The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!
⭐ 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 entertaining & fun 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.
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🛋️ 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 hosting a big family dinner or just hanging out in pajamas, the layout makes it easy.
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🍽️ EAT, DRINK & LINGER
The Kitchen: fully stocked for preparing real meals and easy hosting — 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.
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🛌 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.
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🌞 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 & Entertaining • 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.
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CLEANING
Professional cleaning, hotel-quality linens, and full turnover included — no extra linen or supply fees.
Easy access to Kent Narrows, Historic Stevensville, Queenstown, Wedding Venues, and day trips to St. Michaels, Naval Academy, Annapolis, Easton, and Oxford.
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❤️ 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.
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⭐ THE LANDING IS PERFECT FOR…
Family vacations, multigenerational trips, friends’ getaways, bachelorette parties, celebrations, 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.
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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Pets allowed: dogs less than 23 kg per pet (limit one pet total)
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Smoking
Smoking is not permitted
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
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
Frequently asked questions
Does The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground! have a pool?
Yes, this property has an outdoor pool.
How much does it cost to stay at The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!?
As of 4 April 2026, prices found for a 1-night stay for 2 adults at The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground! on 27 April 2026 start from NZ$1,420, 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 The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground! 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 The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!?
On-site parking is available at the property.
What time is check-in at The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!?
Check-in begins at 4:00 PM.
What time is check-out at The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!?
Checkout is at 11:00 AM.
Where is The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground! 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
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
Peter W.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 17 March 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!
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.
Nick S.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 19 January 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!
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!
kelly h.
Stayed 3 nights in Mar 2026
Response from VrboOwner on 17 March 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!
About the host
Hosted by Jenna Jacobson
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.