The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!

Top rated by guests
Waterfront home in Kent Island - the perfect place to stay on your vacation to Maryland’s Eastern Shore.
The Coffee Bar is a highlight at The Landing. With a french press, Keurig, and nespresso machine - along with a welcome pack of coffee pods - you will enjoy waking up with a freshly brewed cup while enjoying the peaceful views.
Our record player is a great way to unwind and enjoy an evening with friends and family. We have about 15 records you can feel free to listen to during your stay.
Interior
Interior
review stars
10Outstanding
(3 Ratings)
"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 ..."
Peter W.
Don't miss out! Price and availability may change
10 / 10
Outstanding(3 Ratings)

House in Kent Island, MD

12 guests · 5 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

⭐ 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.



🛋️ 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.



🍽️ 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.



🛌 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 & 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.



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, 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.

Amenities at The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!

Non-smoking
Pets allowed
Family friendly

Map of Kent Island, MD


Ratings and reviews

10 / 10
Outstanding(3 Ratings)
10 / 10Outstanding·Jan 2026
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.
10 / 10Outstanding·Jan 2026
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.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground! pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.