Holiday rentals with a patio in Oak Bluffs

The exterior of a charming two-story house is viewed from the front, featuring a wrap-around porch adorned with hanging flower baskets. Lush greenery surrounds the entrance, and a clear blue sky looms above, enhancing the welcoming atmosphere of the property.

5 out of 5 average rating, 14 reviews

Updated cottage/ ocean views

Location! Location! Location! Leave your worries and car behind, this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated 3 bdr and1.5 baths, offering the perfect combination of cottage charm and modern updates. Enjoy ocean views from our wrap around porch and owner's suite enclosed balcony. Large backyard allows for private outdoor enjoyment. Prime location for enjoying all Oak Bluffs has to offer.

A spacious living area is bathed in natural light, featuring a light-colored sectional sofa and a wooden coffee table. The room is adorned with potted plants, and a large flat-screen television is mounted on the wall. A dining area with a modern light fixture is visible in the background.

4.94 out of 5 average rating, 18 reviews

Charming Oak Bluffs Retreat

Escape to this peaceful Oak Bluffs retreat featuring 4 bedrooms, 2 full modern baths, and an updated kitchen. The finished basement has two overflow rooms with beds (bedrooms 5 and 6 in the photos), a half bathroom, and a media and gaming area, offering plenty of space to unwind. The private outdoor yard offers a trellised deck, grill, kid-friendly tree platform and ample parking. This home is perfect for both relaxation and socializing and is centrally located between the island’s down towns.

The exterior of a historic home is displayed, featuring a shingle-style facade and a white front door. Lush green lawns surround the house, complemented by neatly trimmed shrubs and flowering plants. A clear sky with scattered clouds creates a serene atmosphere.

4.96 out of 5 average rating, 23 reviews

Spacious Waterfront w Private Beach sleeps 10

This historic home with a private beach in Edgartown sleeps 6 in the main house and 4 in the guesthouse. Perfect for entertaining, enjoying family or reconnecting with friends. The main house has an open concept kitchen, dining room and living room with a large deck facing the water. Plenty of space to lay out and relax plus an enclosed porch for late night card games and drinks. The home is a leisurely 10 min walk into Edgartown for morning croissants at Rosewater and dinner at The Atlantic.

A charming home is framed by a gravel pathway leading through landscaped gardens. The exterior features a warm wood finish, complemented by thoughtful plantings and natural stone accents. A wooden trellis adds vertical interest beside the entrance, enhancing the welcoming atmosphere of the property.

5 out of 5 average rating, 25 reviews

Quaint Roomy Ranch

Enter this light filled and airy home with soaring cedar lined ceilings and an entire southern facing wall of windows. This surprisingly spacious home has enough room for the whole family and more. Kids will love having the bunk room to themselves while parents can enjoy the rest of the living area in peace. Located in a quiet neighborhood, this is a perfect family retreat. Enjoy the expansive deck while you grill lunch or dinner and finish up the evening with s'mores by the fire pit.

4.98 out of 5 average rating, 41 reviews

A charming two-story house is featured, showcasing shingle-style architecture and a welcoming front porch. White pillars support a broad balcony, while large windows allow for natural light. The well-maintained exterior is accented by a well-paved path and surrounding greenery.

Home in East Chop

Pinkletink Plantation

Your family will be close to everything when you stay at this centrally-located place. Less than a mile from the heart of Oak Bluffs and Circuit Ave., where you'll find all the famous restaurants, harbor & night life. A half mile from Eastville Beach (fabulous sunsets). Take a morning stroll around "the chop"-East Chop & walk or run a 5K. Less than 2.5 miles from Farm Neck Golf Club- & 2.5 miles to State Beach. It has a well equipped kitchen, laundry, outside shower, & back yard!

5 out of 5 average rating, 106 reviews

A sandy beach stretches along the shoreline, meeting the calm blue waters. People are seen enjoying the sun and swimming. Beach umbrellas and some distant structures are visible under a clear sky with a few clouds.

Guest suite in Falmouth

Location Location Location! Beach, Bike, Ferry

STEPS to beach, bike path, trails, restaurants, shopping, bus to MV Ferry Gorgeous studio/in law apartment, private entry, own parking + patio Open plan living/sleeping area + en suite bathroom Queen bed + queen sleeper sofa: sleeps max 4 Fresh linens, towels, personal care products, first aid, hairdryer, iron Mini kitchen w fridge, air fryer, microwave, toaster oven, dishwasher, cutlery, crockery, coffee maker Our famous home baked goodies! Coffee/tea/milk/sparkling water provided

An inviting living room features a light-colored sofa and a natural wood coffee table. Artwork and plants add warmth, while natural light fills the space through ample windows. A large television is mounted on the wall, providing entertainment options for guests.

