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Waterfront vacation rentals in Kent Island

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Kent Island waterfront rentals

Waterfront apartment rentals

Guest favorite
A two-story building is shown, featuring a metal roof and a wooden balcony adorned with potted plants. Outdoor furniture is visible on the balcony, and multiple windows can be seen on the building's exterior.
Apartment in Chestertown
4.98 out of 5 average rating, 107 reviews

RIVER WATCH

PeggyRating, 5 stars4 weeks ago
It was an extremely lovely apartment overlooking the beautiful Chester River! The apt was spotless, warm, inviting & had lots of amenities. Walter was beyond helpful: he rescued me when my rental car broke down out of town on the highway in the rain. You can’t ask for more than that!! Thank you for a wonderful stay!!
Top guest favorite
A spacious dock area displays two Adirondack chairs positioned for enjoying the water views. The wooden platform features a vibrant finish, with boats visible in the distance and trees lining the shoreline under a partly cloudy sky.
Apartment in Pasadena
5 out of 5 average rating, 22 reviews

Relaxing Waterfront Apartment!

VictoriaRating, 5 stars6 days ago
WOW! My family and I cannot say enough great things about Jeanne's Airbnb already planning our next trip! First off the property is an oasis in itself with a massive deck overlooking the inlets of Chesapeake Bay we woke up every morning to a beautiful blue heron eating breakfast right on the dock, having access to kayaks to explore the waterways was a huge bonus too, not to mention the gazebo with a fire pit we enjoyed roasting marshmallows and talking about the days adventures as a family. The inside of the Airbnb is extremely well thought out with every amenitie that anyone could ever ask for, from a well stocked and equiped kitchen, to the king size master bed with luxurious soft linenes, to the heated fan that greets you after a perfect water pressure shower. Seriously, this place is perfect a hidden gem for sure with easy access to so many wonderful Maryland attractions. Can't say enough great things about this experience and Airbnb can't wait to return!
Top guest favorite
A serene view of the Severn River is captured, bordered by lush greenery and blooming flowers. The calm water reflects the sky and surrounding landscape, while trees create a natural frame. Sunlight casts gentle shadows over the grassy area, enhancing the tranquil setting.
Apartment in Annapolis
4.98 out of 5 average rating, 115 reviews

One bedroom apartment in Annapolis

AmyRating, 5 stars6 days ago
Lisa’s place was amazing! My daughter and I had a great visit. The location is perfect for going into Annapolis. We will definitely be back. Thank you for a great few days!
Guest favorite
A cozy living area displays a flat-screen TV on a rustic wooden console. A round coffee table sits center-stage, surrounded by comfortable seating. Light enters through angled windows, highlighting the warm wood flooring and inviting decor elements.
Apartment in Wye Mills
4.77 out of 5 average rating, 66 reviews

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

TimRating, 5 stars1 week ago
Host was responsive, rental was as pictures with no surprises and clean upon arrival. Would stay there again
Top guest favorite
An aerial view showcases a large grassy area surrounding a heated pool, with several lounge chairs positioned nearby. A fire pit is set with white adirondack chairs. Two properties are visible, featuring balconies and umbrellas enhancing the outdoor space.
Apartment in Stevensville
5 out of 5 average rating, 48 reviews

Heron Roost

EmilyRating, 5 stars1 week ago
This was unanimously our family's favorite AirBnB! Dana and Mike are the dream hosts! Our accommodations prior to our scheduled arrival were cancelled last minute and they immediately jumped in to help. They were extremely considerate of our privacy whilst being right next door but also quick to respond when we reached out to them. We could not of asked for a better mini-vacay in the middle of our travels. The beautiful surroundings, welcoming accommodations and hosts, attention to detail throughout amenities and decor, and impeccable cleanliness were top-notch. We really enjoyed the heated pool too. The kitchen and grill were easy to navigate and stocked with all essential items needed to prepare meals. The Monocle Meat Company and Lovepoint Deli & Wine are great local shopping options. If cooking is not in your plans, Avanti has amazing pizza. Thank you Dana and Mike for going above and beyond to make us feel at home! Heron Roost is now our must stay place when visiting MD.
Guest favorite
A well-maintained inground pool can be seen surrounded by a spacious deck featuring lounge chairs and shaded seating areas. Lush greenery and trees create a natural backdrop, enhancing the outdoor space’s tranquility with direct views of the water.
Apartment in Arnold
4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

JennaRating, 5 stars9 months ago
Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.
Top guest favorite
A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.
Apartment in Essex
4.97 out of 5 average rating, 272 reviews

A place unique on sue creek

BritneyRating, 5 stars4 days ago
This place was so peaceful. I really felt comfortable and relaxed. It’s a very beautiful area.
Guest favorite
A serene waterfront view is captured at sunset, revealing the reflection of sunlight shimmering on the water. Boats are moored at the dock, and foliage frames the image, creating a tranquil atmosphere. The horizon is lined with trees under a warm golden sky.
Apartment in Dundalk
4.86 out of 5 average rating, 7 reviews

Waterfront Romantic Studio

JuanRating, 5 stars6 days ago
Michaels place was amazing enjoy every minute of it wish I could had stayed longer but I know for a fact when I come back I will be staying here.

