We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Southport Vacation Rentals

Revenue impacts this sort order. Learn more.

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 mi
49 rentals in Southport.
Westport 'Gold Coast' across from Southport beach, vacation rental in Southport
Westport 'Gold Coast' across from Southport beach, vacation rental in Southport
Westport 'Gold Coast' across from Southport beach, vacation rental in Southport

Westport 'Gold Coast' across from Southport beach

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Payment Protection

A New England Jewel with Scenic Beauty, vacation rental in Southport
A New England Jewel with Scenic Beauty, vacation rental in Southport
A New England Jewel with Scenic Beauty, vacation rental in Southport

A New England Jewel with Scenic Beauty

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection

Sunny Studio APT above historic Westport Mill, vacation rental in Southport
Sunny Studio APT above historic Westport Mill, vacation rental in Southport
Sunny Studio APT above historic Westport Mill, vacation rental in Southport

Sunny Studio APT above historic Westport Mill

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Gem by the Sound Summ, vacation rental in Southport
Gem by the Sound Summ, vacation rental in Southport
Gem by the Sound Summ, vacation rental in Southport

Gem by the Sound Summ

Rental Home
0 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming Cottage By The Sea on Fairfield Beach, vacation rental in Southport
Charming Cottage By The Sea on Fairfield Beach, vacation rental in Southport
Charming Cottage By The Sea on Fairfield Beach, vacation rental in Southport

Charming Cottage By The Sea on Fairfield Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stylish 1bd/1ba Apt + Pool - Downtown Fairfield, vacation rental in Southport
Stylish 1bd/1ba Apt + Pool - Downtown Fairfield, vacation rental in Southport
Stylish 1bd/1ba Apt + Pool - Downtown Fairfield, vacation rental in Southport

Stylish 1bd/1ba Apt + Pool - Downtown Fairfield

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

4 BR Classic Country House in CT, vacation rental in Southport
4 BR Classic Country House in CT, vacation rental in Southport
4 BR Classic Country House in CT, vacation rental in Southport

4 BR Classic Country House in CT

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Fairfield Old Post Road with pool - walk to  NYC train and Beach, vacation rental in Southport
Fairfield Old Post Road with pool - walk to  NYC train and Beach, vacation rental in Southport
Fairfield Old Post Road with pool - walk to  NYC train and Beach, vacation rental in Southport

Fairfield Old Post Road with pool - walk to NYC train and Beach

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Spacious 5 Bed/2 Bath w. Lg Yard + Game Room + Min. from Beach, vacation rental in Southport
Spacious 5 Bed/2 Bath w. Lg Yard + Game Room + Min. from Beach, vacation rental in Southport
Spacious 5 Bed/2 Bath w. Lg Yard + Game Room + Min. from Beach, vacation rental in Southport

Spacious 5 Bed/2 Bath w. Lg Yard + Game Room + Min. from Beach

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning direct waterfront beach house!, vacation rental in Southport
Stunning direct waterfront beach house!, vacation rental in Southport
Stunning direct waterfront beach house!, vacation rental in Southport

Stunning direct waterfront beach house!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Cozy getaway in Fairfield - EXPERTLY SANITIZED, vacation rental in Southport
Cozy getaway in Fairfield - EXPERTLY SANITIZED, vacation rental in Southport
Cozy getaway in Fairfield - EXPERTLY SANITIZED, vacation rental in Southport

Cozy getaway in Fairfield - EXPERTLY SANITIZED

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Westport Paradise With Every Amenity!, vacation rental in Southport
Westport Paradise With Every Amenity!, vacation rental in Southport
Westport Paradise With Every Amenity!, vacation rental in Southport

Westport Paradise With Every Amenity!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Fairfield CT, Historic District w/Heated Pool;Walk to Town/Restaurants, vacation rental in Southport
Fairfield CT, Historic District w/Heated Pool;Walk to Town/Restaurants, vacation rental in Southport
Fairfield CT, Historic District w/Heated Pool;Walk to Town/Restaurants, vacation rental in Southport

Fairfield CT, Historic District w/Heated Pool;Walk to Town/Restaurants

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

A private summer compound in Westport, CT - total seclusion yet close to it all, vacation rental in Southport
A private summer compound in Westport, CT - total seclusion yet close to it all, vacation rental in Southport
A private summer compound in Westport, CT - total seclusion yet close to it all, vacation rental in Southport

A private summer compound in Westport, CT - total seclusion yet close to it all

Rental Home
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Spectacular direct waterfront with rooftop hot tub 360 degree views, vacation rental in Southport
Spectacular direct waterfront with rooftop hot tub 360 degree views, vacation rental in Southport
Spectacular direct waterfront with rooftop hot tub 360 degree views, vacation rental in Southport

Spectacular direct waterfront with rooftop hot tub 360 degree views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 30
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Mill Pond Retreat, vacation rental in Southport
Mill Pond Retreat, vacation rental in Southport
Mill Pond Retreat, vacation rental in Southport

Mill Pond Retreat

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautiful home on private beach, sleeps 11! Bring your family and friends!, vacation rental in Southport
Beautiful home on private beach, sleeps 11! Bring your family and friends!, vacation rental in Southport
Beautiful home on private beach, sleeps 11! Bring your family and friends!, vacation rental in Southport

Beautiful home on private beach, sleeps 11! Bring your family and friends!

