Holiday rentals with outdoor seating in Siasconset

4.94 out of 5 average rating, 131 reviews

A cozy family room features a slip-covered sofa and two light-colored armchairs, arranged around a wooden coffee table. A brick fireplace complements the space, and a flat-screen TV is mounted above it. Light from the window illuminates the warm wooden flooring.

Home in Mashpee

Newly Renovated! Seconds to sand, fire pit, A/C

Recently Renovated! This Cape Cod Cottage is completely refreshed top to bottom. Less than 60 seconds to the sand. Cape cod vacations do not get any better than this! Located on idyllic Monomoscoy Island known for its gorgeous wildlife and stunning waterways, our home is the perfect choice to rent on Cape Cod. We are less than 10 Mins to Mashpee Commons and famous Mashpee Town Beach, Less than 5 mins to New Seabury and the Popponesset Inn, and only 15 mins to downtown Falmouth. Linens included!

4.97 out of 5 average rating, 111 reviews

The cottage exterior features a charming shingled façade with multiple windows and decorative planters. An American flag is displayed near the entrance, and a small storage area is located on one side. Gravel surrounds the cottage, contributing to the inviting curb appeal.

Cottage in Nantucket

Attractive 3 Bedroom/2 Bath in Town

Enjoy walking proximity to downtown, shopping, dining, bike paths and more. Sun-splashed and comfortable, this updated cottage is in impeccable condition, tastefully decorated and fully stocked. The first floor suite has a queen bed and bath. Second floor has two bedrooms (one double bed and one two single beds), a shared bathroom and laundry. The private backyard has a patio with a sectional sofa and dining table. Outdoor shower. Central air with individual room control. All linens supplied.

A living area features a comfortable sofa adorned with decorative pillows and a glass-top coffee table. Two bar stools are positioned at a nearby counter, and a chair is set to the side. Natural light streams through large windows showcasing plants in the outdoor space.

4.85 out of 5 average rating, 117 reviews

Beach "Loft"

Enjoy The Beach Loft Apartment's convenient proximity to beaches, town and S’conset. Located 4 miles from the ctr. of the Historic District and 1 mile to Nobadeer beach our lofty spacious 900 sq. ft., 10 foot ceiling height apartment is the lower level (basement) of our home. Yet you will have complete privacy with separate parking as well as separate entrance and your own outdoor deck. The neighborhood is 3 acre zoning. It is secluded and quiet with many pine trees, oak and sassafras trees.

A charming entrance to a coastal home is highlighted by a set of steps leading to a pastel blue door. Flower pots are positioned on either side of the door, and a wooden railing frames the steps, adding a welcoming touch.

4.94 out of 5 average rating, 121 reviews

Captain's House 1750 In town

Our 1750 house is just over a block from the cobblestones of Main St. and only one block from the harbor. You can walk from the Hy-Line Ferry. At night, just walk home from dinner at any restaurant in town. There are 3 bedrooms (1 has a bunk bed) and two and a half baths. In the morning, walk next door for great coffee and cinnamon muffin. Have a cookout and eat in our small backyard area. Come for a visit! (Restaurants, Buses and Cars can cause some noise FYI) Drip coffee maker/filters too!

4.95 out of 5 average rating, 203 reviews

Cuddle In Cottage near Surfside Beach

This charming Nantucket chic decorated cottage is your ideal vacation spot. Perfect for 2 and a max of 4 people. The cottage is less than a mile from Surfside Beach, voted the islands favorite, and across the street from a bike path offering biking to the beach or town a safe and easy option. The cottage boasts privacy with fully stocked kitchen, in and out door shower, radiant heat, AC unit in the bedroom, 2 flat screen TV's, top drawer linens, towels, beach chairs and an out door grill.

A modern kitchen is featured, with sleek cabinetry and stainless steel appliances. A large refrigerator and gas stove are visible. Stone countertops provide ample workspace, complemented by a breakfast bar with four blue chairs. Natural light streams through the window, enhancing the open atmosphere.

4.96 out of 5 average rating, 134 reviews

Updated, modern and charming condo!

Updated, modern and charming condo in central Nantucket. 1,120 square feet, totally accommodates 8 people. Living room has a cozy electric fireplace for chilly Nantucket nights. Full kitchen .Lush private back yard with a patio, grill, hammock, and a relaxing outdoor shower. Two parking spots in the front of the house. Central location is walkable to downtown, grocery stores, coffee shops, restaurants, and night clubs.Close to a couple of bus stations taking you to all parts of the island.

4.97 out of 5 average rating, 109 reviews

Relaxation Awaits! Mid-Island Retreat

Our guest suite is a separate wing of the main house. It is separated by a locked door. You have your own separate private entrance. Perfect honeymoon suite. You must come into the backyard of the main house to access your suite. We do not allow pets in our guest suite. Our Airbnb is not suitable for infants or children. There is an additional guest fee of $150 per guest per night after the initial two guests. And please let us know if you are bringing a car so we can arrange parking.

