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.

House on 12 Samoset in Oak Bluffs

House on 12 Samoset in Oak Bluffs

8 guests·4 beds·1 bath

$4,700 week

2 Narraganssett Ave.

2 Narraganssett Ave.

22 guests·9 beds·4 baths

$15,150 week

63 Tradewinds Rd.

63 Tradewinds Rd.

4 guests·2 beds·2 baths

$4,250 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

$6,300 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

86 Washington Ave

86 Washington Ave

5 guests·2 beds·2 baths

$2,800 week

Seaside Cottage near Inklwell

Seaside Cottage near Inklwell

2 guests·1 bed·1 bath

$3,200 week

Victorian on Ocean Park in Oak Bluffs

Victorian on Ocean Park in Oak Bluffs

9 guests·5 beds·3 baths

$7,300 week

Sun Filled Waterfront Home with Pond View

Sun Filled Waterfront Home with Pond View

8 guests·4 beds·2 baths

$5,550 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

MVCMA Campground cottage walk to beach

MVCMA Campground cottage walk to beach

8 guests·4 beds·2 baths

$4,300 week

50 Pondview Dr

50 Pondview Dr

6 guests·3 beds·2.5 baths

$6,100 week

380 Seaview Ave

380 Seaview Ave

12 guests·5 beds·4 baths

$9,000 week

12 Chickawaukee Street

12 Chickawaukee Street

4 guests·2 beds·1.5 baths

$2,500 week

13 Hubbard Lane

13 Hubbard Lane

6 guests·3 beds·2 baths

$4,750 week

26 Inca Road

26 Inca Road

8 guests·4 beds·3 baths

$8,800 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

2 Monahegan Ave.

2 Monahegan Ave.

8 guests·4 beds·2 baths

$4,500 week

3 Coral Ave

3 Coral Ave

6 guests·3 beds·2.5 baths

$3,100 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

$9,200 week

Cinderella Cottage in Oak Bluffs

Cinderella Cottage in Oak Bluffs

8 guests·4 beds·2 baths

$8,400 week

East Chop Cottage

East Chop Cottage

7 guests·3 beds·2 baths

$3,500 week

Nashawena Park Steps from Inkwell Beach

Nashawena Park Steps from Inkwell Beach

8 guests·4 beds·2 baths

$6,800 week

5 Rock Ave

5 Rock Ave

8 guests·4 beds·2 baths

$4,400 week

Charming Cottage in Great Oak Bluffs Location

Charming Cottage in Great Oak Bluffs Location

6 guests·2 beds·3 baths

$4,600 week

73 Wing Road

73 Wing Road

6 guests·3 beds·2 baths

$4,250 week

Beautiful Beachy Classic with Reverse Floor Plan

Beautiful Beachy Classic with Reverse Floor Plan

8 guests·4 beds·2 baths

$5,050 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

$4,050 week

Contemporary Cape with open floor plan

Contemporary Cape with open floor plan

5 guests·2 beds·2 baths

$2,800 week

Newly Renovated Top to Bottom for Summer 2023

Newly Renovated Top to Bottom for Summer 2023

8 guests·4 beds·2 baths

$6,150 week

House on 27 Ocean Avenue in Oak Bluffs

House on 27 Ocean Avenue in Oak Bluffs

10 guests·6 beds·3 baths

$14,650 week

Renovated Bayes Hill Home with Pool

Renovated Bayes Hill Home with Pool

8 guests·4 beds·2 baths

$14,500 week

Endless Summer in East Chop

Endless Summer in East Chop

8 guests·3 beds·2 baths

$4,900 week

3 Bedroom Campground Cottage

3 Bedroom Campground Cottage

6 guests·3 beds·2 baths

$3,500 week

In Town Victorian with large back yard