Waterfront house rentals

Top guest favorite
Home in Stevensville
5 out of 5 average rating, 21 reviews

Chessie Cottage - Chesapeake Bay

CarolineRating, 5 stars1 month ago
We had the BEST time staying at this beautiful home this past weekend while we were in town for a wedding. The location is absolutely perfect for a peaceful weekend on the water and this house is a DREAM. Thank you so much for letting us stay at your incredible home!
Top guest favorite
A spacious living area features large windows offering unobstructed views of the water. A comfortable sectional sofa is complemented by decorative cushions. A coffee table is positioned in front, with planters adding greenery. A wall-mounted television is visible, alongside a cozy fireplace.
Home in North Beach
5 out of 5 average rating, 142 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

StephanieRating, 5 stars6 days ago
This was our second time staying at Kimberly’s home, and it was just as magical as we remembered. The views of the water are absolutely stunning—whether you’re enjoying your morning coffee or winding down in the evening, it’s hard to look away. The location is perfect: peaceful but just a short walk to shops and restaurants. We also really appreciated the Peloton and treadmill—such a bonus for staying active during our trip. Everything was spotless and thoughtfully prepared. Honestly, we didn’t want to leave. Already looking forward to our next visit!
Top guest favorite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge
4.99 out of 5 average rating, 171 reviews

Sunset Breezes - quiet waterfront retreat

MicheleRating, 5 stars2 months ago
Scott and Melinda's place was perfect for a peaceful getaway for our family of 5. The water was so nice to wake up to and fall asleep hearing the water move by! The thought of all the basic needs and had everything easily accessible from fresh eggs from their chickens, a great variety of coffee pods and creamer, and all the other small needs that come up while staying in an airbnb. This was great since it is off the beaten path. If you are looking for some peaceful family time or a secluded retreat with friends, this is a perfect place!
Top guest favorite
A wooden dock extends into the calm waters, leading to a two-story, gray house with white accents. The home features multiple windows and a spacious deck overlooking the water, surrounded by green grass and trees. The shoreline is lined with rocks.
Home in Stevensville
5 out of 5 average rating, 46 reviews

Away at the Bay: New Home on the Chesapeake Bay!

PaigeRating, 5 stars2 weeks ago
Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.
Top guest favorite
A spacious outdoor area features a stone fire pit surrounded by chairs, overlooking a serene waterfront. A boat is docked in the distance, and a bright red umbrella provides shade. Lush green grass and a wooden deck create a welcoming atmosphere.
Home in Pasadena
5 out of 5 average rating, 16 reviews

Rock Creek Cottage, Waterfront

SandyRating, 5 stars3 weeks ago
The place was spotless and had all the amenities we needed for a 4 day stay. We enjoyed the water view and had a crab feast on the deck overlooking the water. It was a perfect Memorial Day weekend.
Top guest favorite
A scenic view of a spacious green lawn bordering a tranquil waterway. A white house is positioned near the water's edge, surrounded by trees and a clear blue sky. The peaceful setting is enhanced by the gentle reflection of the landscape in the water.
Home in Oxford
5 out of 5 average rating, 57 reviews

Stunning Chesapeake waterfront home

AlanoudRating, 5 stars2 weeks ago
We had a truly wonderful stay at this beautiful home! The place was spotless and very well maintained, and we felt comfortable from the moment we arrived. There were plenty of activities to enjoy as a family, and we created some unforgettable memories here. The host was incredibly friendly and responded quickly to any questions we had, which made everything even more enjoyable. The surroundings are absolutely stunning, and the sunset views were nothing short of magical. We would love to come back again!
Guest favorite
A spacious living area is highlighted by large windows allowing natural light. Modern furniture includes a sectional sofa and accent chairs, complemented by a sleek coffee table. A large television is mounted on the wall, while indoor greenery adds a touch of nature.
Home in Edgewater
4.98 out of 5 average rating, 124 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

JeanRating, 5 stars1 month ago
This house was perfect for our large family. It had everything we needed and was very comfortable. The place was very clean and nicely decorated. The kitchen is well stocked with plenty of dishes and cookware for a large group.
Guest favorite
The exterior view features a multi-level bayfront retreat with a circular architecture. A wooden dock extends over the water, providing access to the shore lined with rocks. Lush greenery surrounds the property, contributing to a serene water-facing environment.
Home in Stevensville
4.95 out of 5 average rating, 20 reviews

Bayou on the Bay

AaronRating, 5 stars2 days ago
Very nice stay!! We enjoyed the place and thought it was super nice. Would highly recommend

