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Orleans Holiday Vacation with Pools

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    C$1,394 Average
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    Travellers to Orleans are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    14 Matching Rentals in OrleansView all 226 rentals
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Executive Waterfront Luxury Home. A/C; Heated Pool & Elevator1 / 29
    (1)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Sauna
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxurious Orleans Home with Private Salt Pool, Sleeps 10 (linens included) Peak Summer Weekly Rates: $9,000 - $9,500 Rents Saturday to Saturday during peak season Located on a large private lot in South Orleans, this luxurious property provides the highest level of amenities and diverse indoor and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Cable/satellite TV
    • Grill
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Orleans resort with water views, heated pool & spa; sleeps 15 (linens included) Peak Summer Weekly Rates: $15,900- $17,800 Rents Sunday to Sunday during peak season   Please click on the 'Virtual Tour' to see a 3D tour of the home Your multi-generational or multi-family summer vacation has...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Updated East Orleans 6 Bedroom Home with Pool (linens included) Peak Summer Weekly Rates: $7,300 - $8,900 Rents Sunday to Sunday during peak season. Linens included NEW Kitchen for 2018! Fully remodeled kitchen with high end appliances. It's the best of all worlds at this unique East Orleans...
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    East Orleans, Orleans 02643
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    30 Chestnut is a bright, charming home in a private, wooded location only steps from a rustic beach on Little Pleasant Bay, where you can take evening walks or explore the shoreline in our double kayak. This is a quiet, serene environment with a large patio where you can cook dinner on the grill,...
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    East Orleans, Orleans 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Updated, Spacious & Private, Sleeps 12 with Carriage House and Pool *Pool and Carriage House Open Memorial Day to Columbus Day 4 BR Main House available for rent year round at listed rates* Peak Summer Weekly Rates:  $9,450 - $10,500 Rents Sunday to Sunday in Peak Season Linens Included A short...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Classic Cape1 / 14
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Parking
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 11, 2014
    From the moment we drove up the driveway to the time when we finally left, our girls weekend was spectacular! This house that we rented was all we expected and more! Spacious...
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    About this property
    Classic Cape with bright, modern, free-flowing interior and central air conditioning in a tiny neighborhood on a private road in the woods (but only 2 miles to local stores). Private access to secluded salt-water beach on shallow bay, great for kayaking and beach-combing. Two master suites with...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Sauna
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Orleans resort-style compound with heated pool & spa, fire pit and cabana (linens included) Peak Summer Weekly Rates: $16,900-$18.500 Rents from Sunday to Sunday during peak weeks Come enjoy Thanksgiving on the Cape! Sit by the fire pit after a wonderful family dinner. Please click on the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    55 Barley Neck Rd (ID #131073) ~ Waterviews, Private Pool, Central A/C ~ Meetinghouse Pond 2019 Season! Sweet Retreat on Barley Neck in East Orleans! This bright and airy home has gentle slopping views of Meeting House Pond, a private pool, new screen room and patio/outdoor fire pit. Close to the...
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    East Orleans, Orleans 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spotless vacation apartment in lower level of home with private entrance with in-ground pool. 2 bedroom and 1 bath, Kitchens, living room and a groomed yard make this the perfect home for a family vacation. Less than a mile from child friendly Skaket beach on Cape Cod bay and 5 minutes from Nauset...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    10 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Orleans Estate (3 structures) with large heated pool, on Town Cove, Sleeps up to 24 Peak Summer Weeks from $24,500  Linens included Weddings not permitted on property   Please click on the 'Virtual Tour' to see a 3D tour of the home Please note:  This property rents Sunday to Sunday in summer for...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 10 Bedrooms, 8 Bathrooms, Sleeps 24
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    Newly updated, heated pool, sleeps 12: 051-O1 / 34
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 17, 2018
    Orleans was new for our group of 12 family and friends that travel to the Cape every year. Loved it, we were located 1 mile from Nauset Beach, bars and restaurants close to the...
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    About this property
    East Orleans; magnificent updated historic home, heated pool, A/C, perfect family vacation; Sleeps 13 Peak Summer Weekly Rates: $9,500 - $12,000 Rents Saturday - Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home   The interior of this beautiful 1920...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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