Holiday rentals with outdoor seating in Nantucket

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 private outdoor area features green lounge chairs arranged around a small table, with a patio woven into the grassy landscape. A barbecue grill is positioned nearby, and the exterior of the cottage is framed by lush hedges and a pergola, creating a serene environment.

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 bright and inviting living space features a white sectional sofa accented with colorful throw pillows and a soft blanket. A round white coffee table sits at the center, complemented by a decorative tray. Soft textures and natural light create a warm ambiance.

4.97 out of 5 average rating, 71 reviews

Beachy House on the edge of Brant Point

Our Beachy house, furnished with a fun, beachy theme is located near Children's Beach, walking distance from the ferry & close to town on the edge of Brant Point. We are less than a block from the harbor & beach, across from White Elephant Hotel and Lola 41. This cute little 3 bedroom house has been renovated & updated with a yard surrounded by hedges, 1 parking spot (small driveway). A small yard offers a grill & outdoor dining for 4. The backdoor off of driveway leads into master bedroom.

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, 132 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.

4.92 out of 5 average rating, 219 reviews

The cottage is set in a charming garden with flowering cherry trees, surrounded by a white picket fence. Its two-story structure features a shingle exterior, and lush greenery enhances the outdoor space, providing a tranquil setting just off a quiet street.

Guest suite in Nantucket

Cozy cottage just off Main Street

Perfect location. Modern cottage. block off Main St. Cozy for 2, gas burning fireplace & AC. Well-equipped, open floor plan, lvg room/galley ktch/dining/ full bath WD down. Upstairs, queen bdr. and 1/2 bath. Private outdoor deck. Outdoor shower too! Beach chairs & towels, tote, cooler, umbrella, hair blower, iron. We care about the details like ironed sheets, good pillows, new mattress, & fluffy towels.! We don't provide parking & discourage bringing a car. Parking at a premium in season.

A charming home with a shingled exterior is set against a clear blue sky. It is surrounded by a well-maintained lawn and lush greenery. A spacious deck is visible at the rear, furnished with seating, while a gravel pathway leads to a pair of white Adirondack chairs.

5 out of 5 average rating, 23 reviews

Large yard, deck & hot tub 4 bedroom, sleeps 8

**Min stay: peak season 5 nights / shoulder season 4 nights/ off season 3 nights** Tucked in off the road lies a 4 bedroom home with a spacious yard, hot tub, fire pit, and deck suitable for dining or entertaining. The modest upstairs expands to a basement with a large living area, two bedrooms, and a kitchenette. The large deck is equipped for dining or entertaining. It also features an outdoor shower for after a long day at the beach. **House is winterized for cold weather stays**

A bright and airy guest suite features a spacious bed with decorative pillows, set against light-colored walls. Sheer curtains allow soft natural light to fill the room. Wooden flooring complements the light decor, while a dresser and small cabinet provide additional storage space.

4.98 out of 5 average rating, 169 reviews

"Upon a Rock" Peace & Quiet - Mid island retreat!

Our guest suite is a separate wing on the main house. It is separated by a locked door. You have your own separate private entrance. You must come into the backyard of the main house. Look for the arbor with BAIRD written on top. These is an extra charge for any guests after the first 2 guests.,$150 per guest per night. Our guest suite is not suitable for children. We do not allow pets. If you were bringing a car please let us know in advance so we can make parking arrangements

4.98 out of 5 average rating, 146 reviews

A charming two-story home is framed by vibrant flowerbeds featuring lush hydrangeas in shades of purple and blue. A porch with hanging plants complements the façade, which displays a flag. The greenery and flowers enhance the property's inviting exterior.

Guest suite in Nantucket

Derrymore Place - an island gem

Located in a quiet neighborhood off of Cliff Road, guests can relax in a spacious 350 sq/ft beautiful bedroom with a comfortable king size bed and single day bed (w/trundle). There is a 3 piece private bathroom with washer/dryer. A full size pull out sofa is available in the very large kitchenette/game room. A 300 sq/ft comfortable sitting room with sofa, cable television, wine fridge and high top table is for your exclusive use. A private entrance allows guests to come and go freely.

