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Condo holiday rentals in Oak Bluffs

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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 living area features a mounted television above an electric fireplace, surrounded by a wall adorned with nautical decor. A glass coffee table sits on a patterned area rug, while high-backed bar stools are positioned at a kitchen counter nearby.
Condo in Oak Bluffs
5 out of 5 average rating, 3 reviews

Island Inn - Residential Suite - 31G - Dog-friendl

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 an electric fireplace with crystal glass stones, TV for relaxing downtime, while WiFi keeps you connected with loved ones and helps you plan your island adventures The kitchenette is equipped with a full-sized fridge, stove, microwave, dishwasher and coffeemaker, along with silverware, plates, cups, cookware, and utens

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
4.9 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 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!

Guest favourite
The exterior of a two-story house is depicted, featuring grey shingles and white trim. A small balcony is visible on the upper level, surrounded by vibrant pink flowers and lush greenery. A white picket fence frames the garden area in front of the house.
Condo in New Seabury
5 out of 5 average rating, 17 reviews

Beach, Steps Away, * Reduced Seasonal Rental *

Off Season Monthly Rate Reduction now avaliable This is a special place where many great spring, summer, fall and holiday memories have been made. It's unique premium proximity to the beach makes it extremely convenient and friendly for couples and families. No roads ever need to be traveled to directly access the beach, making it stress free for folks with kids. Beautiful view of Nantucket Sound. Immediate surrounding neighbors include some of the nicest beach homes around. Relaxing & fun.

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, 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 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 Vineyard Haven
4.73 out of 5 average rating, 26 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.

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.

Guest favourite
A charming exterior of a two-story home is framed by a white picket fence. The light brown siding and decorative gable accentuate the inviting architecture. Lush greenery and flowering bushes are visible, complemented by a sunny blue sky.
Condo 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
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, 167 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 West Falmouth
4.91 out of 5 average rating, 54 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

Popular amenities for Oak Bluffs condo rentals

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 $211 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!

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