Pet-friendly vacation rentals in Siasconset

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, 25 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.

A charming white house is set against a clear blue sky. Lush greenery surrounds the property, with a gravel driveway leading to the attached garage. The front yard features well-maintained shrubs, and the roof is adorned with simple, traditional architecture.

4.91 out of 5 average rating, 69 reviews

"Summer Escape" at South Cape Beach Estates.

This newly remodeled and furnished house offers the epitome of the Cape Cod lifestyle in the private South Cape Beach Estates, a place perfect for family time and relaxation. This location has it all: it's just steps away from the Great River Boat Ramp, a beach at Waquoit Bay, the Mashpee town beach, South Cape Beach, and both Popponesset Marketplace and Mashpee Commons. The neighborhood also has private areas with a playground for kids and a place perfect for volleyball, fishing and kayaking.

4.95 out of 5 average rating, 22 reviews

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

May 26-27, 31; June 3-4 are $199/night July 26-Aug 1 available at $1575/night (6 nights) Please email me to discuss these dates and options. Memorial Day rentals commence: Saturday Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. Our home overlooks the un-heated pool (opens May 15th), beach and bay. We include: Bikes, Kayaks, and a Barnstable beach pass. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six (6) adult guests. (other group size options available).

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 serene garden setting features a stone pathway winding through lush greenery. A figure in traditional attire stands amidst the foliage, bordered by various plants and a bird feeder. The area is accented with gravel and stone elements, creating a tranquil atmosphere.

4.84 out of 5 average rating, 117 reviews

New Seabury Retreat. Butchart Gardens' Inspired

A Tranquil Escape in New Seabury 5-Bedroom Cape Cod Home with Garden Oasis Inspired by Butchart Gardens Welcome to your year-round retreat, tucked away in a private setting among towering oaks in the heart of New Seabury, Cape Cod. This beautifully maintained 5-bedroom home offers the perfect blend of coastal charm and modern comfort. Step outside into your own slice of paradise—a professionally designed garden inspired by the world-famous Butchart Gardens of Victoria, British Columbia.

4.9 out of 5 average rating, 30 reviews

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.

Home in Madaket

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.

4.92 out of 5 average rating, 13 reviews

Newly Renovated Huckleberry House - 6 Bed in Town

Newly renovated! This historic home is just steps away from Downtown, making it the perfect home-base for your group. This 6 bedroom, 4 bathroom home can accommodate 15 guests. Amenities include an oversized yard (rare for a location in Town), outdoor shower, custom playhouse, and brick patio for grilling. Inside, the house offers classic Nantucket architecture with coastal-inspired decor and multiple entertainment areas. *Draft photos posted - new photos with art hung are coming!*

4.94 out of 5 average rating, 229 reviews

A gravel pathway winds through a lush forest, flanked by tall trees and dense greenery. Brightly colored signage can be seen attached to some trees. A narrow dirt path leads off to the right, inviting exploration.

Guest suite in Mashpee

Cottage on the Bay

Welcome to our charming Cape Cod cottage nestled on the tranquil shores of Popponessett Bay! This cozy space has been cherished by our family for generations, offering a quintessential Cape Cod experience. Located on a private point, our cottage provides stunning bay views and a serene atmosphere perfect for relaxation. Conveniently situated between Popponessett Market Place (2miles) and Mashpee Commons (2.6miles) you're close to shopping, dining, and entertainment options.

5 out of 5 average rating, 35 reviews

The two-story home is situated along a quiet street, enhanced by natural light and surrounded by lush greenery. A front porch with railings is visible, offering a welcoming entrance. Nearby structures and mature hedges contribute to the charming neighborhood atmosphere.

Home in Siasconset

‘Sconset Charmer, steps to beach

Adorable and equipped 2 BR 1.5 bath home nestled in the heart of ‘Sconset Village. Short stroll to beach, Bluff Walk, market and restaurants. New living and dining room furniture, new beds and bedding. Front and side decks with outdoor furniture, grill, and smokeless fire pit. Gas-burning stove fireplace makes for cozy off-season retreat. Extra high speed internet, extended cable package and Roku smart TV. One parking space, and easy shuttle access into ACK center.

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!

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.

4.91 out of 5 average rating, 35 reviews

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

Newly renovated home in the heart of New Seabury! You'll love the breathtaking golf course view from our backyard, where you can enjoy a heated saltwater pool, a large deck, and a patio with a fire pit. Our spacious home offers a fully equipped kitche, a coffee bar and plenty of open space for family gatherings. 5 minutes from the stunning South Cape beach, and surrounded by attractions like the Children's Museum and Mashpee Commons.

4.9 out of 5 average rating, 153 reviews

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.

Apartment in Nantucket

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 Siasconset pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

An aged stone monument stands prominently in a sunny park. Surrounding it are well-maintained trees and shrubbery, while traditional shingled buildings are visible in the background, reflecting the historic charm of the area.

5 out of 5 average rating, 9 reviews

Historic Downtown Nantucket Home - Up to 12 Guests

The charming townhouse exterior features a two-story design with dormer windows and a textured shingle facade. Vibrant hydrangeas enhance the landscaping, blooming against the backdrop of a brick pathway leading to the dual entrances. A clear blue sky serves as a backdrop.

