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Osterville Vacation Rentals & Homes with Swimming Pool - 148 Rentals Available.

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148 Vacation rentals

Filters applied: Swimming pool

1 / 43

Osterville House

  • 6
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,571.00

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from $2,571.00 / night

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1 / 37

Osterville House

  • 5
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,857.00

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from $2,857.00 / night

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1 / 28

Osterville House

  • 6
  • 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$3,571.00

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from $3,571.00 / night

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1 / 29

Osterville House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,072.00

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from $1,072.00 / night

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(3)

1 / 64

Osterville House

  • 10
  • 22
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,857.00

Excellent (3 reviews)

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from $2,857.00 / night

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1 / 30

Osterville House

  • 4
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$500.00

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from $500.00 / night

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1 / 43

Osterville House

  • 6
  • 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,142.00

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from $2,142.00 / night

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1 / 18

Osterville House

  • 5
  • 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,142.00

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from $1,142.00 / night

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1 / 44

Osterville House

  • 6
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,857.00

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from $2,857.00 / night

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1 / 21

Osterville House

  • 6
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$3,571.00

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from $3,571.00 / night

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(1)

1 / 43

Osterville House

  • 7
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,285.00

Excellent (1 reviews)

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from $1,285.00 / night

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1 / 50

Osterville House

  • 5
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,572.00

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from $1,572.00 / night

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1 / 50

Osterville House

  • 5
  • 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,214.00

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from $2,214.00 / night

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Your search has been expanded 19.8 miles to include more rentals

(5)

1 / 54

Barnstable House - 6.4 miles away

  • 5
  • 10
  • 7 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Ask about children

$572.00

Excellent (5 reviews)

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from $572.00 / night

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(1)

1 / 16

West Yarmouth House - 8.1 miles away

  • 4
  • 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$1,260.00

Excellent (1 reviews)

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from $1,260.00 / night

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(9)

1 / 22

Sandwich House - 6 miles away

  • 6
  • 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Our group of 17 recently held a family reunion for one week at this property. The group included young children, teens and adults, and everyone was sad to leave as the week went far too fast. Beautiful property that was extremely well maintained by...”
- Review left on 08/18/2015

$928.00

Excellent (9 reviews)

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from $928.00 / night

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(1)

1 / 14

Sandwich House - 6.9 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$367.00

Excellent (1 reviews)

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from $367.00 / night

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(1)

1 / 8

Dennis Port Apartment - 13.8 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$182.00

Excellent (1 reviews)

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from $182.00 / night

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1 / 25

Dennis Port Condo - 12.3 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$250.00

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from $250.00 / night

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1 / 29

Vineyard Haven House - 17.9 miles away

  • 4
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$680.00

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from $680.00 / night

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1 / 23

Edgartown House - 18.9 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,787.00

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from $1,787.00 / night

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1 / 33

Edgartown House - 18.9 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,143.00

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from $1,143.00 / night

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1 / 29

Edgartown House - 17.9 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$2,143.00

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from $2,143.00 / night

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1 / 12

Edgartown House - 19.1 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$208.00

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from $208.00 / night

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1 / 27

West Tisbury House - 19.3 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$329.00

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from $329.00 / night

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1 / 41

Brewster House - 19.2 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly

$514.00

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from $514.00 / night

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1 / 26

Marstons Mills House - 1.7 miles away

  • 5
  • 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$514.00

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from $514.00 / night

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1 / 34

West Harwich House - 14.8 miles away

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly

$862.00

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from $862.00 / night

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(1)

1 / 49

West Barnstable House - 5.1 miles away

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly

$529.00

Excellent (1 reviews)

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from $529.00 / night

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1 / 44

Brewster House - 18.9 miles away

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$719.00

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from $719.00 / night

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(1)

1 / 25

Brewster House - 19.8 miles away

  • 3
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$567.00

Excellent (1 reviews)

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from $567.00 / night

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1 / 21

Brewster House - 19.2 miles away

  • 3
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$301.00

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from $301.00 / night

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(1)

1 / 28

Yarmouth Port House - 11 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly

$684.00

Excellent (1 reviews)

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from $684.00 / night

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1 / 58

Brewster House - 15.6 miles away

  • 10
  • 22
  • min stay varies
  • Swimming pool
  • Child friendly

$1,480.00

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from $1,480.00 / night

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1 / 23

Brewster House - 17.9 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly

$402.00

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from $402.00 / night

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1 / 51

Dennis House - 14.1 miles away

  • 8
  • 17
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$837.00

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from $837.00 / night

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1 / 27

Brewster House - 19.4 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$675.00

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from $675.00 / night

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(1)

1 / 45

Hyannis Port House - 4.3 miles away

  • 6
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,142.00

Excellent (1 reviews)

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from $2,142.00 / night

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1 / 72

Marstons Mills House - 1.3 miles away

  • 6
  • 15
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$2,142.00

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from $2,142.00 / night

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1 / 52

Sandwich House - 9.1 miles away

  • 5
  • 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$571.00

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from $571.00 / night

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