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Kent Island Vacation Rentals

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Vacation Rentals in Kent Island

Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, 23 reviews
"We'd stay there again but with modified expectations based on our experience. The 'water view' is quite distant and obtuse. The water is hundreds of yards away, and separated from the house by several suburban style homes and an unpaved road."
The price is CA $280
CA $569 total
includes taxes & fees
Jul 16 - Jul 17
Relax on Kent Island in 3 Bedroom Home w/Waterview
Waterfront Cottage on the Eastern Shore
9.4 out of 10, Exceptional, 3 reviews
"Very much as pictured in ad. Convenient to we did venue we were attending"
The price is CA $818
CA $1,548 total
includes taxes & fees
Jun 27 - Jun 28
Waterfront Cottage on the Eastern Shore
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Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, 9 reviews
"My husband and I both LOVED this property!!! The houseboat was beautifully decorated, so relaxing and in a great area. We cant wait to go back!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, 7 reviews
"Very clean and well maintained property. We had a great time crabbing on the pier out back and just relaxing. The property is in an excellent location and the host was very quick to answer any questions."
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
9.8 out of 10, Exceptional, 6 reviews
"Overall the home is beautiful. There is a gorgeous mostly well stocked kitchen and 3 bedrooms with beds for couples. One of the king beds listed is a pull out couch in the pool house. The biggest con of this place is that there are no blackout curtains or anything to block the sun in the bedroom so for our June visit the rooms were very bright at 5:45AM. We also had to go out and buy some of our own things that you'd think would be included (garbage bags). Other than that its a beautiful home...
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cozy place close to the city dock
10.0 out of 10, Exceptional, 55 reviews
"We enjoyed our 2 nights at Cozy Place Close to the docks. Easy access and personalized connection with Nathalie were appreciated! We enjoyed the French and sail boating themes in the apartment, aligned the Annapolis maritime history! The docks are a short drive and old Town Annapolis was pleasant and historical! We recommend Cozy Place to others!"
Cozy place close to the city dock
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 189 reviews
"Beautiful grounds in a peaceful, isolated neighborhood. Absolutely as described in the listing. Hosts were helpful and responsive and absolutely everything we needed to enjoy the weekend was there."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, 86 reviews
"Nice house in a great location."
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
10.0 out of 10, Exceptional, 64 reviews
"Pat and Ken were THEE BEST hosts I have E V E R had at any rental. Since my divorce last year I’ve had to use a lot of rentals to spend time with my kids and words cannot explain how amazing these people and this location were. All of it was a huge breath of healing that I needed with my kids and I. So so so amazing."
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
Anchor's Away in the Heart of Eastport!
9.8 out of 10, Exceptional, 31 reviews
"Property is very convenient to the USNA and DTA. You can walk, but they're a good 25-30 minutes and parking was available even during Commissioning week and at the local restaurants. Plus, we could park about 25 feet from the door of the VRBO all the time. It is a first floor, easy to access door. There is a full kitchen and fridge, a comfy couch, and a nice bathroom. It's really like a nice hotel suite. A couple idiocycracies however. The bed pulls down from the wall, which gives you more play...
Anchor's Away in the Heart of Eastport!
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, 63 reviews
"Wonderful Weekend! We had the pleasure of staying at Waterfront Oasis for a long weekend to celebrate my husband’s birthday and it was truly amazing! We were welcomed lovingly and we were provided with a tour of the property. We were blown away by the luxury suite and the beautiful views. We enjoyed the access to the pool, patio with plenty of room to relax on the sofas, and the grilling area was perfect! Being able to walk down to the dock to watch sunsets was just breathtaking. We loved every...
The price is CA $376
CA $685 total
includes taxes & fees
Jul 7 - Jul 8
Waterfront Oasis of Annapolis Star
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, 184 reviews
"This house is perfect for stayiing in the historic distict of Annapolis. Very comfortable and clean. One and one half baths, a private patio, and the best part is the off street parking with a private garage; very hard to find in this beautiful area. John, the manager was so helpful and answered all my questions. If ever in Annapolis again, we will definately stay here."
Directly Across from Gate One & Steps from the Waterfront
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, 66 reviews
"Jim was amazing and answered our questions, etc. almost immediately. He was wonderful and very accommodating. Cozy cottage, loved it."
Amazing views, short walks to great dining!
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, 44 reviews
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, 44 reviews
"This was my Mom's first vacation since the covid pandemic and this location really made it special! She was a kid again in the swings and I found her out there each morning. The location is great, the house is HUGE, and it was full of amazing amenities. Would definitely stay again."
The price is CA $545
CA $1,046 total
includes taxes & fees
Jul 10 - Jul 11
Charming Annapolis WaterVIEW Home
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 15 reviews
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 199 reviews
"We love staying at Magee Cottage. It has all you need to relax and enjoy such a comfortable home on the water. This is our second stay and we’ll hurry back in a few months for more of the good life!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, 90 reviews
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, 84 reviews
"We took this trip to celebrate my 48th bday and to get away from the busy life in Washington DC. It is not only a beautiful little boat house but the location is great. We sampled most of the restaurants in the area via walking. We enjoyed our time in the roof top looking at the sunset, water and boats. It was extremely relaxing and beautiful. We hope to have the opportunity to come back."
The price is CA $244
CA $544 total
includes taxes & fees
Jun 27 - Jun 28
Cass-Away Luxury Houseboat
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See all available properties in Kent Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Kent Island you may be interested in

The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, 345 reviews
"The Inn is a wonderful place - very nice atmosphere, and excellent attentive service. What I liked best is that it was peaceful. I went for a peaceful get-away - and I especially loved the balmy air, the gentle breezes, the gardens, and the birds. Heard and saw so many wonderful birds! And you can meander around the surrounding lanes, and end up down by the water. All so nice!"
The price is CA $326
CA $397 total
includes taxes & fees
Jul 21 - Jul 22
The Inn at Chesapeake Bay Beach Club
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, 70 reviews
"Quiet and beautiful. The staff was very professional and friendly. I felt like I was home. Looking forward to my next visit!!!"
The price is CA $319
CA $408 total
includes taxes & fees
Jun 26 - Jun 27
Kent Island Resort
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kent Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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