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New downtown 2 bedroom condo, both kings, with central AC in Oak Bluffs

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The iconic Vineyard Vines building in Oak Bluffs
Whale Tail is located on the second floor
Steps from almost every activity in OB!
Up to the left for Whale Tail
Welcome to Whale Tail!

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 6750 sq ft

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Kitchen
  • Air conditioning
  • Free WiFi

Explore the area

View in a map
Oak Bluffs, MA
  • Circuit Avenue
    ‪1 min walk‬
  • Inkwell Beach
    ‪6 min walk‬
  • Oak Bluffs Town Beach
    ‪8 min walk‬
  • Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪15 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 2

1 King Bed

Living Room 1

1 Double Sofa Bed

PRIMARY BEDROOM

1 King Bed

1 bathroom

Bathroom

Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Kitchen
Balcony
Dining area

About this property

New downtown 2 bedroom condo, both kings, with central AC in Oak Bluffs

Welcome to 'Whale Tail', one of the most iconic and talked-about properties in Oak Bluffs! Located directly above Vineyard Vines, this stunning pink, blue, and white gingerbread-style condo offers the perfect mix of charm, luxury, and unbeatable convenience.

Freshly renovated from top to bottom, this premium second level space features nickel gap walls, central A/C and heat, a beautifully designed kitchen with brand, new stainless appliances, quartz countertop, and backsplash, and dining for six along with all-new furnishings and amenities. There are two lovely king bedrooms and a comfortable pop-up sleeper in the living room which is perfect for a child or two. Every detail has been carefully curated to make your stay stylish, relaxing, and easy.

The location couldn’t be better: you’re just steps from Circuit Avenue’s shops, bars, and restaurants, and a short stroll to the ferry, harbor, and Oak Bluffs’ popular beaches. The property also sits feet from the historic Campground Cottages, offering a quiet, storybook backdrop while still being in the center of it all.

Whether you’re sipping coffee on the deck, walking to dinner, or catching a sunset by the water, this condo offers the ideal Martha’s Vineyard experience: central, comfortable, and completely unforgettable.

Property manager

Scott Savage
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Fireplace

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  • Washer
  • Dryer
  • Free WiFi
9.8 out of 10, (68 reviews)
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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Please throw all used towels into the shower
No need to strip the beds we will take care of that
Please set the ÅC to 74 upon departure
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number c0544702210

We should mention

This property does not have any lifts

About the area

Oak Bluffs

Located in Oak Bluffs, this holiday home is in the city centre. The area's natural beauty can be seen at Inkwell Beach and Cape Cod Beaches, while Cottage Museum and Martha's Vineyard Film Center are cultural highlights. Flying Horses Carousel and Oak Bluffs Fishing Pier are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with horse riding and mountain biking.
Map
Oak Bluffs, MA

What's nearby

  • Circuit Avenue - 1 min walk - 0.0 km
  • Oak Bluffs Harbor - 5 min walk - 0.4 km
  • Oak Bluffs Ferry Terminal - 6 min walk - 0.6 km
  • Inkwell Beach - 6 min walk - 0.6 km
  • Oak Bluffs Town Beach - 8 min walk - 0.7 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 14 min drive

Restaurants

  • ‪Lookout Tavern - ‬6 min walk
  • ‪Portuguese-American Club - ‬3 min drive
  • ‪Back Door Donuts - ‬2 min walk
  • ‪Black Joy - ‬10 min walk
  • ‪Offshore Ale Co. - ‬3 min walk

Frequently asked questions

Is New downtown 2 bedroom condo, both kings, with central AC in Oak Bluffs pet-friendly?

No, pets are not allowed at this property.

How much is parking at New downtown 2 bedroom condo, both kings, with central AC in Oak Bluffs?

This property doesn't offer parking.

What time is check-in at New downtown 2 bedroom condo, both kings, with central AC in Oak Bluffs?

Check-in begins at 4:00 PM.

What time is check-out at New downtown 2 bedroom condo, both kings, with central AC in Oak Bluffs?

Checkout is at 10:00 AM.

Where is New downtown 2 bedroom condo, both kings, with central AC in Oak Bluffs located?

Located in the heart of Oak Bluffs, this holiday home is within a 10-minute walk of Circuit Avenue and Inkwell Beach. Trinity Park Tabernacle and Cottage Museum are just steps away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Valerie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We LOVED this condo. It is the perfect location in Oak Bluffs and very walkable. The condo itself was very clean and the use of space was impeccable. Scott was lovely and easy to work with - highly recommend!
Stayed 4 nights in Aug 2025

10/10 Excellent

Tajuana TJ B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
So many good things to say about this rental. Where do I begin? First, this place has the coastal charm of historic MV homes, but with the modern touch and conveniences that my family prefers when vacationing. The property is in an amazing location right off Circuit Avenue, allowing the opportunity to sit on the upstairs deck or downstairs porch and enjoy the energy and movement on the active street. We enjoyed sitting out upstairs after a long day out and the rocking chairs downstairs while waiting for everyone to come down before heading out on excursions. With a little effort we were able to find parking, even on busy nights. The place is laid out perfectly and thoughtfully and was stocked with everything we needed for our vacation. I used the blender for smoothies most mornings. The range of kitchenware was great quality. The beach chairs and towels came in handy for our day at the beach. We also used the chairs for the drive-in movie at the YMCA. (I also popped popcorn on the stove to take with us). The beds were so comfortable, my girls even noticed. The water pressure in the shower was good. There was an overall light, peaceful feeling to the place, which was a bonus. Not to mention, check-in was a breeze and communicating with Scott was smooth and straightforward. We clearly enjoyed our stay there and would recommend this gem to anyone wanting to have easy access to all the Oak Bluffs has to offer.
Stayed 5 nights in Aug 2025

10/10 Excellent

Taylor H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We couldn’t have asked for a better experience. We were scrambling to find a place in Oak Bluffs. after another host of a different property canceled last minute last-minute cancellation from another property. If anyone knows, it's extremely hard to find housing in OB that close to August, so our options were very limited. So we stumbled upon this property.This spot not only saved our trip, it completely exceeded expectations. The location was incredibly convenient to walk to everything we love: shops, restaurants, the harbor, and more.The unit was spotless and well-maintained, and we especially loved spending time each day out on the balcony. It was perfect for soaking in the vibrant downtown atmosphere with a morning coffee. I just want to comment on the beds too, it was the best sleep I've gotten all year hahaParking around Circuit Ave was an initial concern but there was typically long-term parking available near the church or around the corner.Scott was an exceptional host. Since it was a new property, he was very clear in answering any questions we had and advising us about every step of check-in. He responded to our texts within minutes (never more than 10!), which made everything smooth and stress-free.We’ve been coming to Oak Bluffs for 7 years, and this is hands-down one of the best locations we’ve stayed in. We’ve already reached out to book again for next year!Highly recommend this property to anyone looking for a clean, comfortable, and relaxing stay.
Us sitting on the balcony!
Our bedroom
The kitchen where we baked cookies for three days. They had appliances and cooking tools for everything.
We watched movies in the living room.
Stayed 4 nights in Aug 2025

About the host

Hosted by Scott Savage

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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