5 out of 5 average rating, 46 reviews

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.

4.96 out of 5 average rating, 162 reviews

A modern kitchen features a spacious island with two black bar stools. Stainless steel appliances, including a microwave and toaster, complement quartz countertops. Natural light fills the space through large windows, revealing a glimpse of greenery outside.

Cottage in Oak Bluffs

Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

Cottage in Chappaquiddick

A bright living space features white walls and a wooden ceiling with ample natural light. A round coffee table is centered in the room, surrounded by a sofa and wicker chairs. A side table holds a lamp, and a colorful artwork is displayed on the wall, with ocean views visible through windows.

5 out of 5 average rating, 9 reviews

Beachfront Cottage w. Yard + Town Access

Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

Guest suite in West Falmouth

A cozy living area features a comfortable gray sofa with decorative pillows and a wooden coffee table. Natural light fills the space, highlighting a dining table with four chairs. A doorway leads to the kitchen, while a wall-mounted TV provides entertainment options.

4.99 out of 5 average rating, 195 reviews

The Sea-Cret Garden, Guest Apartment

Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

A spacious, newly constructed home is showcased with a dark blue exterior and white accents. The façade features a prominent front porch with chairs and a large garage. A gravel driveway leads to the entrance, framed by a lush green lawn and trees.

4.98 out of 5 average rating, 42 reviews

The Blue Lagoon, Oak Bluffs

Come enjoy this beautifully designed, brand new home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An outdoor patio with gas grill is the perfect spot to relax after a day at the beach. Just a few steps away is the lagoon where you can paddle board, kayak, dig clams, or just take in the amazing sunsets! Summer rentals are Saturday to Saturday. Please send a message if you have any questions.

An open floor plan is showcased, featuring a light-toned sectional sofa with decorative pillows. A wooden dining table and chairs are positioned nearby, with a stylish pendant light overhead. The kitchen is visible in the background, equipped with modern appliances and a large window providing natural light.

5 out of 5 average rating, 42 reviews

NEW Modern Open Floor Plan House in Heart of OB

Come stay in our home in the heart of Oak Bluffs. Located just steps away from circuit ave, 3 blocks to the start of town and a 10 minute walk to the beach your are in the perfect spot to enjoy all the vineyard has to offer. Neighborhood is up and coming, lots being built residential and commercial, but its got that quirky charm we are excited to be a part of . Most importantly we welcome ALL <3

Popular amenities for rentals with patio in Oak Bluffs

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Flat rentals with a patio

Flat in Tisbury

4.67 out of 5 average rating, 3 reviews

Private Studio Apartment Retreat in the VH Woods!

4.88 out of 5 average rating, 66 reviews

A spacious bed is dressed in white linens with a patterned accent blanket and matching decorative pillows. Light wooden furniture complements the blue walls, and a tall cabinet is positioned nearby, enhancing the room's overall comfort and functionality.

Flat in Falmouth

Sunshine Beautiful

4.82 out of 5 average rating, 17 reviews

A bright living room features multiple seating options, including a light-colored sofa, a striped chair, and a woven side table. Natural light streams through the large windows, illuminating the space. A television is positioned in front of a light-colored cabinet, while decorative elements enhance the ambiance.

Flat in West Falmouth

Charming West Falmouth walk to bikeway and beach

4.71 out of 5 average rating, 28 reviews

An outdoor patio area is surrounded by lush gardens featuring blooming flowers and greenery. Two blue chairs are positioned near a table underneath a large umbrella, providing a shaded space for relaxation. The backdrop includes a well-maintained building with multiple glass doors.

Flat in Aquinnah

Quiet & Serene in Aquinnah

A spacious deck features wooden flooring with a white railing, offering views of lush green grass and the distant ocean. The setting includes nearby houses and vehicles on a quiet street, with a bright sky dotted with clouds overhead.

Flat in Oak Bluffs

BRAND NEW Walk to Beach Owner's Suite with Balcony

4.94 out of 5 average rating, 69 reviews

A welcoming sitting area features a comfortable sofa and a small dining table with two chairs. Natural light filters through the large window, highlighting the wood grain of a side table and a floral area rug. Decorative artwork is displayed on the walls.

Flat in Cataumet

Cape Heaven

A historic two-story blue house features a grey shingle roof and red doors. Symmetrical windows adorn the facade, while neatly trimmed shrubs line the front yard. The property is set back from the road, with a driveway visible and trees providing shade.

Flat in North Falmouth

4.67 out of 5 average rating, 3 reviews

Cozy Nest in North Falmouth Village

5 out of 5 average rating, 28 reviews

A bright living room is seen with large windows offering views of the pond. A comfortable sofa, accent chair, and dining table are arranged harmoniously within the space. Natural light illuminates the wooden floor, highlighting a cozy area rug underfoot.

