Holiday rentals with a fireplace in Oak Bluffs

Stunning 4/2.5 Water View, Hot Tub, Dogs ok (fee)

Custom home with beautiful water views of Lagoon Pond. Surrounded by Land Bank and Sheriff's Meadow, this very private home offers easy access to miles of hiking trails and pristine waters. Enter the home from the covered porch; the main level features an open floor plan, high ceilings in the living areas - open to the dining room and kitchen, where large windows frame the Lagoon. Sleeps up to 8. Outdoor shower! Wifi speed 430 MBPS download speed Dogs ok with owner approval ; fee applies

Charming 3-Bedrm w/Loft.New Construct! Walk 2 town

A stylish place to stay, perfect for group trips. 15min walk from town and Inkwell beach. NEW construct, beautiful open layout home is just what you have been looking for. Every bedrm has its OWN full bath. The kitchen is modern and stylish. The open layout design, leads outside to the deck, to a peaceful yet fun backyard. As you sit on the mahogany deck, you will smell the tasty delights coming from the grill of the outdoor kitchen. This home is my home and I want to share it with you.

Spacious 1 Bedroom Apt - 3 min walk to the Beach!

A perfect place for 1 -4 people to stay! You will have plenty of room, shared use of a grill, backyard, and outdoor dining area. Location is great - it's only a 3 minute walk to the lagoon/beach, 20 minute walk to the Oak Bluffs harbor, 25 minute walk to downtown Oak Bluffs, and 7 minute drive to State Beach. We also have central AC and heating! The owners live upstairs with two young kids (4 & 6) and a dog. As such, this listing is for early-risers ready to enjoy the island mornings :)

The Island Collection MV: The Hideaway

This beautiful 3 bedroom home is located in a quiet area on Martha’s Vineyard by Lagoon Pond. When you walk inside, you will be delighted by the stone fireplace and the comforting ambience. It presents gorgeous “costa esmeralda” granite counter tops with solid cherry cabinets, stainless steel appliances, and a kitchen which integrates to the dining area. From there, the french doors invite you to a patio surrounded by artisan landscaping. Tenant brings own linens/sheets/towels/beach towels.

WATERFRONT Cottage, Downtown w/ Beach

DIRECT WATERFRONT in-town beach house with walk-out beach and onsite private parking. This recently renovated 1 bedroom, 1.5 bath, 2-story house is located directly across the street from the famous Black Dog Tavern, right on the bustling year-round Vineyard Haven harbor. This property is no doubt one of the most unique residential properties on Martha’s Vineyard given its proximity to the harbor, ferry terminal, stores, restaurants, bike rentals, beaches & so much more. You will love it!

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

A Nostalgic Space: Your Martha's Vineyard Getaway!

Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from a memorable family vacation to a serene couples retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive. The home was completely updated in 2019, with an all new interior that is bright and fresh! It features an open floor plan, with a bright kitchen, all new appliances and new finishes. You can't beat the location of this home!

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on a quiet semi-private road with beautiful views of Vineyard Sound. This inviting coastal retreat features 3 bedrooms, 2 private en-suite baths, 1 semi-private en-suite bath, a fully equipped kitchen, gas fireplace, cable TV, WiFi, and air conditioning. Relax on the second-floor deck with water views or enjoy outdoor dining on the patio with the BBQ grill. Conveniently located near the Martha’s Vineyard ferry, bus station, beaches, shops, and town.

Valentine's Retreat Hot Tub Fire Pit Trails Beach

LOCATION LOCATION ✅ Rated Top 5% of Homes ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood ✅ HotTub, Fire Pit, Trails at your door step, perfect for peaceful strolls or energetic hikes through lush landscapes. AND Flexibility, with Every detail curated for comfort and style, you'll feel at home the moment you step inside. Located with the island's natural beauty around you, unwind and reconnect with nature.

NEW Beautiful Waterfront, Firepit & Private Dock

Welcome to Weather Permitting, a relaxing Cape Cod retreat perfect for families and groups. Enjoy beautiful water views, cozy gathering spaces, and direct pond access from the private dock. Spend your days relaxing by the water, lounging on the deck, or exploring nearby beaches and local attractions. - 6 min drive to Seconsett Beach - 10 min drive to South Cape Beach - 15 min drive to Mashpee Commons shopping & dining Experience Mashpee with us & learn more below!

First-class 4+ BR Lagoon Pond Camp

Ultimate getaway house! Situated on Lagoon Pond in Oak Bluffs. Sleeps 10 plus 2 in the optional guest cottage. The house is under 2 miles from OB center - convenient for walking and bike riding. Beach access! The house boasts a pizza oven, outdoor nooks (hammocks!), and a spacious yard. There are amenities galore including, but not limited to: an outdoor shower, grill, board games, wifi, towels, linens, etc. 1 week min stay, Sunday turnovers in July & August.

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!