Search 105,200+ Vacation Rentals

Osterville Vacation Rentals & Homes with Swimming Pool - 148 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

148 Vacation rentals

Filters applied: Swimming pool

1 / 43

Osterville House

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

$2,571.00

Inquire

from $2,571.00 / night

1 / 37

Osterville House

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

$2,857.00

Inquire

from $2,857.00 / night

1 / 28

Osterville House

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

$3,571.00

Inquire

from $3,571.00 / night

1 / 29

Osterville House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,072.00

Inquire

from $1,072.00 / night

(3)

1 / 64

Osterville House

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

$2,857.00

Excellent (3 reviews)

Inquire

from $2,857.00 / night

1 / 30

Osterville House

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

$500.00

Inquire

from $500.00 / night

1 / 43

Osterville House

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

$2,142.00

Inquire

from $2,142.00 / night

1 / 18

Osterville House

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

$1,142.00

Inquire

from $1,142.00 / night

1 / 44

Osterville House

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

$2,857.00

Inquire

from $2,857.00 / night

1 / 21

Osterville House

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

$3,571.00

Inquire

from $3,571.00 / night

(1)

1 / 43

Osterville House

  • 7
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,285.00

Excellent (1 reviews)

Inquire

from $1,285.00 / night

1 / 50

Osterville House

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

$1,572.00

Inquire

from $1,572.00 / night

1 / 50

Osterville House

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

$2,214.00

Inquire

from $2,214.00 / night

Your search has been expanded 19.8 miles to include more rentals

(5)

1 / 54

Barnstable House - 6.4 miles away

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

$572.00

Excellent (5 reviews)

Inquire

from $572.00 / night

(1)

1 / 16

West Yarmouth House - 8.1 miles away

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

$1,260.00

Excellent (1 reviews)

Book

from $1,260.00 / night

(9)

1 / 22

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

$928.00

Excellent (9 reviews)

Inquire

from $928.00 / night

(1)

1 / 14

Sandwich House - 6.9 miles away

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

$367.00

Excellent (1 reviews)

Inquire

from $367.00 / night

(1)

1 / 8

Dennis Port Apartment - 13.8 miles away

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

$182.00

Excellent (1 reviews)

Inquire

from $182.00 / night

1 / 25

Dennis Port Condo - 12.3 miles away

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

$250.00

Inquire

from $250.00 / night

1 / 29

Vineyard Haven House - 17.9 miles away

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

$680.00

Inquire

from $680.00 / night

1 / 23

Edgartown House - 18.9 miles away

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

$1,787.00

Inquire

from $1,787.00 / night

1 / 33

Edgartown House - 18.9 miles away

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

$1,143.00

Inquire

from $1,143.00 / night

1 / 29

Edgartown House - 17.9 miles away

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

$2,143.00

Inquire

from $2,143.00 / night

1 / 12

Edgartown House - 19.1 miles away

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

$208.00

Inquire

from $208.00 / night

1 / 27

West Tisbury House - 19.3 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$329.00

Inquire

from $329.00 / night

1 / 41

Brewster House - 19.2 miles away

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

$514.00

Inquire

from $514.00 / night

1 / 26

Marstons Mills House - 1.7 miles away

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

$514.00

Inquire

from $514.00 / night

1 / 34

West Harwich House - 14.8 miles away

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

$862.00

Inquire

from $862.00 / night

(1)

1 / 49

West Barnstable House - 5.1 miles away

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

$529.00

Excellent (1 reviews)

Inquire

from $529.00 / night

1 / 44

Brewster House - 18.9 miles away

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

$719.00

Inquire

from $719.00 / night

(1)

1 / 25

Brewster House - 19.8 miles away

  • 3
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$567.00

Excellent (1 reviews)

Inquire

from $567.00 / night

1 / 21

Brewster House - 19.2 miles away

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

$301.00

Inquire

from $301.00 / night

(1)

1 / 28

Yarmouth Port House - 11 miles away

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

$684.00

Excellent (1 reviews)

Inquire

from $684.00 / night

1 / 58

Brewster House - 15.6 miles away

  • 10
  • 22
  • min stay varies
  • Swimming pool
  • Child friendly

$1,480.00

Inquire

from $1,480.00 / night

1 / 23

Brewster House - 17.9 miles away

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

$402.00

Inquire

from $402.00 / night

1 / 51

Dennis House - 14.1 miles away

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

$837.00

Inquire

from $837.00 / night

1 / 27

Brewster House - 19.4 miles away

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

$675.00

Inquire

from $675.00 / 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)

Inquire

from $2,142.00 / night

1 / 72

Marstons Mills House - 1.3 miles away

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

$2,142.00

Inquire

from $2,142.00 / night

1 / 52

Sandwich House - 9.1 miles away

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

$571.00

Inquire

from $571.00 / night