Holiday rentals in Lagoon Pond

Guest suite in Oak Bluffs

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

Lovely 2 BR Oak Bluffs Apartment

*To returning guests: Airbnb has restructured their fees; so while our nightly price may look higher at first glance, it is our same pricing overall This private apartment is on the 1st floor of a family home with a personal entrance & parking; owners and their son live upstairs. There are no shared spaces. It is a mile from Oak Bluffs Center, a half mile from the Cottages and Farm Neck Golf Course, and across the street is a bike path. The bus stop is on the corner for easy island wide travel!

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4.95 out of 5 average rating, 442 reviews

The front exterior of the house is shown surrounded by lush greenery, featuring a well-maintained lawn. A pathway leads to the entrance, and the porch offers seating. Two sun loungers are positioned on the grass, inviting relaxation in the open space.

4.93 out of 5 average rating, 153 reviews

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. 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. Updated 7/25/2025 we do not have any more firewood on the property.

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An open living area is highlighted by high ceilings and large windows allowing natural light. A comfortable sectional sofa with a blue and white throw sits atop a textured rug. The kitchen area features a white island with seating, connecting to a lofted space above.

4.98 out of 5 average rating, 92 reviews

New Pristine Luxury Home on Martha's Vineyard

This brand new, stylish luxury home is located in a quiet neighborhood in Oak Bluffs and is centrally located; close to town, beaches, steamship, bike path and more. Our entirely private home has 2 bedrooms with King size beds and loft sleeping area with 2 sets of bunk beds, making it a perfect stay for 2 families with children. This home is equipped with everything you need. Parties are not permitted at this home as it is in a quiet residential neighborhood.

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The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

4.93 out of 5 average rating, 327 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

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The exterior of a charming two-story house is shown, featuring a wrap-around porch with multiple seating options. The porch is adorned with wooden chairs, and the front yard is grassy, providing ample space for outdoor relaxation. Large windows reflect natural light, contributing to the inviting ambiance.

4.81 out of 5 average rating, 134 reviews

Beautiful 3 bedroom in Oak Bluffs, walk to beach

Located in Martha's Vineyard, close to beach, bike path, oak bluffs center, art and culture, parks,and the airport. You’ll love my place because of the outdoors space with a wrap around farmers porch, the proximity to the ferry, walking distance to neighborhood beach, less than 2 miles from ferry, screened in porch, central a/c, hardwood floors and an open floor plan. Real Cape Cod feel with modern amenities. Most of my guest come back year after year!

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4.97 out of 5 average rating, 114 reviews

A scenic view is captured showcasing a vibrant sunset over the water, with sailboats gently floating. The sky displays rich hues of orange and pink, reflecting on the calm surface, creating a serene atmosphere.

Guest house in Tisbury

MV King bed, Water Views, Near Bike Path- Bus stop

Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay. :)

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Superhost

The charming Cape Cod-style home is framed by lush greenery and a well-kept yard. A welcoming red staircase leads to the front door, while gravel paths and decorative stones outline the landscape, inviting guests to explore the outdoor space.

4.88 out of 5 average rating, 76 reviews

Oak Bluffs 4BR • 5 Min Drive to Downtown

Just 5 minutes from Downtown Oak Bluffs and nearby beaches, this spacious 4-bedroom home sleeps up to 8 guests and offers comfort, privacy, and a peaceful cul-de-sac setting. Enjoy an open-concept living area, fully equipped kitchen, private deck with BBQ, and large backyard with hot/cold outdoor shower. Both full bathrooms are newly renovated with floor-to-ceiling tiled showers and luxury top-shelf bath amenities for a spa-like experience.

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A spacious, newly constructed home is showcased with a dark blue exterior and white accents. The façade features a prominent front porch with chairs and a large garage. A gravel driveway leads to the entrance, framed by a lush green lawn and trees.

4.98 out of 5 average rating, 58 reviews

The Blue Lagoon, Oak Bluffs

Come enjoy this beautifully designed, brand new home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An outdoor patio with gas grill is the perfect spot to relax after a day at the beach. Just a few steps away is the lagoon where you can paddle board, kayak, dig clams, or just take in the amazing sunsets! Summer rentals are Saturday to Saturday. Please send a message if you have any questions.

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A raised ranch is surrounded by lush greenery, with large windows allowing natural light to fill the interior. A spacious deck extends from the front, providing outdoor seating options. The home is elevated, partially obscured by surrounding trees, and features a charming sloped roof.

4.79 out of 5 average rating, 261 reviews

Central location for your vacation

An apartment in a peaceful Raised Ranch! Your Martha’s Vineyard sanctuary. Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proximity. 8 minutes away from ferry. Great for family vacation, Island explorations, work trips, hosting wedding guests, wellness retreat, or just a simple gateway, this home will compliment your Martha’s Vineyard experience.

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Guest suite in Oak Bluffs

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

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4.98 out of 5 average rating, 211 reviews

4.96 out of 5 average rating, 320 reviews

The cottage is adorned with warm, glowing string lights that outline the roof and windows, creating a welcoming ambiance. A lush wreath decorates the front door, while charming wood paneling and multiple windows enhance the inviting exterior.

Cottage in Tisbury

Not Your Great Aunt's Island Cottage

In the heart Vineyard, 1930's cottage, lovingly updated by architect-owner. • Stylish decor, open floor plan, granite terrace • 2 blocks to Main St/harbor/ferry/town beach/playhouse • Central Air • Easily walkable to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

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