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Condo holiday rentals in Oak Bluffs

Find and book unique condos on Airbnb

Quick stats about condo rentals in Oak Bluffs

  • Total holiday rentals

    Explore 30 holiday rentals in Oak Bluffs

  • Nightly prices starting at

    Oak Bluffs holiday rentals start at $199 AUD per night before taxes and fees

  • Verified guest reviews

    Over 730 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    30 of Oak Bluffs holiday rentals include Wi-Fi 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!

Top-rated condo rentals in Oak Bluffs

Guests agree: These condos are highly rated for location, cleanliness and more.

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A cozy sleeping area features a spacious bed adorned with white linens. A decorative beach-themed sign is displayed on the wall. A wooden nightstand with a lamp sits beside the bed, and a flat-screen TV is mounted on the opposite wall, enhancing the room's functionality.
Condo in Oak Bluffs
5 out of 5 average rating, 4 reviews

Island Inn - Residential Suite - 29G - Dog-friendl

Your stay in this charming first-floor corner one and half-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 stre

An outdoor pool surrounded by lounge chairs offers a refreshing space for relaxation. Umbrellas provide shade, and trees and greenery frame the area. The pool is populated with guests enjoying the water, contributing to a lively, family-friendly environment.
Condo in Mashpee
5 out of 5 average rating, 3 reviews

Beautiful Spacious 2 BR 2BA Condo CapeCod 6/26-7/3

Beautiful & spacious 1st-floor, one-level 2BR/2BA condo at Sea Mist Resort on wonderful Cape Cod. Family-friendly full amenity resort w/Huge indoor & outdoor pools, large indoor jacuzzi, sauna, gym, tennis, BBQs & mini golf. PRIME CENTRAL LOCATION minutes to beautiful beaches, restaurants, shops, ice cream, supermarket & scenic bike paths. close to ferries to Martha’s Vineyard & Nantucket, perfect for unforgettable day trips. Perfect home base for relaxing & exploring all Cape Cod has to offer !

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.
Condo in Oak Bluffs
4.91 out of 5 average rating, 22 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 light blue, multi-level condo building is captured with distinctive architectural features, including round windows and a turret. Balconies are visible, surrounded by landscaped greenery and a stone retaining wall. The building is set against a clear sky, suggesting a pleasant coastal ambiance.
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
A blue-painted condo building is positioned near a seaside road. The entrance features a short pathway leading to a wooden boardwalk that extends toward the ocean. Clear blue skies are visible, with the ocean seen in the background.
Condo in Oak Bluffs
5 out of 5 average rating, 29 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 bright living area features a navy blue sectional sofa and a wooden dining table with four chairs. Light streams in through a large window adorned with green curtains, complementing a coastal-themed wall art piece. A cozy area rug lies beneath a wooden coffee table.
Condo in Tisbury
4.71 out of 5 average rating, 28 reviews

Heart of VH, w/ac, pool & harborview

Enjoy your stay on Martha’s Vineyard in Causeway Harborview condos with this 2 bedroom/1 bathroom unit. - Views of the harbor from the unit - Pool & Laundry on-site - Parking on-site - Walk to ferry, restaurants, shops and beach - Bike to Oak Bluffs - All linens provided - Fully equipped kitchen with coffee and tea provided - Beach gear provided My goal is to provide guests with a 5-star experience, if there is anything that can improve your experience that isn’t listed, just ask!

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.
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.

Guest favourite
A welcoming outdoor seating area is furnished with a white sofa and dark wicker chairs, complemented by yellow accents. A patterned rug lies beneath, and an umbrella provides shade, creating an inviting spot for relaxation among trees and natural surroundings.
Condo in New Seabury
4.88 out of 5 average rating, 42 reviews

Cape Esacpe at New Seabury

Relax with the whole family at this little Cape escape. This is a cozy 2 bedroom one bathroom condo. Walk to beaches, restaurants, bars, and shops. Visit The Popponesset Market place for food ,mini gold, and ice cream after your day at the beach. Also located directly across from The Popponesset Inn, a popular wedding venue, whether you are there for a wedding or just want to eat at the upscale restaurant, it's a beautiful place to visit. (Market place only open in summer season)

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.
Condo 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.

Top Guest favourite
Condo in Tisbury
4.97 out of 5 average rating, 65 reviews

Short Walk into Town - Nice Comfortable Reasonable

Renovated modern ground floor unit in a two family house in Vineyard Haven. Only a short walk down the hill to the ferry terminal, and Main Street, with plenty of shops and restaurants, a supermarket, movie theatre, the famous Black Dog bakery and restaurant, the Martha's Vineyard museum, the beach and waterfront, the large Veterans Memorial park, and more. Public transportation to the other towns is easily accessible. A car is not necessary as it is with more remote locations.

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.
Condo in Oak Bluffs
4.9 out of 5 average rating, 261 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.

Top Guest favourite
Condo in New Seabury
4.97 out of 5 average rating, 174 reviews

New Seabury Cape Condo | Pool & Beach Escape

Top 5% of Air Bnbs! Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

Popular amenities for Oak Bluffs condo rentals

Destinations to explore

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