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Kent Island Rentals

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Price: high to low

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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

$341

Price per night from

$403

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 50 minutes

Price per night from

$1,990

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$460

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

$472

New! Charming Farmhouse in Historic Village Center

Stevensville house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$182

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

$157

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$657

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$395

Small Boat in Annapolis!

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$158

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$651

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,315

Lochhaven house for rent

Edgewater house

3 bedrooms / 1 bathroom / sleeps 2

Price per night from

$132

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$592

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,034

Location,location,location,walk to city dock,free

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$317

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

Edgewater house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 24 minutes

Price per night from

$517

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$2,416

NEW! Classic Family Home: Water View, Walk to Pier

Mayo house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 9 minutes

Price per night from

$213

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$452

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$287

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

$807

*BOOK NOW* Beautiful Cottage in historic Annapolis

Annapolis cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$372

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$283

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

$948

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$316

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$553

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

$796

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$806

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$330

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$445

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 47 minutes

Price per night from

$867

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$264

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$289

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

$489

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 25 minutes

Price per night from

$862

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

$334

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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