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*Waterfront* 5BR w/ Pool + Firepit on Kent Island!

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A large, single-story house with a garage, surrounded by a well-maintained lawn and trees, with a lake in the background.
A swimming pool with a curved edge, surrounded by a fence, and a view of a lake and trees in the background.
A circular outdoor seating area with a central fire pit surrounded by chairs, set against a backdrop of a lake and trees.
A cozy living room with a sectional sofa, a small table, and a fireplace. Large windows allow natural light and views of the outdoors.
A spacious living area with a high ceiling, large windows, and a dining setup.

Reviews

9.8 out of 10
Exceptional
Located at the waterfront, this vacation home accommodates 12 guests with 5 bedrooms and 3 bathrooms. It features 1 outdoor pool and a patio for relaxation. Guests can enjoy water views and partake in nearby activities such as sailing, kayaking, and swimming. This property is pet-friendly and located near golf, shopping, and water sports.

Highlights

  • Family fun awaits
    Top-rated for families.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Discover nearby landmarks
    Near Chesapeake Bay
5 bedrooms3+ bathroomsSleeps 12

Popular amenities

  • Outdoor pool
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View map
Stevensville, MD
  • Place, Northern Chesapeake Bay
    ‪8 min walk‬
  • Place, U.S. Naval Academy
    ‪38 min drive‬
  • Place, Annapolis City Dock
    ‪42 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪69 min drive‬

Where you'll sleep

5 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Bunk Beds

Bedroom 4

1 Queen Bed

Bedroom 5

1 Double Sofa Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Shower only · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo

Bathroom 4

Toilet

Spaces

Deck or patio
Kitchen
Kitchenette
Separate dining area
Garden

About this property

*Waterfront* 5BR w/ Pool + Firepit on Kent Island!

FEATURED IN BETHESDA MAGAZINE JULY ‘26 ISSUE ⭐THE HIGHLIGHTS
• Private waterfront setting on Kent Island
• Resort-style pool with water views
• Firepit with Adirondack chairs on sand
• Walk to the Bay beach for sunsets
• 5 bedrooms + multiple living spaces
• Kids playroom + games
• Playground newly installed
• Big dining tables for meals together
• “Car bar” for fun outdoor setups
• Record player for laid-back evenings
• Eastern Shore decor

We are EXTRA kid-friendly: playroom, pirate bunk room, baby gear (baby tub, diaper genie, high chair, pack n play, stools for the sink all included), toys, kid-sized beach chairs, kids books, fenced pool (when open), lawn games, children’s pool cabana, and an awesome playground.

⸻

🛋️ MADE FOR GATHERING

The Great Room: soaring ceilings, panoramic water views, and space for everyone to spread out.
• Oversized sectional + electric fireplace
• Record player + 65” TV
• Dining table with water views
• Kids play area

The Living Room: the softest sofa, swivel chairs, and over a dozen board games

The “Unplug Zone”: TV-free gathering space in front of a decorative fireplace and art by local artist Kim Hovell.

Whether you’re having a family dinner or just hanging out in pajamas, the layout makes it easy.

⸻

🍽️ EAT, DRINK & LINGER

The Kitchen: fully stocked for preparing real meals together — from waffle mornings to seafood feasts.
• Full-size appliances + dishwasher
• Waffle maker, bakeware, and serving dishes
• Two indoor dining areas (seats 18 total)

☕ “But First, Coffee” Bar
Keurig, Nespresso, French press, and logo mugs for the perfect cup.

⸻

🛌 SLEEP WELL

At The Landing, all beds are freshly made with white linens and duvet and two types of pillows depending on whether you like soft or firm.

• Primary Suite: King bed, panoramic water views, spa-like bath with soaking tub, coffee bar, TV, laundry, and office nook
• Bedroom 2: Queen bed, water views, TV (shares full bath)
• Kids Bunk Room: Two sets of bunks (sleeps 4) with playful pirate theme
• Bedroom 4: Queen bed, en-suite bath, TV, coastal décor
• The Landing Lounge (Bedroom 5): Daybed converts to queen sleeper; barn door + blackout drapes for privacy. Features “The Landing” logo wall.

