Family-friendly holiday rentals in Nantucket

Sweet Dreams Romantic Guest Cottage.....'Sconset

This Cottage is Limited for a Couple!!! Non-Smoking-no pets Check In 3 pm luggage drop off is fine Check Out 10:30 Sweet Dreams is a lovely two-story free-standing building next to my home, outside table & Gas Grill, Beach chairs-towels also supplied. The center village & beach 4-minute walk Some evenings you can fall asleep to the soothing sound of the ocean waves crashing ashore!! (depending on wind) Central heat/air, Flat screen TV/Gas grill/ Patio table chairs A little slice of heaven!!

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.

Entire Townhome in Madaket

Enjoy the best sunsets on Nantucket from the deck of our cozy 3 story townhome. We are located on a quiet cul de sac next to Wild Goose Cove, a half mile to Starbuck beach and less than a mile to Madaket Beach and Millie's restaurant. Also close to the Wave Bus stop & bike path, which make it easy to get around. It's a bright and breezy end unit. There are two decks for relaxing and socializing. Recently renovated, the unit is fully furnished and equipped for a memorable summer getaway.

Spouter Cottage

A unique upside down two bedroom cottage with a deck and a view of the Harbor. A curated space with antique beams, handcrafted doors, flooring and cabinetry, antiques and fine art. It all lends a vintage feel to an up to date with all the amenities home. There is a private small side yard and garden with outdoor grill and seating. This is not a party house, it’s a sensitive house, I live right on the property, adjacent to the cottage, you have full privacy but no shenanigans.

Designer Cottage just off Main Street

Modern cottage with a perfect location (one block off Main Street). Comfortable space for two. Well-equipped (with gas fireplace & AC), open floor plan, living room/galley kitchen/dining/ full bath with WD, queen BR and 1/2 bath upstairs. Private outdoor deck with outdoor shower too! We care about the details like ironed sheets, good pillows, new mattress, & fluffy towels, everything you need for a carefree vacation! We don't provide parking & discourage bringing a car.

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!

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.

Private Beach Cottage in Historic Sconset!

Charming one bedroom beach cottage in Codfish Park, Siasconset Local Realtor says "You have climbing roses and hydrangeas in the summer, you can walk up the shell path up to the Sconset Market — it's Norman Rockwell at its finest, a really magical Sconset spot," he said. "Wake up in the morning, walk up to the store for your coffee and the paper, then take a little stroll down to the beach, which you can see from the property!”

BRIGHT & STYLISH 2BD,1BT with deck & BBQ

Newly renovated 2BD, 1BT first floor in convenient mid island area that is great for a family or small group of friends. Great living area,TV. Dining table and chairs, laundry W/D, fully equipped kitchen(fridge/freeze, oven, microwave, coffeemaker, toaster), window units A/C. Could sleep up to 5 people. Deck with outdoor shower and BBQ. Parking for 1 car.The bus stop is right on the corner.

The Mermaid Suite, walk to Beaches, 15 min to town

The Mermaid Suite is an efficiency apartment within walking distance to Nobadeer, Stones and Fisherman's Beaches. Well equipped with queen bed, desk, galley kitchen, full bath, outdoor shower, private entrance, linens, towels, parking, a/c and heating, etc. The Studio is a spacious 400 sq. ft. Secluded, private location. Comfortable, Cozy, and convenient.

Outside of Town Cottage (Renovated 2025)

Mid-Island Home . 1/2 mile to downtown . Cottage renovated in '25 . NEW- Appliances, Furniture, Beds, Shower, TV, Flooring, Carpet, Paint . Sleeps 4 comfortably . No Pets, please . The WAVE bus stop at end of Street . Outside Shower . 1 Mile to Children's Beach, 2.5 miles to Cisco beach, 2 Miles to Surfside beach, 2.5 miles to Miacomet beach.

Private 1 Bedroom Walk-Out Basement Apt

Convenient mid island location. We are within walking distance to town, Surfside Beach and numerous restaurants. The bus stop is right on our doorstep and the bike path is directly across the street.