Holiday rentals with outdoor seating in Nantucket County

A spacious backyard features a well-maintained lawn surrounded by privacy hedges and blooming trees. Lounge chairs are positioned for relaxation, while a seating area with a table invites outdoor dining. A inviting path leads to the entrance of the cottage-style home, enhancing outdoor enjoyment.

4.88 out of 5 average rating, 24 reviews

South of Town Surf Shack. Best Deal on Island.

Redecorated for summer 2025 with new linens and Casper beds! While the exterior is the picture perfect Nantucket cottage home surrounded by hydrangeas, you will be surprised by the casual, surf-vibe of the decor. Enjoy the best of Nantucket by walking to Town (under 1 mi) at this prime location property. The lot has privacy hedges and borders conservation land. This property has a separate living area home to two of the homeowner's employees. No parties, dinner parties, or events are allowed.

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, 114 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!

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.

4.96 out of 5 average rating, 132 reviews

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.

Apartment in Nantucket

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.

An open-concept living area features a comfortable seating arrangement with two armchairs and a sofa. A large flat-screen TV sits on a wooden console. A circular dining table with four chairs is placed near the kitchen, which displays modern appliances and wooden cabinetry.

4.9 out of 5 average rating, 29 reviews

Beautiful Custom Nantucket Home

Our custom built home is located on a private, natural and secluded location in the beautiful Fishers Landing neighborhood in Madaket. It is perfect for a family of 4. The home is close to beaches, crabbing, bike paths and Madaket Millies. We have a large private landscaped yard for the kids to play in. We also have a great deck in the back of the house for outdoor dinners, an outdoor shower with and BBQ area. It's a great house in a great spot and we have many happy repeat guests.