Oak Bluffs Vacation Rentals

Oak Bluffs Vacation Rentals

Experience the vibrant culture of Martha's Vineyard with our Oak Bluffs vacation rentals. From Victorian cottages to modern beachfront homes, our properties offer comfort and convenience.

Victorian on Ocean Park in Oak Bluffs

Victorian on Ocean Park in Oak Bluffs

9 guests·5 beds·3 baths

$7,300 week

House on 12 Samoset in Oak Bluffs

House on 12 Samoset in Oak Bluffs

8 guests·4 beds·1 bath

$4,700 week

Oak Bluffs/Niantic Park

Oak Bluffs/Niantic Park

8 guests·4 beds·2 baths

$7,050 week

17 High Meadow Lane

17 High Meadow Lane

8 guests·4 beds·4.5 baths

$7,000 week

Contemporary Cape with open floor plan

Contemporary Cape with open floor plan

5 guests·2 beds·2 baths

$2,800 week

Lovely Home in Fresh Pond Estates

Lovely Home in Fresh Pond Estates

8 guests·4 beds·3 baths

$7,750 week

East Chop Cottage

East Chop Cottage

7 guests·3 beds·2 baths

$3,500 week

House on 89 Ocean Avenue in Oak Bluffs

House on 89 Ocean Avenue in Oak Bluffs

14 guests·7 beds·3 baths

$15,000 week

380 Seaview Ave

380 Seaview Ave

12 guests·5 beds·4 baths

$9,000 week

House on 19 Ocean Avenue in Oak Bluffs

House on 19 Ocean Avenue in Oak Bluffs

13 guests·7 beds·3 baths

$10,500 week

Condo/Townhome on 2 Pennacook Avenue in Oak Bluffs

Condo/Townhome on 2 Pennacook Avenue in Oak Bluffs

4 guests·2 beds·2 baths

$4,000 week

In Town Victorian with large back yard

In Town Victorian with large back yard

10 guests·5 beds·1 bath

$6,500 week

Ocean Park 2 bedroom condo- waterview

Ocean Park 2 bedroom condo- waterview

4 guests·2 beds·1 bath

$2,700 week

26 Inca Road

26 Inca Road

8 guests·4 beds·3 baths

$8,600 week

5 Rock Ave

5 Rock Ave

8 guests·4 beds·2 baths

$4,350 week

House on 15 Pequot in Oak Bluffs

House on 15 Pequot in Oak Bluffs

10 guests·5 beds·3 baths

$8,000 week

2 Narraganssett Ave.

2 Narraganssett Ave.

22 guests·9 beds·4 baths

$14,900 week

Summer Tradewinds

Summer Tradewinds

10 guests·5 beds·3 baths

$7,000 week

Nashawena Park Steps from Inkwell Beach

Nashawena Park Steps from Inkwell Beach

8 guests·4 beds·2 baths

$6,750 week

Ocean Park Home with Water view 7 bedrooms

Ocean Park Home with Water view 7 bedrooms

14 guests·7 beds·4 baths

$12,750 week

Charming Cottage in Great Oak Bluffs Location

Charming Cottage in Great Oak Bluffs Location

6 guests·2 beds·3 baths

$4,300 week

Charming Home on Nashawena park Steps to Inkwell

Charming Home on Nashawena park Steps to Inkwell

8 guests·4 beds·2 baths

$7,000 week

House on 3 Canonicus in Oak Bluffs

House on 3 Canonicus in Oak Bluffs

8 guests·4 beds·1 bath

$8,800 week

Copeland Gem Downtown Oak Bluffs

Copeland Gem Downtown Oak Bluffs

10 guests·5 beds·2 baths

$9,500 week

53A Ocean Avenue

53A Ocean Avenue

14 guests·7 beds·4 baths

$21,000 week

Endless Summer in East Chop

Endless Summer in East Chop

8 guests·3 beds·2 baths

$5,350 week

Renovated Victorian Cottage with a/c

Renovated Victorian Cottage with a/c

6 guests·3 beds·2 baths

$6,700 week

Oak Bluffs Victorian less than block from Beach

Oak Bluffs Victorian less than block from Beach

8 guests·5 beds·2 baths

$5,500 week

13 Hubbard Lane

13 Hubbard Lane

6 guests·3 beds·2 baths

$8,100 week

4 Canonicus Ave

4 Canonicus Ave

9 guests·4 beds·2.5 baths

$10,000 week

2 Monahegan Ave.

2 Monahegan Ave.

8 guests·4 beds·2 baths

$4,500 week

House on 24 Winemack in Oak Bluffs

House on 24 Winemack in Oak Bluffs

6 guests·3 beds·2 baths

$8,500 week

63 Tradewinds Rd.

63 Tradewinds Rd.

4 guests·2 beds·2 baths

$4,150 week

Beautiful Beachy Classic with Reverse Floor Plan

Beautiful Beachy Classic with Reverse Floor Plan

8 guests·4 beds·2 baths

$5,700 week

House on 27 Ocean Avenue in Oak Bluffs

House on 27 Ocean Avenue in Oak Bluffs

10 guests·6 beds·3 baths

$13,900 week

50 Pondview Dr

50 Pondview Dr

6 guests·3 beds·2.5 baths

$6,050 week

28 Pequot Ave.

28 Pequot Ave.

10 guests·5 beds·2.5 baths

$9,850 week

Private lagoon beach

Private lagoon beach

7 guests·3 beds·2 baths

$4,000 week

MVCMA Campground cottage walk to beach

MVCMA Campground cottage walk to beach

8 guests·4 beds·2 baths

$4,300 week

Charming Farmhouse with Central A/C Close to Town

Charming Farmhouse with Central A/C Close to Town

8 guests·3 beds·3 baths

$4,100 week

Condo/Townhome on 21 Kennebec Avenue in Oak Bluffs

Condo/Townhome on 21 Kennebec Avenue in Oak Bluffs

4 guests·2 beds·1 bath

$3,700 week

Renovated Victorian steps from Inkwell with a/c

Renovated Victorian steps from Inkwell with a/c

8 guests·4 beds·2 baths

$5,950 week

Sun Filled Waterfront Home with Pond View

Sun Filled Waterfront Home with Pond View

8 guests·4 beds·2 baths

$5,700 week

Updated Salt Box Close to Town

Updated Salt Box Close to Town

6 guests·3 beds·2 baths

$4,150 week

Newly Renovated Top to Bottom Meadow View Farms

Newly Renovated Top to Bottom Meadow View Farms

8 guests·4 beds·3 baths

$9,850 week

Seaview Condo in Oak Bluffs

Seaview Condo in Oak Bluffs

4 guests·2 beds·2 baths

$3,300 week

Cinderella Cottage in Oak Bluffs

Cinderella Cottage in Oak Bluffs

8 guests·4 beds·2 baths

$10,350 week

26 Bridle Path Road

26 Bridle Path Road

8 guests·3 beds·3.5 baths

$5,750 week

House on 6 West Meadow Lane in Oak Bluffs

House on 6 West Meadow Lane in Oak Bluffs

12 guests·4 beds·2 baths

$11,200 week

Renovated Victorian Home near Oak Bluffs Harbor

Renovated Victorian Home near Oak Bluffs Harbor

10 guests·6 beds·2 baths

$6,500 week

Newly Renovated 8 Bedroom Home Steps to Beach

Newly Renovated 8 Bedroom Home Steps to Beach

16 guests·8 beds·3 baths

$11,950 week

House on 9 Pequot Avenue in Oak Bluffs

House on 9 Pequot Avenue in Oak Bluffs

8 guests·4 beds·2 baths

$7,800 week

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