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The Landing at Kent Island a Luxury Waterfront Retreat with a Private Pool

Waterfront holiday home with private pool and kitchen

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Welcome to the breathtaking views and private pool at The Landing at Kent Island.
You'll feel like you're staying at a 5-Star luxury resort.
For the safety of the younger members of the family, the pool is fenced.
Looking for a beach day? There's a public beach just a 10 minute walk from the home.
The entrance to the home is a beautifully-decorated foyer with open views to the main level living spaces.
5 bedrooms3+ bathroomsSleeps 12

Popular amenities

  • Barbecue grill
  • Pool
  • Dryer
  • Washer
  • Fireplace
  • Kitchen

Explore the area

View map
  • Place, Romancoke Wharf County Park
  • Place, Matapeake State Park
  • Place, U.S. Naval Academy
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Rooms & beds

5 bedrooms (sleeps 12)

Bunk Room

2 Single Bunk Beds

King Suite

1 King Bed

Main Floor Den

1 Double Sofa Bed

Queen Suite

1 Queen Bed

Queen Waterfront

1 Queen Bed

3 bathrooms, 1 half bathroom

Full Hall Bath

Bathtub or shower · Toilet

King EnSuite

Bathtub · Toilet · Shower only

Main Floor Powder Room

Toilet

Queen Ensuite

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden
Dining area

About this property

The Landing at Kent Island a Luxury Waterfront Retreat with a Private Pool

Welcome to The Landing at Kent Island– your private waterfront retreat on Maryland’s Eastern Shore.

Nestled on a picturesque acre plus with sweeping water views, The Landing is the perfect blend of privacy, comfort, and fun. This beautifully maintained Eastern Shore Colonial combines timeless elegance with modern amenities, offering guests an unforgettable waterfront getaway just minutes from the Bay Bridge.

Outdoors, the property shines with a spacious backyard and resort-style in-ground pool, complete with a family-friendly safety gate. Enjoy multiple outdoor dining and lounge areas, a fire pit for evening gatherings, and stunning views of the water, where blue herons, ospreys, and other local wildlife are frequent visitors.

Inside, thoughtful design and welcoming touches create the ideal setting for families and groups. The gourmet kitchen, with breakfast bar seating for two and a kitchen table for six, flows into a sun-filled entertainment room featuring a large sectional sofa, children’s play area, dining table, and flatscreen TV. Whether you’re hosting friends, entertaining kids, or enjoying a quiet evening, every space is designed for relaxation and connection.

Sleeping Arrangements:
King Suite: King bed + twin daybed, spa-style bath, office & laundry (sleeps 2)
Queen Suite: Queen bed + private bath (sleeps 2)
Queen Waterfront Room: Wake up to water views (sleeps 2)
Kids’ Bunk Room: Two twin-over-twin bunks (sleeps 4)
Main Level Den: Daybed that converts to Queen Sleeper Sofa (sleeps 2)
Plus: full hall bath upstairs & powder room on the main floor.

Amenities You’ll Love:
Fully stocked kitchen with waffle maker, frozen drink maker
Resort-style pool with safety gate
Outdoor games including cornhole, croquet, and boccee, unique "car bar"
Multiple outdoor dining areas & waterfront ire pit for s'mores
High-speed Wi-Fi & smart TVs
Washer/dryer & luxury linens
Family-friendly extras like high chair, baby bathtub, kids’ dishes, play area & lemonade stands
Two coffee bars - in kitchen and King Suite
Sunroom with electric fireplace, second full dining, family and playroom
Community Beach - free access and 10 minute walk with the house. Pack up the beach chairs from the house and walk them over in the provided beach cart.

The Vibe:
Mornings with coffee on the deck. Afternoons by the pool. Evenings watching the sunset over the water. Whether you’re entertaining friends, planning a family gathering, or sneaking away for a quiet escape, The Landing makes it easy to slow down and enjoy.

Location:
Downtown Annapolis – 25 min
Washington, D.C. – 45 miles
Baltimore – 46 miles

House Rules:
No smoking, pets, or parties
Primary renter must be 25+ and present
Residential neighborhood with quiet hours
Check-in: 4 PM | Check-out: 11 AM

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed, service animals permitted
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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
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 deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Stevensville

Located in Stevensville, this holiday home is on the waterfront. Captain Avery Museum and Annapolis Maritime Museum are cultural highlights, and travellers looking to shop may want to visit Bay Bridge Market Place Shopping Center and Annapolis City Dock. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Stevensville, MD

What's nearby

  • Romancoke Wharf County Park - 6 min drive - 4.5 km
  • Matapeake State Park - 13 min drive - 11.2 km
  • Chesapeake Bay Bridge - 28 min drive - 25.7 km
  • Annapolis City Dock - 42 min drive - 42.6 km
  • U.S. Naval Academy - 44 min drive - 43.4 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 39 min drive

Restaurants

  • ‪Kentmorr Restaurant & Crab House - ‬10 min drive
  • ‪Kent Island Elks Lodge - ‬9 min drive
  • ‪Silver Swan - ‬12 min drive
  • ‪Dirty Dave's Island Tiki Bar - ‬10 min drive
  • ‪Awkward Town - ‬5 min drive

Frequently asked questions

Does The Landing at Kent Island a Luxury Waterfront Retreat with a Private Pool have a pool?

Yes, this property has an outdoor pool.

Is The Landing at Kent Island a Luxury Waterfront Retreat with a Private Pool pet-friendly?

No, only service animals are welcome at the property.

What time is check-in at The Landing at Kent Island a Luxury Waterfront Retreat with a Private Pool?

Check-in begins at 4:00 PM.

What time is check-out at The Landing at Kent Island a Luxury Waterfront Retreat with a Private Pool?

Checkout is at 11:00 AM.

Where is The Landing at Kent Island a Luxury Waterfront Retreat with a Private Pool located?

Situated on the waterfront, this holiday home is 0.3 mi (0.5 km) from Chesapeake Bay and 2.6 mi (4.1 km) from Romancoke Wharf County Park. Matapeake State Park and Paul Reed Smith Guitars are also within 12 miles (20 km).

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About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Languages:

English

Premier Host

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