Entire home

Orleans Oasis on Pleasant Bay, Estate with 2 homes & heated pool; 137-O

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your current months are January, 2025 and February, 2025.
January 2025
February 2025

Photo gallery for Orleans Oasis on Pleasant Bay, Estate with 2 homes & heated pool; 137-O

Exterior
Fridge, microwave, oven, stovetop
A heated pool
Interior
Property grounds

Reviews

10 out of 10

Exceptional

Entire home

6 bedrooms7 bathroomsSleeps 14325 sq m

Popular amenities

  • Gym
  • Parking available
  • Washer
  • Pet-friendly
  • Pool
  • Barbecue grill

Explore the area

Map
Orleans, MA
  • Orleans Bowling Center
    8 min drive
  • Rock Harbor Beach
    10 min drive
  • Skaket Beach
    12 min drive
  • Hyannis, MA (HYA-Barnstable Municipal)
    30 min drive

Room options

Similar properties

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Orleans Oasis on Pleasant Bay, Estate with 2 homes & heated pool; 137-O

This property is professionally managed by Pretty Picky Properties.

Orleans Oasis on Pleasant Bay, 2 Homes and Heated Pool; "Beam Reach"

Sleep up to 14
Rents Friday to Friday in Peak Season
Linens Included, Beds Made
Pets Under 25 Pounds Considered

Pool is open from Memorial Day to Columbus Day weekend

Welcome to your private oasis on Pleasant Bay. At the end of the road you will find this private setting which features 2 homes located right on the water. Windward and Leeward are two wonderful homes that will provide you and your family of up to 14 with great Cape Cod memories. There is a beach area just outside the back door of the Windward home. And there is a heated pool between the two houses for those who prefer a pool to the Bay.

Windward was completely remodeled recently. All new furnishings and a brand new kitchen. Sit in the living room and enjoy tremendous views of Pleasant Bay. There are a total of 3 bedrooms in Windward. The first features a queen size bed with an ensuite bath. The views are amazing from here! The second bedroom has a comfy king size bed along with an ensuite bath. The third bedroom is located through the walk-in closet and offers a twin-over-full bunk bed. There is a private entrance to this room off of the front porch. These two bedrooms are set up perfectly for a family with kids. There is also a half bath, brand new kitchen and laundry. And of course the home is outfitted with central AC and Wi-Fi.

Leeward is on the other side of the pool and features 3 more bedrooms. On the main level you will find a cozy living room, full kitchen and a large screened in porch. There is also a dining room, full bath and two bedrooms on this level. The first bedroom features two twin beds. The other bedroom has a queen size bed and an ensuite bath. Upstairs you'll find a suite perfect for a family with kids. There is a king size bed plus two twin beds up there in addition to a full bath.

The Leeward home also features a wonderful media room in the lower level. A brand new 75” TV is ready for movie night! There is a cozy sectional sofa, a kitchenette, small refrigerator and a popcorn machine making this the best spot for movie night or in case the weather doesn't cooperate. There is also a full bath, exercise equipment and laundry facilities down stairs.

And while the homes are beautiful on the inside you will undoubtedly spend most of your time enjoying the outdoors. The pool, which has a gate around the outside for safety, is heated so it's a great option even in June or September (pool is heated from Memorial Day – Columbus Day). There is a large table inside the pool area for dining al fresco! And the views from the pool area are awesome. There is an outdoor fire-table for enjoying the evenings under the stars listening to the water against the shoreline. And of course no Cape vacation home is complete without an outdoor shower! In addition, the owners provide kayaks and stand-up-paddle boards.

This property offers a wonderful Cape escape. You will feel like you've gone back to a simpler time but thanks to all the modern amenities you'll still enjoy today's creature comforts. A SONOS system, central AC, heated pool, flat screen TV's and Wi-Fi throughout will allow you to enjoy your vacation in comfort.

Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 225. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.

This property offers a 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived.

Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod.

It's your vacation. Get Picky!
During your stay at this holiday home, you're just a quick walk from Cape Cod Beaches. You'll find features such as a gym and an arcade/games room. The holiday home offers free WiFi and a private pool.
  • Air-conditioned home with private pool, kitchen and washing machine
  • Free WiFi
  • On-site recreation includes a gym
  • 10 minutes on foot from Cape Cod Beaches and a 5-minute drive from Captain's Cove Golf Course
As a guest of Orleans Oasis on Pleasant Bay, Estate with 2 homes & heated pool; 137-O, you'll find a fitness centre, barbecue grills, and an arcade/games room. The front desk is open around the clock.

Property manager

Pretty Picky Properties

Languages

English

Property amenities

Beach

  • On the beach

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Kitchenette
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 6.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Living room
  • Separate dining area

Entertainment

  • Games
  • Stereo
  • TV with cable/satellite channels
  • Video games

Outdoor areas

  • Barbecue grill
  • Porch/lanai

Laundry

  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront

Things to do

  • Arcade/game room
  • Gym
  • Heated pool
  • Kayak
  • Table tennis
  • Kayaking nearby
  • Swimming nearby
  • Whale watching nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 3,500 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Service animals are exempt from fees.

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.
Property Registration Number C0082522240

Property is also known as

455295

Orleans Oasis on Pleasant Bay, Estate with 2 homes & heated pool; 137-O Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 15 out of 15 reviews" "
Rating 8 - Good. 0 out of 15 reviews" "
Rating 6 - Okay. 0 out of 15 reviews" "
Rating 4 - Poor. 0 out of 15 reviews" "
Rating 2 - Terrible. 0 out of 15 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Terry R., Torrington, CT USA

Liked: Cleanliness
Siblings and spouses
6 siblings and spouses, property provided everything we needed. Even 5 braved the cooler weather and used the heated pool. We highly recommend this property
Stayed 4 nights in Sep 2024

10/10 Excellent

Narciso R.

