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Massachusetts | Cape Cod

Second Wind

Name: Second Wind
Brand: KEY.co

10 bedrooms·10.5 bathrooms·24 guests·5900 sq/ft

Views of the water

Pool

Hot tub/Jacuzzi

Along the picturesque shores of Town Cove, this expansive Orleans estate offers three beautifully updated residences across 1.3 waterfront acres, with space for groups of up to 24. The Main House provides generous gathering areas, an updated kitchen, multiple dining spaces, and an inviting enclosed porch overlooking the grounds. The Carriage House adds a second full kitchen, dining area, comfortable lounge spaces, and private accommodations, while the Guest House offers another beautifully finished kitchen, welcoming living spaces, and captivating views of Town Cove. Outdoor living revolves around a large heated pool and spa, poolside outdoor kitchen, fire pit, spacious lawn, and direct access to Town Cove for kayaking and paddleboarding. The Guest House also features its own hot tub overlooking the water, creating another peaceful place to unwind. Orleans Center’s restaurants and shops are within walking distance, while Nauset Beach and Skaket Beach are less than a five-minute drive away, making this remarkable waterfront estate an exceptional setting for memorable Cape Cod getaways.

Our promise

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KEY Curation Notes

An Orleans estate on Town Cove, sleeping 24 across three houses on a single property in the heart of Orleans Village. The main house has five bedrooms and five and a half baths, the carriage house has two bedrooms and two and a half baths, and the guest house has three bedrooms and three baths.

Pool and spa open Memorial Day through Columbus Day, with an outdoor kitchen under a pergola, a fire pit, and multiple grilling stations between the structures. The pool deck overlooks Town Cove — sunset cocktails by the fire pit with water views is the defining experience here.

Town Cove access with owner-provided kayaks and SUP boards — launch from the property and explore Nauset Cove and Nauset Marsh. There's a town boat ramp next door; bring your own boat and motor directly to Nauset Beach.

Leave the cars in the driveway — Orleans Village center is walkable, with the Rock Harbor Grill, shops, and the Firebirds Cape League games all within easy reach. The kitchen in the main house has two refrigerators, two dishwashers, and a butler's pantry with wet bar and beverage refrigerator, purpose-built for large groups.

Three large seating areas spread across the main and carriage houses give a group of 24 enough space to gather or disperse as needed. Multiple laundry areas, central AC throughout, high-speed Wi-Fi. Pool is open Memorial Day through Columbus Day. Linens and bed making included. Pets considered up to 25 lbs. Weddings not permitted. KEY.co can arrange grocery delivery so you arrive fully stocked.

Amenities

Indoor

Air conditioning

Dryer

Internet

Washer

Outdoor

Outdoor grill

Heated pool

Hot tub/Jacuzzi

Pool

Corn hole boards

Misc

Beach chairs

Kayak(s)

Stand-up paddle board(s)

Beach towels

Boat friendly

Elevate your stay with add-on services

Book a home, then customize your experience. From beach gear delivery to pre-arrival groceries and private chefs, we coordinate everything you need so you can make memories in the waves and stories at sunset.

Private chef

In-home massage

Beach rentals

Pre-arrival groceries

Alcohol delivery

Private driver

Bedroom details

Bedroom 1 - Main Level (Main House): King

Bedroom 2 - Second Level (Main House): King

Bedroom 3 - Second Level (Main House): Queen + Twin

Bedroom 4 - Second Level (Main House): King

Bedroom 5 - Lower Level (Main House): Two Twins

Bedroom 6 - Main Level (Carriage House): King

Bedroom 7 - Second Level (Carriage House): Queen + Two Twins

Bedroom 8 - Guest House Main Level: Queen

Bedroom 9 - Second Level (Guest House): Single Over Double Bunk + Twin + Trundle

Bedroom 10 - Second Level (Guest House): King

Location

Inside the destination

Neighborhood: Orleans Center - Located in the heart of Orleans Village on picturesque Town Cove. You can walk to everything in Orleans Center, including some of the best restaurants in town, village shops and of course, ice cream. There are four ice cream shops within walking distance. - Town Cove is a great place to drop an owner-provided kayak or SUP and explore the inland waterways of Nauset Cove and Nauset Marsh. - Two world-famous beaches are less than a 5-minute drive away, Nauset Beach on the Atlantic or Skaket Beach on Cape Cod Bay.

Parking information

During peak hours at town beaches, parking stickers are required. Of course, most of our properties are directly on or within easy walking distance of private, neighborhood association beaches, so no pass is required. For those properties that aren’t right on or within walking distance a pass is necessary. You can stop by the town offices to pick up a weekly pass or pay per visit. Beach passes are issued by vehicle so are not transferable.

