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Island Life! Kent Island Waterfront with Pool-Bring your boat!

Riverfront guesthouse with an outdoor pool and a hot tub

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Photo gallery for Island Life! Kent Island Waterfront with Pool-Bring your boat!

3 bedrooms, iron/ironing board, travel crib, free WiFi
Smart TV, fireplace
Smart TV, fireplace
Outdoor dining
Exterior

Reviews

10 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Laundry
  • Air conditioning

Explore the area

View in a map
Stevensville, MD
  • Place, Matapeake State Park
    ‪9 min drive‬
  • Place, Chesapeake Bay Bridge
    ‪14 min drive‬
  • Place, Sandy Point State Park
    ‪18 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪52 min drive‬

Room options

About the neighborhood

Stevensville

This guesthouse is located 2.7 mi (4.4 km) from Paul Reed Smith Guitars and within a 10-minute drive of Island Dog Park. This guesthouse has private in-room pools along with an outdoor pool and free in-room WiFi.
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What's nearby

  • Paul Reed Smith Guitars - 6 min drive - 2.2 miles
  • Matapeake State Park - 9 min drive - 4.5 miles
  • Chesapeake Bay Bridge - 14 min drive - 8.2 miles
  • Sandy Point State Park - 18 min drive - 10.1 miles
  • U.S. Naval Academy - 30 min drive - 19.2 miles

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 34 min drive

Restaurants

  • ‪McDonald's - ‬7 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Cracker Barrel - ‬20 min walk
  • ‪Dunkin' - ‬8 min drive
  • ‪Friendly Food Store - ‬7 min drive

About this property

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Beautiful 2 story secluded private waterfront retreat with shared pool and hot tub access. Bring your boat and tie up to the dock for fishing or sunset cruises. 4ft average water depth at dock. Easy boat rides to local restaurants and historic towns await. 5 minute car ride to Kent Island's great restaurants and wedding venues. Convenient access to Rt 50 and only15 minutes to Annapolis. Great for Bridal parties. Bedrooms: King Bedroom Suite on main floor. Two Queen Bedroom loft area another Bedroom with three (3) full beds. Enjoy everything the Eastern Shore has to offer. The home has interior stair access from garage to the second and third floor living areas.
It does not have an elevator. Enjoy the all the conveniences and amenities this home has to offer. A great place to call homebase while you're away and enjoy Kent Island's best restaurants, dock bars and wedding venues. Nestled on 22 acres of private waterfront. Stroll on the pier or catch some crabs. Jump in the pool--relax in the hot tub. Bring your boat! This place has it all.

Need more room? There is a second home on this property listed as VRBO# 4131073 called Island Life 2 which sleeps 8 people!

Location! Location! Location! We perfectly situated near Kent Island finest Restaurants, Dock Bars and Wedding Venues:
Kent Narrows: 4.7 miles
Chesapeake Bay Beach Club-2.3 miles
Kent Island Resort-2.9 miles

Other popular destinations cities are only minutes away:
Annapolis- 15 miles
Baltimore- 40 miles
Washington DC- 45 miles
Easton- 30 miles
St. Michael's -37 miles

This is a Non-Smoking House.
Also No Pets, Parties or Large Groups (12 max).

The Space:
This Home is situated on a 22 acre private waterfront estate. Nature lovers will be in their glory with Kent Islands wildlife all around you. Bring the kids bikes--we have a 1/4 mile private drive for the to ride and explore. Bring your boat or catch some crabs off the dock!

The first floor has the Kitchen, Dining Room, Living Room, Half Bathroom, Master Bedroom, Full Bathroom and a Washer/Dryer.

Located on the second floor is Three Bedrooms:
Bedroom 2: Loft area with (2) Queen Beds
Bedroom 3: Bedroom with (3) Full Beds

Upstairs Bedrooms and Living Room have Smart TV's with streaming services.
The House also has WIFI, A/C, Heating, Washer/Dryer, Microwave, Dishwasher, Coffee Maker (Both Keurig and Drip), most common spices for the cooks in the group and a fully outfitted Kitchen with all essentials.

Blankets, pillows, linens and bath towels ARE provided with the home.

Guest Access:
You will have full access to the entire house and property, with the exception of the main home and its immediate area, garage, and exterior buildings.

Other Things to Note:
- The home has a set of stairs inside the garage which access the main floor of the guest home. There is an interior set of stairs on the interior to reach the upper floor where the additional bedrooms are located. The house has covered wrap around porches on the main level. These areas are private and for your use only. There is a grill in this area too for your use. There is a set of private stairs from the main level on the waterfront side of the home for convenient access to the pool and hot tub area.