⸻

🌞 OUTDOOR FUN

💦 Private Pool (April–October)
Fully fenced when open, with loungers, umbrellas, and big water views. It feels like your own little resort.

🔥 Firepit on the Water
Eight Adirondack chairs, propane firepit, and solar lights — perfect for s’mores, stories, and early-morning coffee.

🦀 Outdoor Dining
• Dining table for 10
• Bistro table for two
• “Car Bar” for crab feasts, buffets, or lemonade stands

🌊 Waterfront + Beach Access
Located on Chews Creek (great views and wildlife — swimming not recommended). A 10-minute walk brings you to the community Bay beach for sunsets and sandy toes.

Beach chairs and lawn games are provided.

—

CLEANING

Professional cleaning, hotel-quality linens, and full turnover included — no extra linen or supply fees.

⸻

📍 KENT ISLAND LOCATION

You’re minutes from:
• Wineries & waterfront seafood
• Marinas & boat rentals
• Golf
• Parks, trails & art galleries
• Groceries, Target & Starbucks

Easy access to Kent Narrows, Historic Stevensville, Queenstown, Wedding Venues, and day trips to St. Michaels, Naval Academy, Annapolis, Easton, and Oxford.

⸻

❤️ A NOTE FROM YOUR HOST

The Landing was designed to be a place where people feel comfortable, welcomed, and cared for. Hosting is personal to me, and I’m always available to help make your stay easy and special — whether that’s recommendations, questions, or making sure everything feels just right.

⸻

⭐ THE LANDING IS PERFECT FOR…

Family vacations, multigenerational trips, friends’ getaways, or anyone looking for a warm, fun, waterfront escape with room to actually enjoy being together where both kids and grown-up can have fun!

THINGS TO KNOW

You may access the entire home and yard with the exception of the garage and the two locked closets upstairs.

Our neighbor, Kim, is lovely and will be available to assist you during your stay.

Primary guest must be 25+ and be present for the duration of the stay. Events not permitted.

The Landing is located in a quiet residential neighborhood. The onsite caretaker is the next-door neighbor.

Please note that part of Island life is having well water. As a result, bottled water is recommended for drinking / cooking.

No smoking anywhere on property (inside or outside). No parties or events.

Swim in pool, beach, and waterfront at your own risk, no lifeguard, owner and manager assume no liability.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:30 AM
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Children

Children allowed: ages 0–17
Children are welcome at this property
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit one pet total)
Pets are allowed at this property
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Smoking

Smoking is not permitted
No smoking allowed at this property

Check-out instructions

The host requires you to complete the following before checking out:
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Please return the pool gate key to the hook in the mudroom.
Hope you enjoyed your stay and have a safe trip home!!
Failure to complete these may result in a negative review from the host.
Swim, boat, use playground, and use pool and waterfront at your own risk. Owner not liable for any incidents.
No smoking anywhere on the property (inside nor outside). Any evidence of smoking inside or outside will result in a $1,500 fine.
Please note that part of Island life is having well water. As a result, bottled water is recommended for drinking / cooking.

Important information

You need to know

Property # 4927498vb
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
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. Chesapeake Bay Bridge and Captain Avery Museum are local landmarks, and travellers looking to shop may want to visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. Travelling with kids? Consider Paul Reed Smith Guitars and Annapolis Maritime Museum. Kayaking and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and ecotours nearby.
Map
Stevensville, MD

What's nearby

  • Northern Chesapeake Bay - 8 min walk - 0.7 km
  • Sandy Point State Park - 25 min drive - 27.5 km
  • Chesapeake Bay Bridge - 25 min drive - 28.2 km
  • U.S. Naval Academy - 38 min drive - 41.6 km
  • Annapolis City Dock - 42 min drive - 43.4 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 40 min drive

Restaurants

  • ‪Kent Island Elks Lodge - ‬9 min drive
  • ‪Kentmorr Restaurant & Crab House - ‬10 min drive
  • ‪Dirty Dave's Island Tiki Bar - ‬10 min drive
  • ‪Matapeake Cafe - ‬13 min drive
  • ‪P's Pool Party! - ‬10 min drive

Frequently asked questions

Does *Waterfront* 5BR w/ Pool + Firepit on Kent Island! have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at *Waterfront* 5BR w/ Pool + Firepit on Kent Island!?

