Apartment holiday rentals in Oak Bluffs

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Top-rated apartment rentals in Oak Bluffs

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The open living area features a neutral color palette with a comfortable sofa and an accent chair. A dining table is set for four, while a flat-screen TV is mounted above a simple fireplace. Natural light enters through the large windows, enhancing the welcoming ambiance.
Apartment in Oak Bluffs
5 out of 5 average rating, 3 reviews

Island Inn - Two Bedroom Suite - 2A - Dog-freindly

This charming first-floor one-bedroom retreat, featuring a queen bed, offers the quintessential Martha’s Vineyard experience. The open living and dining area invites cozy gatherings, allowing you to stay connected with your guests even while preparing fresh, island-inspired meals in the fully equipped kitchen. Stocked with silverware, plates, cups, cookware, and utensils, it has everything you need for effortless dining. Relax in the evening on the sofa, enjoying a favorite movie on the flatscre

A covered balcony is seen from the exterior, featuring a small bistro dining set. Adjacent to the balcony, a path leads to the beach, with unobstructed views of the ocean. Lush greenery and white gravel enhance the outdoor setting.
Apartment in Oak Bluffs
4.9 out of 5 average rating, 21 reviews

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Planning a family or couple's getaway to Martha's Vineyard? Then you'll love calling this delightful Oak Bluffs vacation rental your home-away-from-home. The quaint 2-bedroom, 2-bath condo offers beautiful beach views, cozy nautical decor, and a covered balcony perfect for socializing with a nice glass of wine. When it's time to explore the island, peruse the shops, restaurants, and lighthouses, or take a ride on the famous Flying Horses Carousel. A memorable Massachusetts vacation starts here!

Guest favourite
A round black table is positioned between two comfortable chairs adorned with patterned upholstery. Atop the table, a decorative floral arrangement includes blue and white flowers, complemented by greenery. A couple of neatly stacked books are also visible.
Apartment in Oak Bluffs
4.84 out of 5 average rating, 51 reviews

Serenity on Martha's Vineyard

This 2BR, 2 Full Bath Condo with air condition (AC) and elevator access is located across the street from State Beach (AKA the "Ink Well") in Oak Bluffs. It's on the top floor, recently redecorated, with all the amenities for a wonderful vacation. Both bedrooms have Smart TVs & AC. Free Wi-Fi. Great location, within walking distance to the ferry, beach and downtown Oak Bluffs, restaurants and shops. Car not needed! Get ready to relax and unwind. It's the perfect location! Welcome to Serenity!

Top guest favourite
A serene view of the ocean is framed by white wooden architecture. The calm water reflects a clear blue sky, while a sandy beach lies in the foreground, accompanied by a stone jetty. Benches are positioned along the walkway, inviting relaxation.
Apartment in Oak Bluffs
5 out of 5 average rating, 28 reviews

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

Enjoy one of the most desirable locations on the Vineyard!! Enjoy AMAZING sunrises & gorgeous ocean views from this lovingly kept, super clean condo. Literally across the street from town beach, adjacent to Waban Park, a few blocks to Ocean Park, Flying Horses, Steamship Authority & downtown Circuit Avenue (restaurants, shops)! Bring a car (one unreserved parking spot) or walk over from the boat. Bike delivery & storage available. We hope to see you this summer in this fantastic summer condo!

Guest favourite
A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.
Apartment in Tisbury
4.92 out of 5 average rating, 49 reviews

Private 3bdrm Condo Tashmoo Woods

This 3 bedroom (3 king) 2 1/2 baths newly renovated condo is in a private setting with screened in porch. New kitchen, gas grill on deck, outdoor shower. -Access to the Tashmoo Woods Association pool, tennis courts and play ground. -Close to West Chop beaches. -Two miles from downtown Vineyard Haven. On bus route, but best to have a car. -The primary bedroom (king bed) is downstairs and the 2 upstairs bedrooms share a bath (shower only). Minimum rental 5 days, 1 week in summer.

An outdoor saltwater pool is framed by comfortable lounge chairs under clear blue skies. Lush greenery surrounds the pool area, providing a serene atmosphere for relaxation and enjoyment. A set of steps leads into the inviting water.
Apartment in Mashpee
5 out of 5 average rating, 3 reviews

1BR Condo w/ Balcony in Mashpee, MA

Escape to this inviting 1-bedroom condo at Sea Mist Resort in Mashpee, MA. With 2 full bathrooms, a fully equipped kitchen, a private balcony, and a cozy living area with a sofa bed, this home is ideal for small families or couples. Enjoy amenities like indoor and outdoor pools, in-suite laundry, free Wi-Fi, shared BBQs, and a games room. Minutes from South Cape Beach and local attractions, this charming retreat offers the perfect blend of comfort, convenience, and coastal charm.

