Vacation Rentals & Apartments in Annapolis

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10 apartments

Luxury Waterfront home with private pier and guest house

Annapolis house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$908

Great rentals within 20 miles that match your search

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

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$1,941

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

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$1,941

Waterfront Getaway - View of bay from your bed

Romancoke studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$228

The Annapolis General House

Parole house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$685

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

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$1,891

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$1,118

Waterfront pier, putting green just minutes from downtown Annapolis

Riva house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$726

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$321

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Tracys Landing house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$728

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