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Osterville Vacation Rentals & Homes with Swimming Pool - 135 Rentals Available.

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135 Vacation rentals

Filters applied: Swimming pool

1 / 28

Osterville House

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

$3,572.00

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from $3,572.00 / night

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 / 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 / 50

Osterville House

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

$1,142.00

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from $1,142.00 / night

1 / 44

Osterville House

  • 6
  • 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 / 37

Osterville House

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

$1,785.00

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from $1,785.00 / night

1 / 50

Osterville House

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

$1,429.00

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from $1,429.00 / night

Your search has been expanded 19.8 miles to include more rentals

(7)

1 / 22

Sandwich House - 6 miles away

  • 6
  • 22
  • 7 nights min
  • Swimming pool
  • Ask about children
  • 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

$1,070.00

Excellent (7 reviews)

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from $1,070.00 / night

(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 / 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 / 29

West Harwich House - 14.5 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$514.00

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from $514.00 / night

1 / 41

Edgartown House - 19.3 miles away

  • 6
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$643.00

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from $643.00 / night

1 / 40

Brewster House - 19.2 miles away

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

$440.00

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from $440.00 / night

1 / 49

West Tisbury House - 18.9 miles away

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

$1,286.00

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from $1,286.00 / night

1 / 21

Mashpee House - 6.3 miles away

  • 3
  • 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$428.00

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from $428.00 / night

1 / 33

Oak Bluffs House - 17.1 miles away

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

$700.00

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from $700.00 / night

1 / 31

Hyannis Port House - 4.3 miles away

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

$2,142.00

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from $2,142.00 / night

(1)

1 / 37

Edgartown House - 19.3 miles away

  • 3
  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,179.00

Excellent (1 reviews)

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from $1,179.00 / 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 / 34

Falmouth House - 13.6 miles away

  • 9
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,429.00

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from $1,429.00 / 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 / 38

Edgartown House - 18.5 miles away

  • 5
  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,143.00

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from $1,143.00 / night

1 / 41

Vineyard Haven House - 16.5 miles away

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$673.00

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from $673.00 / 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 / 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

1 / 18

Yarmouth House - 9.4 miles away

  • 3
  • 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$285.00

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from $285.00 / night

1 / 42

Edgartown House - 17.8 miles away

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

$3,858.00

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from $3,858.00 / night

1 / 71

Marstons Mills House - 1.3 miles away

  • 7
  • 15
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,142.00

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from $2,142.00 / night

1 / 27

Brewster House - 19.4 miles away

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

$462.00

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from $462.00 / night

1 / 11

Brewster House - 19.7 miles away

  • 3
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$462.00

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from $462.00 / night

1 / 41

Edgartown House - 19.1 miles away

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

$858.00

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from $858.00 / 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 / 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 / 31

Harwich House - 15.1 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$825.00

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from $825.00 / night

1 / 43

Edgartown House - 18.3 miles away

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

$1,286.00

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from $1,286.00 / night

1 / 24

Cotuit House - 2 miles away

  • 3
  • 9
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$671.00

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from $671.00 / night