Osterville Vacation Rentals & Homes with Swimming Pool - 135 Rentals Available.
135 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
$3,572.00
from $3,572.00 / 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
$2,000.00
from $2,000.00 / night
439 Sea View Avenue
Osterville House
- 6 bedrooms 6
- 6 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
31 Parker Road
Osterville House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$500.00
from $500.00 / 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
83 Bunker Hill Road
Osterville House
- 5 bedrooms 5
- 7 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,000.00
from $1,000.00 / night
80 Seapuit Road
Osterville House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,142.00
from $1,142.00 / night
111 Oyster Way
Osterville House
- 6 bedrooms 6
- 8 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,000.00
from $2,000.00 / night
140 Ice Valley Road
Osterville House
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,785.00
from $1,785.00 / night
30 Oakdale Path
Osterville House
- 5 bedrooms 5
- 6 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,429.00
from $1,429.00 / night
Your search has been expanded 19.8 miles to include more rentals
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
- Ask about children
- Air conditioning
$1,070.00
from $1,070.00 / night
5 Bedroom LUXURY HOME with inground HEATED POOL in Historic Barnstable Village
Barnstable House - 6.4 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- 7 nights min
- Nearest beach 5 mi
- Swimming pool
- Ask about children
$786.00
from $786.00 / night
CHAPH - Park House Luxury Home, Private Pool surrounded by Bluestone Patio, Bea
Edgartown House - 17.8 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$929.00
from $929.00 / night
Salt Water Pool, Steps to Private Beach, Exclusive Quiet Neighborhood :023-H
West Harwich House - 14.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$514.00
from $514.00 / night
LEMAA - Katama Luxury Home - Private Heated Pool with Pool Bar and Patio, Privat
Edgartown House - 19.3 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 14 14
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$643.00
from $643.00 / night
Brand New Custom Brewster Home with Pool, 4 Min Walk to Private Beach 105-BF
Brewster House - 19.2 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$440.00
from $440.00 / night
MERRY - Merry Farm Summer Estate, Heated Pool, Set on 28 Acres, Open Meadows and
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
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
GOLDF - Outstanding Summer Home with Pool, Screened Porch, and Patio Area, Assoc
Oak Bluffs House - 17.1 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$700.00
from $700.00 / 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
FERR2 - Katama Area, Heated Pool, Main and Guest House, Large Private Yard, Bik
Edgartown House - 19.3 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 9 9
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,179.00
from $1,179.00 / night
YAEGM - Field Club, Exquisite New Luxury Home Offering Heated Pool, Pool House,
Edgartown House - 19.2 miles away
- 7 bedrooms 7
- 6 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$2,143.00
from $2,143.00 / 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
$1,429.00
from $1,429.00 / night
BRIGY - Outstanding Designer Luxury Home, 18 X 30' Pool, Expansive Bluestone P
Oak Bluffs House - 16.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$929.00
from $929.00 / night
NAIDN - Exclusive Luxury Home, Heated 18 x 42 Gunite Pool, Spectacular Patios,
Edgartown House - 18.5 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 9 9
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,143.00
from $1,143.00 / 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 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,215.00
from $1,215.00 / night
MANNB - Designer Home with 18 x 30 Heated Pool, Spacious Deck and Screened Porch
Edgartown House - 19.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$715.00
from $715.00 / night
102 Constance Avenue
Yarmouth House - 9.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$285.00
from $285.00 / night
YASED - STUNNING EDGARTOWN VILLAGE LUXURY COMPOUND, HEATED POOL BORDERED BY LARG
Edgartown House - 17.8 miles away
- 7 bedrooms 7
- 6 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$3,858.00
from $3,858.00 / 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
$2,142.00
from $2,142.00 / night
Secluded with Private Pool, Pets Considered -181-B
Brewster House - 19.4 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$462.00
from $462.00 / 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
$462.00
from $462.00 / night
CHU10 - Designer Luxury Katama, Heated Pool, Bluestone Patios, Private Decks, Si
Edgartown House - 19.1 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$858.00
from $858.00 / night
JOHNT - Perfect Katama Location, Heated Pool 20 X 40, Beautiful Private Yard, 1
Edgartown House - 18.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 7 7
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$686.00
from $686.00 / night
WEISM - Outstanding Tri -Level Katama Home, Pool, new 18 x 40 Heated Saltwater
Edgartown House - 19.8 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$558.00
from $558.00 / night
Modern Harwich Home with Heated Salt Water Pool: 001-HR
Harwich House - 15.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$825.00
from $825.00 / night
FULLS - Exquisite, Chic, Edgartown Village Compound, Heated Pebble Tec Pool, Poo
Edgartown House - 18.3 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,286.00
from $1,286.00 / night
255 Little River Road
Cotuit House - 2 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 9 9
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$671.00
from $671.00 / night
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