House holiday rentals in Oak Bluffs

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Top-rated house rentals in Oak Bluffs

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Guest favourite

Home in Oak Bluffs

4.93 out of 5 average rating, 180 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and the outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, 6/21) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Guest favourite

Home in Edgartown

4.96 out of 5 average rating, 195 reviews

Brand new gorgeous 2 bedroom guest house.

This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

Guest favourite

Home in Oak Bluffs

4.78 out of 5 average rating, 225 reviews

Central location for your vacation

An apartment in a peaceful Raised Ranch! Your Martha’s Vineyard sanctuary. You are not able to get your car over? No problem, we can rent you one. Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proximity. 8 minutes away from ferry. Great for family vacation, Island explorations, work trips, hosting wedding guests, wellness retreat, or just a simple gateway, this home will compliment your Martha’s Vineyard experience.

Guest favourite

Home in Oak Bluffs

4.91 out of 5 average rating, 151 reviews

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Superhost

Home in Oak Bluffs

4.82 out of 5 average rating, 184 reviews

Waterview, Private, Walk to Beach, Mile to Town

Ask the host about ferry reservations if they appear to be sold out! Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing.

Guest favourite

Home in Oak Bluffs

4.97 out of 5 average rating, 233 reviews

Sweet little post and beam

A 700 sq ft post& beam guest house that sleeps 2 people. Open kitchen, living, dining area with full bath. Stairs lead to a full second story bedroom- a queen size bed, half bath, separate seating area. Private back patio and outdoor shower. Cozy off season cottage as well- radiant heat and AC. Central location to everything you want to see! Easy bike to town/beach. Very quiet and spacious. Everyone says "so much nicer in person than in the photos". Come see for yourself!

Guest favourite

Home in Oak Bluffs

4.92 out of 5 average rating, 225 reviews

Unique Luxury Yurt w/ Free kayaking

Step into this unique yurt house! As soon as you walk in, you'll be greeted with a one-of-a-kind experience, from the textured concrete floors to the large circular skylight. Every detail is carefully planned, and you'll have the opportunity to unwind in a spacious private yard. Spend your evenings stargazing, take advantage of complimentary paddling, participate in our scheduled chicken feedings, do yoga in the roomy loft, and revel in the splendor of your exclusive island yurt!

Guest favourite

Home in Oak Bluffs

4.94 out of 5 average rating, 150 reviews

Walk to Town, beach and amazing location 113A

Walk to all Oak Bluffs has to offer. 5-10 mins. to harbor, town, beach and dining. Amazing location! This three unit property offers a shared patio and deck space along with all the amenities. It is private and well appointed. 3 flat screen Televisions, wifi, appliances, tile and wood floors, granite counters, outdoor shower, gas grill and best of all it's all brand new. This 2 bedroom unit will provide you with an excellent home base to explore Oak Bluffs and Martha's Vineyard.

Guest favourite

Home in Edgartown

4.94 out of 5 average rating, 103 reviews

Walk To Town - Beautiful Edgartown Cottage

Walk to downtown Edgartown in minutes while staying in this newly renovated 2-story home in the heart of Upper Main St. The 3-bedroom, 2-bathroom house has been completely renovated, with brand new bathrooms, kitchen appliances, etc. You cannot beat the location of this home! You're a short 10 min walk from Edgartown's amazing restaurants & shops, in addition to a short bike ride to Katama's famous South Beach or Oak Bluff's State Beach. Both easily accessible via bike paths.

Guest favourite

Home in Oak Bluffs

5 out of 5 average rating, 121 reviews

The Oak Bluffs House - Walk to Beach & Town

Come stay in our home located in the ❣️ of Oak Bluffs •8 minute walk to public beach •5 minute walk to town •10 minute walk from Ferry to house, no car needed! Grocery store, Deli, Beer/Wine located just steps away from the house ! **Please Read ** Myself & my partner Max live on the property in a separate apartment on the bottom floor of the main house. We have our own entrance/exit and will NOT share any indoor spaces with you and your guests

Guest favourite

Home in Oak Bluffs

4.94 out of 5 average rating, 124 reviews

The Lighthouse

Visit The Lighthouse! A passive solar, Bright and spacious contemporary home located in beautiful East Chop. Home is nicely appointed with 2-3 large bedrooms, 2 full baths, soaking tub. Outdoor shower and private tree lined yard with deck. Walking distance to semi private beach, town and ferry. Come relax in the window seat with a book. Have a glass of wine on the deck. Soak up the sun at the beach. This home provides true comfort!

Guest favourite

Home in Edgartown

5 out of 5 average rating, 128 reviews

Close to Edgartown Village Center!

This 1800 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has 3 bedrooms and a loft and sleeps 9. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!