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Osterville Vacation Rentals & Homes with Swimming Pool - 157 Rentals Available.

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157 Vacation rentals

Filters applied: Swimming pool

1 / 37

Osterville House

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

$2,000.00

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from $2,000.00 / night

1 / 43

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

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

(1)

1 / 64

Osterville House

  • 10
  • 22
  • 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

1 / 31

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

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

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

1 / 18

Osterville House

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

$1,000.00

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from $1,000.00 / night

1 / 44

Osterville House

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

$2,000.00

Inquire

from $2,000.00 / night

1 / 50

Osterville House

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

$1,142.00

Inquire

from $1,142.00 / night

1 / 37

Osterville House

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

$1,786.00

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from $1,786.00 / night

1 / 50

Osterville House

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

$1,428.00

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from $1,428.00 / night

Your search has been expanded 19.8 miles to include more rentals

(4)

1 / 54

Barnstable House - 6.4 miles away

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

$786.00

Excellent (4 reviews)

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from $786.00 / night

1 / 7

Dennis Port Condo - 14 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$100.00

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from $100.00 / night

1 / 29

Falmouth House - 13.5 miles away

  • 8
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly

$500.00

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from $500.00 / night

1 / 26

Oak Bluffs House - 14.7 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$929.00

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from $929.00 / night

1 / 50

Edgartown House - 17.5 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,986.00

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from $1,986.00 / night

1 / 22

Vineyard Haven House - 17.6 miles away

  • 5
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$500.00

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from $500.00 / night

1 / 32

Edgartown House - 19.8 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$558.00

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from $558.00 / night

1 / 50

Edgartown House - 17.1 miles away

  • 7
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$3,572.00

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from $3,572.00 / night

(1)

1 / 38

Edgartown House - 19.2 miles away

  • 5
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,215.00

Excellent (1 reviews)

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from $1,215.00 / night

1 / 27

Edgartown House - 19.4 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$786.00

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from $786.00 / night

1 / 38

Edgartown House - 18.8 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$500.00

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from $500.00 / night

1 / 34

Edgartown House - 19.8 miles away

  • 5
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$650.00

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from $650.00 / night

1 / 30

West Tisbury House - 19.5 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$658.00

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from $658.00 / night

1 / 35

Edgartown House - 19.5 miles away

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$579.00

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from $579.00 / night

1 / 56

Edgartown House - 17.6 miles away

  • 8
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,501.00

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from $1,501.00 / night

1 / 24

Edgartown House - 18.9 miles away

  • 3
  • 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$686.00

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from $686.00 / night

1 / 38

Edgartown House - 17.8 miles away

  • 4
  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$929.00

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from $929.00 / night

1 / 38

Oak Bluffs House - 16.7 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$929.00

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from $929.00 / night

1 / 35

Edgartown House - 19.6 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$715.00

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from $715.00 / night

(8)

1 / 34

Dennis Port House - 13.9 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$429.00

Excellent (8 reviews)

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from $429.00 / night

1 / 27

Dennis Port House - 12.3 miles away

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

$229.00

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from $229.00 / night

1 / 39

Edgartown House - 19.2 miles away

  • 7
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$2,143.00

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from $2,143.00 / night

1 / 38

Edgartown House - 17.8 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$929.00

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from $929.00 / night

1 / 36

Edgartown House - 17.6 miles away

  • 6
  • 11
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,715.00

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from $1,715.00 / night

1 / 39

Edgartown House - 18.9 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$929.00

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from $929.00 / night

1 / 26

Oak Bluffs House - 18.5 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$715.00

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from $715.00 / night

1 / 20

Edgartown House - 17.7 miles away

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,358.00

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from $1,358.00 / night

1 / 40

Edgartown House - 19 miles away

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$572.00

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from $572.00 / night