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Oak Bluffs Town Beach, Oak Bluffs, Massachusetts, United States of America
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Oak Bluffs Town Beach vacation rentals

We found 1,404 vacation rentals — enter your dates for availability

Discover a selection of 1,500 vacation rentals near Oak Bluffs Town Beach, Oak Bluffs that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $116 per night, and houses and condos are popular options for a stay near Oak Bluffs Town Beach. Either way, you'll find a rental for everyone's needs.
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Houses

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Condos/Apartments

View 133 Condos/Apartments

Cabins

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Cottages

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Bungalows

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Townhouses

View 36 Townhouses

Studios

View 65 Studios

Find the best place to stay — Oak Bluffs Town Beach

Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!

Sleeps 7 · 4 Bedrooms · 2 Bathrooms
$263 avg/night
(79)

Charming Home with WiFi, Near Beaches & Marina - Dog-Friendly

Sleeps 6 · 2 Bedrooms · 1 Bathroom
$116 avg/night
(58)

NEW! Family-Friendly Tisbury Escape - Walk to Town

Sleeps 9 · 5 Bedrooms · 2 Bathrooms
$259 avg/night
(5)

Arrowsmith Cottage - Near Eastville Point Beach - Oak Bluffs-Martha's Vineyard

Sleeps 4 · 2 Bedrooms · 1 Bathroom
$245 avg/night
(60)

Make Lasting Memories In This Adorable Vineyard Cottage!

Sleeps 4 · Studio · 1 Bathroom
$199 avg/night
(109)

Dog-friendly condo with pool, tennis courts, & picnic area - close to beach

Sleeps 4 · Studio · 1 Bathroom
$179 avg/night
(44)

Search 1,404 vacation rentals

Top rated rentals — Oak Bluffs Town Beach
Stayed Dec 2022

After ten years of VRBO, this is number one!!!

The house:A+, the location A+, this home was so beautifully equipped for cooking and fun, great bedding, great books, a great home to have a number of people or just two, and the kitchen is a great space for cooking without that “I’m not at home” fee...

Kate F.
Kate F.
Stayed Dec 2022

Cozy and well stocked!

We had a great time over the holidays. The house is spacious, clean, well decorated, and has more than the basics. We spent alot of time in the living room full of natural light and enjoyed cooking our meals in the kitchen which has pretty much every...

Natalie R.
Natalie R.
Stayed Dec 2022

Perfect Getaway

My girlfriends completely enjoyed staying in this adorable cottage. The three of us met on the Vineyard way back in 1989. We were all working at the Atlantic Connection and Seasons which are no longer around. I was a waitress, my friend worked in the...

Meghan A.
Meghan A.

weymouth

Stayed Oct 2022

A bit of a disappointment

I have stayed at Island Inn each year when I visit Martha’s Vineyard It is a beautiful property with kitchens in each type of room I’ve stayed in. I stayed in a new building this trip and out first morning there my husband and I both slipped several...

Maryann J.
Maryann J.
Stayed Oct 2022

Reasonably-priced Resort on the Vineyard

The only one we have been able to find, frankly. Alas, we never come in the summer so we missed the pool again but there were plenty of people playing tennis and we walked to the ever-lively Nomans Restaurant. Joseph Sylvia Beach and downtown OB we...

Benjamin L.
Benjamin L.
Stayed Sep 2022

Comfortable homey visit

My friends and I were in town for a wedding and enjoyed being within walking distance (20 min) of Oak Bluffs. John is a great property owner and was very responsive to our questions and flexible with check-in time based on the ferry schedule. Appreci...

Bridey
Bridey
Stayed Sep 2022

Better to be pleasantly surprised than let down

The property is conveniently located for any activity. It is quite small but manageable. Our biggest gaff was that the property was advertised as two BR and two baths. Not so. 1 - 1/2 baths. We would have passed this by had we known that. The second...

Fred G.
Fred G.
Stayed Sep 2022

Picture perfect

Wonderful house in a beautiful setting. Photos do it no justice. Location is very convenient to “downtown” and the waterfront. Bedrooms were large and so comfortable. Kitchen was well equipped and there is lots of room, indoors and out, to gather. We...

Sandy M.
Sandy M.

Arlington, VA

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How many vacation rentals are available around Oak Bluffs Town Beach, Oak Bluffs?

Our 2023 property listings offer a large selection of 1,404 vacation rentals around Oak Bluffs Town Beach. From 1,241 house rentals to 133 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses near Oak Bluffs Town Beach?

Yes, of course. Vrbo has 1,241 Houses near Oak Bluffs Town Beach. Our other popular types of vacation rentals near Oak Bluffs Town Beach include:

  • Condos/Apartments: 133 rentals available
  • Cabins: 104 rentals available
  • Cottages: 104 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool near Oak Bluffs Town Beach?

Yes, you can select your preferred vacation rental with pool among our 243 vacation rentals with pool available near Oak Bluffs Town Beach. Please use our search bar to access the selection of vacation rentals available.