Pet-friendly holiday rentals in Nantucket

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.

Spectacular Waterfront Townhouse

Step right out to the water! This amazing waterfront townhouse overlooks Nantucket Harbor and offers splendid views. This unique corner townhouse has two expansive deck spaces and beach views from the living space. The renovated townhouse offers 2 upstairs bedrooms, 2.5 baths, and 2 sleeper couches. The upstairs master has a balcony overlooking the harbor and all windows with waterfront views. Location is prime. Rental comes with 1 parking spot and AC units. July Sat-Sat Weekly rental available

Exquisite Oceanside Madaket Getaway

Location-Location-Location! The best way to experience Madaket Beach, Smith's Point, and More! Beach access at your finger tips. Take in ocean views and sunsets. Enjoy the perfect blend of modern comforts/upgrades and preservation of details that evoke the history and spirit of this seafaring island. Beautiful original hardwood floors, tasteful touches of a bygone nautical era, and more pair with exquisite furnishings, elegant kitchen and living room appliances, hydrangea gardens, and more.

Two-Bedroom Luxury Condo

This two-bedroom suite is located in a restored historic building in Town and the only unit in the building accessed through the original front door. Recently refurbished, the unit elegantly combines Nantucket style with modern accents and upgrades. Minutes from Main St, walking distance to Steps Beach, and a block from free public transportation. There is a shared patio in the back of the building with a gas grill and outdoor furniture. Completely new furniture/mattresses and upgraded HVAC!

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.

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.

Martha's Vineyard Cottage: Walk to Town and Beach

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

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.

Quiet Cul-de-Sac near Sconset

Located on a quiet cul-de-sac across from Sconset Golf Club, this classic Nantucket home offers a peaceful retreat with views of Sankaty Head Lighthouse. Just a ten-minute bike ride to Sconset village and a short walk to the free island shuttle. Filled with natural light, the home features a spacious yard, outdoor shower, and all the essentials for an easy summer stay—beach gear, bikes, and more included.

Katama Barn

Selected dog friendly, Immaculate beach house this is the perfect property to bike to the beach and then to dinner in Edgartown. 1.2 miles from beach South Beach, and 1 mile from Edgartown's Main Street. Outdoor shower, large private yard.heated bathroom floors, a/c, heat, modern kitchen, brand new appliances/washer dryer, sleeping loft, and separate storage loft. Location, location, location.

Entire Home w/ yard: Pet Friendly & Renovated

New master suite and outdoor shower added for summer 2026! Fully fenced in back yard with irrigated grass. This pristine property offers access to all of Nantucket's amenities, bike to town or the beach! Moments from multiple shops, restaurants and jogging/bike paths. The home has been completely updated giving the whole family space to enjoy. Off-street parking for multiple vehicles.

Beautiful home in Naushop

A well appointed Nantucket house for 10 guests, centrally located on the island. There is easy bike or car access to town and beaches. Although most families would want to visit during late spring, summer, or early fall, the property is available throughout the year. We have gone to great lengths to make the home comfortable and accommodating to our guests’ wishes.