Liked: Cleanliness
Perfect
We had a perfect stay. Beautiful property and houses. Great for family and friends.
Stayed 8 nights in Aug 2024

10/10 Excellent

James R., Needham

Liked: Cleanliness
Spectacular Property
Beautiful property, great location, 1st class amenities. Perfect spot for relaxation and fun by the water (and pool). Organized and efficient check-in and check-out, and great communication with property management. I hope to return soon..
Stayed 4 nights in Jun 2024

10/10 Excellent

Donna L., United States

Liked: Cleanliness
Perfect Family Poolside/Waterview Retreat
Superb. Two houses with a pool in between. Beautifully appointed property, agent was very helpful and answered every question. Secluded yet close to Cape shopping and restaurants. Very thoughtful decorating with plenty of comfy chairs, and fully decked out kitchens. Warm pool. Wonderful!!
Stayed 10 nights in Sep 2022

10/10 Excellent

Jennifer S.

Liked: Cleanliness
Fabulous property for families
This was an absolutely beautiful property. Both houses were well appointed with enough space for everyone to eat, sleep and play. The beds and linens were all very comfortable. The provided kayaks and SUP were used almost everyday. Having beach chairs and life jackets on property was also very appreciated. We cooked every dinner and had plenty of room at both tables inside and out to seat everyone. Also appreciated that there was an abundance of indoor and outdoor dishes for large groups. The kids had a blast in the basement media and game areas. The adults enjoyed the screened in porches to avoid the bugs! We just loved our time and the space provided.
Stayed 7 nights in Jul 2022

10/10 Excellent

Michael S.

Liked: Cleanliness
DELIGHTFUL GETAWAY IDEAL FOR FAMILIES
dELIGHTFUL GETAWAY
Stayed 7 nights in Jul 2022

10/10 Excellent

Andrew O.

Liked: Cleanliness
Beautiful, Peaceful Getaway
We stayed at the wonderful property with my family and my brother’s family to celebrate the life of my mother. The property is so conducive to having 2 families with the 2 separate homes. We enjoyed the heated pool, kayaks and paddle boards. There is a nice fire pit area overlooking the water, but we ran out of time to use it. We found both properties immaculate, well stocked, and plenty of space for both families to gather for meals and hang out. Only recommendation would be nonstick pans and backs on the kayaks. We loved our stay and definitely recommend this property!
Stayed 7 nights in Jun 2022

10/10 Excellent

Tom Y.

Liked: Cleanliness
Reunion
All went well
Stayed 3 nights in Jun 2022

10/10 Excellent

Brian G.

Liked: Cleanliness
Awesome for families!
I stayed here with my family, our daughter and my in-laws for Memorial Day Weekend. We had a blast! Both homes are nicely appointed and the pool is fantastic. We would stay again.
Stayed 3 nights in May 2022

10/10 Excellent

Peter H.

Liked: Cleanliness
Very nice
I would just suggest having some bath soap, shampoo and conditioner in the showers.
Stayed 3 nights in Nov 2021

10/10 Excellent

Shaun R.

Liked: Cleanliness
Wonderful property! Perfect for families!
Our family has been coming to the Chatham/Orleans area on the cape for over 20 years and this property has officially become our favorite. 2 beautiful, spacious homes with a heated pool right on the water with private beach access. Don’t think you can ask for much more than that. We will definitely plan on coming back again!
Stayed 7 nights in Sep 2021

10/10 Excellent

Jean O.

Liked: Cleanliness
Cape at its BEST!
Fabulous property! Exceeded our expectations in every way!
Stayed 7 nights in Jul 2021

10/10 Excellent

Ginny M.

Liked: Cleanliness
Stellar Stay :)
What a great spot! Everyone in my group LOVED this property. Both houses are set up pretty perfectly and leave you wanting for nothing. Tons of quality dishes, glassware, plastic ware and pots and pans. All beds quite comfy and common areas and porches very tranquil and spacious. We hardly left the property! Views, views, views everywhere :) On site beach and pool are very inviting and with all the toys you need. We did have a problem with the pool heat not up to par. Property manager was very quick to respond and sent out a pool guy to have it fixed ASAP. Property is maintained beautifully. The lush plantings were picked with care and there is a nice flow between homes. I do feel you could use more outdoor lighting. We spent a lot of time walking between homes, firepit. pool and beach. At night the footing could be a little difficult. Hard to eat out by grill at night. Some "fairy lights" by firepit would be a very nice touch and add some safe but festive pretty lighting ;) We loved every minute of our week and can't wait to go back our only regret is that we didn't stay for 2 weeks.
Stayed 7 nights in Jul 2021

10/10 Excellent

Gisela P.

Liked: Cleanliness
the weather was perfect as was the property
My expectations were exceeded by the real property. It immediately felt open spaced, well cared for and the views when entering were so beautiful. Great architect designed this space. There was plenty of all to have our meals for 13 inside the house and out. Paddle boards and kayaks were used and there was just a little walk to Pleasant Bay...just down the slope and lawn. We definitely like to come again. Any questions were immediately attended to. My whole family enjoyed it and wants to come again. Thanks for a lovely stay.
Stayed 3 nights in May 2021

10/10 Excellent

Randi L.

Liked: Cleanliness
Cape Vacation
We had a great time staying at this property! It is absolutely beautiful. Location is perfect and the pool was great. We would definitely be thrilled to come back!