Oak Bluffs Vacation Rentals

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MILTD

Perfect in Town Location. Just 1 to 2 blocks to Beach, Town Center & Harbor Area, Walk to and from the Ferry

Centrally located in the heart of Oak Bluffs, walk 1-2 blocks to the beach, public tennis courts, and town & harbor areas. This wonderful large home has a large wrap-around porch for relaxing, 7...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$8,500 - $9,500

Clean Fee:

$500 per week

Tax: State & Local:

11.7

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Pool, Lower Patio and Main Living Level Deck

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BROWL

Stunning Tri-Level Home, Heated Pool, Screened Porch, Beautifully Landscaped, Walk to Association Tennis Courts

Featured MVVR Listing:

Beautiful Coastal Inspired Retreat features multiple living spaces, a pool, a bluestone patio area, and a deck with an outdoor dining and grill area. This beautiful home is...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$4,400 - $9,000

Clean Fee:

$550 per week

Tax: State & Local:

11.7

Pool Heated to 80 degrees included in rental rate last Saturday in June to the first Saturday in September.

Pool Heated to 80 degrees, June & September weeks additional $300 propane surcharge per week.

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Yard , Deck Main House. Guest House just to the left

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DONAK

Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$7,000 - $9,000

Clean Fee:

$550 per week

Tax: State & Local:

11.7

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POWDA

Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$6,000 - $9,000

Clean Fee:

$600 per week

Tax: State & Local:

11.7

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Back of Home with Spacious Deck, overlooks Large Landscaped Yard

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VANA2

Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$6,500 - $8,500

Clean Fee:

$450 per week

Tax: State & Local:

11.7

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INGAE

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$4,630 - $8,350

Clean Fee:

$500 per week

Tax: State & Local:

11.7

Rates reduce for available weeks in June & July - see calendar for adjusted rates

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HUN28

Lovely New 3 Bedroom, 3.5 Bath Home, 15 min walk to Oak Bluffs Center, Inkwell Beach and Town Beach, Sleeps 8, 3 Bedrooms, Plus Loft, 3.5 Baths

Please note: This beautiful new home is in the process of being furnished into April. The photos provided are a sampling of the decor. All furnishings and household items will...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$5,230 - $8,010

Clean Fee:

$450 per week

Tax: State & Local:

11.7

3 night minimum stay required, May, June, September, October, 4 night minimum July to 7/19

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CORAG

Lovely, Newly Updated Oak Bluffs Home. Multiple Indoor/Outdoor Living/Lounge Areas, Sleeps 8, 10/15 minute Walk to the Vilage Center.

Note: All photos are virtually staged photos by the owner, all new furnishings will be arriving throughout the winter months.

Welcome to Noble House, a beautifully updated home nestled in a charming neighborhood just...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$1,650 - $8,000

Clean Fee:

$400 per week

Tax: State & Local:

11.7

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HOD28

Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.

Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters.

Summer Joy! Set in the heart of...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$5,000 - $7,850

Clean Fee:

$650 per week

Tax: State & Local:

11.7

Rates reduced for available weeks in June & July - see calendar for adjusted rates

8-minute walk from the ferry dock in Oak Bluffs and 5 minute walk to the Ink Well Beach, and Oak Bluffs Center from the house.

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CURRM

Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$7,700 - $7,700

Clean Fee:

$500 per week

Tax: State & Local:

11.7

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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PRIAN

Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$7,500 - $7,500

Clean Fee:

$750 per week

Tax: State & Local:

11.7

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GLEDE

Stunning New Custom Luxury Home, Oak Bluffs, 18 x 36 Heated Saltwater Pool, Bluestone Patio, 4 Bedrooms 3.5 baths

Tucked just on the outskirts of Oak Bluffs downtown area this spacious architect-designed custom home offers families and friends an outstanding vacation experience.

Professionally designed by a noted architect this outstanding...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$7,500 - $7,500

Clean Fee:

$600 per week

Tax: State & Local:

11.7

Pool Heated to 81 degrees July & August included in Rental Rate

Pool Heated to 81 degrees June & September additional $300 Propane Surcharge

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DENAL

Charming, 4-bedroom Oak Bluffs Home, pristinely maintained! The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,000 - $7,500

Clean Fee:

$450 per week

Tax: State & Local:

11.7

Parking for two cars only, no on-street parking!

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JOHNL

"Endless Summer Vacation" Stylish, Newly Update 3 + Bedroom, Sleeps 8, East Chop Area of Oak Bluffs, Deck Living & Dining Area, Screened Porch,

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,500 - $7,500

Clean Fee:

$330 per week

Tax: State & Local:

11.7

Owner will rent off weekend dates to accommodate the need for ferry tickets July weeks.

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BURBR