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Kent Island Rentals

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74 Houses

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$184

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

Price per night from

$453

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

Price per night from

$401

Responds fast! avg. 54 minutes

Price per night from

$458

KI Golf House-A PAR for the Course & Mile to Beach

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$516

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$487

New! Stunning Waterfront with pool for Naval Academy families!

Stevensville house

4 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 1 hour 16 minutes

Price per night from

$745

Kent Island House with Pool and Bay Views!

Stevensville house

3 bedrooms / 3 bathrooms / sleeps 13

Responds fast! avg. 1 hour 16 minutes

Price per night from

$369

Newly-managed Waterfront Kent Island home

Stevensville house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$416

Great rentals within 20 miles that match your search

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

Price per night from

$785

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$297

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that you could ever need and is very unique and quaint. The location is more than perfect (we literally were in walking distance of everything, shops, restaurants, etc.) and did not even have to get into the car to drive anywhere the entire time. The backyard has a wonderful porch where you can sit outside and converse with friends or even sip your coffee in the morning. The view is phenomenal! You have a wonderful panoramic view of the water from your bedroom window and the beds are very comfortable (which is a must for me). If you are planning on a trip to experience St. Michael's whether it is a romantic weekend getaway or a family (group) outing I would hands down recommend this house.

Price per night from

$516

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$352

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

Price per night from

$487

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 23 minutes

Price per night from

$859

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$344

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$218

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$218

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$321

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 9

“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite. As for the house itself, we couldn't have asked for more. It is spacious, clean, and has all of the amenities you could want. I must also mention that it was a breeze and a pleasure working with the folks at Grandview. They are incredibly responsive, and make a great effort to ensure that you enjoy your stay.

Price per night from

$549

Vintage Bungalow-cozy, walkable, free pkg.

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$487

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 3 minutes

Price per night from

$859

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Price per night from

$6,870

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,117

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$441

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$567

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$916

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$205

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$382

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$431

Annapolis Area Shagrila Resort

Davidsonville house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 57 minutes

Price per night from

$458

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,145

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$801

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 17 minutes

Price per night from

$136

22 Fleet St. - Best Spot for Commissioning Week, Newly-Renovated & Historic!

Annapolis condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$302

Ship's Cove Inn and Resort

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$2,290

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$189

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$573

Viewing 38 of 74
rentals in Kent Island

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Top Destination reviews

Love Point Waterfront
A diamond in the Love Point!!!!

We have been renting this home for the last few years & our exprience has always been excellent! The home is very well maintained (Very very clean) & the interior decor is beautifully done. Property has a beautful backyard towards the bay with some good outdoor furnitures & barbeque grills. Paula ensures that the property is well stocked with the necessities (be it extra towels to fishing rods to ping pong tables...). Paula is very friendly & responsive; its a joy to deal with a landlord like her. Overall this is an excellent property nestled by the bay!!!!see more

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