59 South Shore RdSurfside

Contact an Agent $55,000/wk Rental #3952 ROC Number: C0421841970
Request a Rental- Bedrooms: 9
- Bathrooms: 9.5
- Capacity: 18
- Air Conditioning
- Beach Chairs
- Beach Towels
- Blender
- Cable TV
- Deck
- Internet Access
- Microwave
- Parking
- Patio
- Patio/Deck Furniture
- Porch
- Swimming Pool
- Yard
Luxurious Nantucket Vacation Rental with Pool, Entertainment Wing, and Prime Central Location
This stunning Nantucket vacation rental is a centrally located compound offering resort-style amenities and exceptional design—perfect for unforgettable summer gatherings. Ideally situated near everything essential to island living, the property sits on the bike path to the South Shore and is close to Miacomet Pond, mid-island shopping, and NRTA stops.
Flooded with natural light, the home features soaring vaulted ceilings, a state-of-the-art primary kitchen, and a second commercial-grade kitchen—making it an ideal choice for hosting and entertaining. The outdoor space includes a beautiful pool, free-standing pool house, and a sunny courtyard designed for relaxation and al fresco dining.
The east wing of the compound is a showstopper: an entertainment center complete with a full bar, shuffleboard, billiards table, wood stove, and a spacious seating area that opens to the porch and courtyard—seamlessly blending indoor and outdoor living.
With its luxurious layout, incredible amenities, and convenient location, this compound stands out among Nantucket summer rentals as one of the island’s most extraordinary vacation rentals on Nantucket for families, groups, or those looking to indulge in the ultimate island escape.
First Floor Description
Enter this luxurious Nantucket summer rental through the spacious mudroom on the west wing of the home. Head into the central, light-filled, living, dining, and kitchen area to find beautiful vaulted ceilings, a spacious kitchen with an island and bar seating for four, a breakfast nook, a coffee bar, and of course, the finest kitchen appliances. The cozy living area is appointed with a large sectional couch and chairs, an electric wood stove, a flat-screen television, and doors opening up to the porch and pool area. On the other side of this open-concept living area, find a dining table for eight and doors revealing the courtyard and additional outdoor dining and lounging space. Pass through office space, a light-filled dining room with enough space for a large gathering, with an adjacent bathroom appointed with a glass-enclosed tiled shower, to reach the east wing of the home. The east wing entertainment center offers ample space for activities with a full bar, live-band set up, shuffleboard, billiards table, wood stove, and a seating area, with doors opening up to an outdoor porch and the courtyard. Beyond the entertainment area is the commercial-grade catering kitchen with multiple refrigerators and freezers and a commercial range. Completing the first floor is a powder room.
Second Floor Description
On the west wing of this home, head upstairs to the private primary bedroom. At the top of the stairs, find a spacious ensuite bathroom with a beautiful freestanding bathtub, a glass-enclosed tiled shower, double vanity, and access to a private outdoor balcony overlooking the courtyard. To the right of the stairs find the bedroom, appointed with a king bed, two walk-in closets, and an indoor balcony that overlooks the central living and dining spaces on the first floor. Access the other half of the second floor by the spiral staircase to find a sitting area overlooking the kitchen and living room, and additional office space.

Property Rates.
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Starting Rate Apr - 27, 2025 Call for Rates May - 04, 2025 Call for Rates May - 11, 2025 Call for Rates May - 18, 2025 Call for Rates May - 25, 2025 Call for Rates Jun - 01, 2025 Call for Rates -
Starting Rate Jun - 08, 2025 Call for Rates Jun - 15, 2025 Call for Rates Jun - 22, 2025 Call for Rates Jun - 29, 2025 Call for Rates Jul - 06, 2025 $55,000 Jul - 13, 2025 $55,000 -
Starting Rate Jul - 20, 2025 $55,000 Jul - 27, 2025 $55,000 Aug - 03, 2025 $55,000 Aug - 10, 2025 $55,000 Aug - 17, 2025 $55,000 Aug - 24, 2025 $55,000 -
Starting Rate Aug - 31, 2025 $55,000 Sep - 07, 2025 Call for Rates Sep - 14, 2025 Call for Rates Sep - 21, 2025 Call for Rates Sep - 28, 2025 Call for Rates Oct - 05, 2025 Call for Rates -
Starting Rate Oct - 12, 2025 Call for Rates Oct - 19, 2025 Call for Rates Oct - 26, 2025 Call for Rates Nov - 02, 2025 Call for Rates Nov - 09, 2025 Call for Rates Nov - 16, 2025 Call for Rates