brbrPlease note that we maintain a pet-free home; while we love animals, we are unable to accommodate them on our property.brbrMartha’s Vineyard has long been a beloved vacation destination, offering a wide range of activities, including stunning beaches, fine dining, shopping, golf courses, tennis courts, deep-sea fishing, sailing, kayaking, and so much more.brbrFor more photos follow us on Instagram @vineyardhome24.brhttps://www.instagram.com/vineyardhome24brbrPlease read the Contract and Rider - agreeing to book with VRBO is agreeing to the terms in the Contract and Rider.
Bed 3

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Bath 2

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Sleep 6

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Exceptional(7)

$2904.84

/ Nightly
Private Vacation Home

101 Ocean Ave. On the corner of Inkwell beach and Ocean park.

Oak Bluffs, Massachusetts, United States

Perched on the corner of Ocean Park overlooking Nantucket Sound and across the street from the beach, this elegant home in Oak Bluffs historic Copeland District is one of the premiere houses on Martha's Vineyard. Wide porches surround three sides of the house. A glass enclosed porch with antique wicker swings is the perfect spot to enjoy band concerts in the gazebo, view the annual August fireworks display, or simply enjoy the ocean across the street. A side porch with a large teak table invites grilling and al fresco dining, while another porch offers a table for breakfast or lunch and plush arm chairs for watching the sun rise, reading, napping, or enjoying an unobstructed view of the Atlantic Ocean and the horizon. brbrbrAcross the street from the beach and a five minute walk to the town of Oak Bluffs, the Flying Horses Carousel, and the ferry terminal, this home is perfectly situated. In addition to six light-filled, airy bedrooms, (one with an anteroom that sleeps 2) an open attic loft with picture windows and two skylights sleeps four.brbrThe house boasts a spacious living room, large comfortable den, a fully equipped antique pool room, and hardwood floors and high ceilings throughout. The newly renovated eat-in kitchen is equipped for the serious cook or those who'd rather take it easy. Surrounded by lawns and gardens, a large enclosed yard makes the house perfect for vacationing with children, impromptu sports, and family reunions.brbrSide cottage also available to rent separately (https://www.vrbo.com/3194607), sits beside the house on the property and features kitchen, bathroom, bedroom w/ 1 queen size bed and living room w/ futon.
Bed 7

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Bath 5

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Sleep 14

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Exceptional(2)

$706.48

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Apartment

Inca Gardens Apartment w Large Patio and Deck - Pets OK

Oak Bluffs, Massachusetts, United States

Inca Gardens is a 2nd-floor apartment of a cute house located in a quiet area of Martha's Vineyard between Oak Bluffs and Vineyard Haven. This vacation rental is the entire 2nd floor of this home. You will have the exclusive use of two large wrap-around decks and a large backyard patio with a fire pit, lounge area, and dining area. The owner is a master gardener and esthetician. This shows in her wonderful flowers, yard and attention to detail. The owner lives in the first floor of this home. There are two private and separate entrances to the home to insure your peaceful vacation. brThe apartment is 1,200 square feet. The exterior space is almost 2,000 additional square feet.brbrThe home was recently remodeled and the entire inside was repainted. The owners have really gone all out to make a good impression to their guests along with our advice on how to make an appealing and welcoming home. brbrThere is a private side area with parking for two cars. brbrHigh-Speed Internet (1 Gigabyte Plan) and a large eat-in kitchen and dining area complete this home. brbrPETS: We charge a $25 fee per night for up to one pet which must be under 30 pounds. No pets are allowed at the house per the lease unless a fee is paid. There is a small quiet Shitsu in the bottom apartment that only barks if the front door downstairs is knocked on. Otherwise, it sleeps all day. Properly documented service animals (not support animals) are allowed per Airbnb policy and also per prevailing laws. The fee helps us defray the cost of additional cleaning and additional wear and tear. brbrParking for two cars and two private entrances are on the right side of the house. You will have total privacy. On the left side of the house is the owner's parking and entrance which is not visible from your apartment. brbrThe home is in a quiet area of the island in between Vineyard Haven and Oak Bluffsbr- Eastville Beach is half a mile awaybr- Oak Bluffs and the Flying Horses Carousel is 1.6 miles awaybr- Gingerbread houses & Main St. are 1.4 miles awaybr- Car or bikes are RecommendedbrbrFIXTURESbrThis property is one of the most affordable apartments available on MV. The owners took an existing two-story home and converted it into two apartments. One guest (out of 25) mentioned that the fixtures are dated. In our opinion, there is no reason to replace bathroom fixtures if they are in good working order. Fixing Dated is not something that is compatible at this price point. We work hard to earn 5-star ratings and hope that our guests will measure this apartment to other properties at this price point and not some of the homes that rent for 10 times this amount.brIn other words, we are five stars for the price.brbrNOISEbrThe apartment you are renting is on the second floor so it is the quieter of the two. The owner lives on the first floor. This apartment has a door with a sign on it to keep closed. This connects the apartments via a staircase. When closed no sound comes through from either apartment. We have had one mention of sound in 25 rentals. It is natural for there to be some noise transmission in a wood-construction house where one apartment is over the other. I mention this to simply set expectations.brbrThere is a cleaning fee payable with every staybrWe require our lease to be signedbrWe require a credit card hold for a security deposit. This is a Credit Hold and not a charge
Bed 3

