Home Vacation Home Rentals By Owner In Oak Bluffs, MA

Showing 40 Of 248 Vacation Rentals
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Exceptional(31)

$949.45

/ Nightly
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(54)

$546.05

/ Nightly
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
Bed 3

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Bath 1

Bath

Sleep 7

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Exceptional(9)

$826.58

/ Nightly
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.
Bed 4

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Bath 2

Bath

Sleep 9

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$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

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Bath 2

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Sleep 6

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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

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Bath 2

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Sleep 8

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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

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Bath 2

Bath

Sleep 8

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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

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Bath 4

Bath

Sleep 8

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$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

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Bath 3

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Sleep 6

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