4.96 out of 5 average rating, 161 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.

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, 252 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.

A modern kitchen features soft green cabinetry and a white countertop, complemented by natural wood beams overhead. Pendant lights illuminate the space, and a vase with fresh flowers rests on the kitchen island, adding a touch of color to the functional design.

4.9 out of 5 average rating, 148 reviews

Great Condo In Town!

Great two bedroom condo in town renovated in winter 2025 - new kitchen and updated bathroom. If arriving by ferry, you're just a ten minute walk from dropping off your bags and being on vacation. Convenient to restaurants, bars, shopping and everything town offers. Queen bed in master and single in second bedroom. Couch in living room is a pullout as well as option for blow up mattress. The condo is on the second floor.

Popular amenities for Nantucket outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.95 out of 5 average rating, 65 reviews

An outdoor patio area features a round wooden table surrounded by chairs and a large umbrella for shade. Two wicker armchairs are positioned nearby on a brick surface. Lush greenery and a casual beach cottage are visible in the background under a clear blue sky.

Home in Siasconset

Charming Sconset cottage in Codfish Park

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!

4.96 out of 5 average rating, 257 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.

The colonial-style house is framed by mature trees and lush greenery. A gravel pathway leads to the front entrance, which is highlighted by a blue front door and symmetrical windows. The spacious front yard features well-maintained grass, enhancing the home's inviting appearance.

5 out of 5 average rating, 13 reviews

Foggy Notion

4.94 out of 5 average rating, 148 reviews

A wooden deck extends from the contemporary home, featuring two Adirondack chairs positioned to overlook a serene, natural setting with vibrant autumn foliage. Sunlight filters through trees, enhancing the peaceful atmosphere of the private yard.

Home in East Chop

The Lighthouse

The exterior of a classic Nantucket home is displayed, featuring weathered gray shingles and multiple windows. A welcoming front porch is visible, leading to a central door. A rooftop deck is apparent on top, surrounded by lush greenery and nearby structures.

4.94 out of 5 average rating, 33 reviews

Beautiful Classic, Historic Nantucket Home In Town

4.9 out of 5 average rating, 114 reviews

A charming beach house is set on a lush green lawn, featuring a picnic table and two lounge chairs arranged for relaxation. The house has multiple windows, and its exterior is made of wood, harmonizing with the surrounding nature.

Home in Edgartown

Katama Barn

4.97 out of 5 average rating, 247 reviews

A charming post and beam guest house is set amidst lush greenery, featuring an inviting entrance with a peaked roof. The landscape is softly accented by manicured shrubs and a path leading to the front door, enhancing the serene outdoor environment.

Home in Oak Bluffs

Sweet little post and beam

Apartment rentals with outdoor seating

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, 41 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

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, 83 reviews

The Cisco Loft

A stone pathway leads through a landscaped garden toward an outdoor seating area, where wooden chairs surround a table. A gas grill is visible under the trees, and greenery provides a natural backdrop to the space.

5 out of 5 average rating, 11 reviews

NEW Garden Apartment in Miacomet

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

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, 58 reviews

PRICE DROP Coastal Getaway 1BRM Apartment w/BBQ

An open living area is featured, showcasing a bright orange pull-out couch with decorative pillows. A surfboard is mounted on the wall. Light-filled ambiance is created by recessed lighting, complemented by a small dining area and kitchen bar equipped with high-backed chairs.

4.88 out of 5 average rating, 84 reviews

Easy Nantucket Downtown Apartment

Condo rentals with outdoor seating

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, 75 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.

4.94 out of 5 average rating, 54 reviews

Pawsitively Pet Friendly 2 Bedroom Condo

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.

4.96 out of 5 average rating, 78 reviews

Newly renovated one-bedroom condo in Town

A living and dining area features a light-colored stone coffee table and a wooden dining set with two chairs. A gray sofa with decorative pillows is positioned next to a lamp, while a coastal-themed artwork adorns the wall, contributing to a relaxed ambiance.

Condo in Oak Bluffs

Island Inn - Residential Suite - 35G - Oak Bluffs,

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.