Osterville Vacation Rentals & Homes with Swimming Pool - 157 Rentals Available.
157 Vacation rentals
Filters applied: Swimming pool
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
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
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
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
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
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
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
$1,786.00
from $1,786.00 / 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
$1,428.00
from $1,428.00 / night
Your search has been expanded 19.8 miles to include more rentals
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
79 Chase Ave - 2 Bedroom
Dennis Port Condo - 14 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$100.00
from $100.00 / night
Classic Cape Cod private home
Falmouth House - 13.5 miles away
- 8 bedrooms 8
- 4 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
$500.00
from $500.00 / 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
$929.00
from $929.00 / night
FINNM - Luxury Retreat, Heart of Edgartown Village, Heated Salt Water Pool, 500
Edgartown House - 17.5 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,986.00
from $1,986.00 / night
MONEN - Vacation Retreat, Heated Pool, AC, WiFi, Close Proximitity to Towns and
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
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
AGARH - Luxurious Estate Home, Waterfront, 18 x 40 ft Heated Pool, Hot Tub, Ex
Edgartown House - 17.1 miles away
- 7 bedrooms 7
- 6 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$3,572.00
from $3,572.00 / 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
REINJ - Gorgeous Katama Home, Heated Pool, Large Private Pool Patio and Landsca
Edgartown House - 19.4 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$786.00
from $786.00 / night
KULIJ - Stylish Custom Coastal Design Home, Luxury Appointments, Heated Pool, Po
Edgartown House - 18.8 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$500.00
from $500.00 / night
TALLA - Katama South Beach, 20 x 40 Heated Gunite Pool, Walk or Bike to the Bea
Edgartown House - 19.8 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$650.00
from $650.00 / night
WOODJ - Gorgeous Retreat, Pool 18 X 36', Lush Landscaped Yard, Expansive Deck an
West Tisbury House - 19.5 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$658.00
from $658.00 / night
CHURS - Luxury Katama Home, Heated Pool, Large Patio Area, Private Yard
Edgartown House - 19.5 miles away
- 6 bedrooms 6
- 3 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$579.00
from $579.00 / 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
$1,501.00
from $1,501.00 / 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
CHAP2 - Edgartown Compound with Main and Guest Cottage, Heated Pool, Village Are
Edgartown House - 17.8 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 9 9
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$929.00
from $929.00 / 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
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
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
$429.00
from $429.00 / 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
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
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
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
$1,715.00
from $1,715.00 / 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 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$929.00
from $929.00 / 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
$715.00
from $715.00 / night
OCONS - Ferry Tickets open weeks, Luxury Main and Guest House, Heated Pool, A/C,
Edgartown House - 17.7 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,358.00
from $1,358.00 / night
WALSB - New Contemporary Luxury Home, Heated Pool 18 x 40, Luxury Amenities, Sc
Edgartown House - 19 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$572.00
from $572.00 / night
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