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Kent Island Rentals

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101 Houses

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$183

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

$458

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

$464

Responds fast! avg. 55 minutes

Price per night from

$464

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

$1,971

Golf..Fish..Hunt..Shop - A PAR for the Course & Mile to Beach on Kent Island

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$783

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

$812

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

$1,971

Kent Island House with Pool and Bay Views!

Stevensville house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 25 minutes

Price per night from

$368

Seize the Bay at Waterfront Kent Island home with Hot Tub (Open!)

Stevensville house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Price per night from

$415

Great rentals within 20 miles that match your search

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 37 minutes

Price per night from

$870

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$348

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$325

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$221

Main House at Grandview at Pleasure Point

Bozman house

4 bedrooms / 3 bathrooms / sleeps 9

“Family Fun at Grandview” Our group of grandparents, children with spouses, & grandchildren spent a week in the main house at Grandview. We had a great time in the pool, on the docks, in the porches, & exploring this very large & private property. We also enjoyed the shopping, restaurants, & Maritime Museum in St. Michaels. It was a very hot week & the many fans that were provided made it comfortable. The kitchen was well equipped to handle a large group & we had a great seafood feast on the picnic tables by the pool.

Price per night from

$673

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$221

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$1,038

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

$493

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

$725

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$870

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,160

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$405

Great deal 4 Bedroom House Near the Ferry Park

Rock Hall house

5 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$163

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$1,913

Tentrr Signature Site - Wye Island View

Grasonville tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 27 minutes

Price per night from

$232

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

5 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$2,319

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Neavitt manor house

25 bedrooms / 25 bathrooms / sleeps 50

Price per night from

$8,694

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$2,319

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

Sherwood house

8 bedrooms / 10 bathrooms / sleeps 12

Price per night from

$2,898

Brazilian Artsy Townhome- The wooded getaway

Cape Saint Claire house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$286

Cozy cottage with expansive backyard and firepit!

Tracys Landing house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$286

Cozy Downtown Annapolis Apartment

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$247

West Annapolis Hidden Gem

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$114

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 3 hours 6 minutes

Price per night from

$381

Annapolis Area Shagrila Resort

Davidsonville house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$915

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 34 minutes

Price per night from

$182

Comfort & Luxury near downtown, mall, coffee shops and more

Annapolis apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$195

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Cape Saint Claire house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$400

Viewing 38 of 101
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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