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Vacation Rentals in Southport, CT and nearby

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    All 24 Rentals in the Southport Area
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    The following rentals are within 20 miles of Southport, Connecticut.

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    $185
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    1 / 17
    5 of 5 stars (5) Excellent
    Greenwich
    3 Bedrooms / 1 Bathroom / Sleeps 5
    travelers have booked this property
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    $98
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    1 / 24
    5 of 5 stars (2) Excellent
    Port Jefferson Station, NY
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    $275
    / Night
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    1 / 15
    Pound Ridge, NY
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    $225
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    1 / 21
    5 of 5 stars (1) Excellent
    Stamford
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Stamford, Connecticut 06903
    5 of 5 stars Reviewed August 17, 2014
    Sehr schönes Ferienhaus in waldreicher Umgebung, mit vielen Annehmlichkeiten im Haus, luxeriös eingerichtet mit netten Details. Country Market um die Ecke und gute Anbindung an...
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    $350
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    1 / 37
    South Salem, NY
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Wheelchair access
    • Elder access
    • x
    About this property
    This wonderful 2500sqf, 3 bedroom 2.5 bathroom home located on 6 acres is decorated with modern and contemporary art creating a homey and comfortable environment which you will enjoy during your stay here. The privacy and quiet is paralleled only by the view of the woods which you can see from the... View all property information
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    Location Information
    South Salem, Westchester County 10606
    From
    $795
    / Night
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    1 / 42
    Weston
    5 Bedrooms / 4 Bathrooms / Sleeps 8
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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,... View all property information
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    Location Information
    Weston, Connecticut 06883
    From
    $700
    / Night
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    1 / 24
    Rowayton
    2 Bedrooms / 7 Bathrooms / Sleeps 5
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    We live in a private association called Bell Island. We are surrounded by incredible views of Long Island Sound and Farm Creek Preserve and our beaches are reserved for use by residents and their guests only. Our home is on a tidal estuary called Farm Creek. The creek is fed by the Long Island... View all property information
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    Location Information
    Rowayton, Norwalk 06853
    From
    $986
    / Night
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    1 / 16
    Westport
    4 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Westport, Connecticut 06880
    From
    $300
    / Night
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    1 / 14
    Fairfield
    6 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    PLEASE NOTE - WE ONLY RENT BY THE MONTH! THAT IS THE MINIMUM STAY. Our family beach house is available for rent for both months this coming summer in 2015. Right on the sand, our beach house faces the Long Island Sound. The house has 6 bedrooms and an airy open plan lower floor, perfect for... View all property information
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    Location Information
    Fairfield, Connecticut 06824
    From
    $350
    / Night
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    1 / 2
    Rowayton
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Use of sailboat,paddelboard,kayak and small motor boat, swim and tennis in rowayton ct. 06853- walk to quaint village- furnished apt. For 2, with balcony on your own private swimming beach. Balcony overlooks the beach and the sound.-train 55 min. To grand central nyc. Unique vacation spot!... View all property information
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    Location Information
    Rowayton, Norwalk 06853
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    From
    $775
    / Night
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    1 / 3
    Milford
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    4 bedroom, 3 full bathroom , Beach house, directly on the water View all property information
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    Location Information
    Milford, Connecticut 06460
    From
    $194
    / Night
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    1 / 18
    Stamford
    1 Bedroom / 1 Bathroom / Sleeps 3
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This exquisite property located in the heart of downtown Stamford offers luxurious apartments. Residents will enjoy great amenities such as a furnished sky terrace with outdoor grills & fire pits, a lounge & screening room and a 24 hr fitness center. The fabulous apartments at The Blvd offer... View all property information
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    Location Information
    Stamford, Connecticut
    From
    $8,000
    / Month
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    1 / 76
    Fairfield
    5 Bedrooms / 5 Bathrooms / Sleeps 7
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    5 bedroom, 5 bath for rent in ultra exclusive Greenfield Hills area. Approx. 2 1/4 majestic acres, with a distant winter view of the Long Island Sound. A tranquil pond to the east, adjoining the Stillman Wildlife Preserve, Evergreens to the North, this estate is surrounded by multi million dollar... View all property information
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    Location Information
    Fairfield, Connecticut 06824
    From
    $246
    / Night
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    1 / 13
    Stamford
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    At this premier luxury 5 story community with a suburban feel, there is an assortment of urban amenities like award-winning landscaped grounds, a resort-style heated swimming pool and a 24 hour fitness center for residents to enjoy. The beautiful apartment homes at Stamford Corners offer residents... View all property information
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    Location Information
    Stamford, Connecticut
