Kent Island Holiday Rentals from €635: Search Short-Term Rentals

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Holiday Rentals in Kent Island

"We loved everything about the Kent Island House! Would book again in a hot minute"

"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."

"Clean, Spacious, and exactly as advertised! "

includes taxes & fees

26 Jan - 27 Jan

"The home accomodated"

"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"

"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...

"Great property and location to everything is ideal. Would definitely book this place again. "

"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"

"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "

"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."

"What a fantastic location, central to everything in the city. Parked the car and walked everywhere. The house is perfect!!"

includes taxes & fees

20 Jan - 21 Jan

"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"

"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "

"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...

"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "

"Great location! Beautifully furnished! I stayed here for a month and loved it. The property manager is awesome. Responds to requests within minutes. Book it you won’t be disappointed!"

"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"

"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."

"This home is a wonderful place to stay. We enjoyed so much about it: the fully-equipped kitchen with spices and every appliance you might need, bathrooms with rain showers/good water pressure, decks for outdoor lounging, plenty of space and nice furnishings in the living room, and a quiet neighborhood that isn't too far away from the downtown area. We would love to come back again!"

"Liz was great from the jump. Gave clear directions for check in/out. Place was super cute and super convenient to downtown Annapolis!"

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

"We stayed one night for New Year’s Eve. And everything was awesome. We also had a great dinner in your restaurant"

includes taxes & fees

19 Jan - 20 Jan

"Historic charm and clean."

includes taxes & fees

22 Jan - 23 Jan

"We loved everything about the Kent Island House! Would book again in a hot minute"

Find out more about Kent Island

Everything you need to know about Kent Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kent Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kent Island holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kent Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kent Island holiday rentals we have selected for you start as low as €635 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kent Island rentals

At Expedia, we put the best Kent Island holiday 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 holiday.

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

5/5 Excellent

"Upscale facility with caring and attentive staff that go above and beyond to make you feel welcomed and comfortable. "

A verified traveller stayed at Hyatt Place Kent Narrows & Marina

Posted 18 hours ago

5/5 Excellent

"The Governor Calvert House is a beautiful, historic building centrally located in the heart of downtown. All the staff were very friendly and accommodating and many great restaurants, boutiques, and bars are just a short walk away. Has long been my hotel of choice when in Annapolis during the state's legislative session. "

A verified traveller stayed at Historic Inns of Annapolis

Posted 2 days ago

Country Inn & Suites by Radisson, Annapolis, MD

5/5 Excellent

Good Annapolis Option

"This is a good inexpensive hotel near the Annapolis mall. Staff and breakfast service is always good. We appreciate the layout of the suites since they provide plenty of room along with microwave, fridge, and comfortable bed. Grocery is convenient-right across street. Hotel has been around for many years but seems to be relatively well maintained."

A verified traveller stayed at Country Inn & Suites by Radisson, Annapolis, MD

Posted 8 days ago

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Holiday Rentals in Kent Island

Plan, book, stay with confidence

Check prices for these dates

Holiday Rentals in Kent Island

Pool and Bay Views on wrap around deck in Kent Island

Circa 1700 Chesapeake Colonial home on the National Register.

Relax on Kent Island in 3 Bedroom Home w/Waterview

Beautiful Chesapeake Bay Views -pet friendly

Chesapeake Houseboat Getaway on Kent Island, Maryland

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Freshly renovated 3-story home 1 block from USNA!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Recently Renovated Annapolis Home - Conveniently Located

The Blue Crab Beach House - Free beach passes

2-story, riverfront home with private dock, inviting deck & dog-friendly yard

Charming Annapolis WaterVIEW Home

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

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

The Inn at Chesapeake Bay Beach Club

Kent Island Resort

Pool and Bay Views on wrap around deck in Kent Island

Find out more about Kent Island

Recent reviews of Kent Island properties

Hyatt Place Kent Narrows & Marina

SpringHill Suites by Marriott Annapolis

Historic Inns of Annapolis

Sonesta ES Suites Annapolis

Hilton Garden Inn Annapolis Downtown

Graduate by Hilton Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Courtyard by Marriott Annapolis

Crowne Plaza Annapolis, an IHG Hotel