Holiday rentals with a patio in Oak Bluffs

Updated cottage/ ocean views

Location! Location! Location! Leave your worries and car behind, this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated 3 bdr and1.5 baths, offering the perfect combination of cottage charm and modern updates. Enjoy ocean views from our wrap around porch and owner's suite enclosed balcony. Large backyard allows for private outdoor enjoyment. Prime location for enjoying all Oak Bluffs has to offer.

The Lobster Pot: Lake Tashmoo, beachfront

Welcome to The Lobster Pot, your cozy beach cottage on the tranquil shores of Martha's Vineyard. Nestled on the waterfront, this charming retreat is ideal for a paradise getaway. Wake up to the soothing sound of waves, enjoy panoramic ocean views from your private deck, and relax in the gentle sea breeze. With its inviting décor and relaxed ambiance, The Lobster Pot offers a perfect blend of relaxation and adventure. Savor fresh seafood, stroll along the sandy beach, or enjoy stunning sunsets.

Charming Oak Bluffs Retreat

Escape to this peaceful Oak Bluffs retreat featuring 4 bedrooms, 2 full modern baths, and an updated kitchen. The finished basement has two overflow rooms with beds (bedrooms 5 and 6 in the photos), a half bathroom, and a media and gaming area, offering plenty of space to unwind. The private outdoor yard offers a trellised deck, grill, kid-friendly tree platform and ample parking. This home is perfect for both relaxation and socializing and is centrally located between the island’s down towns.

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! Transferable FERRY TIX for 7/3-7/10, 7/17-7/24, 7/24-7/31, 8/21-8/28 Rent bikes or take island buses or taxis/Ubers.

Quaint Roomy Ranch

Enter this light filled and airy home with soaring cedar lined ceilings and an entire southern facing wall of windows. This surprisingly spacious home has enough room for the whole family and more. Kids will love having the bunk room to themselves while parents can enjoy the rest of the living area in peace. Located in a quiet neighborhood, this is a perfect family retreat. Enjoy the expansive deck while you grill lunch or dinner and finish up the evening with s'mores by the fire pit.

Pinkletink Plantation

Your family will be close to everything when you stay at this centrally-located place. Less than a mile from the heart of Oak Bluffs and Circuit Ave., where you'll find all the famous restaurants, harbor & night life. A half mile from Eastville Beach (fabulous sunsets). Take a morning stroll around "the chop"-East Chop & walk or run a 5K. Less than 2.5 miles from Farm Neck Golf Club- & 2.5 miles to State Beach. It has a well equipped kitchen, laundry, outside shower, & back yard!

Location Location Location! Beach, Bike, Ferry

STEPS to beach, bike path, trails, restaurants, shopping, bus to MV Ferry Gorgeous studio/in law apartment, private entry, own parking + patio Open plan living/sleeping area + en suite bathroom Queen bed + queen sleeper sofa: sleeps max 4 Fresh linens, towels, personal care products, first aid, hairdryer, iron Mini kitchen w fridge, air fryer, microwave, toaster oven, dishwasher, cutlery, crockery, coffee maker Our famous home baked goodies! Coffee/tea/milk/sparkling water provided

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!

Lake Street Haven- Sleeps 8 and short walk to town

Lake Street Haven — Walk to Town, Sleeps 8 | 4BR, 3BA + Outdoor Shower & Firepit Escape to Lake Street Haven, a beautifully decorated 4-bedroom, 3-bathroom private home located in the heart of Vineyard Haven. Just a short walk to town, Owen Park Beach, and the ferry, this coastal retreat blends charm, comfort, and convenience for your Martha’s Vineyard getaway. Whether you’re here for a family vacation, girls’ getaway, or island retreat, Lake Haven offers the perfect home base.

Entire home newly renovated in August 2025

Step into your serene island getaway at 5 Pine Tree Lane, with 4 bedrooms (4 beds) and nestled in the heart of beautiful Martha’s Vineyard. This brand-new home blends modern comfort with Vineyard charm perfect for families, groups of friends, or couples looking for a relaxing escape. Walking distance to a neighborhood beach, year round ferry access (1mi) and shopping. This home was thoughtfully designed and offers everything you need for a peaceful and memorable experience.

Martha's Vineyard Cottage: Walk to Town and Beach

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.