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.

5 Rock Ave

5 Rock Ave

8 guests·4 beds·2 baths

$4,550 week

50 Pondview Dr

50 Pondview Dr

6 guests·3 beds·2.5 baths

$6,300 week

73 Wing Road

73 Wing Road

6 guests·3 beds·2 baths

$4,150 week

Oak Bluffs Victorian less than block from Beach

Oak Bluffs Victorian less than block from Beach

8 guests·5 beds·2 baths

$5,000 week

Ocean Park 2 bedroom condo- waterview

Ocean Park 2 bedroom condo- waterview

4 guests·2 beds·1 bath

$2,500 week

Oak Bluffs Charm

Oak Bluffs Charm

6 guests·3 beds·2 baths

$2,500 week

House on 9 Pequot Avenue in Oak Bluffs

House on 9 Pequot Avenue in Oak Bluffs

8 guests·4 beds·2 baths

$7,250 week

Summer Tradewinds

Summer Tradewinds

10 guests·5 beds·3 baths

$6,600 week

13 Hubbard Lane

13 Hubbard Lane

6 guests·3 beds·2 baths

$4,700 week

Endless Summer in East Chop

Endless Summer in East Chop

8 guests·3 beds·2 baths

$4,650 week

Oak Bluffs Near Lagoon

Oak Bluffs Near Lagoon

6 guests·3 beds·2 baths

$5,500 week

Renovated Victorian Cottage with a/c

Renovated Victorian Cottage with a/c

6 guests·3 beds·2 baths

$6,750 week

MVCMA Campground cottage walk to beach

MVCMA Campground cottage walk to beach

8 guests·4 beds·2 baths

$4,100 week

Sun Filled Waterfront Home with Pond View

Sun Filled Waterfront Home with Pond View

8 guests·4 beds·2 baths

$5,350 week

Seaside Cottage near Inklwell

Seaside Cottage near Inklwell

2 guests·1 bed·1 bath

$3,500 week

3 Coral Ave

3 Coral Ave

6 guests·3 beds·2.5 baths

$3,400 week

Ocean Park Home with Water view 7 bedrooms

Ocean Park Home with Water view 7 bedrooms

14 guests·7 beds·4 baths

$13,050 week

House on 356 Winne Avenue in Oak Bluffs

House on 356 Winne Avenue in Oak Bluffs

6 guests·3 beds·3 baths

$8,650 week

53A Ocean Avenue

53A Ocean Avenue

14 guests·7 beds·4 baths

$21,000 week

Lovely Home in Fresh Pond Estates

Lovely Home in Fresh Pond Estates

8 guests·4 beds·3 baths

$6,750 week

86 Washington Ave

86 Washington Ave

5 guests·2 beds·2 baths

$2,700 week

Beautiful Beachy Classic with Reverse Floor Plan

Beautiful Beachy Classic with Reverse Floor Plan

8 guests·4 beds·2 baths

$5,600 week

Renovated Bayes Hill Home with Pool

Renovated Bayes Hill Home with Pool

8 guests·4 beds·2 baths

$18,700 week

Oak Bluffs Close to Town

Oak Bluffs Close to Town

6 guests·3 beds·2 baths

$3,300 week

House on 3 Canonicus in Oak Bluffs

House on 3 Canonicus in Oak Bluffs

8 guests·4 beds·1 bath

$9,000 week

East Chop Cottage

East Chop Cottage

7 guests·3 beds·2 baths

$3,500 week

63 Tradewinds Rd.

63 Tradewinds Rd.

4 guests·2 beds·2 baths

$4,250 week

Renovated Victorian steps from Inkwell with a/c

Renovated Victorian steps from Inkwell with a/c

8 guests·4 beds·2 baths

$5,600 week

12 Chickawaukee Street

12 Chickawaukee Street

4 guests·2 beds·1.5 baths

$2,500 week

Oak Bluffs/Niantic Park

Oak Bluffs/Niantic Park

8 guests·4 beds·2 baths

$6,800 week

Nashawena Park Steps from Inkwell Beach

Nashawena Park Steps from Inkwell Beach

8 guests·4 beds·2 baths

$6,600 week

In Town Victorian with large back yard

In Town Victorian with large back yard

10 guests·5 beds·2 baths

$6,150 week

House on 50 Pond View Drive in Oak Bluffs

House on 50 Pond View Drive in Oak Bluffs

6 guests·3 beds·2 baths

$6,500 week

2 Narraganssett Ave.

2 Narraganssett Ave.

22 guests·9 beds·4 baths

$16,100 week

House on 24 Winemack in Oak Bluffs

House on 24 Winemack in Oak Bluffs

6 guests·3 beds·2 baths

$9,500 week

28 Pequot Ave.

28 Pequot Ave.

10 guests·5 beds·2.5 baths

$9,800 week

House on 27 Ocean Avenue in Oak Bluffs

House on 27 Ocean Avenue in Oak Bluffs

10 guests·6 beds·3 baths

$14,550 week

House on 12 Samoset in Oak Bluffs

House on 12 Samoset in Oak Bluffs

8 guests·4 beds·1 bath

$4,700 week

10 Seaview Avenue

10 Seaview Avenue

10 guests·5 beds·5 baths

$14,500 week

House on 19 Ocean Avenue in Oak Bluffs

House on 19 Ocean Avenue in Oak Bluffs

13 guests·7 beds·3 baths

$12,650 week

Newly Renovated Top to Bottom for Summer 2023

Newly Renovated Top to Bottom for Summer 2023

8 guests·4 beds·2 baths

$7,000 week

Downtown Oak Bluffs Walk to beach and Town

Downtown Oak Bluffs Walk to beach and Town

12 guests·6 beds·3 baths

$18,900 week

Charming Home on Nashawena park Steps to Inkwell

Charming Home on Nashawena park Steps to Inkwell

8 guests·4 beds·2 baths

$6,300 week

Contemporary Cape with open floor plan

Contemporary Cape with open floor plan

5 guests·2 beds·2 baths

$2,800 week

26 Bridle Path Road

26 Bridle Path Road

8 guests·3 beds·3.5 baths

$6,150 week

17 High Meadow Lane

17 High Meadow Lane

8 guests·4 beds·4.5 baths

$7,000 week

Newly Renovated Top to Bottom Meadow View Farms

Newly Renovated Top to Bottom Meadow View Farms

8 guests·4 beds·3 baths

$9,650 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

$9,600 week

26 Inca Road

26 Inca Road

8 guests·4 beds·3 baths

$9,350 week

Newly Renovated 8 Bedroom Home Steps to Beach

Newly Renovated 8 Bedroom Home Steps to Beach

16 guests·8 beds·3 baths

$10,950 week

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