4.91 out of 5 average rating, 11 reviews

Chic townhouse, walk to town

A charming historic house with a shingle exterior is observed. The front porch features a light blue door and a quaint railing adorned with white flowers. Two windows are situated on the facade, allowing natural light to enhance the warm tones of the structure.

4.78 out of 5 average rating, 9 reviews

Beautiful 3-bedroom house in Nantucket

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

A charming two-story house features a wraparound porch with large windows, allowing for plenty of natural light. A well-maintained garden surrounds the home, and a gravel driveway leads to the entrance. An American flag is displayed, enhancing the welcoming atmosphere.

4.83 out of 5 average rating, 30 reviews

Updated house .3 miles to beach peaceful

Chappaquidick contemporary cottage with sauna

A two-story house is situated among trees with fresh green leaves. A wooden staircase leads to the entrance on the upper level, while a gravel driveway provides access to the home. The exterior features dark wood siding complemented by teal trim.

5 out of 5 average rating, 24 reviews

Chappy Beach House

A landscaped garden surrounds the exterior of the home, featuring a variety of green plants and vibrant orange flowers. A decorative birdbath stands amidst the foliage, accentuating the natural beauty of the outdoor space.

4.89 out of 5 average rating, 44 reviews

New Seabury French Chateau Inspired

Pet-friendly home rentals with a pool

5 out of 5 average rating, 14 reviews

Nantucket home with Pool!

A comfortable seating area is presented on a wooden deck, facing a clear blue pool. Sunlight reflects off the water, while lush greenery frames the space, providing a sense of privacy. A stylish patterned rug enhances the inviting outdoor atmosphere.

4.77 out of 5 average rating, 26 reviews

Pool! Large 4 bedroom+bunk room mid-island!

An outdoor patio area features a large red umbrella shading a dining table surrounded by six decorative chairs. A gas grill stands nearby, with vibrant flowering shrubs adding a natural touch to the serene environment.

Condo in New Seabury

4.5 out of 5 average rating, 20 reviews

2BR dog-friendly 2-story condo with community pool

A heated in-ground pool is surrounded by a spacious patio, featuring a dining set with green chairs and an umbrella for shade. Lush trees are visible in the background, providing natural cover and enhancing the outdoor space's open feel.

5 out of 5 average rating, 3 reviews

Private home with heated pool near the beach!

A private pool area is surrounded by lush greenery and landscaped gardens. An attached hot tub is visible next to the pool. Lounge chairs are arranged on the concrete patio beneath a shaded umbrella, providing a comfortable space for relaxation.

5 out of 5 average rating, 4 reviews

4BR house with private pool, cabana, AC, & grill

4.67 out of 5 average rating, 3 reviews

Home in Mashpee

New place to stay

Private pool, hot tub, minutes from beach!

Private, pet-friendly home rentals

Home in Cotuit

Shoestring Bay Views Walk 2 Water, Kayak & Garden

A spacious living area features a large sectional sofa arranged around a coffee table, with natural light illuminating the space. A stone fireplace is present, complemented by a flat-screen television mounted on the wall. Adjacent is a dining area visible in the background.

Home in Cotuit

4.89 out of 5 average rating, 9 reviews

Spacious Beach House in Cotuit

A single-story house features a shingled exterior with green shutters and a welcoming front entrance. The front porch includes steps leading to a door, framed by lush greenery and an expansive lawn.

4.71 out of 5 average rating, 49 reviews

Cozy house for 4, 5 min walk from beach

A private outdoor deck features colorful striped chaise lounges and a round table with chairs. Potted flowers add a touch of nature, while the surrounding greenery provides a tranquil setting. Natural wood flooring enhances the inviting atmosphere of the outdoor space.

Cottage in Nantucket

4.8 out of 5 average rating, 15 reviews

Sweet Private Cottage nr beach/bike/bus ~ Dogs ok!

The exterior of the home features a wooden façade with a sloped roof. Two light blue chairs are positioned on a wooden deck, which is accessed by steps leading down to a grassy area surrounded by trees. A red star decoration is mounted on the wall.

5 out of 5 average rating, 3 reviews

Updated Chappaquiddick Home For Rent

An aerial view captures a cozy cottage surrounded by lush greenery and a serene waterfront. The calm water reflects the clear blue sky, and the distant shoreline is lined with gentle waves. The natural landscape invites exploration and relaxation.

4.91 out of 5 average rating, 11 reviews

Waterfront Oasis

The exterior of a half-cape house built circa 1850 is displayed, featuring traditional siding and a sloped roof. Lush green shrubbery surrounds the property, complemented by white fencing. A flowering plant adds a touch of color near the entrance, showcasing the home's quaint appeal.

Cottage in Nantucket

4.7 out of 5 average rating, 27 reviews

In-Town 1850s Cottage

A quaint cottage is set back from the road, framed by a white picket fence and lush green grass. Two evergreen trees provide natural shade, while windowed walls reflect the surrounding landscape. The exterior features a light gray shingled facade and a welcoming entrance with a blue door.