**Availability & rates are subject to change.






Starting at $3,600

3 Green Hollow Road

  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
  •  3 Green Hollow Road
Bedrooms: 5      Bathrooms: 3  Sleeps: 10      Area: Tom Nevers   
Beautiful and meticulously maintained upside down home on three private acres. Recently completely renovated and decorated and furnished. Light and airy sun filled interior with cathedral ceilings. (...)

Starting at $6,500

38 Pleasant Street

  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
  •  38 Pleasant Street
Bedrooms: 6      Bathrooms: 6  Sleeps: 10      Area: Town   
Prime Nantucket Town location- this 6 bedroom, 5 ½ bathroom home was recently renovated and is located close to Main Street, shops and restaurants. The main house comprises 5 bedrooms and a 6th (...)

Starting at $12,000

1 Derrymore Road

  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
  •  1 Derrymore Road
Bedrooms: 5      Bathrooms: 6  Sleeps: 12      Area: Cliff   
New custom home off Cliff Rd with in-ground salt water pool and infinity spa. This home was built for entertaining and family gatherings. Enter to a large comfortable living room with fireplace. An (...)

Starting at $5,000

32 Monomoy Road

  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
  •  32 Monomoy Road
Bedrooms: 6      Bathrooms: 6  Sleeps: 12      Area: Monomoy   
This property features extraordinary views of Nantucket Harbor and town and has undergone a masterful transformation for the 2016 season. An upside down house, it has six bedrooms and five and (...)

Starting at $1,000

13 Longwood Drive

  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
  •  13 Longwood Drive
Bedrooms: 3      Bathrooms: 3  Sleeps: 8      Area: Tom Nevers   
A serene setting with a three bedroom and three and a half bathroom Upside Down house located in tom Nevers. Just a few miles from the quaint town of Sconset. First floor: Den with sleep sofa and (...)

Starting at $9,500

34 Fair Street

  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
  •  34 Fair Street
Bedrooms: 4      Bathrooms: 4  Sleeps: 8      Area: Town   
Attractively updated 4 Bedroom & 4 Bath Antique near Main Street. From the front entry, to the right is living room with comfortable seating. On the left is a cozy Den/Library with large Flat Screen (...)

Starting at $3,500

26 Codfish Park Rd

  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
  •  26 Codfish Park Rd
Bedrooms: 2      Bathrooms: 1  Sleeps: 4      Area: Sconset   
Adorable 2 bedroom, 1 bath Codfish Park cottage just steps from the beach.The queen bedroom and the bedroom with two twin beds share a hall bathroom with a combination tub/shower.The living room has (...)

Starting at $5,500

4 Traders Lane

  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
  •  4 Traders Lane
Bedrooms: 4      Bathrooms: 3  Sleeps: 7      Area: Town   
Heart of the Historic District in an equisite neighborhood near Main Street on a quiet lane three blocks to Nantucket's downtown shopping and restaurants. The Captain Peleg Bunker House, circa 1750, (...)

Starting at $5,000

14 New Mill Street

  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
  •  14 New Mill Street
Bedrooms: 5      Bathrooms: 5  Sleeps: 10      Area: Town   
This newly renovated five bedroom, four-and-one-half bath antique is the perfect marriage of Nantucket charm and all the modern amenities - including high end appliances, furnishings, and (...)

Starting at $5,500

54 Fair Street

  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
  •  54 Fair Street
Bedrooms: 5      Bathrooms: 4  Sleeps: 10      Area: Town   
Supremely located comfortable and classic beach house with both direct views and access to one of the islands best swimming beaches. Newly renovated eat- in kitchen equipped with custom cabinetry, (...)

Starting at $5,500

9 Judith Chase Lane

  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
  •  9 Judith Chase Lane
Bedrooms: 4      Bathrooms: 3  Sleeps: 8      Area: Town   
This home is located on a quiet lane in Town. Four bedrooms, three baths. First floor: Foyer leads into a living room/dining area, kitchen and family room with french doors out to private patio area (...)

Starting at $19,500

5 Sandy Drive

  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
  •  5 Sandy Drive
Bedrooms: 4      Bathrooms: 3  Sleeps: 8      Area: Brant Point   
Lovely family vacation home located on one of the most highly sought after streets in desirable Brant Point. Large lawn, wonderful covered porch perfect for lazy Nantucket summer days, grilling and (...)

Starting at $9,000

11 Hulbert Avenue

  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
  •  11 Hulbert Avenue
Bedrooms: 5      Bathrooms: 3  Sleeps: 8      Area: Brant Point   
Large two story five bedroom house with views of the harbor. Great in town location close to shops, beaches and resturants. Brant Point is one of the most desirable areas of the island. Great for (...)

