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Oak Bluffs Vacation Rental home in Martha's Vineyard MA | ID 41757

Waterfront Oak Bluffs Retreat | 4BR | Kayaks, Mooring, Dock
Oak Bluffs, Sengekontacket Pond Vacation Rental - ID 41757

4 BR
2 ½ baths
Sleeps 8
Beds: 2 queens, 1 double, 2 twins
Beach: 3.6 mi to Oak Bluffs Town Beach and 5.0 State Beach (Joseph Sylvia State Beach)
Daily
Weekly
Monthly
Off-season 2025/26
$1,071
Summer 2026
 
Off-season 2026/27
$1,071
Off-season 2025/26
$7,525 - $7,850
Summer 2026
$10,850
Off-season 2026/27
$8,350 - $10,850
Off-season 2025/26
 
Summer 2026
 
Off-season 2026/27
 
State and local taxes of 11.7% will apply
Listed by Donna
Active
Less than a month
Property ID 41757
3
Description

Description

Experience the magic of Martha’s Vineyard from this exceptional waterfront retreat overlooking scenic Sengekontacket Pond in Oak Bluffs. Offered for rental for the very first season, this beautifully appointed 4-bedroom, 2.5-bath home with enclosed outdoor shower combines breathtaking water views, peaceful privacy, and classic island charm for the ultimate Vineyard getaway.

Nestled in a quiet private neighborhood, the home offers panoramic pond views from nearly every room, creating a serene backdrop for your summer escape. Spend your days kayaking on the calm waters, relaxing on the expansive mahogany deck, or enjoying spectacular sunsets around the fire pit.

Guests enjoy access to an exclusive community dock directly across the street, plus clubhouse amenities including tennis and pickleball courts and scenic walking trails. Four kayaks are included for exploring the pond, and private mooring access makes this an ideal retreat for boating enthusiasts.

Perfectly located just minutes from Oak Bluffs’ vibrant shops, restaurants, beaches, bike paths, and the iconic Jaws Bridge, the home offers the perfect balance of convenience and tranquility.<br /> <br /> The Home<br /> Entering on the main level, guests are welcomed into a bright foyer that opens to a spacious kitchen with eat-in dining area and a stunning cathedral-ceiling family room — all designed to maximize the incredible water views. Large sliding doors lead directly to the expansive mahogany deck, perfect for outdoor dining, morning coffee, or evening cocktails overlooking the pond.<br /> <br /> Upstairs, the private primary suite features a queen bed, full bath, cathedral ceilings, and sweeping water views that make every morning feel special.<br /> <br /> The lower level includes three additional guest bedrooms:<br /> One spacious bedroom with a double bed, sitting area, and direct outdoor access<br /> One bedroom with a double bed and beautiful pond views<br /> One bedroom with two twin beds and full-size windows overlooking the water<br /> <br /> This level also includes a full bath and a separate enclosed laundry area for added convenience.<br /> <br /> Amenities<br /> - Waterfront location on Sengekontacket Pond<br /> - Panoramic water views from every room<br /> - Private neighborhood setting<br /> - Community dock access<br /> - Four kayaks included<br /> - Private mooring access<br /> - Clubhouse amenities<br /> - Tennis & pickleball courts<br /> - Walking trails<br /> - Expansive mahogany deck with outdoor dining<br /> - Fire pit area with Adirondack chairs<br /> - Laundry area<br /> - Minutes to Oak Bluffs, beaches, bike paths, and Jaws Bridge<br /> <br /> Whether you’re seeking peaceful mornings on the water, active days exploring the island, or unforgettable evenings watching the sunset, this exceptional Vineyard retreat offers the quintessential Martha’s Vineyard summer experience. read more show less

Location

Location - Oak Bluffs, Sengekontacket Pond

Nearest beach: 3.6 mi to Oak Bluffs Town Beach and 5.0 State Beach (Joseph Sylvia State Beach)

41.4196681 -70.5729071 0
Photos

Photos

Pricing & Availability

Pricing & Availability

1
Minimum Stay Requirements:
  • Off-season 2025/26
    3 nights
  • Summer 2026
    7 nights
  • Off-season 2026/27
    3 nights
  • Summer 2027
    7 nights
Available
Unavailable
Check-in Only
Check-out Only
Unknown

Calendar Last Updated: June 02, 2026

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  • Price JUNE 2026
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     $7,525      1 2 3 4 5
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     $10,850  27 28 29 30      
  • Price JULY 2026
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  • Price AUGUST 2026
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  • Price SEPTEMBER 2026
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  • Price OCTOBER 2026
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Additional availability info: Partial weeks are available if open. This is a Saturday to Saturday vacation rental.

