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Southport Holiday Rentals

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    Don't let other travellers get your favourite Southport area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Southport
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    Southport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Southport
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    The following rentals are within 25 kilometres of Southport.
    #2 - Your own place on the Beach near Silver Sands Park1 / 16
    (1)Excellent
    Silver Lane
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Premiere beach property1 / 12
    (2)Excellent
    Milford
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Terrace
    • Private Garden
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 April 2019
    This was by far one of the best stays we have stayed at in the last several years. Home is immaculate, all linens are provided, it’s cozy and the owner Mary was an amazing host...
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    About this property
    Our home is located in beautiful Woodmont Beach and sits directly across the street from the water. Main floor of the house has a full kitchen for cooking, dining area with table and 6 chairs living room with L shaped sofa and flat screen tv, one bedroom with queen bed, two night stands and a six...
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    Location Information
    Milford, Connecticut 06460
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Serene Connecticut Retreat - Luxury 2 bedroom apt1 / 21
    (3)Very good
    Stamford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2018
    Liz was always available to answer our questions and help with local amenities. The garden was beautiful and secluded with lots of flowers. A perfect spot for two people.
    Reviewed 21 August 2015
    The apartment was in a lovely setting, attached to the family house, but totally private. Liz the landlord was very friendly, helpful and knowledgeable of the area. The...
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    About this property
    Completely updated apartment in lovely rural setting but close to everything. Get away without going very far. Take a break from sterile hotel rooms while on business. Private entrance, 2 bedroom, 1.5 bath, fully equipped kitchen, dining room, living room, french doors to patio, balcony off...
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    Stamford, Connecticut 06903
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Milford
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The first floor apartment is bright, sunny and airy. The beach is right across the street with unobstructed views of Charles Island. You can also walk right over to a seasonal Greek restaurant next door, or to Silver Sands State Park for more recreational activities. We are right next door if you...
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    Milford, Connecticut 06460
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Fairfield
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Housekeeping Included
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This new contemporary beach house has an open floor plan on the first floor with an 8' granite island that seats 4. Fireplace has a 60' Smart TV that hangs from it. Beautiful dining area seats 10. Outdoor gas grill easily facilitates eating al fresco. Each floor has an outdoor furnished deck. Each...
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    Location Information
    Fairfield, Connecticut 06824
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Weston
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Patio
    • Air Conditioning
    • Internet Access
    • Balcony
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Master Bedroom with four additional bedrooms -- two are double height with lofts. The home features 18' soaring ceilings, an incredible wrap around deck overlooking lawns and gardens. Large Italian eat-in kitchen/family room. Office for 4. Home theater. Whole-house B&O system. Badminton, ping pong,...
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    Location Information
    Weston, Connecticut 06883
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    Silver Lane
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Air Conditioning
    • Waterfront
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk along pristine beaches and a sandbar to explore Charles Island; this quaint cottage is a unique getaway vacation rental for up to 7 guests! Providing 3 bedrooms and 1.5 baths, this beach home rests in a quiet setting just 2 miles from the beautiful town green area - lined with a variety of...
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    Location Information
    Silver Lane, Connecticut 06460
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Westport
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Terrace
    • Outdoor Dining Area
    • Cable/satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Elegant home was professionally designed to capture the spectacular views of the Ocean. The home was completely remodeled recently and includes a rich interior with state of the art kitchen appliances, wood burning fireplace, washer/dryer, central A/C and internet. Near the end of a quiet...
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    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Easton
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Terrace
    • Central Heating
    • Balcony
    • Patio
    • Grill
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 'Home Away From Home' is an expansive yet cozy and inviting space to hang with family and friends or for a romantic getaway. It is located in the idyllic town of Easton but borders (just 1.5 miles) the charming and thriving town of Fairfield, CT featuring five miles of shoreline on the Long...
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    Location Information
    Easton, Connecticut 06612
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
    Easton
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our large and luxurious home is open to you for your enjoyment and relaxation. With 4 en-suite bedrooms and 2 additional bedrooms, the house is able to comfortably accommodate large groups of people for short stays. The house is in immaculate condition and boasts luxury appointments and and...
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    Location Information
    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
    Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Washer
    • Ocean Views
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Right across from the beach - penfield and jennings. Easy access for everyone. Amazing 3 br / 2 full bath furnished 1700 sq. Ft. Home on fairfield beach road. Right across the street from the beach! Walk to the train and to town – restaurants, shopping, and theatre. Great alternative to corporate...
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    Location Information
    Fairfield, Connecticut 06824
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS PROPERTY IS AVAILABLE FOR SHORT/LONG TERM RENTALS TO WESTPORT OR PROSPECTIVE WESTPORT RESIDENTS ONLY!! New modern house with roof deck 3 houses from Saugatuck river/bay. Upside down house with 3 bedrooms and master bath on 1st floor. Sun filled living area, kitchen and European wet bath on...
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    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LOCATION, LOCATION, LOCATION... MY HOME IS CENTRALLY LOCATED, SO EVERYTHING YOU NEED AND WANT IS EASILY ACCESSIBLE. IT'S CLOSE TO THREE BEACHES, DOWNTOWN SHOPPING, RESTAURANTS, HISTORIC WESTPORT COUNTRY PLAYHOUSE, AND RAILROAD STATION! IT'S ALL JUST MINUTES AWAY BY CAR, AND NOT ALL THAT FAR TO...
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    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Stratford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch the boats go by and enjoy coastal living during your stay at this 4-bed, 2-bath home in Stratford! With essentials like a fully equipped kitchen for homemade meals, cozy living spaces to reconnect with the kids, and a dreamy front porch, this vacation rental is a true crowd-pleaser. In...
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    Location Information
    Stratford, Connecticut 06615
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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