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Holiday Rentals with Pools in Orleans

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    Travellers to Orleans are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    14 Matching Rentals in OrleansView all 300 rentals
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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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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    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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    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 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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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • 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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    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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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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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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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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 2018 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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    Executive Waterfront Luxury Home. A/C; Heated Pool & Elevator1 / 29
    (1)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2018
    We just had a glorious week enjoying the incredible views, the majestic house and pool, and of course the natural beauty of the Cape. We have rented our fair share of properties...
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    About this property
    This 6000 sq-ft luxury Estate is a gracious oasis of tranquility with mesmerizing views suitable for family vacations & executive corporate retreats. This luxurious estate features four large Master Bedroom Suites, Elevator, A dinning room that seats 16, Large Living Room, Great Room, Game/Media...
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    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 16
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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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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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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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    Location Information
    Orleans, Cape Cod 02642
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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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    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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