Condo holiday rentals in Oak Bluffs

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Top-rated condo rentals in Oak Bluffs

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Superhost

Condo in Oak Bluffs

5 out of 5 average rating, 3 reviews

Island Inn - Residential Suite - 32G - Dog-freindl

Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comfortable with all the essentials. The cozy living and dining area features a TV for relaxing downtime, while WiFi keeps you connected with loved ones and helps you plan your island adventures. The kitchenette is equipped with an apartment-sized fridge, stove, microwave, and coffeemaker, along with silverware, plates, cups, cookware, and utensils—everything you need to enjoy a convenient and s

Condo 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

Condo 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

Condo 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

Condo 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.

Top Guest favourite

Condo in New Seabury

4.95 out of 5 average rating, 82 reviews

Beach Cottage 3nts/4th Free Aug - Oct Mashpee MA

Enjoy our 1 br condo with the BEST view of all the condos, steps from Deans Pond! Walk to Popponesset Market Place, Popponesset Inn & Nantucket Sound. Stroll the beach, hike through conservations areas. Visit quaint shops, restaurants, antique stores! Enjoy morning coffee & evening cocktails on our private deck with that Spectacular View! Spa Rain shower bath, chef's kitchen. Egyptian Cotton Sheets!! NO: Pets-Smoking-Vaping-Parties NO Micro Fiber Sheets!

Guest favourite

Condo in Oak Bluffs

4.9 out of 5 average rating, 255 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

Condo in Falmouth

4.7 out of 5 average rating, 27 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

Condo 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

Condo in New Seabury

4.97 out of 5 average rating, 156 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).

Guest favourite

Condo in Falmouth

5 out of 5 average rating, 8 reviews

Spacious 2BR by the Sea in Falmouth

This inviting 2-bedroom condo at Beachside Village Resort offers comfort and charm with Queen beds, twin beds, a sleeper sofa, and a fully equipped kitchenette. Ideal for up to 6 guests, enjoy ocean views, air conditioning, and access to the resort's pool and BBQ area. Just steps from Surf Drive Beach and close to Cape Cod's top attractions, it's perfect for a relaxing family or group escape.

Guest favourite

Condo in West Falmouth

4.9 out of 5 average rating, 40 reviews

Lovely W Falmouth Home steps to bikeway & more!

Hello and welcome to our home in the heart of West Falmouth Village! Immerse yourself in the charm of this historic locale, just a stroll away from West Falmouth Harbor, the bike path, village store, renowned restaurants, and the sparkling Shining Sea Bike Path. -Child and pet friendly -Well stocked kitchen -Central Air & Heat throughout -Linens & bath and beach towels provided