    From
    $220
    / Night
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    1 / 12
    Stamford
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    At this premier luxury 5 story community with a suburban feel, there is an assortment of urban amenities like award-winning landscaped grounds, a resort-style heated swimming pool and a 24 hour fitness center for residents to enjoy. The beautiful apartment homes at Stamford Corners offer residents... View all property information
    Make Inquiry
    Location Information
    Stamford, Connecticut
    From
    $233
    / Night
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    1 / 17
    Stamford
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This exquisite property located in the heart of downtown Stamford offers luxurious apartments. Residents will enjoy great amenities such as a furnished sky terrace with outdoor grills & fire pits, a lounge & screening room and a 24 hour fitness center. The fabulous apartments at The Blvd offer... View all property information
    Make Inquiry
    Location Information
    Stamford, Connecticut
    From
    $1,000
    / Night
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    1 / 47
    Greenwich
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Lauren Berger Collection is proud to be recognized as one of the best Vacation Rental companies in the world by the best, The Vacation Rental Guide. A forty-five minute drive from Manhattan but a world away from the clamor, this serene, elegant home is set on an acre of rolling lawns in one of... View all property information
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    Location Information
    Greenwich, Connecticut GREENWICH
    From
    $195
    / Night
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    1 / 8
    5 of 5 stars (13) Excellent
    Port Jefferson, NY
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (13) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    A true retreat! Peace and serenity....these will be your thoughts as you look out and view the harbor and magnificient woods located on 3 acres! We are minutes away from a very lively town with many restaurants, theatre and shopping! We have beautiful restaurants on the water as well!! This... View all property information
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    Location Information
    Port Jefferson, Long Island 11777
    5 of 5 stars Reviewed October 16, 2014
    Just as the review below I cannot say enough about this great vacation retreat. This is truly a wonderful vacation destination. Port Jefferson village is a great small village...
    5 of 5 stars Reviewed September 22, 2014
    This is a lovely rental with friendly hosts and walk-to-town convenience. We enjoyed the beautiful seclusion, lovely view (especially at night when the harbor lights are aglow...
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    From
    $250
    / Night
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    1 / 14
    Saint James, NY
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Beautiful 4 bedroom 2 bath Long Island home nestled in the historic village of Saint James on the North Shore. This space is the main floor of a ranch house located a convenient 60 miles away from New York City but a world away in vacation experience. It is easily accessible by car or train.... View all property information
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    Location Information
    Saint James, Long Island 11780
    From
    $350
    / Night
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    1 / 24
    Port Jefferson, NY
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This five bedroom Harbor View home is only steps away from town and the dock, located in the village of Port Jefferson. It has the most amazing harbor views with stairs that lead straight to the harbor where you will find outstanding restaurants, night clubs, bars and shops! There is always... View all property information
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    Location Information
    Port Jefferson, Long Island 11777
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    From
    $47
    / Night
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    1 / 8
    Danbury
    2 Bedrooms / 2 Bathrooms / Sleeps 3
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Newly refurbished cottage directly on the shores of Lake Candlewood in Danbury CT with access to a private dock and the lake. The cottage has 2 bedrooms and 2 bathrooms with a fireplace in the living room and a pellet stove on the enclosed porch that heats the entire house in the winter.... View all property information
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    Location Information
    Danbury, Connecticut 06811
    From
    $6,500
    / Week
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    1 / 12
    East Setauket, NY
    5 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Ping Pong Table
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    A wonderful summer getaway with stunning waterfront views, a few steps away from private beach access. This house sits on 2 full acres of land with steps leading down to the beach great for getting jet skiing, getting a tan or fishing, secluded from the busy streets of Long Island. Including a full... View all property information
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    Location Information
    East Setauket, Long Island 11733
    From
    $150
    / Night
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    1 / 14
    Darien
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Cozy home on private street with water access to Holly Pond and Long Island Sound. The perfect place to get away from the city while only a 45 minute Metro North Train to Grand Central Station NYC. Three metro north stations all less than 10 minute drive from house. The nearest station is only a 20... View all property information
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    Location Information
    Darien, Connecticut 06820
    From
    $9,000
    / Month
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    1 / 6
    Westport
    3 Bedrooms / 6 Bathrooms / Sleeps 7
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Ocean Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This direct waterfront getaway boasts an open floor plan with spectacular full water views throughout. Experience glorious energizing sunrises and exquisite sunsets to begin and end your magical days in this tranquil setting. Custom modern European inspired gourmet kitchen with top of the line... View all property information
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    Location Information
    Westport, Connecticut 06880