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Osterville Vacation Rentals & Homes with Swimming Pool - 54 Rentals Available.

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54 Vacation rentals

Filters applied: Swimming pool

Your search has been expanded 19.8 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

Responds fast! Avg. 3 hours 37 minutes

$1,064.00

Excellent (1 reviews)

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from $1,064.00 / night

(1)

1 / 8

Dennis Port Apartment - 13.8 miles away

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

$258.00

Excellent (1 reviews)

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from $258.00 / night

1 / 29

South Dennis House - 12.4 miles away

  • 3
  • 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$786.00

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from $786.00 / night

1 / 38

Dennis Port Condo - 12.5 miles away

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

$572.00

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from $572.00 / night

(6)

1 / 16

Dennis Port House - 12.7 miles away

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

$108.00

Excellent (6 reviews)

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from $108.00 / night

1 / 30

Harwich House - 18.3 miles away

  • 8
  • 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$775.00

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from $775.00 / night

(4)

1 / 17

Dennis Port House - 13.2 miles away

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$271.00

Very Good (4 reviews)

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from $271.00 / night

1 / 35

Dennis Port House - 12.4 miles away

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

$429.00

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from $429.00 / night

1 / 18

West Harwich House - 14.2 miles away

  • 6
  • 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$750.00

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from $750.00 / night

(8)

1 / 27

Dennis Port House - 13.9 miles away

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

$750.00

Excellent (8 reviews)

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from $750.00 / night

1 / 27

Edgartown House - 18.7 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$850.00

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from $850.00 / night

1 / 27

Edgartown House - 18.5 miles away

  • 5
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,430.00

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from $1,430.00 / night

1 / 20

Edgartown House - 17.6 miles away

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

$3,571.00

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from $3,571.00 / night

1 / 28

Edgartown House - 18.2 miles away

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

$1,857.00

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from $1,857.00 / night

1 / 17

Edgartown House - 18.4 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$571.00

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from $571.00 / night

1 / 28

Edgartown House - 17.8 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,071.00

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from $1,071.00 / night

1 / 46

Edgartown House - 17.7 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$2,143.00

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from $2,143.00 / night

1 / 20

Edgartown House - 18.9 miles away

  • 5
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$857.00

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from $857.00 / night

1 / 35

Oak Bluffs House - 17.1 miles away

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

$571.00

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from $571.00 / night

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

1 / 29

Edgartown House - 19.4 miles away

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$571.00

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from $571.00 / night

1 / 33

Edgartown House - 18.9 miles away

  • 4
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,286.00

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from $1,286.00 / night

1 / 23

Edgartown House - 18.3 miles away

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

$1,430.00

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from $1,430.00 / night

1 / 21

Edgartown House - 18.5 miles away

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

$857.00

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from $857.00 / night

1 / 30

Edgartown House - 18 miles away

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

$1,430.00

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from $1,430.00 / night

1 / 30

Oak Bluffs House - 16.7 miles away

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

$1,143.00

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from $1,143.00 / night

1 / 29

Edgartown House - 17.9 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$2,857.00

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from $2,857.00 / night

1 / 30

Edgartown House - 17.9 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$786.00

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from $786.00 / night

1 / 29

Vineyard Haven House - 17.9 miles away

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

$841.00

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from $841.00 / night

1 / 29

Edgartown House - 17.9 miles away

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

$3,072.00

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from $3,072.00 / night

1 / 22

Edgartown House - 17.9 miles away

  • 4
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$750.00

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from $750.00 / night

1 / 39

Edgartown House - 17.9 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$3,571.00

Inquire

from $3,571.00 / night

1 / 32

Oak Bluffs House - 17.6 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,071.00

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from $1,071.00 / night

1 / 30

Edgartown House - 19.2 miles away

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

$786.00

Inquire

from $786.00 / night

1 / 22

Edgartown House - 17.5 miles away

  • 6
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$5,000.00

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from $5,000.00 / night

1 / 30

Edgartown House - 18.1 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,430.00

Inquire

from $1,430.00 / night

1 / 31

Edgartown House - 19.8 miles away

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

$929.00

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from $929.00 / night

1 / 13

Edgartown House - 19.1 miles away

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

$286.00

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from $286.00 / night

1 / 36

Vineyard Haven House - 17.9 miles away

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,093.00

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from $1,093.00 / night

1 / 23

Edgartown House - 18.9 miles away

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

$1,786.00

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from $1,786.00 / night