Five Bays Oasis - Image 1
Five Bays Oasis - Image 2
Five Bays Oasis - Image 48
1/48

Five Bays Oasis

4 bedrooms·3.5 bathrooms·9 guests·3,700 sq/ft
Beach access
Pool

Set in the charming village of Osterville, this spacious 3,700 plus square foot residence offers an inviting Cape Cod escape just six minutes from Dowses Beach and moments from local favorites including Fancy’s Market. Thoughtfully updated and designed with summer gatherings in mind, the home combines a peaceful residential setting with easy access to the beach, village shops, and everything that makes the Cape so special. Pick up provisions from the market, spend the afternoon by the water, then return home for a leisurely evening under the stars. Inside, generous proportions and multiple gathering spaces make it easy for everyone to settle in. The main level features both a spacious family room and a separate living room, each furnished for relaxed lounging, while a lower level adds another TV lounge and dedicated game room. The well appointed kitchen pairs stainless steel appliances and granite countertops with a peninsula for casual dining, while a separate dining room comfortably seats eight. Four bedrooms occupy the second level, including a spacious king suite with a private bath featuring both a walk in shower and jetted tub, two queen bedrooms, and a family friendly bunk room with two twin beds and an additional single. The heart of summer living unfolds outside, where an inviting heated saltwater pool is surrounded by an expansive stone patio designed for long afternoons and easy entertaining. Lounge beside the water, gather around the shaded dining table for an al fresco meal, or settle around the wood burning fire pit as evening falls. A gas grill and enclosed outdoor shower add to the effortless outdoor experience, while rooftop solar panels provide year round energy to the home. With its generous living spaces, resort like backyard, and coveted Osterville location, this is a Cape Cod retreat made for slowing down, gathering together, and savoring summer.

Our promise

Satisfaction Guarantee

We've reviewed thousands of homes and approve only the best. Each one is professionally managed and vetted for comfort and style, raising the bar for every stay.

KEY Curation Notes

Heated saltwater pool with an unusually designed stone patio — oversized, wood-burning fire pit, umbrella-shaded dining, and lounge seating. Enclosed outdoor shower. The outdoor setup is a genuine gathering space.
Three full TV lounges plus a lower-level game room across 3,700+ sq ft. Main level: family room and separate living room. Lower level: third lounge plus games. The interior is oriented around multiple places for a group to spread out.
Six-minute drive to Dowses Beach on Nantucket Sound. Fancy's Market — a local institution with a butcher, cheese, wine, and prepared food — is half that distance. Five Bays Bistro, one of the Cape's better restaurants, is in Osterville village.
Four bedrooms, all upstairs. King primary suite with private bath and jetted tub. Two queen bedrooms sharing a full bath. Bunk room with two twins and a single. 3.5 baths total; laundry in the half bath. Sleeps 9.
Solar-powered home — rooftop panels supply year-round electricity. Rents Saturday to Saturday in peak season; pets considered.

Amenities

Indoor
Entertainment room
TV
Air conditioning
Internet
Microwave
Outdoor
Heated pool
Pool
Patio
Outdoor shower
Poolside lounge seating
Misc
Rooftop solar panels
WiFi
Beach chairs
Beach towels

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

Private chef

In-home massage

In-home massage

Beach rentals

Beach rentals

Pre-arrival groceries

Pre-arrival groceries

Alcohol delivery

Alcohol delivery

Private driver

Private driver

Bedroom details

Bedroom 1 - Second Level: King
Bedroom 2 - Second Level: Queen
Bedroom 3 - Second Level: Queen
Bedroom 4 - Second Level: Twin + Single Over Single Bunk

Location

Inside the destination

Neighborhood: **Osterville Village** - Just a six-minute drive to sandy Dowses Beach; half that distance to popular Fancy’s Market, pick up some of Howie’s Cheese and wine, crackers, and head to the beach for sunset.

Parking information

Garage parking is available.

We're here to help

Whether you have questions on this home or want us to source other options, we're a message away!

Reviews

Jane

We enjoyed our end-of-summer stay very much. The kids loved the heated pool & all the floating devices. (We heard the tall pines were going to be removed and that would sure help with the debris issue.) Everyone was impressed with the knife set & much-better-than-standard flatware! ... thanks for a fun week.

Policies

Check-in: 4:00 PM
Check-out: 10:00 AM
Quiet Hours: 8:00 PM - 8:00 AM
No smoking allowed
No events allowed
Pets welcome

Cancellation policy

Plans change, we get it.

Enjoy peace of mind when booking with KEY.co.

Partial Refund: Receive a 75% refund 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

Beach pass provided

All bed linens and bath towels are provided at the premises.

Utilities to the property during the rental term will be provided. Such utilities include electricity, cold and hot water, natural gas (if applicable), heat, and trash removal.

Provided with a starter set of cleaning/paper products. There will be paper towels and bath tissue to start your week. Similarly, you will be provided with cleaning products like dish soap, laundry detergent, all-purpose cleaners, etc. We ask that you 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.
  • If the property becomes unavailable or uninhabitable due to fire, casualty, or legal violation, rent will be prorated or refunded accordingly. The landlord is not liable for additional losses.