Book Today!
Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a private pool, a kitchen, and a washing machine.

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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Internet access

Parking and transportation

  • Onsite parking options include a garage

Things to do

  • Communal pool
  • Hot tub
  • Outdoor pool
  • Playground

Conveniences

  • Laundry facilities

Outdoors

  • Barbecue grill
  • Dock
  • Firepit
  • Garden
  • On a river

Accessibility

  • No elevator

More

  • Smoking not allowed

Room amenities

Bedroom

  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Private pool
  • Smart TV with cable/satellite channels

Food and drink

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dining table
  • Dishwasher
  • Ice maker
  • Kitchen
  • Kitchen island
  • Lobster/crab pot
  • Meal delivery service
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

More

  • Air conditioning
  • Dryer
  • Fireplace
  • Heating
  • Iron/ironing board

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

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

Rules

Adult supervision is required for pool and hot tub use as well as for children under 13 on the pier..

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Safety features at this property include a smoke detector and a deadbolt lock
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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a smoke detector and a deadbolt lock.

Additional information about polices, regulations, and more:

  • There are no elevators.

Property is also known as

Private Waterfront Retreat Guesthouse
Private Waterfront Retreat Stevensville
Private Waterfront Retreat Guesthouse Stevensville

Frequently asked questions

What's there to do around this guesthouse?

This guesthouse is located in Stevensville, close to Matapeake State Park, Chesapeake Bay Environmental Center, and Love Point State Park. Paul Reed Smith Guitars is also within a driving distance of 2.6 mi.

Will I be able to park at Island Life! Kent Island Waterfront with Pool-Bring your boat!?

Yes, there is a garage.

Is this guesthouse adjacent to a casino?

No, this guesthouse is not connected to a casino.

Is there an indoor pool at this guesthouse?

No, this guesthouse doesn't have an indoor pool; however, there are an outdoor pool and a hot tub.

What will couples enjoy most about a stay at Island Life! Kent Island Waterfront with Pool-Bring your boat!?

At this riverfront guesthouse, couples will welcome the many amenities including a private pool and a fireplace along with an outdoor pool.

Are there hot tubs at Island Life! Kent Island Waterfront with Pool-Bring your boat!?

Yes, this guesthouse has a spa tub.

Does this guesthouse offer breakfast?

No, this guesthouse doesn't offer breakfast.

Does this guesthouse allow pets to stay free of charge?

No, pets aren't allowed at this guesthouse.

Does Island Life! Kent Island Waterfront with Pool-Bring your boat! have connecting rooms?

No, there aren't connecting guestrooms at this guesthouse.

How far is the airport from this guesthouse?

The closest major airport to this guesthouse is Easton, MD (ESN-Easton - Newnam), which is 24.8 mi away (34 minutes by car). Another top airport is Baltimore Washington Intl. Airport (BWI), which is around 24.4 mi away.

Are there rooms with balconies at Island Life! Kent Island Waterfront with Pool-Bring your boat!?

Yes, every accommodation at Island Life! Kent Island Waterfront with Pool-Bring your boat! comes with a balcony with some featuring water views.

Island Life! Kent Island Waterfront with Pool-Bring your boat! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 193 out of 198 reviews
Rating 8 - Good. 4 out of 198 reviews
Rating 6 - Okay. 0 out of 198 reviews
Rating 4 - Poor. 0 out of 198 reviews
Rating 2 - Terrible. 1 out of 198 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Kimberly C.

Liked: Cleanliness
Absolutely amazing property with superb host! The place is packed with "little" details that anyone would need! Such a clean place and peaceful property! Highly recommend!Also, this place is nestled in a country-like setting but so conveniently close to nearby eats and Target! Cannot say enough about the communication with the host and overall stay!
Stayed 4 nights in Sep 2025

10/10 Excellent

Cassandra H.

Stayed 9 nights in Jul 2025

10/10 Excellent

Maura M.

Liked: Cleanliness
We had a wonderful stay at John’s place - it was absolutely beautiful and the property was wonderful. John was very responsive and the listing was exactly as pictured!
Stayed 3 nights in Aug 2025

10/10 Excellent

Vicki F.

Liked: Cleanliness
Beautiful and private property. Close to grocery stores and restaurants. Lots of things to do. The hosts were very welcoming and made us feel at home.
Stayed 3 nights in Jul 2025

10/10 Excellent

Michelle K.

