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Holiday Rentals with Pools in Orleans

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    $1,433 Average
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    Travellers to Orleans are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    11 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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    10 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • 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 Open June weeks JUST REDUCED 20%! (click the rates tab for the new rates) Rents Sunday to Sunday during peak season   Please click on the 'Virtual Tour' to see a 3D...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    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
    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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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Sauna
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    Suitability
    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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    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-$17,800 Week of June 10th JUST REDUCED 10%! (click the rates tab for the new rates) Rents from Sunday to Sunday during peak weeks Please click on the 'Virtual Tour'...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Parking
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This exceptional compound is one-of-a-kind with a Main House, Carriage House and private pool. The Main house has a restaurant quality kitchen which will bring out the Iron Chef in you. Ample seating in the dining area with separate bar. Entertaining is easy in the Living Room with HDTV and DVD, it...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • DVD Player
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private 1.4 acre East Orleans compound with direct saltwater access The ultimate vacation escape - enjoy fresh saltwater breezes and spectacular views from this beautiful 1.4 acre estate on exclusive Snow Point in East Orleans. The compound features a stunning main house with enclosed patio and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxurious Orleans getaway with main, carriage, and pool house! Exceptional property with architect-designed Main House with a restaurant quality kitchen that features a commercial 8 burner stove and separate grill for pancakes and bacon, Sub Zero refrigerator and wine cooler and 3 sinks. A large,...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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