Search 105,200+ Vacation Rentals

Osterville Pet-Friendly Vacation Rentals, Homes & More - 142 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

142 Vacation rentals

Filters applied: Pet Friendly

1 / 19

Osterville House

  • 3
  • 6
  • 1 night min
  • Ask about children
  • Pet friendly

$257.00

Inquire

from $257.00 / night

1 / 16

Osterville House

  • 6
  • 10
  • 1 night min
  • Ask about children
  • Pet friendly

$642.00

Inquire

from $642.00 / night

1 / 14

Osterville House

  • 3
  • 6
  • 1 night min
  • Ask about children
  • Pet friendly

$357.00

Inquire

from $357.00 / 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 / 24

Osterville House

  • 3
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$251.00

Inquire

from $251.00 / night

1 / 26

Osterville House

  • 3
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$285.00

Inquire

from $285.00 / night

1 / 19

Osterville House

  • 5
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$1,714.00

Inquire

from $1,714.00 / night

(3)

1 / 31

Osterville House

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$285.00

Excellent (3 reviews)

Inquire

from $285.00 / night

1 / 25

Osterville House

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$457.00

Inquire

from $457.00 / night

(1)

1 / 19

Osterville House

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$271.00

Excellent (1 reviews)

Inquire

from $271.00 / night

1 / 34

Osterville House

  • 3
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$614.00

Inquire

from $614.00 / night

1 / 15

Osterville House

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Pet friendly

$122.00

Inquire

from $122.00 / night

1 / 51

Osterville House

  • 9
  • 12
  • 1 night min
  • Ask about children
  • Pet friendly

$2,571.00

Inquire

from $2,571.00 / night

Your search has been expanded 18.3 miles to include more rentals

(2)

1 / 17

Oak Bluffs Cottage - 14.9 miles away

  • 6
  • 10
  • min stay varies
  • Nearest beach 0.2 mi
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 17 minutes

“Great house and location! If you are looking for something with space, as well as the ability to walk to the bars and restaurants in Oak Bluffs, this is the house for you! Great location and great porch for those nights when you want to hang in....”
- Review left on 07/20/2014

$501.00

Excellent (2 reviews)

Book

from $501.00 / night

(5)

1 / 25

Yarmouth House - 9.6 miles away

  • 5
  • 10
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 1 minutes

“My family rented the house for one week. It was exactly as described. We had plenty of room for ourselves and our guests. The beds were comfortable and they provide the linens. With 3 bathrooms and an outdoor shower no one was ever waiting. This is...”
- Review left on 09/08/2016

$280.00

Very Good (5 reviews)

Book

from $280.00 / night

(10)

1 / 23

Mashpee House - 7.5 miles away

  • 5
  • 16
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
“My family truly enjoyed our stay. The proximity to nearby attractions, restaurants, and beaches made it easy to have fun, while the private setting let us really feel that we were "away from it all". This newer home with central A/C was ready for a...”
- Review left on 08/23/2016

$425.00

Excellent (10 reviews)

Inquire

from $425.00 / night

(7)

1 / 21

Sandwich House - 14.6 miles away

  • 4
  • 10
  • min stay varies
  • Nearest beach 1 mi
  • Ask about children
  • Pet friendly
“A couple of friends and I decided to rent a house for New Years last minute. After searching for hours, we found, and secured, this house within three days. The owner is cool, very organized, and understanding. Along with that, the house was a great...”
- Review left on 01/19/2016

$360.00

Very Good (7 reviews)

Book

from $360.00 / night

(11)

1 / 21

South Yarmouth House - 8.9 miles away

  • 5
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

Responds fast! Avg. 2 hours 1 minutes

“The landlord Alex was very gracious. Everything we needed was provided which was very convenient since we traveled so far. The house was clean and spacious. Centrally located on the cape so we could travel easily in both directions. The beach is only...”
- Review left on 10/20/2016

$290.00

Excellent (11 reviews)

Book

from $290.00 / night

(1)