Superhost
A private balcony offers a scenic view of well-maintained green lawns and a gazebo, creating a tranquil outdoor experience. The balcony features decorative wooden railings, while the open sky above enhances the feeling of spaciousness.
Apartment in Oak Bluffs
4.76 out of 5 average rating, 17 reviews

Ocean View Gem, Walk to it All, No Car Needed!

Lovely 2 BR/1 BA condo sleeps up to 4 guests. Amazing location with spectacular views! Experience island living at its finest. Martha’s Vineyard vacationers dream! Enjoy walking everywhere: Inkwell Beach, Circuit Avenue, Biscuits, OB ferry and harbor, Campground Cottages, Tabernacle, shops, restaurants and more! Have a front seat to Illumination fireworks, spectacular sunrises and romantic sunsets on the private balcony. No car needed; however, parking is available if required.

The exterior of the home features a sloping roof with multiple skylights and is surrounded by well-kept greenery. A paved pathway leads to the main entrance, set against a backdrop of bright blue sky and lush, manicured landscaping.
Apartment in Oak Bluffs
4.92 out of 5 average rating, 13 reviews

Spectacular Martha's Vineyard Island Home!

This is our beautiful Hidden Cove home on Martha's Vineyard we call Shangri-La! Spectacular setting with a great peaceful view overlooking Sengekontacket Pond with the Ocean beyond. The property features a shared Pool, Tennis Courts & Dock. Our house is conveniently located midway between the Oak Bluffs & Edgartown town centers. When the presidents visit the Vineyard this is the area they come to relax (at the Farm Neck Golf Club which is right up the street).

Guest favourite
A modern kitchen is displayed, featuring wood cabinetry and granite countertops. Stainless steel appliances, including a stovetop and microwave, are visible. A tile backsplash adds texture, complementing the overall design. A stainless steel sink is situated next to the counter, enhancing functionality.
Apartment in Oak Bluffs
4.9 out of 5 average rating, 260 reviews

Stunning. Walk to Beach, Town and Harbor 113B

Walk to all Oak Bluffs has to offer. 5-10 minutes to harbor, town, beach and restaraunts. Amazing location! This three unit property offers a shared patio and deck space along with all the amenities. It is private and well appointed. 2 flat screen Televisions, wifi, appliances, tile throughout, granite counters, outdoor shower, gas grill. This 400 square foot unit will provide you with an excellent home base to explore Oak Bluffs and Martha's Vineyard.

Superhost
The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.
Apartment in Falmouth
4.68 out of 5 average rating, 31 reviews

Condo in Falmouth MA

The Condominium is just 10 minutes from Falmouth and Falmouth Heights, where you can enjoy the road race and 4th of July fireworks. It’s a quick 20-minute drive to the ferry to Martha's Vineyard and Nantucket, and only 5 minutes to the ocean. Guests can unwind in the stand-alone game room with arcade games or relax by the fire pit, take a swim in the pool, or explore the flax pond for kayaking and fishing. Perfect for both relaxation and adventure!

Superhost
A bright living room is showcased, featuring white sofas and a light wood coffee table. A decorative shelving unit lines the wall, filled with various items. Large windows allow natural light to fill the space, and soft curtains frame the view of the outdoors.
Apartment in Edgartown
4.8 out of 5 average rating, 5 reviews

Brand New 2BR Condo w/ Pool. No Pets!

This beautifully renovated condo is in the heart of Edgartown. 5 min walk to downtown shops, restaurants, and waterfront. This unit has 2-bedrooms & 1.5-baths. The master has a king bed and half bath, and the second bedroom features a queen bed and full bath. Enjoy a spacious living room with high ceilings, a full kitchen, and access to outdoor spaces with a pool. Sleeps 4, this condo is the perfect base for your Martha's Vineyard adventure!

Top guest favourite
A welcoming living area features a comfortable sectional sofa and two wooden armchairs arranged around a circular coffee table. Natural light fills the space, highlighting a large area rug on the hardwood floor. A well-equipped kitchen is visible in the background.
Apartment in New Seabury
4.97 out of 5 average rating, 162 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).

Popular amenities for Oak Bluffs apartment rentals

Quick stats about apartment rentals in Oak Bluffs

  • Total holiday rentals

    Explore 30 holiday rentals in Oak Bluffs

  • Nightly prices starting at

    Oak Bluffs holiday rentals start at € 147 per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Wifi availability

    30 of Oak Bluffs holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oak Bluffs rentals

  • 4.9 Average rating

    Oak Bluffs stays are highly rated by guests – averaging 4.9 out of 5!

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