Flat in Falmouth

Peaceful Pond view apartment close to beach

House rentals with a patio

4.91 out of 5 average rating, 101 reviews

The exterior of a two-story residential building is displayed, featuring light gray siding and dark blue shutters. A well-maintained lawn surrounds the home, complemented by two coniferous trees and various shrubs. The entrance is marked by a solid black door, enhancing the home’s facade.

Home in Barnstable

Serene Haven w/ No Shared Spaces | Cape Cod

5 out of 5 average rating, 19 reviews

A modern home with light grey siding is featured in the background, surrounded by landscaped gardens. A heated saltwater pool, with clear blue water, is framed by grey stone paving. Lounge chairs and shaded seating are situated beside the pool, enhancing the outdoor space.

Home in Popponesset

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

5 out of 5 average rating, 9 reviews

A cozy living area is highlighted by high, exposed wooden beams and a stone fireplace. Two patterned armchairs and a gray sofa are arranged on an area rug, while a circular wooden coffee table holds decorative items. Natural light filters through the windows, enhancing the warm ambiance.

Home in West Tisbury

3BR Home, Fenced Yard, Free use of car, Pets ok!

A custom-built home is depicted with a charming shingle exterior and a symmetrical roof. The front porch is flanked by well-maintained landscaping, including flower beds. Several windows allow natural light to illuminate the inviting entryway, creating an accessible and welcoming façade.

4.88 out of 5 average rating, 8 reviews

Lovely Farm View on Llewellyn

The exterior of the home is surrounded by a lush green lawn and trees. A spacious deck with umbrellas offers shaded seating areas. The house features multiple levels, blending with the natural landscape, and includes a patio area with lounge chairs.

4.97 out of 5 average rating, 38 reviews

Spacious 4-Bedroom home with outdoor dining

A bright living room features comfortable leather seating arranged around a central area rug, with natural light flowing through large windows. A ceiling fan hangs above, and a dining area is visible in the background, providing a cozy space for relaxation and gatherings.

5 out of 5 average rating, 3 reviews

Spacious 3BR Stay Near Oak Bluffs

4.91 out of 5 average rating, 34 reviews

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

Home w/ golf view, salted heat pool, mins to beach

An outdoor space is featured with a patio surrounded by well-maintained greenery. A dining table set with chairs is shaded by bright red umbrellas, providing a pop of color. Lush grass and established shrubs create a comfortable and inviting atmosphere.

4.94 out of 5 average rating, 18 reviews

Gorgeous and spacious MV getaway

Apartment rentals with a patio

4.96 out of 5 average rating, 78 reviews

A modern living area features a comfortable sofa adorned with cushions, a decorative table, and a vase with flowers. A spacious kitchen is visible in the background, equipped with stainless steel appliances and stylish bar seating for two. Natural light filters through framed windows.

Apartment in Nantucket

Newly renovated one-bedroom condo in Town

4.9 out of 5 average rating, 30 reviews

A two-story home is set amid lush greenery, featuring a well-manicured lawn and a large tree offering shade. The exterior displays classic architectural elements, with white siding and black shutters. A sign marked '1846' is visible beside the pathway, inviting exploration.

Apartment in Falmouth

Heart of downtown, walk to ferry, bikeway & beach!

4.82 out of 5 average rating, 74 reviews

A spacious sleeping area features a large bed with neutral bedding and colorful accent pillows. A TV is mounted on the wall. Natural light filters through a sliding glass door, which opens to an outdoor area with a small table and chairs.

Apartment in Dennis Port

Cozy Studio Just Steps Away From the Beach!

Apartment in East Dennis

4.73 out of 5 average rating, 15 reviews

Bright & Breezy Bayside Condo

4.88 out of 5 average rating, 41 reviews

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.

Apartment in Popponesset

Cape Esacpe at New Seabury

4.94 out of 5 average rating, 69 reviews

A historic stone building is prominently displayed, showcasing a vibrant red entrance and outdoor seating area. Surrounding areas feature neat gardens and pavement that complement the structure. A clear sky and early light enhance the building's architectural details and inviting atmosphere.

Apartment in New Bedford

Millie's-Historic New Bedford, 2BR, water views

4.97 out of 5 average rating, 68 reviews

A bright and airy studio features a queen bed with a soft blanket, paired with a small dining table and chairs. The kitchenette is equipped with modern appliances, while a flat-screen TV hangs above. A large window opens to a private balcony with outdoor seating.

Apartment in West Dennis

Oct + Nov Discount | Central | Private Balcony