Rental Home
6 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Westport "Gold Coast" across from Southport beach, vacation rental in Southport
Westport "Gold Coast" across from Southport beach, vacation rental in Southport
Westport "Gold Coast" across from Southport beach, vacation rental in Southport

Westport "Gold Coast" across from Southport beach

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Fabulous private home on desirable street in Westport., vacation rental in Southport
Fabulous private home on desirable street in Westport., vacation rental in Southport
Fabulous private home on desirable street in Westport., vacation rental in Southport

Fabulous private home on desirable street in Westport.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Elegant Beachfront, beautiful views. Come enjoy!, vacation rental in Southport
Elegant Beachfront, beautiful views. Come enjoy!, vacation rental in Southport
Elegant Beachfront, beautiful views. Come enjoy!, vacation rental in Southport

Elegant Beachfront, beautiful views. Come enjoy!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse, vacation rental in Southport
Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse, vacation rental in Southport
Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse, vacation rental in Southport

Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

STUNNING POOL & SCREENED PORCH! Private home, close to EVERYTHING!!, vacation rental in Southport
STUNNING POOL & SCREENED PORCH! Private home, close to EVERYTHING!!, vacation rental in Southport
STUNNING POOL & SCREENED PORCH! Private home, close to EVERYTHING!!, vacation rental in Southport

STUNNING POOL & SCREENED PORCH! Private home, close to EVERYTHING!!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Fairfield In-Town/Beach Area "Story-Book" Cottage with Pool, vacation rental in Southport
Fairfield In-Town/Beach Area "Story-Book" Cottage with Pool, vacation rental in Southport
Fairfield In-Town/Beach Area "Story-Book" Cottage with Pool, vacation rental in Southport

Fairfield In-Town/Beach Area "Story-Book" Cottage with Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Summer in Westport, CT! - Renovated, Private, Close to everything!, vacation rental in Southport
Summer in Westport, CT! - Renovated, Private, Close to everything!, vacation rental in Southport
Summer in Westport, CT! - Renovated, Private, Close to everything!, vacation rental in Southport

Summer in Westport, CT! - Renovated, Private, Close to everything!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beach Cottage on the Harbor!, vacation rental in Southport
Beach Cottage on the Harbor!, vacation rental in Southport
Beach Cottage on the Harbor!, vacation rental in Southport

Beach Cottage on the Harbor!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks, vacation rental in Southport
Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks, vacation rental in Southport
Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks, vacation rental in Southport

Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning Estate w/ private pond-views from every room!, vacation rental in Southport
Stunning Estate w/ private pond-views from every room!, vacation rental in Southport
Stunning Estate w/ private pond-views from every room!, vacation rental in Southport

Stunning Estate w/ private pond-views from every room!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, vacation rental in Southport
Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, vacation rental in Southport
Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, vacation rental in Southport

Summer Rental: 4 Car Garage 1/4 mile to town of Fairfeild Center

Rental Home
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Vacation Ready: Beautiful House with Heated Pool, vacation rental in Southport
Vacation Ready: Beautiful House with Heated Pool, vacation rental in Southport
Vacation Ready: Beautiful House with Heated Pool, vacation rental in Southport

Vacation Ready: Beautiful House with Heated Pool

Rental Home
6 bedrooms
7 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Pool & beach vacation in Westport, Connecticut, vacation rental in Southport
Pool & beach vacation in Westport, Connecticut, vacation rental in Southport
Pool & beach vacation in Westport, Connecticut, vacation rental in Southport

Pool & beach vacation in Westport, Connecticut

Rental Home
5 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT), vacation rental in Southport
5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT), vacation rental in Southport
5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT), vacation rental in Southport

5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT)

Rental Home
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Historic Updated Carriage House, vacation rental in Southport
Historic Updated Carriage House, vacation rental in Southport
Historic Updated Carriage House, vacation rental in Southport

Historic Updated Carriage House

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Exceptional August rental one block from beach!, vacation rental in Southport
Exceptional August rental one block from beach!, vacation rental in Southport
Exceptional August rental one block from beach!, vacation rental in Southport

Exceptional August rental one block from beach!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beach house - perfect location next to beach and town!, vacation rental in Southport
Beach house - perfect location next to beach and town!, vacation rental in Southport
Beach house - perfect location next to beach and town!, vacation rental in Southport

