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Piece of Katama Heaven near South Beach,Edgartown

Large house with 2 masters suites. Modeled after HGTV Dream House 2015. Large piece of property near ocean and Edgartown center. Clean, sunny with a large custom table on screened in porch which is attached to gourmet kitchen- great area to watch the bunnies, turkeys, deer. Masters have own TVs and one has private deck. Outdoor shower, outdoor kitwo living rooms, each has a TV. Katama is the most requested area to rent - close to Oak Bluffs and Vineyard Haven. Bikes available as is bike trailer

Modern Marvel in Woods Hole - Walk to town & ferry

Beautiful modern masterpiece down a quiet street with quick access to Woods Hole, Shining Sea Bikeway, and the Vineyard ferry. This architecturally significant house was designed by the renowned postmodern architect Charles Moore and built in 1969. An addition providing ample entertaining space - including a dining room, den, loft, and roof deck - was completed in 2021, along with top to bottom refinishing of all rooms. This house has mid-century charm in spades with all the modern conveniences.

The Perfect Family Retreat - New Home in VH

This brand new, recently built 4-bedroom, 3-bathroom home offers the perfect blend of comfort and convenience, situated within walking distance of downtown Vineyard Haven and the Steamship Authority. Step outside into the spacious yard, where you'll find a grill and outdoor dining area. Rejuvenate your senses in the outdoor shower, ideal for refreshing after a day of exploring the island's treasures. The property is also equipped with an E/V charger. Private Deep Water Dock Available as well!

Cheerful, Romantic Retreat for Two

A fully-furnished one-bedroom guest apartment (600sq ft) on two levels attached to our house. Separate entrance. Ensuite-shower and complete kitchen. 3 miles from downtown Edgartown, 5 miles to State Beach. In a peaceful neighborhood abutting miles of state forest trails. WiFi, workspace, laundry, smart TV and air conditioning. It can be difficult to secure a ferry res for your car when planning last minute trips in summer. May we suggest renting a bicycle or use a taxi/ride-share service.

Newly Renovated Cape, walk to Osterville

Welcome to Pond Street and your cape cod summer vacation. This fully renovated single family home is situated in the heart of Osterville on a large half acre lot. The home features an open floor plan with all new finishes inside, central AC and a newly landscaped outdoor entertaining area and putting green! This is a kid-friendly home complete with necessities for infants and children. Just a short walk to downtown Osterville offering the area's best beaches, dining, shops, and much more!

The Pearl: Lovely cottage, close to VH town/ferry

THE PEARL is a lovely retreat for up to two couples. Come relax in this quaint cottage, close to town, beaches and ferry. Located in a quiet, residential neighborhood. Large yard and plenty of off-street parking. Walk to nearby beaches and restaurants. FRIDAY to FRIDAY, weekly rentals only, June 27 - September 5. Significant DISCOUNTS for longer stays. Make an INQUIRY! Can't get your car over? This location can work for you! Rent bikes or take advantage of island buses or taxis/Ubers.

Cape Summer Family Retreat+ FirePit +OutdoorShower

Brand NEW HOME with seasoned hosts looking forward to your 5 star stay! Bring your family and friends to East Falmouth: ★ EV Charger ★ Game Room Haven (Ping pong, pool, shuffle board) + 85"TV ★ Outdoor Shower/Grill /Firepit ★ 10 min from 6+ beaches (Old/Silver beach) ★ 10 min to Mashpee Commons ★ 12 min to Falmouth’s Main St ★ 4 min from Coonamessett Farms ★ Private deck & outdoor dining table ★ Spacious fenced-in backyard (pet-friendly) ★ Deep pond fishing spot 10 min walk

Quiet West Tisbury 2 BDR Suite

We are inviting you to stay in the two bedroom, full bath 1st floor wing of our home which has its own private entrance and hot tub. On 3 acres in a quiet area in the center of the island, the house is in a wooded area that leads to numerous island trails. The town of West Tisbury is 1.5 miles away with a bakery, general store, library and church. Included with your stay is access to the town’s private beach, Lamberts Cove which is an island favorite and only 2 miles away.

2 Acre Waterfront Oasis Overlooking Waquoit Bay

Perched over sparkling Waquoit Bay, this stylishly renovated waterfront home features a 38’ Living and dinning room. Open plan with large picture windows for watching boats, wildlife, and extraordinary sunsets. Entertain while cooking for the whole family in the large luxury kitchen surrounded by barstool seating. Walk down the path to the bay to swim, fish, paddle board, or kayak. Enjoy magnificent sunsets while grilling, sitting around the fire pit or enjoying the hot tub.

Simone by the Sea

Come enjoy this beautifully designed, totally renovated home. This 3 level home features an open floor plan with a fully stocked kitchen, new appliances, Central HVAC, rooftop deck, EV charging station and much more. Spacious 3 bedrooms, 2 bathrooms is within walking distance to the heart of Downtown Oak Bluffs, OB Ferry and beaches. Comforts of home as well as all the beach accessories to enjoy your day in the sand.

Koi Suite: Covered deck, koi pond & free Kayaks!

Open, spacious and sunny vacation home, perfect for families. The property is on safe and private road surrounded by lush trees, lovely gardens and your very own koi pond. Private residence with full kitchen, beach chairs, beach bag/cooler and beach towels provided, along with free kayaking/paddle boarding and chickens on the property that you can feed! One mile from town and a 10 minute bike ride to the beach.

Modern & Spacious Edgartown Home with Pool

Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or stay at home and go for a swim in your own backyard. There is plenty of dining room & deck space to entertain. The bike path and bus shuttle are at the end of the road (a two minute walk away). Downtown Edgartown is less than two miles away for you to enjoy shopping and multiple dining choices.