Waterfont: Yes
Starting at $3,000

23 East Lincoln Avenue

  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
  •  23 East Lincoln Avenue
Bedrooms: 4      Bathrooms: 2  Sleeps: 8      Area: Brant Point   
Light and airy 4 bedroom cottage in the heart of Brant Point. Lovely furnishings, three separate living rooms, new granite kitchen with stainless appliances and a private garden with patio make this (...)

Starting at $8,000

10 Gingy Lane

  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
  •  10 Gingy Lane
Bedrooms: 5      Bathrooms: 6  Sleeps: 10      Area: Town   
This custom designed home, built in 2013, offers three levels of living space as well as covered porches and a patio. The first floor has a high end kitchen that opens into the open dining and (...)

Starting at $4,500

43 Chuck Hollow Rd

  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
  •  43 Chuck Hollow Rd
Bedrooms: 4      Bathrooms: 4  Sleeps: 8      Area: Tom Nevers   
Wonderful house with ocean views to delight. Open floor plan with kitchen, family room and dining space for optimum family time on vacation. First floor has a queen bedroom with a half bath in it as (...)

Starting at $2,750

6 Lyons Lane

  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
  •  6 Lyons Lane
Bedrooms: 4      Bathrooms: 2  Sleeps: 8      Area: Tom Nevers   
Casual summer style four bedroom, two bath home with private yard, easy access to bike friendly roads in Tom Nevers East and a short distance to the beach. Home offers a variety of living spaces (...)

Starting at $23,000

2 Sandy Drive

  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
  •  2 Sandy Drive
Bedrooms: 5      Bathrooms: 5  Sleeps: 12      Area: Brant Point   
This stunning 5 bedroom,5.5 bath home was completed in the fall of 2015. It offers gorgeous views of Nantucket Sound and beach access across the street. Outstanding Brant Point Location near Jetties (...)

Starting at $14,500

82 Orange Street

  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
  •  82 Orange Street
Bedrooms: 5      Bathrooms: 4  Sleeps: 10      Area: Town   
The first floor of this spacious in town rental home boasts the main living areas, two sitting areas, a dining area, a fully equipped kitchen with center island and doors to a lovely porch perfect (...)

Starting at $1,200

68 Washington Street

  •  68 Washington Street
  •  68 Washington Street
  •  68 Washington Street
  •  68 Washington Street
  •  68 Washington Street
  •  68 Washington Street
  •  68 Washington Street
Bedrooms: 1      Bathrooms: 1  Sleeps: 2      Area: Town   
Scallop shack grown into a quaint one bedroom cottage on a soft sand beach. Marvelous Harbor views. This is not a late fall rental(oct-nov etc)

Waterfont: Yes
Starting at $2,415

23C Rhode Island Avenue

  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
  •  23C Rhode Island Avenue
Bedrooms: 2      Bathrooms: 1  Sleeps: 6      Area: Madaket   
Wonderful Smith's Point Beach Cottage. Views of Madaket Harbor. One story cottage. Open living, dining, kitchen area, two bedrooms, one bathroom. Large deck looking out at waterviews. Walk to (...)

Waterfont: Yes
  •  70 Wauwinet Road (14 Fargo Way)
  •  70 Wauwinet Road (14 Fargo Way)
  •  70 Wauwinet Road (14 Fargo Way)
  •  70 Wauwinet Road (14 Fargo Way)
  •  70 Wauwinet Road (14 Fargo Way)
  •  70 Wauwinet Road (14 Fargo Way)
Bedrooms: 4      Bathrooms: 3  Sleeps: 10      Area: Wauwinet   
Fabulous location, beachfront. Waterviews from every room.Secluded and private at the head of Wauwinet Harbor. Virtual Tour http://view.paradym.com/viewer/fusion/1179204/sk/301/prt/10003

Waterfont: Yes
Starting at $4,950

37 Boulevarde

  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
  •  37 Boulevarde
Bedrooms: 3      Bathrooms: 3  Sleeps: 8      Area: Surfside   
Entry way into large living room with a gas fireplace, wonderful kitchen with granite counter tops. There is a den (queen sofa bed) also on this floor with TV and VCR. The second floor consists of (...)

Starting at $5,000

14 South Mill Street

  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
  •  14 South Mill Street
Bedrooms: 5      Bathrooms: 5  Sleeps: 14      Area: Town   
Come down a private drive to this comfortable in-town home with all the conveniences of a first class resort. It is a five minute walk to shops on Main Street. The large bluestone patio has glass (...)

Starting at $3,350

14 A Fargo Way- Boat House

  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
  •  14 A Fargo Way- Boat House
Bedrooms: 2      Bathrooms: 2  Sleeps: 4      Area: Wauwinet   
Waterfront Upside down house! Lower level has an entry foyer, large playroom, laundry room, guest bedroom with bath. The upper level has a living room, kitchen/dining area, cathedral celings and a (...)

Waterfont: Yes