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Nantucket’s Luxury Vacation Rentals


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Fisher Real Estate
Nantucket Luxury Vacation Rentals

Please note that Nantucket 2022 vacation rentals are in high demand and many homes, including these luxury rentals, have many weeks already booked for summer 2022. We are continually adding new rental inventory so please reach out to us directly for additional options.  Also, we are in the process of confirming 2022 rates with homeowners so rates and availability are subject to change. 

For those looking for the best vacation rental homes on Nantucket, these luxury properties are available to lease through Fisher Real Estate. Whether you are seeking high-end construction, a private pool, golf range, movie theater or house with all en-suite bedrooms, these 19 homes are a great place to stay on the island. Which one is your favorite?

4 Old Mill Ct

This light-filled and open floor plan 6 bedroom, 6 bathroom property with 2 bedroom, 2 bathroom cottage has a weekly rate, in peak season, of $59,500. The interior features a master suite on each level while the outdoor spaces feature a heated, in-ground pool and spa with stone-paved terraces which are complimented by an outdoor gas fire pit for chilly New England evenings. Link to rent.

64 Cliff Rd

‘Whale of a Time on Cliff’ is one of the most meticulously maintained vacation homes on the island. The property features a recently constructed (2017) 8 bedroom, 8.5 bath home with pool and fire pit, and is conveniently located in the highly desirable Cliff area.  It comes at a weekly rate, in peak season, of $50,000. Link to rent.

21 Woodbine St

This beautiful, custom-designed home has just been completed and is bright, airy, modern, and has a weekly rate, in peak season, of $50,000. Link to rent.

6 Capaum Pond Rd

This custom-built J. Graham Goldsmith home was designed to accommodate the needs of multigenerational families & features over 7,500 sq ft of living space, custom millwork, designer tile, antique chestnut flooring, pool, spa, bluestone patio, BBQ area & home theater. This house sits high on the Cliff and has it all and is only moments from town and the beaches. You can rent 6 Capaum Pond Rd at a weekly rate, in the peak season, of $48,000. Link to rent.

3 Cliff Lane

Located in the desirable Cliff neighborhood, 3 Cliff Lane offers easy access to the bike path, Steps Beach and town. Two beautifully executed structures offer a large, heated infinity pool with great outdoor space, two covered sitting areas with an outdoor fireplace and an expansive yard. Rent it at a weekly rate, in peak season, of $45,000. Link to rent.

30 Madequecham Valley Rd

Enjoy peace and tranquility in this spectacular oceanfront home in Madequecham at a weekly rate, in peak season, of $44,000. With open and airy interiors, a large pool and just steps from the beach you have everything needed for a unique Nantucket experience. Link to rent.

5 Cudweed Rd

This fabulous Nantucket summer vacation rental is tucked away on a large private piece of land just minutes from Cisco Beach. It can be rented at a weekly rate, in peak season, of $40,000. Link to rent.

66 Cliff Rd

Enjoy a high-end 7 bedroom Cliff Road rental offering all of the amenities for rest and relaxation available at a weekly rate, in peak season, of $40,000. Link to rent.

74A Madaket Rd

Available at a weekly rate, in peak season, of $40,000 this home, just one mile from Main Street, is perfect for large families and groups and sits on two sweeping acres of conservation land. High-end finishes and a spacious floor plan allow for airy and naturally lit rooms that seamlessly transition to outdoor spaces. Exterior living includes a spacious bluestone patio surrounding the heated saltwater pool, a lush rolling yard, and a covered back deck. Link to rent.

21 Quidnet Rd

Situated on 4 acres and high above the Quidnet Moors, 21 Quidnet Road is an exceptional family compound with sweeping views of the Atlantic Ocean, Sankaty Lighthouse, and Nantucket’s Eastern Shore. Available at a weekly rate, in peak season, of $40,000, “High Point” features 6 bedrooms, 6.5 baths, a heated saltwater pool, outdoor spa, fire pit, beautifully landscaped lawns, walking trails, and easy access to Sesachacha Pond beaches. Link to rent.

1 Pochick Ave

Accessible from Surfside Avenue down a long wooded drive, this bucolic 5.7 acre hideaway is nestled within over 30 acres of conservation land. This sprawling estate was reimagined for 2022 with a major remodeling from Carolyn Thayer Interiors, new audio/visual equipment with Sonos and the opening of its celebrated private vegetable gardens, now professionally managed to grow food for residents. It’s available at a weekly rate, in peak season, of $40,000. Link to rent.

45 Hummock Pond Rd

This recently completed (2021) home is set in a six-and-a-half-acre luxury community composed of elegant, high-design homes. Available at a weekly rate, in peak season, of $35,000, this fabulous five-bedroom property features three levels of finished space, three living rooms, an office, and multiple en suite bedrooms. It boasts a gracious screened-in porch, outdoor dining/living area with grill and outdoor fireplace, and is just steps away from the pool and gym. Link to rent.

52 West Miacomet Rd

This fabulous, one-of-a-kind waterfront property has private stairs to the beach and wonderful views of the ocean, dunes, and moors. Over the 2021 winter, they will be adding a new pool and fire pit! Beautiful amenities are located throughout the home and there are ocean views from the second-floor decks. You can rent this property at a weekly rate, in peak season, of $35,000. Link to rent.

122 Tom Nevers Rd

At a weekly rate, in peak season, of $35,000, this exceptional waterfront estate features luxurious construction and an ocean-side pool. This beautifully appointed 5,500 sq ft, 5 bedroom home has a bright, open floor plan with soaring ceilings and stunning water views from every room. Link to rent.

7 Judith Chase Lane

Originally built in 1746 this family estate was completed in 2018 after a three-year historic restoration project by Georgantas Design and Development. With uncompromising quality, style, and luxury in mind, this property consists of a main house and a separate guest house, which can be rented individually or concurrently. You can rent the main house at a weekly rate, in peak season, of $35,000. Link to rent.

28 Bosworth Rd

This is a beautiful 6 bedroom estate in Tom Nevers perfect for the family who loves to embrace the outdoors. Available at a weekly rate, in peak season, of $34,500, the home includes a pool, tennis court, gardens, a great grilling area complete with a pizza oven and a small deck towards the edge of the property for even more views. The interior of the home is well planned to space out sleeping quarters but offers a great open kitchen and dining area for entertaining and gathering. Link to rent.

78 Polpis Rd

A 7 bedroom property sleeping 15 people between the main house and cottage, this property offers the best of the very best for your vacation getaway. This home has been sited to maximize a 180-degree panoramic view of Town and Coatue. Lawn space for games, expansive decks for lounging, a fire pit for those cool nights stargazing and a pool with an immersed jacuzzi, you will leave this vacation completely unplugged and relaxed. This house can be rented at a weekly rate, in peak season, of $32,000. Link to rent.

3 Old Farm Rd

Surrounded by 20 acres of dedicated open spaces, this property provides a serene respite from the hustle and bustle of city life. The property has been impeccably designed, furnished, and decorated, boasting 6 bedrooms, 6+ bathrooms, with over 6,000 square feet of living space. At a weekly rate, in peak season, of $30,000, this home could be your Nantucket oasis! Link to rent.


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Fisher Real Estate