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Kent Island Rentals

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70 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

$340

Responds fast! avg. 27 minutes

Price per night from

$404

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$519

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-Kent Island House with Pool and Bay Views!

Stevensville house

3 bedrooms / 3 bathrooms / sleeps 13

Responds fast! avg. 2 hours 4 minutes

Price per night from

$369

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

$156

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$391

Small Boat in Annapolis!

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$157

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$2,393

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$912

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$153

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$306

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,146

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 58 minutes

Price per night from

$518

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$659

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

$492

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

$790

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$801

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

$655

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$862

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

$862

Waterfront Annapolis Home: Fire Pit & Fishing Pier

Cape Saint Claire house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$334

Downtown Annapolis Home, Walk to Navy Stadium

Annapolis townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$129

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$569

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

$206

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

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$334

Annapolis Home w/ Deck & Whitehall Bay Access

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$236

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$813

Annapolis Area Shagrila Resort

Davidsonville house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 37 minutes

Price per night from

$460

NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!

Lothian house

2 bedrooms / 1 bathroom / sleeps 2

Price per night from

$123

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$190

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$804

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$334

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$311

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

$621

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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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