1 / 18

Yarmouth House - 9.5 miles away

  • 4
  • 8
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 1 minutes

“We had a wonderful stay in Alex's beautiful, comfortable, fully-appointed home. This is a spacious fully-furnished home you could live happily in year-round. We rented for 1 wk. with sister-in-law and husband, totaling 4 adults and one small dog. We...”
- Review left on 05/28/2015

$200.00

Excellent (1 reviews)

Book

from $200.00 / night

(3)

1 / 23

Falmouth House - 9.1 miles away

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Air conditioning
  • Pet friendly
“Welcoming place. My family and I had had a good time staying at this place. Bedrooms were good size, layout of the kitchen and living room were nice along with the interior decoration. They had bikes which we took for a good ride to the beach about 2...”
- Review left on 09/14/2015

$375.00

Very Good (3 reviews)

Book

from $375.00 / night

(1)

1 / 16

Falmouth House - 8.8 miles away

  • 3
  • 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$375.00

Excellent (1 reviews)

Book

from $375.00 / night

(17)

1 / 19

Dennis Port House - 12.4 miles away

  • 2
  • 7
  • 7 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
“The house is close to everything and we felt right at home and so did our dog Brody ( he didn't want to leave) The house has everything you need and then some,close to the beach and a great farm stand and Woofies bakery .This house is so clean and...”
- Review left on 07/15/2016

$115.00

Excellent (17 reviews)

Inquire

from $115.00 / night

(1)

1 / 24

Barnstable House - 3 miles away

  • 4
  • 14
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$600.00

Excellent (1 reviews)

Book

from $600.00 / night

(1)

1 / 21

Barnstable Villa - 5 miles away

  • 4
  • 10
  • min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 1 minutes

$320.00

Excellent (1 reviews)

Book

from $320.00 / night

(1)

1 / 14

Barnstable Villa - 5 miles away

  • 5
  • 10
  • min stay varies
  • Nearest beach 0.2 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 1 minutes

$320.00

Excellent (1 reviews)

Book

from $320.00 / night

(6)

1 / 14

Marstons Mills House - 4.3 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$129.00

Excellent (6 reviews)

Inquire

from $129.00 / night

1 / 50

Cotuit House - 2.7 miles away

  • 7
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$1,642.00

Inquire

from $1,642.00 / night

(1)

1 / 32

Sandwich House - 7.6 miles away

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$501.00

Excellent (1 reviews)

Inquire

from $501.00 / night

1 / 11

Cotuit House - 2.7 miles away

  • 2
  • 4
  • 1 night min
  • Ask about children
  • Pet friendly

$428.00

Inquire

from $428.00 / night

1 / 58

Barnstable House - 0.1 miles away

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

$857.00

Inquire

from $857.00 / night

1 / 31

Marion House - 17.4 miles away

  • 3
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$714.00

Inquire

from $714.00 / night

1 / 21

Edgartown House - 18.3 miles away

  • 3
  • 6
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

$286.00

Inquire

from $286.00 / night

(1)

1 / 42

West Yarmouth House - 6.1 miles away

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

$857.00

Excellent (1 reviews)

Inquire

from $857.00 / night

1 / 18

Yarmouth House - 8.9 miles away

  • 3
  • 7
  • 1 night min
  • Ask about children
  • Pet friendly

$157.00

Inquire

from $157.00 / night

(2)

1 / 14

Sandwich House - 11.2 miles away

  • 3
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$129.00

Excellent (2 reviews)

Inquire

from $129.00 / night

1 / 39

Barnstable House - 0.1 miles away

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$1,071.00

Inquire

from $1,071.00 / night

1 / 23

West Yarmouth House - 6.2 miles away

  • 3
  • 10
  • 1 night min
  • Ask about children
  • Pet friendly

$785.00

Inquire

from $785.00 / night

1 / 23

Brewster House - 15.2 miles away

  • 3
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$285.00

Inquire

from $285.00 / night

1 / 23

Cotuit House - 3.2 miles away

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

$642.00

Inquire

from $642.00 / night

1 / 33

Yarmouth House - 7.1 miles away

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

$1,714.00

Inquire

from $1,714.00 / night