4.91 out of 5 average rating, 197 reviews

A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.

Home in Oak Bluffs

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

4.95 out of 5 average rating, 126 reviews

A light-filled living room is showcased with a comfortable sofa, side chairs, and a flat-screen TV. A brick fireplace is centered in the room, adorned with a round mirror and decorative items. Natural light filters through the windows, enhancing the inviting space.

Home in Edgartown

Walk To Town - Beautiful Edgartown Cottage

Walk to downtown Edgartown in minutes while staying in this newly renovated 2-story home in the heart of Upper Main St. The 3-bedroom, 2-bathroom house has been completely renovated, with brand new bathrooms, kitchen appliances, etc. You cannot beat the location of this home! You're a short 10 min walk from Edgartown's amazing restaurants & shops, in addition to a short bike ride to Katama's famous South Beach or Oak Bluff's State Beach. Both easily accessible via bike paths.

4.96 out of 5 average rating, 109 reviews

A charming cottage exterior features a shingle facade and a spacious wooden deck. Two lounge chairs are arranged invitingly beside a potted plant. Large glass doors offer a view into the interior, while a grill is positioned nearby for outdoor cooking.

Guesthouse in Madaket

Madaket Bright and Airy Guest Cottage

Escape to this charming guest cottage in Madaket, just a short walk from Madaket Beach, known for its stunning sunsets. This peaceful retreat offers a cozy, light-filled space with a well-equipped kitchen and comfortable sleeping arrangements. Enjoy mornings on the private patio, bike scenic paths, or dine at Millie’s. Easily explore Nantucket’s shops, restaurants, and history. End your day with a breathtaking sunset—your perfect island getaway awaits!

A cozy sleeping area features a spacious bed with blue and white striped bedding. Natural light enters through two large windows, illuminating the light-colored walls and ceramic tile floor. A wooden bench at the foot of the bed complements a stylish lamp and decorative wall art.

4.94 out of 5 average rating, 254 reviews

Mid Island Crash Pad

A conveniently located mid-island Crash Pad for the all movers and shakers that visit Nantucket! This gorgeous, newly built one bedroom studio with its own exterior entrance is just a few steps from the bike path and shuttle that takes you right into town. This location and space offer everything you need to be comfortable in between beach jaunts or shopping trips to town. Like a hotel room, we offer a simple and affordable place to stay on ACK.

5 out of 5 average rating, 118 reviews

A private garden patio is showcased, featuring a circular table surrounded by four chairs. Plush cushions in vibrant blue patterns adorn the seating. Nearby, two wooden lounge chairs offer additional relaxation options. Lush greenery and flowers provide a natural backdrop, enhancing the outdoor ambiance.

Apartment in Edgartown

Stylish retreat | walk to town | fire pit

* Private garden patio: table & chairs, propane grill, propane fire pit & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC

Popular amenities for Siasconset outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A cozy seating area is highlighted by a round table and three upholstered chairs arranged around it. A vase filled with sunflowers sits on the table. Natural light filters through the window, illuminating the neutral tones of the paneled walls and the circular mirror above the mantel.

4.98 out of 5 average rating, 65 reviews

Duck Duck Goose - Renovated Historic 6BR Near Town

A light-filled living area features a large gray sectional sofa and a round, textured coffee table. Shelving displays decorative items and a welcoming atmosphere is created by a modern chandelier overhead. Natural light streams through multiple windows, enhancing the bright ambiance.

4.97 out of 5 average rating, 65 reviews

Home in Nantucket

4.97 out of 5 average rating, 258 reviews

The exterior of a newly constructed guest house is shown, featuring a spacious deck with seating arrangements. Surrounding plant beds with fresh landscaping complement the wooden structure, while a gravel pathway leads towards the entrance, creating an inviting outdoor space.

Home in Edgartown

Brand new gorgeous 2 bedroom guest house.

An open living space features a cozy seating area with a grey sofa, two lamps on side tables, and a television nearby. A dining table set for four is visible, alongside a white cabinet and a glimpse of a doorway leading to a bathroom.

5 out of 5 average rating, 13 reviews

Outside of Town Cottage (Renovated 2025)

A bright kitchen and living area are highlighted by a central island with seating. The space includes modern appliances, a television, and a comfortable couch. Natural light enters through multiple windows, enhancing the relaxed ambiance of this inviting room.

5 out of 5 average rating, 34 reviews

Nantucket Getaway with everything you need

4.98 out of 5 average rating, 57 reviews

A modern kitchen is featured with a large island topped with white quartz. Stainless steel appliances are visible, along with an array of utensils. A bright dining area is beyond the kitchen, with sliding glass doors leading to a lush outdoor space. The living area is comfortably arranged with a dark sofa and a TV.