Liked: Cleanliness

Great Family Get Away

My family and I thoroughly enjoyed our stay. The house was clean and inviting when we arrived. My grandchildren loved the pool and hot tub. The location was also a plus. Close to a grocery store and my granddaughters favorite, Target! We also enjoy going into Annapolis. Such a quaint town.John was a wonderful host and available to answer any questions. We certainly will return!
Stayed 9 nights in Jul 2025

10/10 Excellent

Chuck C., Freeland

Liked: Cleanliness
Great spot.
Stayed 7 nights in Jul 2025

10/10 Excellent

Mike Y.

Liked: Cleanliness

Great stay on Kent Island!

We had a great stay at this vacation home. From the time we booked the vacation, communication with the host, John, was great. He is very responsive.The home exceeded our expectations. This location is beautiful, and we enjoyed exploring, swimming in the gorgeous pool, and spending time relaxing with family on the wraparound porches.We would definitely like to stay here again in the future.
Stayed 4 nights in Jul 2025

10/10 Excellent

Charlene U.

Liked: Cleanliness

SPECTACULAR!!!

CONGRATULATIONS! You have found the best house on Kent Island and all of VRBO.We just finished an incredible stay here and were blown away from the moment we pulled up the driveway. The house is spotless, beautifully decorated, and fully stocked with everything you could possibly need. The amenities truly went above and beyond. The outdoor spaces are immaculate and luxurious, with a wraparound porch on both levels and a breathtaking pool. Our family especially enjoyed the daily deer sightings on the property.As for the host, John was extremely hospitable. His attention to detail is unmatched. He was accessible, accommodating, and made sure everything was perfect for our stay.We will forever cherish the family memories we made here. If you're lucky enough to see this place available, book it!
Stayed 5 nights in Jun 2025

10/10 Excellent

Nicolette M.

Liked: Cleanliness

So relaxing!!

This was our first VRBO experience and it was wonderful. The rental provided more than our expectations. It was a beautiful site and extremely clean.The host was friendly, kind and easily reachable. We highly recommend this rental location and host and will check here first for future trips to this area.
Stayed 3 nights in Jun 2025

10/10 Excellent

Deborah C.

Liked: Cleanliness

Family time

This property is amazing. Wonderful location to The Narrows, Annapolis, Saint Michaels, wonderful restaurants, parks and trails. The amenities were perfect. The kitchen was well stocked and there was plenty of paper products , soaps, towels, pool toys. Wonderful for a large family and great for small children. The pool was beautiful.
Stayed 5 nights in Jun 2025

10/10 Excellent

Sharon T.

Liked: Cleanliness

Highly recommend!

We were there for son’s wedding weekend. We could not have been more pleased!
Stayed 3 nights in May 2025

10/10 Excellent

Gina M.

Liked: Cleanliness

Perfect Commissioning Week Getaway

Our family thoroughly enjoyed our stay! It was the perfect location for relaxing away from the busyness of our son’s USNA commissioning week. Beautiful scenery, quiet, peaceful with plenty of fun amenities. My family enjoyed the pool, kayaks, large backyard, cornhole, basketball and bicycle rides. Super close to the grocery store and Target and an easy drive to the Yard. Highly recommended!! Bonus…exceptional host who was super helpful and accommodating! P
Stayed 8 nights in May 2025

10/10 Excellent

Latricia M.

Liked: Cleanliness

Ya Ya Girls Trip

Incredible!!!! This is without a doubt the best VRBO we’ve Ever stayed in. Start to finish you couldn’t ask for More. Exceptional host Gorgeous house and the whole experience was Absolutely Magnificent!!! We’re already booking for next year.
Stayed 3 nights in May 2025

10/10 Excellent

Janet W.

Liked: Cleanliness

Great Getaway

Wonderful house with great water access. Great place to relax and visit and recreate
Stayed 14 nights in Apr 2025

8/10 Good

Ricky W., Fuquay Varina, NC

Liked: Cleanliness

Excellent Propery

Great location, clean and everything was just like it posted. Would 100% stay here again
Stayed 7 nights in Apr 2025

10/10 Excellent

Dylan M.

Liked: Cleanliness
Stayed 3 nights in Dec 2024

10/10 Excellent

Mike W.

