COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Search 105,200+ Vacation Rentals

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

1 / 55

Osterville House

  • 8
  • 20
  • 1 night min
  • Ask about children
  • Pet friendly

$2,000.00

Inquire

from $2,000.00 / night

1 / 19

Osterville House

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

$457.00

Inquire

from $457.00 / 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 / 28

Osterville House

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

$2,857.00

Inquire

from $2,857.00 / night

1 / 24

Osterville House

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

$250.00

Inquire

from $250.00 / night

1 / 26

Osterville House

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

$357.00

Inquire

from $357.00 / night

(2)

1 / 19

Osterville House

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

$271.00

Excellent (2 reviews)

Inquire

from $271.00 / night

(1)

1 / 51

Osterville House

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

$4,285.00

Excellent (1 reviews)

Inquire

from $4,285.00 / night

1 / 36

Osterville House

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

$714.00

Inquire

from $714.00 / night

1 / 30

Osterville House

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

$714.00

Inquire

from $714.00 / night

(2)

1 / 17

Osterville House

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

$140.00

Excellent (2 reviews)

Inquire

from $140.00 / night

1 / 55

Osterville House

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

$2,571.00

Inquire

from $2,571.00 / night

1 / 54

Osterville House

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

$4,000.00

Inquire

from $4,000.00 / night

1 / 56

Osterville House

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

$2,142.00

Inquire

from $2,142.00 / night

Your search has been expanded 18.1 miles to include more rentals

1 / 24

Barnstable House - 7.3 miles away

  • 5
  • 8
  • 14 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$409.00

Book

from $409.00 / night

(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. 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

$573.00

Excellent (2 reviews)

Book

from $573.00 / night

(11)

1 / 18

Sandwich House - 14.6 miles away

  • 4
  • 10
  • min stay varies
  • Nearest beach 1 mi
  • Ask about children
  • Pet friendly

Responds fast! Avg. 3 hours 17 minutes

“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

$321.00

Very Good (11 reviews)

Book

from $321.00 / night

1 / 30

Sagamore Beach House - 12.4 miles away

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

Responds fast! Avg. 1 hour 16 minutes

$311.00

Book

from $311.00 / night

(3)

1 / 15

East Sandwich Cottage - 9.3 miles away

  • 1
  • 4
  • 7 nights min
  • Child friendly
  • Pet friendly

$109.00

Excellent (3 reviews)

Inquire

from $109.00 / night

1 / 8

Sandwich House - 11.2 miles away

  • 3
  • 9
  • 7 nights min
  • Child friendly
  • Pet friendly

$138.00

Inquire

from $138.00 / night

1 / 18

Yarmouth House - 8.9 miles away

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

$257.00

Inquire

from $257.00 / night

1 / 25

Mashpee House - 5.1 miles away

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

$928.00

Inquire

from $928.00 / 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

(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)

Inquire

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)

Inquire

from $1,785.00 / night

1 / 47

Marion House - 18.1 miles away

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

$514.00

Inquire

from $514.00 / night

1 / 39

Dennis House - 12 miles away

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

$571.00

Inquire

from $571.00 / night

1 / 25

Hyannis Port House - 5.3 miles away

  • 4
  • 11
  • 1 night min
  • Ask about children
  • Pet friendly

$285.00

Inquire

from $285.00 / night

1 / 39

Barnstable House - 0.1 miles away

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

$2,142.00

Inquire

from $2,142.00 / night

1 / 32

Waquoit House - 6.8 miles away

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

$472.00

Inquire

from $472.00 / night

1 / 38

Sandwich House - 9.1 miles away

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

$528.00

Inquire

from $528.00 / night

1 / 46

Hyannis Port House - 5.4 miles away

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

$500.00

Inquire

from $500.00 / night

(1)

1 / 46

Sandwich House - 7.6 miles away

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

$1,214.00

Excellent (1 reviews)

Inquire

from $1,214.00 / night

1 / 21

Falmouth House - 12.4 miles away

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

$928.00

Inquire

from $928.00 / 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 / 73

Marstons Mills House - 1.3 miles away

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

$714.00

Inquire

from $714.00 / night

(1)

1 / 16

Falmouth House - 8.8 miles away

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$430.00

Excellent (1 reviews)

Book

from $430.00 / night

(3)

1 / 23

Falmouth House - 9.1 miles away

  • 4
  • 8
  • min stay varies
  • 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

$430.00

Very Good (3 reviews)

Book

from $430.00 / night

(2)

1 / 15

East Sandwich House - 9.8 miles away

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

$280.00

Very Good (2 reviews)

Inquire

from $280.00 / night

(12)

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. 1 hour 8 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

$355.00

Excellent (12 reviews)

Book

from $355.00 / night