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Sleep 6

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Exceptional(54)

$546.05

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Private Vacation Home

Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town

Oak Bluffs, Massachusetts, United States

A comfortable residence, this charming ranch has all the amenities for a perfect vacation. It's quiet location is 1.5 miles from town, yet not too far to bike or walk in when needed. Beaches, ponds, the lagoon, and other recreational facilities are also easily accessible if you want to hop on the bike path (just around the corner) or take a brisk walk. Park on property, several cars. If you have difficulty obtaining ferry tickets I may be able to supply them for some weeks.brbrNicely refinished hardwood floors, tiled kitchen and bath, air conditioning in every room, free washer and dryer, private wooded back yard deck & deck with gas grill & an amazing outdoor shower. TV in the living room with DVD/VCR, video games, high speed wireless internet (WiFi). The house has three bedrooms and will sleep 7 people comfortably. One bedroom has a queen size bed. The second bedroom has a bunk bed, (twin size on top, double bed on bottom). The third bedroom has two twin beds. There is a full size pullout in the living room, as well. Oversized closets and dressers are in each bedroom. Kitchen and Bathroom recently upgraded and remodeled with a lot of new paint, refinished floors, new mattresses, new bedroom furniture, the house is clean and comfortable.brbrSave money renting bikes or Kayaks.. and use mine! One two seater Kayak and one single seater, both are sit on top. I have paddles and life jackets. For the bikes, I have assorted helmets ..not to mention badminton, croquet, clamming rakes, fishing poles, board games, ping pong, etc. Going to the beach.. use my beach chairs, several varieties.brbrFeel safe and secure, safe neighborhood, deadlocks if you want though, outdoor lighting, fire and smoke detectors throughout. Sports safety equipment for bikes and kayaks.brbrShould you decide to rent this listing using mastersard or visa, I have an account with Paypal.brbrbrKeywords: House Oak Bluffs Martha's Vineyard Martha 3 bedrooms kayak bikes grill beach chairs deck outdoor shower air conditioning Wifi internet washer dryer
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Bath 1

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Sleep 7

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Exceptional(9)

$826.58

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Private Vacation Home

Centrally located Oak Bluffs property next to Bike Path

Oak Bluffs, Massachusetts, United States

Welcome to our vacation rental in Oak Bluffs, Martha's Vineyard! Lovely home in the sought after Meadow View Farms community is right on the bike path! This is the perfect combination of tranquility and accessibility. As you step into our space, you'll be greeted by a warm and inviting atmosphere. The 4 bedroom 2 bath spacious open concept living provides a comfortable retreat after a day of exploring the island. With ample natural light and modern amenities, including a/c, outdoor grills, and large outdoor shower. Offers a relaxing environment for you to unwind. Just a short drive away, you can sink your toes into the sandy shores of Inkwell Beach or State beach known for there crystal-clear waters and stunning sunsets. Golf enthusiasts will be delighted to discover that it is also conveniently located near the prestigious Farm Neck Golf Course with public access. Challenge yourself in a game of tennis or golf and take in the breathtaking views of the surrounding landscapes. When you're ready to explore further, Oak Bluffs offers an array of charming shops, restaurants, and entertainment options. Immerse yourself in the vibrant local culture, visit art galleries, or savor delicious seafood at waterfront eateries. The quaint and historic Oak Bluffs Campground is also within reach, showcasing its iconic gingerbread cottages and vibrant community.
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Bath 2

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