Osterville Vacation Rentals & Homes with Swimming Pool - 89 Rentals Available.
89 Vacation rentals
Filters applied: Swimming pool
Your search has been expanded 19.8 miles to include more rentals
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
$1,071.00
from $1,071.00 / night
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
$870.00
from $870.00 / 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
$97.00
from $97.00 / night
Cape Cod cottage-Just 150 feet to Sea Street Beach
Dennis Port House - 13.2 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
$250.00
from $250.00 / 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
$572.00
from $572.00 / night
Beautiful five bedroom home with private swimming pool
Dennis Port House - 13.9 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
Eight bedroom home sleeping 20 with private swimming pool
Harwich House - 18.3 miles away
- 8 bedrooms 8
- 2 bathrooms
- sleeps 20 20
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$715.00
from $715.00 / 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
Three bedroom home sleeping 9 with private swimming pool
South Dennis House - 12.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$251.00
from $251.00 / night
New to our inventory! Oceanfront Heritage Sands condo that sleeps 8.
Dennis Port House - 12.4 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$857.00
from $857.00 / 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
Beautiful Cape with Pool and Air Conditioning Close to Town
Edgartown House - 18.8 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
CUSTOM BUILT HOME WITH POOL NEAR EDGARTOWN GOLF COURSE
Edgartown House - 17.8 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,071.00
from $1,071.00 / night
Beautiful Mink Meadows Five Bedroom Home with Pool
Vineyard Haven House - 17.9 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$679.00
from $679.00 / night
Beautiful Home in Katama with Heated Pool
Edgartown House - 18.9 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,286.00
from $1,286.00 / night
BEAUTIFUL SUNNY HOME IN EDGARTOWN WITH POOL
Edgartown House - 18.9 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$857.00
from $857.00 / night
Beautiful West Tisbury Home with Association Pool
West Tisbury House - 19.3 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$329.00
from $329.00 / night
Beautiful Tri-Level Katama Home with Heated Pool
Edgartown House - 19.8 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$700.00
from $700.00 / night
Katama Luxury with Pool
Edgartown House - 19.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$2,429.00
from $2,429.00 / night
Perfect Katama Luxury Home with Pool
Edgartown House - 18.9 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,786.00
from $1,786.00 / night
Spectacular luxury Edgartown waterfront home
Edgartown House - 17.9 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$3,571.00
from $3,571.00 / night
Beautiful Edgartown Village Home with Pool
Edgartown House - 17.9 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$2,143.00
from $2,143.00 / night
Beautiful Six Bedroom Edgartown Home with Pool
Edgartown House - 17.9 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
Luxury Four Bedroom In-town Edgartown Home with Pool
Edgartown House - 18.2 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,857.00
from $1,857.00 / night
Katama Farmhouse with Pool
Edgartown House - 18.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
Brand New Katama Luxury Home with Pool and Hot Tub
Edgartown House - 19.2 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,357.00
from $1,357.00 / night
LUXURY WATERFRONT WITH POOL & HIGH END AMENITIES
Edgartown House - 17.5 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$5,000.00
from $5,000.00 / night
Great House with a Pool close to Town and South Beach
Edgartown House - 18.7 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
Beautiful Oak Bluffs home on Lagoon Pond with Pool!
Oak Bluffs House - 17.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
Luxury Oak Bluffs Home with 18 X 30' Pool
Oak Bluffs House - 16.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,143.00
from $1,143.00 / night
Close to town 5 bedroom home with pool
Edgartown House - 18.7 miles away
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$850.00
from $850.00 / night
CLASSIC COLONIAL LUXURY HOME IN EDGARTOWN WITH A HEATED POOL
Edgartown House - 18.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,430.00
from $1,430.00 / night
Beautiful Katama Home with Pool
Edgartown House - 17.9 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$715.00
from $715.00 / night
Luxury In-town Edgartown Home with Pool
Edgartown House - 17.8 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,430.00
from $1,430.00 / night
New Contemporary Home with Heated Pool
Edgartown House - 18.5 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,430.00
from $1,430.00 / night
Luxury Edgartown Village Home with Pool
Edgartown House - 18.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$929.00
from $929.00 / night
In-town Luxury Retreat with Pool
Edgartown House - 17.7 miles away
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$2,143.00
from $2,143.00 / night
Great Four Bedroom Home Walking Distance to Town
Edgartown House - 17.6 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$2,857.00
from $2,857.00 / night
MODERN LUXURY HOME WITH RELAXED ATMOSPHERE THAT EMBRACES VINEYARD LIFE
Edgartown House - 17.9 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$2,571.00
from $2,571.00 / night
Beautiful Edgartown home with Pool
Edgartown House - 18.3 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,286.00
from $1,286.00 / night
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