luxury house for rent Vineyard Haven, United States

Set on just under an acre of beautiful, private, manicured grounds, this furnished five-bedroom, four-bath contemporary home offers an exceptional rental opportunity just minutes from the village of Woods Hole. Featuring soaring ceilings throughout, the home boasts a generous, open, light-filled floor plan designed for comfortable coastal living. The chef's kitchen is outfitted with a Viking range, Sub-Zero refrigerator, and ample space for entertaining. A large, elegant private patio with table and chairs is just off the kitchen for al fresco dinning. With its spacious interiors, modern amenities, and serene private setting, this exceptional property is an ideal Woods Hole retreat. The winter/off season rental rate is $5,000 per month plus utilities. The Summer (July & August) weekly rate is $6,500 per week including utilities. Sept. & June: $4,000 per week utilities included. Please reach out with your rental needs. Rental Terms: Other / Short Term - Monthly: $5,000

Escape to the tranquil embrace of this charming two-bedroom guest cottage by the sea! Nestled along the sun-kissed shores, this idyllic retreat promises an unforgettable summer getaway. Wake up to the gentle lullaby of waves, and savor your morning coffee with breathtaking panoramic views of the sparkling sea. Step directly onto the sandy shores from your doorstep, for sun-soaked days of relaxation and access to two private beaches. Wash off the sand in the outdoor shower. Eat-in kitchen with top-of-the-line appliance package. Spacious family and living rooms. With a pull-out sleeper sofa and several beds, this can easily sleep 8 comfortably. Dine in style on two private decks, enjoying fresh seafood and spectacular sunsets, creating cherished memories with loved ones. Discover nearby biking trails, 6 bicycles and helmets included, charming coastal towns, and a plethora of water-based activities for adventurers of all ages. Just a short drive from town, you'll have easy access to restaurants, shops, and local attractions, making your stay even more enjoyable. Book Now for Your Picture-Perfect Summer Escape! Rental Terms: Summer Weekly: $7,500 Per Week

Exclusive oceanfront on Penzance Point - A Classic Cape Cod Summer Awaits. Nestled in the private enclave of Penzance Point, this nostalgic Cape offers a rare blend of seclusion, charm, and sweeping water views. This spacious oceanfront haven hosts 5 bedrooms and 3.5 baths, with stunning vistas from every room and an expansive deck that wraps the home, drawing you into the natural beauty of Buzzards Bay and Woods Hole Harbor. Watch the steady rhythm of boat traffic by day and toast unforgettable sunsets by night. The sun-drenched living room opens effortlessly onto the deck, creating the perfect flow for summer entertaining and relaxed coastal living. A well-equipped kitchen and pantry make dining easy, whether you're whipping up a simple lunch or a seafood feast. Let the sound of rolling waves lull you to sleep, and wake to sea breezes and salt air. Just minutes away, discover the charm of Woods Hole Village and downtown Falmouth with its laid-back eateries, boutique shopping, and maritime allure. Your Cape Cod summer starts here. Rental Terms: Summer Weekly: $7,000 Per Week

There are places that remind you of a different time. Where mornings begin with coffee on the porch. Children spend the day barefoot on the lawn, and evenings end with the sun disappearing into the water while everyone lingers just a little longer. Set on four private waterfront acres in Woods Hole, 122 Gansett Road captures the spirit of old Cape Cod--unhurried, welcoming, and deeply connected to the sea. Thoughtfully modernized, the home preserves its timeless character while offering every comfort expected today. A new chef's kitchen, updated baths, six bedrooms, and generous gathering spaces make it ideal for family vacations that become lifelong traditions. Outside, the days unfold naturally. Swim in the heated pool, relax in the spa, challenge friends to a game of pickleball, wander down to the private association beach, or simply settle into an Adirondack chair and watch one of the Cape's unforgettable sunsets. Just minutes from Woods Hole Village, you'll find charming restaurants, ferry service to Martha's Vineyard, scenic walking trails, and quiet beaches that have drawn generations here. Availability last week in July, August, September and October. $15,500 per week. Rental Terms: Summer Weekly: $15,500 Per Week

Exclusive off season waterfront rental in Falmouth, available until June 1, 2026. Luxurious living in this exceptional 5-bedroom, 4-bath waterfront residence with deep-water dock and sweeping views of the saltwater harbor. Wake each morning to breathtaking sunrises, coffee in hand on your private covered porch, as boats glide by and the harbor comes to life. Designed for effortless luxury and relaxation, the home features upscale interiors that blend refined coastal charm with modern elegance. Sun-filled, spacious living areas invite gathering and entertaining, while the gourmet kitchen is perfectly appointed for culinary creations and hosting family and friends. Five serene bedrooms and four spa-inspired baths provide comfort and privacy, including three ensuite bedrooms with stunning water views. Every detail has been thoughtfully curated to create a tranquil, elevated retreat. Enjoy strolls on the private sandy association beach just moments away, explore the harbor by boat from your own dock, or venture into downtown Falmouth, the ferry to Martha's Vineyard, and local shopping and dining—all just minutes from your door. Rental Terms: Other / Short Term - Per Month Off Season: $12,000