Waterfront condo rentals

Guest favorite
A modern living area features a sleek flat-screen television mounted above a stone fireplace. On either side, wooden shelving units are filled with decorative items and books. The ambient light from the fireplace creates a cozy atmosphere, complemented by neutral wall colors.
Condo in Baltimore
4.89 out of 5 average rating, 236 reviews

Historic Federal hills urban lifestyle

LarellRating, 5 stars1 week ago
I was impressed by how clean and uncluttered Ricky’s place was. It was definitely a benefit that parking was included, though it was a little awkward loading and unloading and getting to and from the parking garage. Garage was a block away and secure with lots of cars nicer than mine haha.
A modern kitchen area presents sleek cabinetry and a white countertop, with a kitchen island featuring open shelving. Light wood flooring complements the space. In the background, a cozy living area is partially visible, showcasing a green sofa and wall art.
Condo in Washington
New place to stay

Ità Vero DC 1-Bdrm Lux Apt

TravoltaRating, 5 stars1 day ago
All I can say is AMAZING! The view’s looking over the water, the building was like a 5 star hotel, concierge etc…. This is a perfect spot to relax and take a breather ❤️❤️❤️❤️❤️
Top guest favorite
A modern living area is depicted with a cozy seating arrangement, featuring a light-colored sofa and armchairs with striped patterns. A stone fireplace serves as a focal point, while ambient lighting is provided by a stylish overhead fixture. Natural light floods in through the windows.
Condo in Baltimore
5 out of 5 average rating, 56 reviews

Harbor Gem

DawnRating, 5 stars6 days ago
We stayed at Gerald's wonderful Airbnb for our daughter's surgery at JH Hospital and it was perfect in every way. It is one of THE best Airbnb's we've stayed in, and we've stayed in many all over the world. His place is clean, stylish yet comfortable (including the mattresses), and well stocked, with lots of appreciated amenities. As a host, Gerald is very helpful, communicative, accomodating, and friendly. It is clear he values and prioritizes his guests' comfort and experience. It is conveniently located - walking distance to everything the Inner Harbor offers, Camden Yards, and much more. We definitely plan on returning to Gerald's place (under better circumstances)!
Top guest favorite
A comfortable living area is displayed, featuring a sectional sofa and a coffee table on a textured rug. A wall-mounted television is visible, alongside a stylish fireplace. The open layout connects to the kitchen area, with warm lighting illuminating the space.
Condo in Annapolis
4.98 out of 5 average rating, 84 reviews

Charming Annapolis Waterfront Condo

JanelleRating, 5 stars4 days ago
Great host, great location. Walkable to great restaurants as right over the bridge from Main Street Annapolis. The pool is literally right in front of the apartment overlooking the water and the boats going by. The place is not huge but location, location, location.
Superhost
A sandy beach stretches along the shoreline, dotted with parasols and beachgoers. Calm waters reflect a clear sky, while a pier juts out in the distance, framed by lush greenery. The serene landscape offers a tranquil view of the surrounding nature.
Condo in Betterton
4.92 out of 5 average rating, 38 reviews

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

SihamRating, 5 stars1 week ago
My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!
Superhost
The living area features a comfortable blue sectional sofa paired with a light-colored accent chair. A round metallic coffee table rests on a patterned area rug. Two lamps with white shades provide soft lighting, while large windows offer natural light and views of the outdoors.
Condo in Annapolis
4.71 out of 5 average rating, 7 reviews

Waterfront Eastport Condo w Rooftop Pool & Parking

IanRating, 5 stars3 weeks ago
Sean’s unit is an amazing option for those who love a great place to relax with an amazing view. Sean is a great host and very communicative.
Top guest favorite
An outdoor covered deck offers seating with a sectional sofa and a coffee table. High chairs are positioned at a bar-style table, with views of greenery and the bay in the distance. The area is brightened by natural light and features a welcoming atmosphere.
Condo in Betterton
5 out of 5 average rating, 18 reviews

Beach Haven Hideout

JenniferRating, 5 stars3 weeks ago
What a perfect weekend get away. The place was perfect. Extremely comfortable beds, lots of pillows and two deck areas outside. We cooked outside 2 nights - and loved seeing the bay from the deck. We used the nearby tennis and basketball courts, and spent the days visiting wineries and neighboring towns, and driving through the countryside. Groceries and restaurants require some planning and some driving. Loved our stay!
Guest favorite
An aerial view captures the condo building with a red roof, framed by a sandy beach and the Chesapeake Bay. A wooden pier extends into the water, where gentle waves create rippling patterns. The surrounding area includes a path lined with trees and beachgoers enjoying the day.
Condo in North Beach
4.96 out of 5 average rating, 26 reviews

Unbelievable beach views for 6

JuliannRating, 5 stars2 weeks ago
Condo was in a perfect location in North Beach area. Loved walking boardwalk and walked 5+ miles daily. Felt very safe in the area, everyone was so friendly. Mexican restaurant and Baia were fantastic. Very peaceful. Condo definitely worth the money. Host was very responsive and let us check in early and was quick to reply to any text questions. Loved the view!

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