Reviews

Helen

My fiance and I rented Second Wind to celebrate his 30th birthday and our engagement with friends + family, and we could not have asked for a better experience. The three houses gave everyone sufficient space to spread out and relax (while some even comfortably worked from home on the weekdays that we were there), while also providing everyone the opportunity to congregate in the main house, by the pool, and on the lawn. The amenities were all top notch, and we fully took advantage of the multiple kitchens + grocery provisioning service to cook and bake every single meal

Policies

Check-in: 4:00 PM

Check-out: 10:00 AM

No smoking allowed

No events allowed

Pets allowed by request

Cancellation policy

Plans change, we get it.

Enjoy peace of mind when booking with KEY.co.

Full Refund: Receive a full refund (excluding credit card fees) when you cancel your reservation at least 120 days before check-in.

No Refund: Reservations canceled 119 days or less before check-in are not eligible for a refund.

Refunds subject to a 5% processing fee of the total.

Things you need to know

Self check-in / check-out

Pool is open Memorial Day - Columbus Day.

This property has a seven-night minimum during the peak season and rents Friday to Friday during peak weeks.

This property offers a three night minimum stay during select weeks in May – June and September – November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived.

You may bring your boat and use the adjacent town boat ramp to motor your way to Nauset Beach by boat.

Fresh sheets and bath towel sets for each guest are provided. A bath towel set includes a bath towel, hand towel and face cloth. Bed linens at the premises are provided – no need to pack them and bring them with you.

A “starter set” of cleaning/paper products is also provided. There will be paper towels and bath tissue to start off your week. Similarly, you will be provided with cleaning products like dish soap, laundry detergent, all-purpose cleaners, etc. Please replace what you use so the guests coming in after you can enjoy the same convenience. Some kitchen trash bags will also be provided.

Restrictions

Guests & Occupancy

No more than the number of guests listed on the lease may occupy the property at any time, including infants, children, and overnight visitors.
Guests are responsible for all damage, loss, or added expenses incurred during the stay (including pay-per-view charges). All known damage or loss must be reported before departure to remain eligible for accidental damage coverage.

Events & Noise

Weddings, receptions, reunions, or any gathering exceeding the approved occupancy are prohibited without prior written approval. Failure to obtain approval will result in a penalty equal to an additional full weekly rental rate.

Prohibited Activities

Pets: No animals, birds, or pets of any kind unless explicitly approved in the lease. Violation fee: $5,000.
Smoking/Vaping: Smoking or vaping is prohibited anywhere on the premises. Violation fee: $5,000.
Illegal Substances & Fireworks: Illegal activities and fireworks are strictly prohibited.
Security Cameras: Tampering with, disabling, redirecting, or obscuring exterior security cameras (e.g., Ring doorbell) is prohibited and may result in lease cancellation. No interior cameras are used.

Equipment & Amenities

Utilities are provided (electricity, water, gas if applicable, heat, trash). Guests must use utilities responsibly and avoid waste.
Appliances & Equipment _(if equipped)_: Appliances and equipment (HVAC, internet, cable TV, dishwasher, washer/dryer, gas grill) are maintained but not guaranteed. No refunds will be issued for outages or malfunctions.
Parking: The number of vehicles parked at the property may not exceed the number listed on the lease and must be parked only in assigned spaces. Camper vehicles or vehicles providing sleeping accommodations are not permitted without prior written approval.

Checkout & Care

Check-in: 4:00–6:00 PM (early arrival only if confirmed). Check-out: 10:00 AM. Guests must text upon departure to notify housekeeping. Late Checkout Fees: $500 per hour (or portion thereof) for up to two hours past checkout. After two hours, additional lease penalties apply. The property must be left clean and in good, habitable condition per the checkout checklist. Lost key fee: $25 per key.

Liability & Disclaimers

Not responsible for lost or stolen items. Guests must pay shipping and handling for any items requested to be returned after departure.
Guests assume all risk for injury, loss, or damage resulting from use or misuse of the property or its fixtures and agree to indemnify the landlord and agent.
May enter the property with reasonable notice to inspect, make repairs, or protect the premises.
Minor or non-material changes to furnishings, fixtures, equipment, or property details do not constitute liability.
Failure to comply with lease terms may result in eviction with as little as two hours’ notice and additional charges equal to a full weekly rental rate, plus legal fees if enforcement is required.
Not liable for additional losses if the property becomes unavailable or uninhabitable due to fire, casualty, or legal violation; rent will be prorated or refunded accordingly.