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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
Outdoor pool
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
Exterior
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 $205
$416 total
includes taxes & fees
Jul 14 - Jul 15
Relax on Kent Island in 3 Bedroom Home w/Waterview
Waterfront Cottage on the Eastern Shore
Fridge, microwave, oven, stovetop
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 $599
$1,134 total
includes taxes & fees
Jun 26 - Jun 27
Waterfront Cottage on the Eastern Shore
Chesapeake Houseboat Getaway on Kent Island, Maryland
Property grounds
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!
Interior
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
Fridge, microwave, oven, stovetop
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
Beach
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
Exterior
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!
Fridge, microwave, oven, stovetop
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.
Property grounds
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
10.0 out of 10, Exceptional, 64 reviews
"Firefly cottage is a beautiful little place, super clean and with every possible convenience - well stocked, with lots of special touches. Terrific hosts and a lovely cottage - we thoroughly enjoyed it! Thank you…. Sheilah"
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
Anchor's Away in the Heart of Eastport!
Fridge, microwave, oven, stovetop
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
Outdoor pool, a heated pool
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 $275
$502 total
includes taxes & fees
Jul 7 - Jul 8
Waterfront Oasis of Annapolis Star
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
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!
View from property
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
Fridge, microwave, oven, stovetop
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
Property grounds
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 $399
$766 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.
Interior
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
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 199 reviews
"This is the perfect place for a private anniversary getaway. The house is very clean and the views are terrific."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun loungers, beach towels
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
Smart TV
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, 84 reviews
"The houseboat is exactly as pictured online, it is clean modern and cozy. Kirby & Cassidy were excellent to work with to plan our trip. When we arrived we found snacks for us in the kitchen which was so thoughtful of our hosts. My husband loves boats so this was the perfect trip for us while our kids were at summer camp. It was so relaxing being on the water, we enjoyed looking out the window in the morning with coffee and sitting on the roof top deck in the evening watching the sunset. We will...
The price is $150
$364 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
Front of property - evening/night
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 $239
$291 total
includes taxes & fees
Jul 21 - Jul 22
The Inn at Chesapeake Bay Beach Club
Kent Island Resort
Aerial view
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 $233
$298 total
includes taxes & fees
Jun 26 - Jun 27
Kent Island Resort
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
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.

Everything you need to know about Kent Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kent Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kent Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kent Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kent Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kent Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kent Island rentals

At Expedia, we put the best Kent Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kent Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kent Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kent Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Kent Island properties
Expedia verified reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
"I can’t say enough good things about this Inn. Location, staff, cleanliness, and amenities were all of a 5 star, first class Inn at Expedia prices. Highly recommend!"
A verified traveler from Reston stayed at Historic Inns of Annapolis
Posted 19 hours ago
Historic Inns of Annapolis