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Osterville Vacation Rentals & Homes with Swimming Pool - 122 Rentals Available.

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122 Vacation rentals

Filters applied: Swimming pool

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 / 37

Osterville House

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

$2,858.00

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from $2,858.00 / night

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

(3)

1 / 64

Osterville House

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

$2,714.00

Excellent (3 reviews)

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from $2,714.00 / night

1 / 30

Osterville House

  • 4
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$714.00

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from $714.00 / 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 / 13

Osterville House

  • 3
  • 5
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$357.00

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from $357.00 / night

1 / 54

Osterville House

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

$4,000.00

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from $4,000.00 / night

1 / 56

Osterville House

  • 4
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$2,142.00

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from $2,142.00 / night

1 / 100

Osterville House

  • 7
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,500.00

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from $2,500.00 / night

1 / 50

Osterville House

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

$2,642.00

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from $2,642.00 / night

Your search has been expanded 19.3 miles to include more rentals

(1)

1 / 16

West Yarmouth House - 8.1 miles away

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

$1,031.00

Excellent (1 reviews)

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from $1,031.00 / night

(1)

1 / 34

Falmouth House - 12.3 miles away

  • 5
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$928.00

Excellent (1 reviews)

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from $928.00 / night

(2)

1 / 44

Marstons Mills House - 1.7 miles away

  • 5
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$500.00

Excellent (2 reviews)

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from $500.00 / night

(2)

1 / 51

Barnstable House - 0.1 miles away

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

$1,785.00

Excellent (2 reviews)

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from $1,785.00 / night

1 / 50

South Dennis House - 14.8 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 / 21

Mashpee House - 6.3 miles away

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

$500.00

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from $500.00 / night

1 / 32

Waquoit House - 6.8 miles away

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

$471.00

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from $471.00 / night

1 / 24

Mashpee House - 7 miles away

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

$642.00

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from $642.00 / night

1 / 38

Sandwich House - 9.1 miles away

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

$528.00

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from $528.00 / night

(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

1 / 33

Mashpee House - 7.1 miles away

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

$357.00

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from $357.00 / night

1 / 38

Falmouth House - 13.6 miles away

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

$1,714.00

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from $1,714.00 / night

1 / 73

Marstons Mills House - 1.3 miles away

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

$714.00

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from $714.00 / night

(11)

1 / 25

Sandwich House - 6 miles away

  • 6
  • 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,200.00

Excellent (11 reviews)

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from $1,200.00 / night

(1)

1 / 8

Dennis Port Apartment - 13.8 miles away

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

$170.00

Excellent (1 reviews)

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from $170.00 / night

(1)

1 / 44

West Dennis House - 11.9 miles away

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

Responds fast! Avg. 2 hours 50 minutes

$374.00

Very Good (1 reviews)

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from $374.00 / night

1 / 42

Edgartown House - 19.3 miles away

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

$715.00

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from $715.00 / night

1 / 45

Edgartown House - 18.7 miles away

  • 6
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$822.00

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from $822.00 / night

1 / 42

Edgartown House - 18.3 miles away

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

$1,036.00

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from $1,036.00 / night

1 / 26

Oak Bluffs House - 18.5 miles away

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

$683.00

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from $683.00 / night

1 / 29

Oak Bluffs House - 17.3 miles away

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

$1,429.00

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from $1,429.00 / night

1 / 54

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 / 56

Edgartown House - 17.6 miles away

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

$1,500.00

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from $1,500.00 / night

1 / 35

Edgartown House - 18.9 miles away

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

$929.00

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from $929.00 / night

1 / 40

Oak Bluffs House - 14.7 miles away

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

$1,358.00

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from $1,358.00 / night

1 / 36

Edgartown House - 17.6 miles away

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

$2,500.00

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from $2,500.00 / night

1 / 19

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 / 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 / 43

Edgartown House - 19.2 miles away

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

$1,072.00

Excellent (1 reviews)

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from $1,072.00 / night