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Holiday Rentals with Pools in Orleans

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    RM 3,660 Average
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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    12 Matching Rentals in OrleansView all 241 rentals
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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 Rents from Sunday to Sunday during peak weeks Please click on the 'Virtual Tour' to see a 3D tour of the home Your multi-generational or multi-family...
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    02653, Orleans, Cape Cod
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    Classic Cape1 / 14
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • Parking
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 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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    02653, Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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   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 full-week or multiple week terms...
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    02653, Orleans, Cape Cod
    Holiday Rental House - 10 Bedrooms, 8 Bathrooms, Sleeps 24
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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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    02653, Orleans, Cape Cod
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    02653, Orleans, Cape Cod
    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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    02642, Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located overlooking the sands of Nauset Beach, this spotless vacation home is as true a Cape Cod experience as you could ever find. Complete with 5 bedrooms and 3 full baths, 2 spacious decks for relaxing and grilling, outdoor shower, wireless Internet, AC on the main level, 4 TVs and all the bells...
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    Location Information
    02653, Orleans, Cape Cod
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Waterfront
    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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    Location Information
    02653, Orleans, Cape Cod
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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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
    02653, Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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