The owners refer to this one-of-a-kind property as Pleasant Plus. This unique beachfront home and certified wildlife habitat is located on Big Pleasant Bay with spectacular panoramic water and big sky views from the Atlantic Nauset barrier beach to the golf course at Chatham's Eastward Ho! Country Club.
Set on a bluff, the main house is an amazing, white-washed, full Post and Beam design. The first floor offers a family-friendly open floor plan with oversized fully equipped kitchen, dining area and living room with vaulted ceiling and open loft. There is one half bathroom in the foyer and one full bathroom with tub/shower at the end of a center hall, as well as two guest bedrooms; one with a queen bed and one with two twin beds.
Step out of the family room onto a full-length deck looking south onto the fall/winter kaleidoscope of down-Cape weather, certified natural wildlife habitat, and relentless local and migratory bird activity.
On the second floor you will find a stunning master bedroom with king-sized bed where you will wake each day overlooking the breathtaking vista. This floor also features a separate full bathroom with shower, a third guest bedroom with one double bed and two small twin beds, and a fully tech-equipped "work from vacation" office setting and/or kid-friendly entertainment area for reading, creating, gaming or just relaxing.
The lower walkout-to-beach level features a large glass-walled indoor bathroom to accommodate guest and beach-goers alike, as well as an all-weather (above freezing) outdoor shower with view of Strong Island.
Stairs descend south from the Bay side of the house to the 1100 square foot boathouse/party house built directly on the private sandy beach where guests can isolate and commune with the Bay's nature and beauty up close and personal at any time, and in any weather.
Pleasant+'s isolation from public activity (down a 1/3 mile private lane, into a gated cul-de-sac) make the property an ideal cathartic getaway from the realities of urban living. Unique features of this all-season home make it possible to experience the wonders of Lower Cape Cod's fall and winter natural and wildlife beauty, all the while remaining engaged and connected as remote work-from-home responsibilities may require.
Amenities include: Panoramic view of Pleasant Bay from all living areas, central heating and air conditioning, high-speed wired and WiFi internet service, full home office/WFH setting, first floor washer and dryer, 3 smart TVs with live streaming service, DVD/VHS player, telephone, light duty laser printer, gas grill, Keurig and drip coffee makers, enclosed outdoor shower, seasonal outdoor furniture, kayak, dinghy, beach chairs and recliners, sporting and aquatic gear, etc. Linens are provided for prime season rentals. For all other weeks, tenants can bring their own linens or rent them.
* Additional Fees: - $300 Cleaning Fee. - $220 Non-Refundable Reservation Fee; $30 Damage Protection Fee; Guest Services Fee - All Applicable Taxes * FREE WIFI * SATURDAY TO SATURDAY RENTAL * NO PETS (no exceptions) * NO SMOKING * OCCUPANCY: 10 (adults and children) * PARKING FOR 4 VEHICLES * Sheets and towels provided on all weeks between May 30 - September 26, 2026. Linens are not included on any off-season stays. Tenants may bring their own or rent for $300.00.
****FREE ACTIVITIES INCLUDED**** To enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area.
Click the Xplorie button or visit the Free Activities page to see the free fun included with this Kinlin Grover Compass rental!
As a guest of Kinlin Grover Compass, you'll receive free golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
About the area
Orleans
Located on the beach, this holiday home is in South Orleans, a neighbourhood in Orleans. The area's natural beauty can be seen at Cape Cod Beaches and Cape Cod National Seashore. Travelling with kids? Consider Chatham Marconi Maritime Center and Adventure Chatham. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
Cape Cod National Seashore - 19 min drive - 15.4 km
Mayflower Beach - 32 min drive - 31.7 km
Hyannis Harbor - 33 min drive - 37.2 km
Getting around
Hyannis Transportation Center - 27 min drive
Hyannis, MA (HYA-Barnstable Municipal) - 28 min drive
Restaurants
Hog Island Beer Co. - 9 min drive
Three Fins Coffee House & Cacao Factory - 8 min drive
Dunkin' - 8 min drive
Dunkin' - 6 min drive
Cumberland Farms - 7 min drive
Frequently asked questions
Is Pleasant Bay Beachfront Property Plus! pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Pleasant Bay Beachfront Property Plus!?
As of 14 May 2026, prices found for a 1-night stay for 2 adults at Pleasant Bay Beachfront Property Plus! on 7 May 2026 start from AU$829, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Pleasant Bay Beachfront Property Plus!?
On-site parking is available at the property.
What time is check-in at Pleasant Bay Beachfront Property Plus!?
Check-in begins at 4:00 PM.
What time is check-out at Pleasant Bay Beachfront Property Plus!?
Checkout is at 10:00 AM.
Where is Pleasant Bay Beachfront Property Plus! located?
Nestled on the beach, this South Orleans holiday home is within 2 mi (3 km) of Cape Cod Beaches, Captain's Cove Golf Course and Captains Golf Course. Pilgrim Lake and Caleb Nickerson House are also within 3 miles (5 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Our extended family of 7 stayed here very comfortably. Lots of time spent on the beach and in the kayaks. We had such an amazing week long vacation at this wonderful beach house. Couldn’t ask for a better experience working with the management company and owners.
We’ll be back ! It’s a wonderful property! Gayle let us get straight to the property instead of having to stop at office to get the key. That was nice considering we were in the middle of a nor’easter! We had plenty of heat, and many games to entertain us.
This house is absolutely beautiful and has direct beach access. It fits two families very comfortably and is in a wonderful area. We stayed here last summer and hope to come again soon!!
This is a nice home and we enjoyed the property / beach but overall we feel the home owner needs to pay a bit more attention to the details. Examples are that the deck and deck furniture is quite aged and in need of cleaning and the "beach house" is basically used for storage of many things and not really a usable family hangout. We also had issues with there being no picnic table on the deck (damaged by a previous renter), the kayak was not on the property until late in the week (due to a mishap with a previous renter), the dishwasher did not work properly, and the second propane tank was just about empty (though previously confirmed with the homeowner that it would be filled). It is important to note that the property manager was fantastic and was able to solve a couple of the issues. We would hesitate to rent this property in the future at this price point, but would certainly work with the property manager for future rental plans.
Linda C.
Stayed 7 nights in Aug 2020
Response from VrboOwner on 1 Oct 2020
Thank you for your 4-star review, and for pointing out details that were not up to expectations. As our first season of summer renting ends, we've taken your suggestions seriously for the Fall: Older deck furniture has been replaced with a new all-season cast aluminum dining set, the kayak and SALTY dinghy have been restaged in the boathouse together with additional beach-themed waterside seating, two filled propane tanks are now available in addition to the one in service, and the dishwasher is in good working order. Thank you for your suggestions and for enjoying the Pleasant Bay remote lifestyle, beach, and wildlife experience with us.
GREAT rental!!! Excellent amenities!!!
Local on bay very relaxing-beach house offered all kids of water toys- a HUGE plus for fun on the water. We will definitely go back. 5 stars for everything!!!!
Fantastic views, space and fun for all ages in a thoughtfully designed and well maintained property that is clearly a special place for the owner and their extended family.