Osterville Vacation Rentals & Homes with Swimming Pool - 93 Rentals Available.
93 Vacation rentals
Filters applied: Swimming pool
101 Carriage Road
Osterville House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$3,571.00
from $3,571.00 / night
71 Sand Point Road
Osterville House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,857.00
from $2,857.00 / night
86 Leonard Road
Osterville House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Ask about pets
$1,072.00
from $1,072.00 / night
405 Sea View Avenue
Osterville House
- 10 bedrooms 10
- 12 bathrooms
- sleeps 22 22
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,142.00
from $2,142.00 / night
31 Parker Road
Osterville House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$642.00
from $642.00 / night
340 Grand Island Drive
Osterville House
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,142.00
from $2,142.00 / night
236 Smoke Valley Road, #B
Osterville House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 5 5
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$357.00
from $357.00 / night
501 Eel River Road
Osterville House
- 6 bedrooms 6
- 9 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$3,571.00
from $3,571.00 / night
22 Sea View Avenue
Osterville House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$2,000.00
from $2,000.00 / night
166 North Bay Road
Osterville House
- 7 bedrooms 7
- 10 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,500.00
from $2,500.00 / night
30 Oakdale Path
Osterville House
- 5 bedrooms 5
- 7 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,642.00
from $2,642.00 / night
Your search has been expanded 19.7 miles to include more rentals
OCEANFRONT HOME Completely Rebuilt Brand New
West Yarmouth House - 8.1 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$1,031.00
from $1,031.00 / night
In-Ground Pool, Large home, Perfect for Multi Family Vacations & Family Reunions
Sandwich House - 6 miles away
- 6 bedrooms 6
- 3 bathrooms
- sleeps 22 22
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,200.00
from $1,200.00 / night
61 Chase Ave
Dennis Port Apartment - 13.8 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$150.00
from $150.00 / night
19 Seaview Lane
Mashpee House - 7 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$535.00
from $535.00 / night
250 Windswept Way
Cotuit House - 2.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$1,857.00
from $1,857.00 / night
185 Associates Road
Falmouth House - 13.6 miles away
- 9 bedrooms 9
- 6 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,714.00
from $1,714.00 / night
86 Falmouth Heights Road
Falmouth House - 12.3 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$785.00
from $785.00 / night
199 Cedar Tree Neck Road
Marstons Mills House - 1.7 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$500.00
from $500.00 / night
14 Grayton Avenue
Hyannis Port House - 4.3 miles away
- 6 bedrooms 6
- 8 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,142.00
from $2,142.00 / night
105 Ice Valley Road
Barnstable House - 0.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$1,714.00
from $1,714.00 / night
11 Oriole Lane
Sandwich House - 9.1 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$471.00
from $471.00 / night
161 Stanhope Road
Waquoit House - 6.8 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$471.00
from $471.00 / night
93 Glenneagle Drive
Mashpee House - 6.3 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$428.00
from $428.00 / night
10 Mashie Circle
Mashpee House - 7.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$357.00
from $357.00 / night
391 Baxters Neck Road
Marstons Mills House - 1.3 miles away
- 7 bedrooms 7
- 9 bathrooms
- sleeps 15 15
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,285.00
from $2,285.00 / night
58 Pleasant Street
South Dennis House - 14.8 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,785.00
from $1,785.00 / night
285 Baxters Neck Road
Marstons Mills House - 1.3 miles away
- 6 bedrooms 6
- 10 bathrooms
- sleeps 15 15
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$714.00
from $714.00 / night
NOW BOOKING FOR 2020! Gorgeous ocean views sleeping 8
Dennis Port House - 12.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$500.00
from $500.00 / night
Six bedroom sleeping 20 with private swimming pool
West Harwich House - 14.2 miles away
- 6 bedrooms 6
- 2 bathrooms
- sleeps 20 20
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$500.00
from $500.00 / night
Two bedroom Heritage Sands condo-Less than 500 feet to shared/private beach
Dennis Port House - 12.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$229.00
from $229.00 / night
Upscale, Resort-like, Heated Pool/Spa, Sleeps 14: 002-H
West Harwich House - 14.8 miles away
- 6 bedrooms 6
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
$838.00
from $838.00 / night
Pristine Marstons Mills Family Estate Sleeps 11, Pool; 160-MM
Marstons Mills House - 1.7 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 11 11
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$422.00
from $422.00 / night
Spacious Modern Home with huge pool! : 011-Y
Yarmouth Port House - 11 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$421.00
from $421.00 / night
Private, Updated 4+ Acre Family Compound, Pool, Water Views, Sunsets: 071-D
Dennis House - 14.1 miles away
- 8 bedrooms 8
- 6 bathrooms
- sleeps 17 17
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$776.00
from $776.00 / night
Private Saltwater Pool, 0.3 Miles to Beach, Central AC: 037-B
Brewster House - 19.7 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$334.00
from $334.00 / night
Stunning Architect-Owned Estate w/pool : 059-WB
West Barnstable House - 5.1 miles away
- 7 bedrooms 7
- 6 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
$553.00
from $553.00 / night
1 bedroom condo-just steps to the beach
Dennis Port House - 12.7 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$90.00
from $90.00 / night
Two Cottages with a Brand New Pool, ½ mile to Private Beach: 048-B
Brewster House - 19.2 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$253.00
from $253.00 / night
New to 2020! In ground pool sleeping 10 on the North Side!!!
Dennis House - 13.4 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$285.00
from $285.00 / night
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.