As of 2 Oct 2026, prices found for a 1-night stay for 2 adults at *Waterfront* 5BR w/ Pool + Firepit on Kent Island! on 7 Dec 2026 start from AU$2,662, 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.

Is *Waterfront* 5BR w/ Pool + Firepit on Kent Island! pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much is parking at *Waterfront* 5BR w/ Pool + Firepit on Kent Island!?

On-site parking is available at the property.

What time is check-in at *Waterfront* 5BR w/ Pool + Firepit on Kent Island!?

Check-in begins at 4:00 PM.

What time is check-out at *Waterfront* 5BR w/ Pool + Firepit on Kent Island!?

Checkout is at 10:30 AM.

Where is *Waterfront* 5BR w/ Pool + Firepit on Kent Island! located?

This family-friendly Stevensville holiday home is located on the waterfront, within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay. Romancoke Wharf County Park is 2.6 mi (4.1 km) away.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 6 out of 7 reviews
Rating 8 - Good. 1 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jenna (host) is amazing! She was super responsive and did everything within her power to ensure we had the things/information we needed to have an enjoyable stay. The property was beautiful and we truly cannot stop talking about lovely our weekend getaway was!
Stayed 2 nights in Sep 2026
Response from VrboOwner on 22 Sept 2026
Christina, thank you so much for the lovely review — I’m glad you enjoyed your weekend. You were such a kind and great guest. I’d love to host you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The space was beautifully decorated, plenty of seating and space for a family getaway and the view was perfect. Our kids enjoyed the playset and the quick walk to the beach. Our host was proactive in communication and very warm and inviting.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 17 Mar 2026
Thank you Peter for your kind review! It meant so much to hear how much your kids loved The Landing!! You’re welcome back any time!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great home for families. Nice communal areas for games and hanging out by the pool. The host was readily available for any communication. Good time had by all.
Stayed 8 nights in Jul 2026
Response from VrboOwner on 13 July 2026
Thank you Luke - you and your family were wonderful guests. I’m grateful you chose The Landing for your stay. I hope you’ll come back again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property is absolutely beautiful. The decor and cleanliness is beyond expectations. The beds were comfortable and plenty of areas to mingle and enjoy family. We celebrated my daughters engagment here and it was beyond special. Just perfect!
Stayed 3 nights in Mar 2026
Response from VrboOwner on 17 Mar 2026
Thank you Kelly! I’m so honored you chose to celebrate your daughter’s engagement at The Landing. You and your family were wonderful guests and I appreciated your kindness and great communication. I’d love to host you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Gorgeous property… four great bedrooms plus a convertible lounge on the ground floor, a huge yard, and an expansive living area connected to the sunroom. We visited in the winter, but the pool, fire pit, and outdoor spaces would be fantastic in the summer.House was well stocked w/ coffee, towels, soaps, etc. Wonderful & responsive host.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 19 Jan 2026
Nick - thank you so much for your kind words. I’m so grateful and appreciated you and your friends being wonderful guests. You’re welcome back anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an amazing time in this charming home.
Stayed 7 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Needs weeds picked from beds, and better cleaning around pool area. Need cleaning supplies in kitchen to clean counters and sink. Vacuum cleaner would be a good idea.Enjoyed fire pit but fence around pool was disturbing. No grille was also disappointing.Host was very good.Thank you, Ron Altieri
Stayed 5 nights in Jul 2026

About the host

Hosted by Jenna Jacobson

Host profile image
Being a host is incredibly meaningful. I love helping families and friends have memorable vacations. Making sure you enjoy your stay, feel comfortable, and have fun is my goal!

Why they chose this property

Kent Island is the largest island in Maryland. I love that the views are beautiful, time sees to slow down, and there is so much nature to see. I also love the restaurant scene and visiting the historic towns and art galleries.

What makes this property unique

The Landing at Kent Island offers the feel of a boutique luxury resort with the privacy and space of a vacation rental home. It caters to all ages and interests from the kid’s playroom, to the custom coffee bar, to the outdoor “car bar,” pool, and our favorite - the fire pit! But best of all are the views. They are simply stunning.
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