Experience the pinnacle of Vineyard living at this extraordinarily updated 9-acre estate, nestled within the exclusive Herring Creek Farm Association. Set along the tranquil shores of Edgartown Great Pond, this 10,000+ square foot residence offers unmatched privacy, refined elegance, and direct access to pristine beaches. The main level showcases timeless design with a grand foyer, sweeping staircase, sunlit formal dining room, gourmet chef’s kitchen, and multiple living areas designed for both relaxation and entertaining. A separate guest wing ensures comfort and privacy for visitors. French doors open to a resort-style outdoor oasis with a heated pool, expansive bluestone patio, and a covered porch with fireplace for elegant al fresco dining. Upstairs, five spacious bedrooms include an expansive primary suite featuring a private balcony with water views, a large walk-in closet, private office, and spa-like bath. Spend your days lounging poolside, enjoying sunset views over the Pond, or following a short private path to your own sandy beach. The Association’s exclusive Atlantic beach is a short golf cart ride away. Framed by beautifully landscaped grounds and open farm fields, this exceptional property offers total seclusion just minutes from downtown Edgartown.

A Cape Cod Quintessential summer retreat with spectacular views of the Ocean and saltmarsh. A wonderful home to create those Cape Cod Memories. This home is located in the Sippewissett area in desirable West Falmouth. The private association beach is steps away where you can swim, sun, kayak and paddle board. With west facing views you will be mesmerized by the amazing sunsets of West Falmouth. This home has a terrific floor plan for large families with numerous gathering areas, and private sitting areas There are views from nearly every room of the home. With close proximity to downtown Falmouth and Woods Hole, you will be able to enjoy the shopping, restaurants, and access the ferry boat to Martha’s Vineyard. No Availability left for 2021. Rental Terms: Summer Weekly: $3,900 Per Week

Escape to this perfect waterfront Cape Cod summer rental getaway that has been newly renovated. Enjoy beautiful water views and a private dock with direct access to Vineyard Sound—no bridges required—this home is a boater's paradise. Dock your boat at the deep-water dock and soak in breathtaking sunsets from the west-facing deck. Not a boater, use the dock to launch a kayak or a float. The main level features a spacious primary suite, while the open-concept living area and modern kitchen create a seamless flow for relaxation and entertainment. Upstairs, you'll find two generous bedrooms and a beautifully updated tiled bath. The lower-level walk-out offers extra space for guests, ensuring comfort for all. Enjoy sun-soaked days at the association beach, just a short stroll away, or rinse off in the outdoor shower after a day on the water. Stay cool with split AC units throughout the home. Whether you're seeking adventure or serenity, this wonderful rental is your gateway to coastal living. Ready to set sail on a dream vacation? Book your stay today! Rental Terms: Summer Weekly: $6,000 Per Week

Winter rental. Welcome to this beautifully renovated ranch in East Falmouth, the perfect Cape Cod getaway for families and friends. Thoughtfully updated throughout, the home features all-new furnishings, new appliances, and a charming deck for enjoying your morning coffee or evening relaxation. Sleeping up to 8 guests, this inviting home offers a large private backyard with plenty of room for outdoor fun, along with a classic Cape Cod outdoor shower to rinse off after a day at the beach. Conveniently located just minutes from Mashpee Commons, you'll enjoy easy access to shopping, dining, beaches, golf, and everything that makes Cape Cod a favorite vacation destination. Whether you're spending the day exploring Falmouth's beautiful coastline, enjoying time with family and friends in the backyard, or unwinding after a day of adventure, this delightful home is the perfect place to create lasting Cape Cod memories Rental Terms: Summer Weekly: $3,200 Per Week

Availability this summer at this beachfront home steps from Old Silver Beach. The house is located in Old Silver Beach Estates on the private, expansive white sandy beach. Enjoy the ocean breeze, and the glorious sunsets. The home is meticulously maintained, with room for eight people (4 bedrooms), and 3 ½ baths. Additionally, there is a spacious family room, kitchen with large dining area and den. The yard has plenty of room for your outdoor activities. This rare opportunity awaits. Amenities: Outdoor shower, A/C, Internet, linens, towels provided. Two week stay is $30,000 Rental Terms: Summer Weekly: $15,000 Per Week

