Kent Island Rentals

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130 Houses

Serene Waterfront Apartment on Kent Island

Stevensville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$229

“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

$458

Price per night from

$458

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

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$1,947

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$802

Waterfront Getaway - View of bay from your bed

Romancoke studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$228

Waterfront home with private pier is A Shore Thing

Chester house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$429

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,947

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$321

Private pier at Waterfront Kent Island home with Hot Tub (Open!)

Stevensville house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$416

Great rentals within 20 miles that match your search

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

$716

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

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$344

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$476

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$859

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,145

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

Price per night from

$2,290

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$400

Great deal 4 Bedroom House Near the Ferry Park

Rock Hall house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Price per night from

$275

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Price per night from

$2,290

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Price per night from

$2,863

Waterfront Condo Amazing Views with Resort Amenities

Annapolis condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$441

Ferry Bridge House

Easton house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

Price per night from

$796

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$457

Huge Beach Bungalow- Yard, Beach Pass, King Beds

North Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$630

Waterfront Getaway, Dock Your Boat and Play!

Mayo camper van

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$343

London Towne Bungalow w/Loft

Edgewater bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$298

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$572

The Fritz

Edgewater house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,546

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$224

New, Book Me! Riverview Retreat on Warehouse Creek

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$315

South River Hangout

Edgewater tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 16

Price per night from

$344

Neptunes by the Water

Cape Saint Claire house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$207

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$682

Charming Charles Retreat

Annapolis house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$430

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Price per night from

$189

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$401

Viewing 38 of 130
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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