Luxury Vacation Rentals

50 Pondview Dr

$6,050 week

Sun Filled Waterfront Home with Pond View

$5,550 week

709 Old County Road

$4,500 week

House on 2 Bold Meadow in Edgartown

$7,350 week

14 Quammox Rd

$4,250 week

103 School Street

$4,200 week

67 Hidden Village Rd

$17,200 week

27 Cormorant Circle

$8,250 week

27 Schoolhouse Rd

$5,000 week

Newly Renovated Top to Bottom for Summer 2023

$5,650 week

1 Essex Court EDG

$7,200 week

Cinderella Cottage in Oak Bluffs

$10,000 week

Renovated Victorian Cottage with a/c

$6,550 week

80 Midland Avenue

$5,500 week

Ocean Park Home with Water view 7 bedrooms

$12,750 week

13 Hubbard Lane

$4,650 week

2 Monahegan Ave.

$4,500 week

House on 3 Canonicus in Oak Bluffs

$7,750 week

29 Pine Street

$9,650 week

22 Grove Avenue

$4,450 week

Oak Bluffs Near Lagoon

$6,250 week

In Town Victorian with large back yard

$6,300 week

206 Spring Hill Road

$7,700 week

11 Katama Farm South

$7,750 week

12A Chasin Road

$4,500 week

175 Meetinghouse Way

$4,550 week

Newly Renovated Top to Bottom Meadow View Farms

$9,650 week

6B Caleb Pond Lane-Mizzen

$3,150 week

Copeland Gem Downtown Oak Bluffs

$8,200 week

Condo/Townhome on 21 Kennebec Avenue in Oak Bluffs

$3,700 week

House on 27 Ocean Avenue in Oak Bluffs

$13,900 week

Stand Along Condo with Pool and A/C

$2,600 week

189 Boulevard

$12,250 week

80 Bellevue Ave VH

$8,750 week

Classic Vineyard home with Guest House

$10,000 week

23 Pierce Lane

$8,300 week

34 Pilgrim Road

$4,900 week

Nashawena Park Steps from Inkwell Beach

$6,750 week

12 Chasin Rd

$16,000 week

House on 99 Marthas Road in Edgartown

$4,400 week

Renovated Victorian steps from Inkwell with a/c

$6,250 week

House on 12 Samoset in Oak Bluffs

$4,700 week

Newly Renovated 8 Bedroom Home Steps to Beach

$11,950 week

50 Edgartown Bay Rd.

$27,000 week

12 Chickawaukee Street

$2,500 week

3 Laura's Way

$4,550 week

6 Mariner Circle, Edgartown

$7,500 week

63 Tradewinds Rd.

$4,150 week

House on 35 West Farm Road in West Tisbury

$3,900 week

Beautiful Beachy Classic with Reverse Floor Plan

$4,800 week

15 Pinehurst ( REAR )

$4,850 week

7-A Katama Farm South

$5,550 week

Updated Salt Box Close to Town

$3,800 week

16 Zoll Rd.

$4,200 week

House on 24 Winemack in Oak Bluffs

$8,500 week

East Chop Cottage

$3,500 week

Lovely Home in Fresh Pond Estates

$7,250 week

64 Saddle Club Road

$3,850 week

Ocean Park 2 bedroom condo- waterview

$2,550 week

53A Ocean Avenue

$21,000 week

House on 19 Ocean Avenue in Oak Bluffs

$10,200 week

House on 50 Pond View Drive in Oak Bluffs

$6,300 week

16 Hillman Drive

$3,850 week

Seaside Cottage near Inklwell

$3,200 week

2 Schoolhouse Rd

$4,800 week

Vineyard Haven Oasis

$4,050 week

11 Town Lot Road

$5,000 week

10 Old Dunham Corner Way

$6,700 week

Victorian on Ocean Park in Oak Bluffs

$7,300 week

41 Smith Hollow

$6,500 week

26 Bridle Path Road

$5,750 week

2 Narraganssett Ave.

$14,900 week

19 Farms End Rd.

$9,800 week

10 Seaview Avenue

$14,600 week

73 Wing Road

$4,300 week

Endless Summer in East Chop

$5,100 week

3 Bedroom Campground Cottage

$3,500 week

8 Quammox Rd

$6,000 week

9 Mattakesett Way

$15,450 week

26 Inca Road

$8,600 week

9 Katama Farm South - Main House+Guest House

$39,150 week

5 Willow Run

$5,600 week

36 Park Ave

$4,100 week

Private lagoon beach

$4,000 week

7 Angevin Lane

$5,500 week

House on 10 Katama Drive in Edgartown

$3,300 week

House on 89 Ocean Avenue in Oak Bluffs

$15,000 week

5 Rock Ave

$4,350 week

House on 356 Winne Avenue in Oak Bluffs

$8,250 week

House on 9 Pequot Avenue in Oak Bluffs

$7,850 week

House on 6 West Meadow Lane in Oak Bluffs

$8,950 week

House on 15 Pequot in Oak Bluffs

$6,500 week

5 Angevin Lane

$5,800 week

3 Coral Ave

$3,000 week

House on 18 Swan Lane in Edgartown

$2,350 week

Renovated Victorian Home near Oak Bluffs Harbor

$6,500 week

Contemporary Cape with open floor plan

$2,800 week

4 Essex Court

$3,850 week

9 Pip'n Road

$2,750 week

Renovated Bayes Hill Home with Pool

$14,200 week

Seaview Condo in Oak Bluffs

$3,300 week

4 Caleb Pond Lane - "Rudder"

$3,400 week

17 High Meadow Lane

$7,000 week

MVCMA Campground cottage walk to beach

$4,300 week

6 Trails End

$8,650 week

37 Stoney Hill Lane

$3,800 week

Oak Bluffs Close to Town

$4,500 week

Charming Home on Nashawena park Steps to Inkwell

$7,000 week

Oak Bluffs Victorian less than block from Beach

$5,500 week

4 Canonicus Ave

$10,000 week

61 Edgartown Meadows Rd

$20,400 week

28 Pequot Ave.

$9,400 week

Charming Cottage in Great Oak Bluffs Location

$4,300 week

Oak Bluffs/Niantic Park

$7,050 week

10 Mayfield Way

$12,500 week

Charming Farmhouse with Central A/C Close to Town

$4,050 week

Summer Tradewinds

$7,000 week

17 Edgartown Bay Road

$11,900 week

380 Seaview Ave

$9,000 week

Lower Makonikey with Beach Access

$6,350 week