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Kent Island Rentals

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74 Results

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74 Houses

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$177

Huge Stevensville House Overlooking Eastern Shore!

Stevensville house

3 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 5 minutes

Price per night from

$474

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

$327

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

$288

Price per night from

$402

KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 17 minutes

Price per night from

$1,529

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$462

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

$470

Great rentals within 20 miles that match your search

Little Boat in Annapolis!

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$141

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$587

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 8

“A best kept secret!” I have had the pleasure of staying at Cliff Point many times. The view cannot be matched, water views more than 180 degrees, sunsets are stunning. But on top of that the house is so comfortable and charming, spacious and cozy. Charming, Chestertown is a short drive away if you would enjoy a Saturday morning at the farmers market, antiquing, or maybe you want to stay on the water and take a kayak out. This is a perfect place for a family vacation or romantic get away, you choose. But do choose to come to Cliff Point it is a best kept secret! I try to get here as often as time allows. And that is not often enough.

Price per night from

$347

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 41 minutes

Price per night from

$336

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$353

Small Boat in Annapolis!

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$142

Charming Eastport Home

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$353

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$234

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$353

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$582

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,176

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$818

Lochhaven house for rent

Edgewater house

3 bedrooms / 1 bathroom / sleeps 2

Price per night from

$118

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$294

Luxury Apartment with Private Entrance

Centreville apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$138

Modern Luxury Rental in North Beach!

North Beach house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$159

St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$587

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$529

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$164

Luxury Boat & Bed 78' Motor Yacht "Laid Off"

Edgewater yacht

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,163

Charming Artists Home in Eastport/Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$441

*BOOK NOW* Beautiful Cottage in historic Annapolis

Annapolis cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 23 minutes

Price per night from

$373

4,000 Sq Ft Annapolis Area Home w/ Backyard Oasis!

Riva house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$435

NEW! Quiet Sailor’s Home with Pier and Bay Vistas!

Tilghman house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$276

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

“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

$785

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$439

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$279

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$279

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

$484

Waterfront Annapolis Area 3BR/3BA Retreat with Private Pier

Edgewater house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$372

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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