Payment Methods: ACH/EFT (transaction fees vary); and personal checks

Fee Breakdown:

INCLUDED IN WEEKLY RATE

Cleaning Fee:

$450

OPTIONAL FEES

Other Fees:

$100 if trash guidelines are not followed per HOA

SECURITY DEPOSIT

Security Deposit:

$1500.00

ADDITIONAL PRICING INFO

State and local taxes of 11.7% will apply

Amenities

Amenities

  • On salt water On salt water

  • Central air Central air

  • Outdoor shower Outdoor shower

  • Washer&dryer Washer&dryer

  • No Pets No Pets

  • Internet Internet

  • Bathtub Bathtub

  • Dock for boat Dock for boat

  • Firepit Firepit

  • Deck, porch or patio Deck, porch or patio

  • BBQ-grill BBQ-grill

  • Boat, kayak, canoe Boat, kayak, canoe



    Green Amenities

    3
    • Heat Pumps Heat Pumps

    • LED lighting LED lighting

    • ENERGY STAR appliances ENERGY STAR appliances

    Reviews

    Guest Reviews

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    About

    About Donna

    Member since:
    5/18/2026
    Response Time:
    Within a day
    Response Rate:
    100%
    I have been a Martha's Vineyard homeowner since 1997 and have had the privilege of owning this home as my second Vineyard property. In fact, I purchased my very first Vineyard home during the very first weekend I ever spent on the island. There was something special about Martha's Vineyard that captured my heart immediately, and that feeling has never faded.

    Over the years, this home has been the setting for countless gatherings with family and friends and many of our most treasured memories. From summer days on the water to quiet evenings watching the sunset, the Vineyard has provided a place to reconnect, relax, and celebrate life's special moments.

    As my daughter begins building a family of her own and I spend more time caring for an aging parent, I felt it was the perfect time to open my home to others. It brings me great joy to share this special place and offer guests the opportunity to create their own unforgettable Vineyard memories.

    I hope you enjoy this home and the island as much as my family has for nearly three decades.

    What is special about this property?
    I can honestly say it was love at first sight. Everything about Sengekontacket Pond and this home drew me in from the moment I saw it, and it has exceeded my expectations every year since.

    What makes this property truly special is its location. Nestled in a quiet private neighborhood with wonderful amenities, the home offers breathtaking water views from every room. The open floor plan, set back from the road, creates a peaceful sense of privacy while still being bright, welcoming, and connected to the surrounding beauty.

    The location also provides the best of both worlds - easy access to Oak Bluffs, Edgartown, beaches, and the island's main roads, while remaining just far enough away from the summer crowds. The bike path and an MVTA bus stop are conveniently located at the entrance to the community, making it easy to explore all that Martha's Vineyard has to offer.

    What is special about your town?
    Oak Bluffs has a unique energy that captures the best of Martha's Vineyard. From the colorful Gingerbread Cottages and historic Flying Horses Carousel to its beautiful harbor, beaches, shops, and restaurants, it offers a perfect blend of history, charm, and coastal fun.

    What makes Martha's Vineyard truly special, however, is its ability to feel both vibrant and peaceful at the same time. Each town has its own personality, from the elegance of Edgartown to the rural beauty of West Tisbury and Aquinnah. Miles of beaches, scenic bike paths, walking trails, farm stands, and stunning waterfront views create endless opportunities to explore.

    For me, the Vineyard is a place where families reconnect, friendships grow, and lifelong memories are made. Whether you're enjoying a day on the water, watching a sunset, or simply slowing down to enjoy island life, Martha's Vineyard has a way of drawing you back year after year.


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