TOP 30 Summer vacation rentals in Oak Bluffs, Massachusetts

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The Flying Seahorse offers charming summer cottage rentals in the picturesque town of Oak Bluffs, Massachusetts. Nestled at 8 Pennacook Avenue, our real estate and travel agency specializes in providing cozy accommodations for your summer getaway. With a prime location near the beach and local attractions, our cottages are perfect for families, couples, and solo travelers looking to relax and unwind. Book your stay with The Flying Seahorse for a memorable summer retreat on Martha's Vineyard.

All Star Martha's Vineyard Bike Rentals is your go-to destination for all your biking needs on the beautiful island of Martha's Vineyard. Conveniently located at 5 Oak Bluffs Avenue in Oak Bluffs, Massachusetts, our store offers a wide selection of high-quality bicycles for rent. Whether you're looking to explore the scenic trails or cruise along the picturesque coastline, we have the perfect bike for you. Our friendly and knowledgeable staff are here to help you choose the right bike and provide any assistance you may need. So come visit us at All Star Martha's Vineyard Bike Rentals and start your biking adventure today!

The Island Inn on Martha's Vineyard by Vacasa is a charming vacation destination located at 30 Island Inn Road in Oak Bluffs, Massachusetts, United States. This condominium resort sits on five acres of beautiful land and is open year-round, offering a perfect New England getaway. The Island Inn on Martha's Vineyard offers a variety of vacation rentals to suit every traveler's needs. Whether you're looking for a cozy retreat for two or a spacious home for the whole family, there is something for everyone. The property boasts 51 vacation rentals with internet access, allowing guests to stay connected during their stay.

Isabelle's Beach House is a charming lodging institution located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, United States. Our family-owned B&B was founded on the principles of hospitality, warmth, and community, making every guest feel like part of our inclusive community. As a gift of Island Joy, we offer 2024 Gift Certificates for a memorable stay at our beach house. Our newly opened boutique in Oak Bluffs, launched in August 2023, serves as a platform for mission-driven businesses and conscious consumers. Summer boutique hours are from May to October, or shop online 24/7 at www.jubileemv.com.

Seacoast Properties is a premier real estate agency and travel agency located at 31 North Summer Street in Edgartown, Massachusetts. Specializing in Martha's Vineyard properties, we offer a wide selection of vacation rentals and homes for sale, from charming cottages to luxurious estates. Our experienced agents are experts in the local market and are dedicated to helping you maximize your sales and rental profits. Martha's Vineyard is a unique resort island known for its rich history, arts, music, and culture. With outstanding restaurants, shops, galleries, and beautiful beaches, there is something for everyone to enjoy. Whether you are looking to buy, sell, or rent a property on the island, Seacoast Properties is here to make your Martha's Vineyard dreams a reality.

Martha's Vineyard Real Estate, located at 63 Winter Street in Edgartown, Massachusetts, is a reputable real estate agency with a rich history dating back to 1972. Originally a peaceful retreat for families to escape to, Martha's Vineyard has since evolved into a bustling community with diverse real estate transactions. Despite the changes over the years, Martha's Vineyard Real Estate still prides itself on building personal connections with clients that last long after the transaction is complete. The agency's agents have a strong working knowledge of the island's real estate market and are committed to providing individual attention to each client.

Ocean Park is a picturesque and popular tourist attraction located at 2 Seaview Avenue in Oak Bluffs, Massachusetts, United States. This charming park offers stunning views of the Atlantic Ocean and features lush greenery, walking paths, and a gazebo perfect for relaxing and enjoying the ocean breeze. Visitors can also enjoy picnics, sunbathing, and various events and performances held at the park throughout the year. Whether you're looking for a peaceful retreat or a fun day out with family and friends, Ocean Park is the perfect destination for nature lovers and outdoor enthusiasts alike.

The YMCA of Martha's Vineyard Ice Arena is a popular tourist attraction located at 91 Edgartown Road in Oak Bluffs, Massachusetts, United States. This state-of-the-art facility offers visitors of all ages the opportunity to enjoy ice skating in a fun and safe environment. Whether you're a beginner or an experienced skater, the YMCA of Martha's Vineyard Ice Arena has something for everyone. Come and experience the thrill of gliding across the ice at this iconic destination on Martha's Vineyard.

Vineyard Family Tennis is a premier tennis institution located at 618 Barnes Road in Oak Bluffs, Massachusetts. Our facility offers top-notch tennis instruction for players of all ages and skill levels. Whether you're a beginner looking to learn the basics or an experienced player striving to improve your game, our experienced coaches are here to help you reach your full potential. In addition to tennis lessons, we also offer fitness programs and health classes to promote overall wellness. Come join our vibrant tennis community and experience the thrill of the game in a welcoming and supportive environment.

Inkwell Beach, located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, is a picturesque natural feature that offers visitors a serene and beautiful setting for relaxation and recreation. This sandy beach is known for its clear waters, gentle waves, and stunning views of the Atlantic Ocean. Whether you're looking to sunbathe, swim, or simply take a leisurely stroll along the shore, Inkwell Beach is the perfect destination for a day of fun in the sun. With its convenient location and tranquil atmosphere, this beach is a popular spot for locals and tourists alike to unwind and enjoy the beauty of the Massachusetts coastline.

The East Chop Lighthouse is a historic landmark located at 229 East Chop Drive in Oak Bluffs, Massachusetts, United States. This picturesque lighthouse is a popular tourist attraction, offering visitors stunning views of the surrounding area and the opportunity to learn about its rich maritime history. The East Chop Lighthouse is a must-visit destination for anyone looking to experience the charm and beauty of Martha's Vineyard.