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Compare 330 Vacation Homes in Southport with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (6)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (19)
"This is a beautiful property. When we arrived, everything was perfect. It is completely stocked, including games for the family, and an unbelievable view of the lake. Communication with the homeowner was wonderful and we definitely plan to come back. We highly recommend this beautiful, clean and well kept home on the lake!."
Lakeside luxury: beautiful, relaxing 4 bedroom home

Business or Weekend escape

9.6 out of 10, Exceptional, (34)
"Very nice owner with great communication. "
The price is AED 275
AED 496 total
includes taxes & fees
13 Apr - 14 Apr
Business or Weekend escape

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"Toocold in Connecticut, host was alway inclose contact, heat was our only issue "
Cheerful 4 bedrooms residential house.

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (29)
"This is a place that feels like home, in a great location and filled with everything you could imagine bringing with you.Beachy vibes, and good energy! Highly recommend!"
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing."
Over Sized Colonial on Private Road.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"Great home with fun ping pong table!"
The price is AED 1,212
AED 2,773 total
includes taxes & fees
13 Apr - 14 Apr
New Beach Home near Stamford Downtown/Shippan

Ocean Front Beach House with Private Beach Access - Newly Renovated!

10.0 out of 10, Exceptional, (14)
"Communication was top notchThe property was very well appointed and perfect for a family gathering The most important part was the accessibility of the bathroom and bedroom for my mom who has mobility issues I was worried about the half step from bedroom to bathroom but I put pick lights on floor to remind her to step upLocation was perfect Especially loved visiting pez!"
Ocean Front Beach House with Private Beach Access - Newly Renovated!

Cottage at Sunny Day- Lakeside, views, kayak, dock

9.8 out of 10, Exceptional, (35)
"This property was very new and clean. It had everything you needed. Every room was comfortable and had its own TV. The open layout of the main floor made for great socializing and eating, and the 180 views of the frozen lake (in February) were beautifully serene. Would definitely come again and maybe next time in the summer! Thanks you for sharing this lovely property."
Cottage at Sunny Day- Lakeside, views, kayak, dock

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Westport Gem - walk to shops, dining, town center, pet-friendly

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"The place was plenty big and had so many rooms so all of the atjletes on Team B*REAL had their own space. We loved the huge island in the kitchen and open space to hang out together."
Spacious Gorgeous Getaway perfect for family reunion or business

Spacious 4-bedroom house with WiFi and AC in awesome Milford

The price is AED 1,192
AED 2,476 total
includes taxes & fees
20 Apr - 21 Apr
Spacious 4-bedroom house with WiFi and AC in awesome Milford

Charming West Haven Home - Walk to Beach!

8.6 out of 10, Excellent, (11)
"Clean house in a convenient and quiet location. Close to many store and restaurants. House was well equipped. Sauna was a nice extra. Only complaints are that the bed in the third bedroom is not for adults and the towels need to be replaced. We would definitely rent the house again when in the area. "
Charming West Haven Home - Walk to Beach!

Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub

Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub

Akasa Ocean Front Oasis- Seasonal Pool, Grill

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was the perfect location for our family to stay as we gathered for an event. Professional communication and my requests were quickly responded to. The location of this property features an absolutely stunning view of the ocean! Highly recommend!"
Akasa Ocean Front Oasis- Seasonal Pool, Grill

Historic Hideaway with Lake Access!

9.8 out of 10, Exceptional, (16)
"This was such a fun place to stay with my family who live in the area but we always have a hard time fitting. We all fit comfortably. It is a well maintained antique home with lots of nice features. The kids had a blast playing hide and seek. The house is very clean and plenty of linens and towels. Kitchen is set up well for a rental. Communication was fantastic. Instructions were easy and clear. I would highly recommend this place. Great little markets nearby and a lovely quiet neighborhood....
Historic Hideaway with Lake Access!

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (18)
"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "
The price is AED 2,156
AED 3,901 total
includes taxes & fees
13 Apr - 14 Apr
Waterview House Walking Distance from Cove Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Southport

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (83)
"House was perfect and in a great location. It was clean, well-stocked and had everything you might need - either winter or summer. The owner was incredibly helpful. Unqualified highest recommendation "
Westport "Gold Coast" across from Southport beach

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (51)
"Really liked Dune. I had a great room that was on the other side from Sea Grape - bar that could be loud. I heard noting from room 31. Could walk to Post Rd and the beach. Ocean view from room. "
The price is AED 826
AED 1,152 total
includes taxes & fees
20 Apr - 21 Apr
DUNE Fairfield Beach

Stamford Suites

3.0 star property
5.6 out of 10, (26)
"Room was very spacious "
The price is AED 625
AED 719 total
includes taxes & fees
25 Apr - 26 Apr
Stamford Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.