Home in Mashpee Neck

Charming Cape House with Private Hot Tub !

5 out of 5 average rating, 28 reviews

Home in New Seabury

Ocean View Cape Cod Beach Cottage

4.95 out of 5 average rating, 128 reviews

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

Apartment rentals with outdoor seating

A spacious living area is showcased, featuring a large sectional sofa and a wooden coffee table. Light-colored walls enhance the brightness, while a mounted television is positioned on a sleek console. A decorative area rug provides a calming contrast to the wood flooring.

5 out of 5 average rating, 10 reviews

Paradise Found

4.88 out of 5 average rating, 164 reviews

A charming waterfront building with a distinct blue facade features multiple balconies lined with railing. A lively outdoor dining area is visible on the lower level. Surrounding structures reflect a lively coastal atmosphere, with clear skies and people enjoying the vibrant setting.

Apartment in Oak Bluffs

WATERFRONT PENTHOUSE OAK BLUFFS

4.95 out of 5 average rating, 42 reviews

The kitchen features sleek countertops, stainless steel appliances, and a unique table supported by a natural wood base. Large windows provide ample natural light, illuminating the space. Cabinets offer storage solutions, while the stove and sink are conveniently positioned for ease of use.

Apartment in Edgartown

Katama Loft

A cozy living area features a yellow loveseat adorned with patterned cushions, positioned beside a woven storage ottoman. Natural light floods in from the window, illuminating the open layout that leads to a dining space and modern kitchen visible in the background.

5 out of 5 average rating, 6 reviews

Nantucket "Bird Nest” private deck & restaurants

5 out of 5 average rating, 5 reviews

Downtown Condo 3 minute walk from Ferries.

A modern kitchen space features stainless steel appliances and a wood-topped island with seating for two. Natural light is provided through the windows, highlighting the white cabinetry and grey tiled backsplash. The kitchen flows into the dining area with a door leading to the outdoors.

4.89 out of 5 average rating, 84 reviews

The Cisco Loft

A cozy bedroom is decorated with soft linens on a spacious bed, complemented by light-colored accent pillows. A stylish bedside table holds a vase of flowers, and a contemporary lamp provides soft lighting. The wall features a calming nature-inspired pattern.

4.9 out of 5 average rating, 60 reviews

PRICE DROP Coastal Getaway 1BRM Apartment w/BBQ

4.95 out of 5 average rating, 86 reviews

The extended front porch features comfortable outdoor seating, including a patterned couch and a hanging chair. A striped runner runs along the wooden floor, while the street below reflects the vibrant town with shops and parked cars in view.

Apartment in Oak Bluffs

Cozy 3 bedroom apartment with King bed on Main St.

Condo rentals with outdoor seating

A private balcony is presented with a wooden table set for two. A vase containing yellow flowers adds a touch of color. Surrounding views of neighboring rooftops are visible under a clear blue sky, creating a peaceful outdoor setting.

4.86 out of 5 average rating, 7 reviews

Cinghiale Penthouse on Centre

Superhost

A landscaped garden area is featured, framed by blooming cherry trees and lush greenery. Outdoor seating is arranged among the plants, offering a peaceful space for relaxation. The exterior of the studio apartment, characterized by traditional architecture, is visible in the background.

4.84 out of 5 average rating, 19 reviews

Brant Point Studio in heart of town

A light gray condo features a quaint design with shingle siding under a clear blue sky. A welcoming entryway is flanked by well-maintained landscaping, including small shrubs. A brick driveway leads to the home, where a balcony and a fenced area are visible on the upper level.

Condo in New Seabury

4.75 out of 5 average rating, 8 reviews

2BR condo near beach & golf with deck, AC, and W/D

A bright living area features large windows that allow natural light to fill the space. A light-colored sectional sofa is complemented by a chaise lounge and a wooden coffee table. A patterned area rug anchors the seating area, while tropical plants add a touch of greenery.

Condo in New Seabury

4.93 out of 5 average rating, 14 reviews

Private Ocean Overlook! Serene Cape Cod Escape

5 out of 5 average rating, 17 reviews

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

Beach, Steps Away, * Reduced Seasonal Rental *

5 out of 5 average rating, 39 reviews

Two bedroom condo, walk to town! Fully renovated

A bright living room is highlighted by wide-planked wooden floors and large windows that invite natural light. A comfortable white sofa is positioned near a wooden coffee table, complemented by two armchairs. Decorative plants and soft furnishings enhance the inviting space.

4.93 out of 5 average rating, 76 reviews

Charming two bedroom Historic District condo.

A spacious corner sofa covered in neutral fabric is accompanied by decorative blue and white throw pillows. A wooden coffee table sits in front, displaying a stack of books and a decorative basket. A large arched window enhances the inviting atmosphere.