Holiday rentals with lake access in Oak Bluffs

Lakefront~Private Beach~Cape Cod family retreat~AC

*NEW*2025 renovated waterfront retreat with private sandy beach on John’s Pond’s calm lagoon - Cape Cod’s warm, swimmable freshwater escape. Perfect for families: kayak, swim, or relax out front. Enjoy the shaded pergola lounge, perfect for outdoor dining and unwinding. Just 15 mins to South Cape & Craigville Beach, 35 to iconic Mayflower. Features open layout, AC, fast WiFi, firepit, kid gear, and gourmet kitchen. Walk to trails, minutes to Mashpee Commons, golfing. Pond days+beach adventures.

Bright townhome with private ponds, pickleball

Beautifully furnished condo is centrally located in a park-like setting. This property is perfect for anyone who loves to explore the outdoors or just relax on the private deck at home. The Sengekontacket Assoc. in Oak Bluffs is a desirable waterfront community easily located off the bike path and on the bus route to town. Private amenities include a freshwater pond just 2-min walk down a quiet road; a large saltwater pond about a 10-min walk to a community dock; and tennis/pickleball courts.

Renovated pond view home near Lamberts Cove beach

Idyllic renovated farmhouse across from Seth's Pond and 0.6 miles from the infamous Lamberts Cove beach. Enjoy the views from the expansive enclosed front porch, play in the 2 acre yard and relax on the back patio with hardlined gas grill. Brand new kitchen, many recent renovations and a fully stocked home ensure a comfortable stay. Terrific mid-island location with easy access to nature hikes, State Road Restaurant, the Lamberts Cove Inn Restaurant, Up Island Cronigs (groceries) and more!

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

Ideal rental for families and friends! Two fully equipped kitchens, two fully furnished outdoor spaces, oversized deck with grill, washer/dryer, sleeps 10 (2 King, 2 Queen, Full over Full bunk beds) 3 living spaces, 2 pack and plays, 2 full baths, outdoor shower, large yard, and central a/c in every room! No ferry ticket? No car? No problem! This home is located close enough to the Vineyard Haven ferry for a quick bike ride or comfortable walk. Walking distance to trails and beach!

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

Swan nest escape

The Swan Nest Escape , nestled on a peninsula in a peaceful private neighborhood, is a charming retreat that offers access to the lake and features a large trail perfect for hiking and exploring nature. The house boasts comfortable accommodations, a fully equipped kitchen, and cozy living spaces designed for your comfort. Whether you’re seeking a romantic escape or a family vacation, our lakeside retreat provides the perfect setting for unforgettable memories.

Spectacular Beach- front home, includes linen

High beamed ceilings with sunny, spacious open kitchen and living room with floor to ceiling windows overlooking the lake. Oversized deck perfect for enjoying the BBQ and view with compfy rocking chairs. Minutes from quaint Falmouth village and Mashpee Commons. Planning a reunion or corporate outing? The house right next door is available for rental! Check out the following listing, "Stunning 4-bedroom Private Fresh Water Beach Front".

The quintessential MV home. Now booking for 2025!

The perfect home for a Vineyard getaway! Pirate's Cove is a charming 4-bed, 4-bath, 2500 sqft. young, Victorian home that sleeps 9. Amenities include new furniture, spacious bedrooms, a beach stone fireplace, air conditioning, a full finished basement with arcade machine, and amazing outdoor spaces on the front porch or in the backyard. The beach, harbor, and downtown are all just a pleasant 15-18 minute walk or short drive/bike ride away.

Surf and Turf Townhouse

Cozy 2 bdr, 1.5 bath townhouse perfect for a family of four looking for an action-packed Martha's Vineyard vacation. We are located right between Oak Bluffs and Edgartown offering easy access to all down-island towns and bike paths. The development provides access to dock on Sengekontacket (where you'll find our two kayaks) a freshwater pond, and tennis/pickle ball courts for you to enjoy.