Beach house - perfect location next to beach and town!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Black Rock Bungalow, vacation rental in Southport
Black Rock Bungalow, vacation rental in Southport
Black Rock Bungalow, vacation rental in Southport

Black Rock Bungalow

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Amazing Beach House On Fairfield Beach, vacation rental in Southport
Amazing Beach House On Fairfield Beach, vacation rental in Southport
Amazing Beach House On Fairfield Beach, vacation rental in Southport

Amazing Beach House On Fairfield Beach

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Captain House in Black Rock-Academic Rental, vacation rental in Southport
Captain House in Black Rock-Academic Rental, vacation rental in Southport
Captain House in Black Rock-Academic Rental, vacation rental in Southport

Captain House in Black Rock-Academic Rental

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Summer Getaway in Fairfield (Beach Passes Included!), vacation rental in Southport
Summer Getaway in Fairfield (Beach Passes Included!), vacation rental in Southport
Summer Getaway in Fairfield (Beach Passes Included!), vacation rental in Southport

Summer Getaway in Fairfield (Beach Passes Included!)

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Steps away from the beach -updated  4bd/2 bath beach house with guest house, vacation rental in Southport
Steps away from the beach -updated  4bd/2 bath beach house with guest house, vacation rental in Southport
Steps away from the beach -updated  4bd/2 bath beach house with guest house, vacation rental in Southport

Steps away from the beach -updated 4bd/2 bath beach house with guest house

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Fairfield Beach House, vacation rental in Southport
Fairfield Beach House, vacation rental in Southport
Fairfield Beach House, vacation rental in Southport

Fairfield Beach House

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Steps to Jennings Beach and the South Benson Marina!, vacation rental in Southport
Steps to Jennings Beach and the South Benson Marina!, vacation rental in Southport
Steps to Jennings Beach and the South Benson Marina!, vacation rental in Southport

Steps to Jennings Beach and the South Benson Marina!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

"Sea-Duced" by the Beach! Four-Bedroom Fairfield Beach Home Near Downtown, vacation rental in Southport
"Sea-Duced" by the Beach! Four-Bedroom Fairfield Beach Home Near Downtown, vacation rental in Southport
"Sea-Duced" by the Beach! Four-Bedroom Fairfield Beach Home Near Downtown, vacation rental in Southport

"Sea-Duced" by the Beach! Four-Bedroom Fairfield Beach Home Near Downtown

Rental Home
4 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Dreamy Beachfront Cottage with NYC views, vacation rental in Southport
Dreamy Beachfront Cottage with NYC views, vacation rental in Southport
Dreamy Beachfront Cottage with NYC views, vacation rental in Southport

Dreamy Beachfront Cottage with NYC views

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM - ACADEMIC YR AVAILABLE, vacation rental in Southport
ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM - ACADEMIC YR AVAILABLE, vacation rental in Southport
ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM - ACADEMIC YR AVAILABLE, vacation rental in Southport

ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM - ACADEMIC YR AVAILABLE

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beach area cape!  Walk to town & beach, vacation rental in Southport
Beach area cape!  Walk to town & beach, vacation rental in Southport
Beach area cape!  Walk to town & beach, vacation rental in Southport

Beach area cape! Walk to town & beach

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Entire House- Walk to Beach!, vacation rental in Southport
Entire House- Walk to Beach!, vacation rental in Southport
Entire House- Walk to Beach!, vacation rental in Southport

Entire House- Walk to Beach!

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Clean as a whistle, happy place! Beachtown!, vacation rental in Southport
Clean as a whistle, happy place! Beachtown!, vacation rental in Southport
Clean as a whistle, happy place! Beachtown!, vacation rental in Southport

Clean as a whistle, happy place! Beachtown!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Spacious Beach AreaHome- Walk to Town, Bike >Beach, vacation rental in Southport
Spacious Beach AreaHome- Walk to Town, Bike >Beach, vacation rental in Southport
Spacious Beach AreaHome- Walk to Town, Bike >Beach, vacation rental in Southport

Spacious Beach AreaHome- Walk to Town, Bike >Beach

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Newly renovated 1 bedroom in historic English Tudor on private ground, vacation rental in Southport
Newly renovated 1 bedroom in historic English Tudor on private ground, vacation rental in Southport
Newly renovated 1 bedroom in historic English Tudor on private ground, vacation rental in Southport

Newly renovated 1 bedroom in historic English Tudor on private ground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming and comfy  bedroom, vacation rental in Southport
Charming and comfy  bedroom, vacation rental in Southport
Charming and comfy  bedroom, vacation rental in Southport

Charming and comfy bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 1
More info
Vrbo.com logo
Check in
Check out

Showing results 1-49 of 49
Frequently Asked Questions about Southport