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Osterville Vacation Rentals & Homes with Swimming Pool - 93 Rentals Available.

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93 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

$2,857.00

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from $2,857.00 / 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

$2,142.00

Excellent (3 reviews)

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from $2,142.00 / night

1 / 30

Osterville House

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

$642.00

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from $642.00 / 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

$3,571.00

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from $3,571.00 / night

1 / 56

Osterville House

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

$2,000.00

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from $2,000.00 / night

1 / 99

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 / 36

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 19.7 miles to include more rentals

(1)

1 / 16

West Yarmouth House - 8.1 miles away

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$1,031.00

Excellent (1 reviews)

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from $1,031.00 / night

(11)

1 / 25

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

$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

$150.00

Excellent (1 reviews)

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from $150.00 / night

1 / 24

Mashpee House - 7 miles away

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

$535.00

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from $535.00 / night

1 / 28

Cotuit House - 2.1 miles away

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

$1,857.00

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from $1,857.00 / 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)

1 / 34

Falmouth House - 12.3 miles away

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

$785.00

Excellent (1 reviews)

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from $785.00 / night

(2)

1 / 37

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

(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

(2)

1 / 51

Barnstable House - 0.1 miles away

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

$1,714.00

Excellent (2 reviews)

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from $1,714.00 / night

1 / 38

Sandwich House - 9.1 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 / 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 / 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

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)

1 / 71

Marstons Mills House - 1.3 miles away

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

$2,285.00

Excellent (1 reviews)

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from $2,285.00 / night

1 / 50

South Dennis House - 14.8 miles away

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

$1,785.00

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from $1,785.00 / 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

1 / 33

Dennis Port House - 12.4 miles away

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

$500.00

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from $500.00 / night

1 / 18

West Harwich House - 14.2 miles away

  • 6
  • 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$500.00

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from $500.00 / 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 / 33

West Harwich House - 14.8 miles away

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

$838.00

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from $838.00 / night

1 / 26

Marstons Mills House - 1.7 miles away

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

$422.00

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from $422.00 / night

(1)

1 / 28

Yarmouth Port House - 11 miles away

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

$421.00

Excellent (1 reviews)

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from $421.00 / night

1 / 51

Dennis House - 14.1 miles away

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

$776.00

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from $776.00 / night

1 / 26

Brewster House - 19.7 miles away

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

$334.00

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from $334.00 / night

(1)

1 / 49

West Barnstable House - 5.1 miles away

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

$553.00

Excellent (1 reviews)

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from $553.00 / night

(5)

1 / 12

Dennis Port House - 12.7 miles away

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

$90.00

Excellent (5 reviews)

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from $90.00 / night

1 / 22

Brewster House - 19.2 miles away

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

$253.00

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from $253.00 / night

1 / 20

Dennis House - 13.4 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$285.00

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from $285.00 / night