Liked: Cleanliness

Christmas on Kent Island

Our host Jon was so nice, checked in with us to make sure all was good, and it was. He had the place decorated for Christmas and even had a tree - we appreciated it very much since we were not home for Christmas. Beautiful setting on Cox creek. The guest house was well maintained and fully equipped kitchen. Very Comfortable beds and bedding which we find unique for VRBOs.
Stayed 7 nights in Dec 2024

10/10 Excellent

Christine S.

Liked: Cleanliness

Wedding Weekend

We came from Texas and California for a wedding weekend on Kent Island, and we chose this fabulous location. There were four adults for the weekend, and we had more than enough room, beautiful accommodations, and an excellent host. The home was as expected ~ Lovely, large, on the water, and fairly secluded on 22 acres. Peaceful and quiet. We highly and enthusiastically recommend!
Stayed 3 nights in Nov 2024

10/10 Excellent

Adam S.

Liked: Cleanliness

great stay for my daughters wedding

John was a great host! property was flawless. Great setting and amenities and just and overall welcoming place for a long weekend. Would definitely go back . Thank you John and family!
Stayed 3 nights in Oct 2024

10/10 Excellent

Ken B.

Liked: Cleanliness

Perfect Family Home-base for a wedding weekend

We had 2 families of 4 adults plus Grandma on Kent Island for a wedding weekend. The location was perfect to get to all of the various parties and meet-ups at the Narrows. Beautiful expanse of a property with views of the water and a great 1/2 mile walk or so to the Starbucks down the street. Well appointed kitchen with coffee pods and snacks, comfy couch and great TVs. We didn't get to use the pool or Jacuzzi but wish we had time to!! The backyard is absolutly gorgeous! Our only suggestion to potential customers with mulitple families like ours would be to pay attention to the sleeping layout. There's 1 king bed primary room with a bathroom/shower downstairs (plus another bathroom). The upstairs is more of a loft-feel with 2 queens in an open space (exposed to noise downstairs), then a bedroom with 3 double beds. Everyone upstairs is sharing one bathroom. We made it work, but something to pay attention to if privacy (snoring LOL) is a concern. Huge thanks to John for being flexible and communicative. We would love to come back and stay here again.
Stayed 3 nights in Oct 2024

10/10 Excellent

Brooke H.

Liked: Cleanliness

Most Memorable Stay!!

My, now, husband and I booked this property over a year ago for our wedding weekend. We were planning everything while living in Australia and to say that this property and John were perfect is an understatement. From the very beginning Johns communication and responsiveness was unbelievable especially with living on the other side of the world. Somehow it got even better. We booked John's place for our wedding party and us to stay for the weekend. He was extremely accommodating and offered up the property as if it was our own. Every question we had was met with a prompt answer. The property alone was so stunning we decided to have our first look and all wedding portraits done on site. Just to share how accommodating John was, he made sure the grass was cut prior to our photos taking place. John has created a memory for us that will never fade. He will always be a part of our wedding story and for that we are forever grateful. We have truly left this property with a forever friend. Anyone who has stayed or is planning to stay with John is incredibly lucky. Thank you for everything! We hope to return one day!
Stayed 4 nights in Oct 2024

10/10 Excellent

Ryan H.

Liked: Cleanliness

Unbelievable Property

John was extremely welcoming and helpful. His property is absolutely beautiful. Our kids had a great job crabbing off the dock, riding around on kayaks, and swimming in the pool.
Stayed 3 nights in Sep 2024

10/10 Excellent

Terri M.

Liked: Cleanliness

Stevensville

It was a great location and place to stay for the weekend of our son's wedding.
Stayed 3 nights in Sep 2024

10/10 Excellent

Kaitlin I.

Liked: Cleanliness

Amazing!! Will be back!

We had the best time!! Everything was amazing. We are already talking about coming back next summer. Clean, comfortable, room for everyone, plenty of activities, great local spots to visit.
Stayed 4 nights in Sep 2024

10/10 Excellent

Dan A.

Liked: Cleanliness

FANTASTIC host, house and location

We have had a yearly trip with family and friends for 34 years and have rented many places in and around Kent Island.. This is the one we will definitely repeat! Between the pool, the dockside, the kayaks, the house and the local amenities - there was always something for every person's taste at the time. The location is easy to get to, close to the boat ramp and has easily navigable water to the dock. The host was very accommodating and helpful to the extreme. He went out of his way to make us feel at home and welcome. Everything was exactly as described and the setup allowed us to bring virtually nothing to support a week of cooking and good times.
Stayed 10 nights in Aug 2024