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Holiday Rentals with Pools in Orleans

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    ₹ 76,508 Average
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    Travellers to Orleans are booking May dates now. Secure your holiday home today, and have the perfect trip.
    16 Matching Rentals in OrleansView all 223 rentals
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    Classic Cape1 / 14
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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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: $7,500 - $7,900 plus tax Rents Sunday to Sunday during peak season. Linens included Fully remodeled kitchen with high end appliances. It's the best of all worlds at this unique East Orleans home. The...
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    East Orleans, Orleans 02643
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    10 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    • 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 'Second Wind' Peak Summer Weeks from $24,900 plus tax Linens included Weddings not permitted on property   Please click on the 'Virtual Tour'tab to take a 3D tour of the home Please note:  This property rents...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 10 Bedrooms, 8 Bathrooms, Sleeps 24
    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* Rents Sunday to Sunday in Peak Season Linens Included   Please click on the 'Virtual Tour'tab to take a 3D...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Orleans resort with water views, heated pool & spa; sleeps 15 Rents Sunday to Sunday during peak season Peak Weekly rates from $13,500 - $16,900 plus taxes Linens included   Please click on the 'Virtual Tour' to see a 3D tour of the home Your multi-generational or multi-family summer...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
    Newly updated, heated pool, sleeps 12: 051-O1 / 34
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Grill
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 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 Rents Saturday - Saturday during peak season Peak Rates $11,250 - $12,500 plus tax Please click on the 'Virtual Tour' to see a 3D tour of the home   The interior of this beautiful 1920 Orleans...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
    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 2020 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
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to your very own private resort on Cape Cod. Located directly on Nauset Harbor on the Eastham\Orleans town line, The Jeremiah House is the place to be for your quintessential Cape Cod getaway. This luxury home is the perfect convergence of classic old Cape Cod architecture and charm with...
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    Orleans, Cape Cod 02642
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    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
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Orleans Oasis on Pleasant Bay, Estate with 2 Homes and Heated Pool; sleeps 14 'Beam Reach' Peak Weekly Summer Rates from $12,500 - $13,500 plus tax Rents Sunday to Sunday in Peak Season Linens Included Welcome to your private oasis on Pleasant Bay. At the end of the road you will find this...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Orleans:  2+ Acres, Pool, Comfortable Luxury, Steps to Beach Peak Summer Weekly Rates: $11,000- $12,200 plus tax Sleeps 12 Rents Saturday to Saturday during peak season Linens and Bed Making Included PLEASE NOTE:  July 4, 2020 is a Saturday To avoid an unpopular rental turnover day on the July...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceanfront Estate with Pool, Spa, 6,600 sq ft of Sumptuous Summer Living Sleeps up to 14 Peak Summer Weekly Rate: $25,000 plus tax Rents Saturday to Saturday in Peak Season   NEW Listing for 2019! Here is the height of luxury on Nauset Heights, overlooking the Atlantic and famous Nauset...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    3 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on a quiet road and just 1.2 miles from Nauset Beach, this three bedroom home is perfectly situated for a serene Cape Cod vacation. Featuring a heated pool, extensive outdoor spaces and an entertaining deck overlooking the marsh, you and your guests will relax in style. Spend the day at...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 6
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