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Holiday Rentals with Pools in Orleans

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    $1,301 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 252 rentals
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    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Classic Cape1 / 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • 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, 6 Bathrooms, Sleeps 10
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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 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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    10 Bedrooms, 9 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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    Orleans, Cape Cod 02653
    Holiday Rental House - 10 Bedrooms, 9 Bathrooms, Sleeps 24
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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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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    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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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Hot Tub
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 6000 sq-ft luxury Estate is a gracious oasis of tranquility with mesmerizing views suitable for family vacations and executive corporate retreats. This luxurious estate features four large master bedroom suites plus two bonus sleeping areas, an elevator, a dining room that seats 16, a large...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Washer
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    40 Fox Ridge Drive, East Orleans MA (ID# 130420) 2017 Season! Light and Bright custom built Post & Beam is perfectly situated on the .62 lot surrounded by perennials for every season of the year including Hollies, white viburnums, PJM Rhodys, Laurel, weeping cherry, Norway Maples to name a few....
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    Location Information
    Orleans, Cape Cod 02643
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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