In Town Victorian with large back yard

10 guests·5 beds·2 baths

$6,300 week

House on 24 Winemack in Oak Bluffs

House on 24 Winemack in Oak Bluffs

6 guests·3 beds·2 baths

$8,500 week

Classic Vineyard home with Guest House

Classic Vineyard home with Guest House

8 guests·4 beds·3 baths

$8,000 week

53A Ocean Avenue

53A Ocean Avenue

14 guests·7 beds·4 baths

$21,000 week

Copeland Gem Downtown Oak Bluffs

Copeland Gem Downtown Oak Bluffs

10 guests·5 beds·2 baths

$8,200 week

Renovated Victorian Home near Oak Bluffs Harbor

Renovated Victorian Home near Oak Bluffs Harbor

10 guests·6 beds·2 baths

$6,500 week

Summer Tradewinds

Summer Tradewinds

10 guests·5 beds·3 baths

$6,900 week

26 Bridle Path Road

26 Bridle Path Road

8 guests·3 beds·3.5 baths

$5,900 week

House on 3 Canonicus in Oak Bluffs

House on 3 Canonicus in Oak Bluffs

8 guests·4 beds·1 bath

$7,200 week

Newly Renovated 8 Bedroom Home Steps to Beach

Newly Renovated 8 Bedroom Home Steps to Beach

16 guests·8 beds·3 baths

$11,400 week

Ocean Park 2 bedroom condo- waterview

Ocean Park 2 bedroom condo- waterview

4 guests·2 beds·1 bath

$2,500 week

House on 356 Winne Avenue in Oak Bluffs

House on 356 Winne Avenue in Oak Bluffs

6 guests·3 beds·3 baths

$8,250 week

Oak Bluffs Charm

Oak Bluffs Charm

6 guests·3 beds·2 baths

$3,000 week

Oak Bluffs Close to Town

Oak Bluffs Close to Town

6 guests·3 beds·2 baths

$3,400 week

House on 9 Pequot Avenue in Oak Bluffs

House on 9 Pequot Avenue in Oak Bluffs

8 guests·4 beds·2 baths

$6,750 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

House on 15 Pequot in Oak Bluffs

House on 15 Pequot in Oak Bluffs

10 guests·5 beds·3 baths

$7,000 week

Oak Bluffs/Niantic Park

Oak Bluffs/Niantic Park

8 guests·4 beds·2 baths

$6,650 week

In Town 3 Bedroom Cape Walk to everything!

In Town 3 Bedroom Cape Walk to everything!

6 guests·3 beds·1 bath

$3,850 week

10 Seaview Avenue

10 Seaview Avenue

10 guests·5 beds·5 baths

$14,850 week

Seaview Condo in Oak Bluffs

Seaview Condo in Oak Bluffs

4 guests·2 beds·2 baths

$3,300 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

Lovely Home in Fresh Pond Estates

Lovely Home in Fresh Pond Estates

8 guests·4 beds·3 baths

$6,550 week

17 High Meadow Lane

17 High Meadow Lane

8 guests·4 beds·4.5 baths

$7,000 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

Private lagoon beach

Private lagoon beach

7 guests·3 beds·2 baths

$4,000 week

Oak Bluffs Near Lagoon

Oak Bluffs Near Lagoon

6 guests·3 beds·2 baths

$4,300 week

Renovated Victorian Cottage with a/c

Renovated Victorian Cottage with a/c

6 guests·3 beds·2 baths

$6,400 week

House on 19 Ocean Avenue in Oak Bluffs

House on 19 Ocean Avenue in Oak Bluffs

13 guests·7 beds·3 baths

$12,250 week

Updated Salt Box Close to Town

Updated Salt Box Close to Town

6 guests·3 beds·2 baths

$3,900 week

Ocean Park Home with Water view 7 bedrooms

Ocean Park Home with Water view 7 bedrooms

14 guests·7 beds·4 baths

$13,150 week

28 Pequot Ave.

28 Pequot Ave.

10 guests·5 beds·2.5 baths

$9,400 week

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