Osterville Vacation Rentals & Homes with Swimming Pool - 122 Rentals Available.
122 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
$2,858.00
from $2,858.00 / 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
$2,714.00
from $2,714.00 / night
31 Parker Road
Osterville House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$714.00
from $714.00 / 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
$4,000.00
from $4,000.00 / 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
$2,142.00
from $2,142.00 / 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 19.3 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
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$1,031.00
from $1,031.00 / 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
$928.00
from $928.00 / 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
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
$1,785.00
from $1,785.00 / 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
$2,142.00
from $2,142.00 / 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
$500.00
from $500.00 / 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
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
$642.00
from $642.00 / 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
$528.00
from $528.00 / 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
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
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
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
In-Ground Pool, Large home, Single or 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
$170.00
from $170.00 / night
#908: Water Views from Multiple Decks, Private Pool, Access to Grand Cove!
West Dennis House - 11.9 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 50 minutes
$374.00
from $374.00 / night
CANNM - Gorgeous Katama Family Compound with Pool, Ferry Tickets, Separate Carr
Edgartown House - 19.3 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$715.00
from $715.00 / night
PAILB - Exquisite all Newly Updated Contemporary Farm House Style Home! Heated P
Edgartown House - 18.7 miles away
- 6 bedrooms 6
- 2 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$822.00
from $822.00 / night
CAS27 - Beautiful New 6 Bedroom Luxury Home for 2020, Heated Pool! Walk to Edga
Edgartown House - 18.3 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 14 14
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,036.00
from $1,036.00 / night
GUCOB - Spacious Family Home, Pool and Patio Area, Centrally located,
Oak Bluffs House - 18.5 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$683.00
from $683.00 / night
TAYLC - Luxurious Home located in The Preserve, 18 x 36 Heated Pool to be Compl
Oak Bluffs House - 17.3 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,429.00
from $1,429.00 / night
MERRY - Merry Farm Summer Estate, Heated Pool, Set on 28 Acres, Open Meadows, Pr
West Tisbury House - 18.9 miles away
- 7 bedrooms 7
- 5 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,286.00
from $1,286.00 / night
WEEKW - CLASSIC, IN-TOWN EDGARTOWN, ENGLISH-COUNTRY CHIC LUXURY HOME WITH POOL A
Edgartown House - 17.6 miles away
- 8 bedrooms 8
- 6 bathrooms
- sleeps 14 14
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,500.00
from $1,500.00 / night
GEORS - Family Friendly Edgartown Home, Heated Pool, 12' x 25', Screened Porch,
Edgartown House - 18.9 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$929.00
from $929.00 / night
HODGW - New Tri Level Luxury Home, Heated Pool with Bluestone Patio Surround
Oak Bluffs House - 14.7 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,358.00
from $1,358.00 / night
CARLP - Distinctive Luxury All New For Summer 2016, Heated Pool 16 x 32, Villag
Edgartown House - 17.6 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 11 11
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$2,500.00
from $2,500.00 / night
MONEN - Lovley Vineyard Haven Home, Heated Pool, AC, Close Proximitity to Towns
Vineyard Haven House - 17.6 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$500.00
from $500.00 / night
DRAPM - Mink Meadows Family Compound, Private Heated Pool, Walk or Drive to Pri
Vineyard Haven House - 16.5 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$673.00
from $673.00 / night
LINEM - Wintucket Cove House, Heated Pool 20 x 40, Edgartown Great Pond Fronta
Edgartown House - 19.2 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,072.00
from $1,072.00 / night
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