Kent Island Rentals

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44 Houses

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

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$1,950

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

Stevensville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$803

Love Point Luxury Waterfront

Stevensville house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Balcony or terrace

All filters match

Price per night from

$802

Waterfront home with private pier is A Shore Thing

Chester house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Balcony or terrace

All filters match

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

Match: Balcony or terrace

All filters match

Price per night from

$1,950

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$321

Great rentals within 20 miles that match your search

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

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$476

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$860

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$1,147

Ferry Bridge House

Easton house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$797

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Match: Balcony or terrace

All filters match

Price per night from

$2,294

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$458

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

Match: Balcony or terrace

All filters match

Price per night from

$2,294

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$573

The Fritz

Edgewater house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$1,548

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$797

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$802

Tranquil Easton Waterfront Property

Easton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$6,880

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

Wittman log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$1,118

Match: Balcony or terrace

All filters match

Price per night from

$384

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Tracys Landing house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Balcony or terrace

All filters match

Price per night from

$727

Take your Leave of Absence around gardens with driveway parking

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Balcony or terrace

All filters match

Price per night from

$426

180-degree water views at unique round house

Shady Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$391

Eastport Gem - Popular house walk to Downtown & USNA

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$400

Luxury Waterfront home with private pier and guest house

Annapolis house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$979

Walk to Main Street from Waterfront Condo with pool and parking

Annapolis condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Balcony or terrace

All filters match

Price per night from

$407

History & Charm Near the Annapolis City Dock

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Balcony or terrace

All filters match

Price per night from

$394

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$465

Match: Balcony or terrace

All filters match

Price per night from

$338

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$465

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Shady Side house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Balcony or terrace

All filters match

Price per night from

$429

Match: Balcony or terrace

All filters match

Price per night from

$407

Match: Balcony or terrace

All filters match

Price per night from

$403

Still Available for 2024 Commissioning Week! Historic gem steps to USNA

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$465

All newly renovated Eastport Retreat - private back patio with parking

Annapolis house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

Match: Balcony or terrace

All filters match

Price per night from

$785

Available for 2024 Commissioning Week Waterfront home mins to USNA

Crownsville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$361

Parking at Stunning On Cloud 9 with private patio pet-friendly

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$500

Stunning Waterfront Home in Round Bay

Severna Park house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$1,451

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