Orleans Homes & Apartments with Swimming Pool - 60 Rentals Available.
60 Vacation rentals
Filters applied: Swimming pool
Luxurious Orleans Home w/Private Salt Pool: 012-O
Orleans House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$539.00
from $539.00 / night
Updated East Orleans 6 Bed with Heated pool: 004-O
East Orleans House
- 6 bedrooms 6
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
$437.00
from $437.00 / night
Orleans Estate w/large heated pool, sleeps 24:39-O
Orleans House
- 10 bedrooms 10
- 8 bathrooms
- sleeps 24 24
- min stay varies
- Swimming pool
- Child friendly
$1,772.00
from $1,772.00 / night
Private Orleans resort-style compound w/heated pool & spa and fire pit: 023-O
Orleans House
- 5 bedrooms 5
- 6 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
$1,147.00
from $1,147.00 / night
Private Orleans resort w/water views, heated pool/spa; sleeps 16 (linens) 009-O
Orleans House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 15 15
- min stay varies
- Swimming pool
- Child friendly
$1,002.00
from $1,002.00 / night
Newly updated, heated pool, sleeps 12: 051-O
Orleans House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 13 13
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$668.00
from $668.00 / night
Great cottage close to Nauset Beach, (linens included): 040-O
Orleans House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
$303.00
from $303.00 / night
55 Barley Neck Rd 131073
East Orleans House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
Oceanfront Estate with Pool, Spa, 6,600 sq ft of Sumptuous Summer Living: 047-O
Orleans House
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
$1,745.00
from $1,745.00 / night
#517 Endless Summer: Private pool, updated, minutes from Skaket Beach!
Orleans House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$299.00
from $299.00 / night
Orleans: 2+ Acres, Pool, Comfortable Luxury, Steps to Beach: 030-OC
Orleans House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
$844.00
from $844.00 / night
Orleans Oasis on Pleasant Bay, estate w/2 homes & heated pool; sleeps 14: 137-O
Orleans House
- 6 bedrooms 6
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$893.00
from $893.00 / night
Your search has been expanded 19.4 miles to include more rentals
Hedgebound of Cape Cod
Truro House - 14.5 miles away
- 8 bedrooms 8
- 6 bathrooms
- sleeps 20 20
- 2 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,833.00
from $1,833.00 / night
OCEANFRONT HOME Completely Rebuilt Brand New
West Yarmouth House - 16.3 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
Private resort, three homes, one property. Walk to the beach, new pool!
Eastham House - 5.2 miles away
- 7 bedrooms 7
- 7 bathrooms
- sleeps 18 18
- min stay varies
- Nearest beach 0.8 mi
- Swimming pool
- Child friendly
$1,145.00
from $1,145.00 / night
3 homes in 1, new pool, walk to beach. Great for multiple families!
Eastham House - 5.4 miles away
- 7 bedrooms 7
- 4 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$917.00
from $917.00 / night
61 Chase Ave
Dennis Port Apartment - 11.3 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
Kingsbury - 3798
Eastham House - 3.8 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$286.00
from $286.00 / night
14 Grayton Avenue
Hyannis Port House - 19.4 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
12 Wapoos Trail
Chatham House - 9.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,214.00
from $1,214.00 / night
58 Pleasant Street
South Dennis House - 8.6 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,786.00
from $1,786.00 / night
166 Barcliff Avenue
Chatham House - 6.8 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,285.00
from $2,285.00 / night
464 Shore Road
Chatham House - 7 miles away
- 4 bedrooms 4
- 6 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,142.00
from $2,142.00 / night
103 Bellamy Lane
Chatham House - 5.8 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$928.00
from $928.00 / night
21 Crestview Circle
Truro House - 16.7 miles away
- 4 bedrooms 4
- 6 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,142.00
from $2,142.00 / night
New to 2020! In ground pool sleeping 10 on the North Side!!!
Dennis House - 9.9 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
Private Saltwater Pool, 0.3 Miles to Beach, Central AC: 037-B
Brewster House - 3.6 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
Two bedroom Heritage Sands condo-Less than 500 feet to shared/private beach
Dennis Port House - 12.5 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
Just Built, 5-bedroom Chatham Beauty w/heated Pool, Overlooks Cranberry Bog 30-C
Chatham House - 7.2 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
$702.00
from $702.00 / 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
Salt Water Pool, Steps to Private Beach, Exclusive Quiet Neighborhood :023-H
West Harwich House - 10.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$399.00
from $399.00 / night
Modern, Magnificent & Private with Heated Pool; 032-B
Brewster House - 4.8 miles away
- 7 bedrooms 7
- 5 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$565.00
from $565.00 / night
Brand New Custom Brewster Home with Pool, 4 Min Walk to Private Beach 105-BF
Brewster House - 4.1 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$662.00
from $662.00 / night
Two Cottages with a Brand New Pool, ½ mile to Private Beach: 048-B
Brewster House - 4 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
Magnificent Mansion, Privacy, Pool, Water Views in Brewster; 417-B
Brewster House - 7.7 miles away
- 10 bedrooms 10
- 10 bathrooms
- sleeps 22 22
- min stay varies
- Swimming pool
- Child friendly
$1,352.00
from $1,352.00 / 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
Spacious Custom Chatham Home Plus Guest House: 051-C
Chatham House - 6.8 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 14 14
- 3 nights min
- Swimming pool
- Child friendly
$1,284.00
from $1,284.00 / night
Elegantly Renovated, Walk 3 Min. to Beach -- 113-B
Brewster House - 3.5 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 13 13
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$565.00
from $565.00 / night
Secluded with Private Pool, Pets Considered -181-B
Brewster House - 4 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$348.00
from $348.00 / night
Six bedroom sleeping 20 with private swimming pool
West Harwich House - 10.6 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
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