Available for two weeks summer rental, 76 Santuit Road is perfectly positioned just one house from the pristine sands of Old Silver Beach. Nestled within the exclusive Old Silver Beach Estates, this property offers convenient access to a private, expansive stretch of white sandy beach, where you can indulge in the soothing ocean breeze and witness breathtaking sunsets on Buzzard Bay. This home is designed to accommodate 7 guests comfortably, featuring 4 bedrooms and 3 bathrooms. The spacious family room is perfect for relaxation, with two bay windows looking out towards the water. A cozy den provides an ideal retreat for quiet moments or reading. Outside, the expansive deck offers ample space for soaking up the sun, hosting a beachside barbecue, or simply enjoying the serene views of Buzzard Bay. Additional amenities include an outdoor shower for refreshing rinses after a day at the beach, air conditioning for ultimate comfort, high-speed internet, and complimentary linens and towels for your convenience. Embrace the ultimate beachside lifestyle and create unforgettable memories at this stunning property. Rental Terms: Summer Weekly: $13,000 Per Week

Located in the lovely seaside Cape Cod village of Cotuit, this renovated, impeccable home features three bedrooms, two and a half baths and new laundry. Entertain in the sun filled brand new eat-in kitchen and large living room with fireplace. Enjoy one floor living with en-suite primary bedroom with sliders out to the deck and two other bedrooms and an office. The deck runs the entire length of the rear of the home and overlooks the private acre yard. Enjoy the convenient location close to shopping, restaurants, town docks and Nantucket Sound beaches. The popular Cotuit Kettleers baseball team games entertain folks of all ages just a short distance away. Other local activities include Cahoon Museum, Cotuit Center for the Arts and Kettle-Ho restaurant. What a wonderful place to enjoy your warm summer days and breezy nights. The pricing includes $800 per night for Memorial Day weekend, $5000 for June 1-27 and $6000 for June 27-July 31. Please contact agent for any other dates. Rental Terms: Summer Weekly: $5,000 Per Week

Spend your Cape Cod vacation in this magnificent property located on Garrison Lane in Osterville. Enjoy your days relaxing by the private pool surrounded by professionally landscaped grounds. Amenities: heated pool, central air, linens and towels provided, high-speed internet and cable tv, outdoor shower, spacious patio & screened-in porch. Sleeps: 8 four queen beds. Barnstable beach pass included. No smoking. Rental price does not include state, regional, local, or community taxes or fees. Rental Terms: Summer Weekly: $15,000 Per Week

Welcome to 147 Scudder Road in Osterville! This charming rental offers the perfect blend of convenience and relaxation, just a short stroll away from Main Street and the pristine shores of Dowses Beach. With its ideal location and cozy atmosphere, this is the perfect retreat for enjoying all Osterville offers. Amenities: Central Air, Wireless Internet, Cable TV, Outdoor Shower, Barnstable Beach Pass. Sleep: 5, two queens and one full. The rental price does not include state, regional, local, or community taxes or fees. Rental Terms: Summer Weekly: $4,800 Per Week

This home is located in the heart of Wianno, only minutes to Dowses Beach and the village of Osterville. The first floor offers an open floorplan including living room, dining, kitchen, half bath, and a large master bedroom with ensuite bathroom. The second floor has three additional bedrooms and one large full bath. Fabulous outdoor space for entertaining. Amenities: Central Air, Outside Shower, Wifi, Cable TV, Linens & Towels Included. Barnstable Beach Pass Provided. No Smoking & Pets. Rental price does not include state, regional, local or community taxes or fees. Rental Terms: Summer Weekly: $7,500 Per Week

Welcome to your ideal summer retreat at 360 Main St, Osterville. This exceptional property offers everything you need for a luxurious and relaxing stay. Enjoy the stunning outdoor amenities, including a sparkling pool, cozy fire pit, fully-equipped outdoor kitchen, and multiple seating areas perfect for entertaining. For sports enthusiasts, a private pickleball court awaits. Inside, the home boasts four beautifully appointed bedrooms, three full baths, and two half baths. The fabulous kitchen is a chef’s dream, and multiple living spaces provide plenty of room for everyone to unwind. Central air conditioning ensures comfort throughout your stay, and an office space offers a quiet retreat for work or reading. The property also features an outside shower for rinsing off after a day at the beach. A Barnstable Beach Pass is included, giving you access to the beautiful Dowses Beach. Located in the charming village of Osterville, you’ll be just minutes away from delightful restaurants, boutique shops, and everything you need for a perfect summer getaway. Experience the best of Cape Cod living at 360 Main St. Your summer escape awaits. No smoking. Rental price does not include state, regional, local, or community taxes or fees. Rental Terms: Summer Weekly: $16,000 Per Week