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Southport Vacation Rentals

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

Westport 'Gold Coast' across from Southport beach

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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A New England Jewel with Scenic Beauty, vacation rental in Southport

A New England Jewel with Scenic Beauty

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Milford Beach House - New Construction!, vacation rental in Southport

Milford Beach House - New Construction!

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Elegant Country Estate with Equestrian Farm, vacation rental in Southport

Elegant Country Estate with Equestrian Farm

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Direct Beach Front Apartment - Discounts available for long term stays., vacation rental in Southport

Direct Beach Front Apartment - Discounts available for long term stays.

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beach Vacation Get-Away – Near All Conveniences. You Decide Which You Want., vacation rental in Southport

Beach Vacation Get-Away – Near All Conveniences. You Decide Which You Want.

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Private 3.5 acre estate  Zen House /Historic mid century modern  / lap pool, vacation rental in Southport

Private 3.5 acre estate Zen House /Historic mid century modern / lap pool

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Beach side rental booking winter 2020\2021 Available December17 2020, vacation rental in Southport

Beach side rental booking winter 2020\2021 Available December17 2020

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS, vacation rental in Southport

Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Cottage By The Sea on Fairfield Beach, vacation rental in Southport

Charming Cottage By The Sea on Fairfield Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, vacation rental in Southport

FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC, vacation rental in Southport

Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Entire Guest House at Fox Pond Farm with Access to In ground Pool, vacation rental in Southport

Entire Guest House at Fox Pond Farm with Access to In ground Pool

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Luxe CT Country Home w/ Hi-end WiFi for WFH & School, vacation rental in Southport

Luxe CT Country Home w/ Hi-end WiFi for WFH & School

6 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Nice Duplex with view of Long Island Sound, vacation rental in Southport

Nice Duplex with view of Long Island Sound

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Cottage located on Historic Estate 1 Hour from NYC!, vacation rental in Southport

Charming Cottage located on Historic Estate 1 Hour from NYC!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy the serenity of the countryside at Pleasant Valley Trails - Home & Acres, vacation rental in Southport

Enjoy the serenity of the countryside at Pleasant Valley Trails - Home & Acres

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Bright Cottage on Silver Sands Beach, vacation rental in Southport

Charming Bright Cottage on Silver Sands Beach

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Home for Your Family Vacation, vacation rental in Southport

Beautiful Home for Your Family Vacation

7 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Cottage in Westport, CT (charming & pristine in fabulous location), vacation rental in Southport

Cozy Cottage in Westport, CT (charming & pristine in fabulous location)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Beachfront, beautiful views. Come  enjoy!, vacation rental in Southport

Elegant Beachfront, beautiful views. Come enjoy!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serene Connecticut Retreat - Luxury 2 bedroom apt, vacation rental in Southport

Serene Connecticut Retreat - Luxury 2 bedroom apt

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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North Stamford Guest House, vacation rental in Southport

North Stamford Guest House

2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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1/2 block to Compo Beach on Long Island Sound!, vacation rental in Southport

1/2 block to Compo Beach on Long Island Sound!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Premiere beach property, vacation rental in Southport

Premiere beach property

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Less than 1 block to the beach in Westport! Long Term Rentals too., vacation rental in Southport

Less than 1 block to the beach in Westport! Long Term Rentals too.

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Modern Waterfront Home  * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY, vacation rental in Southport

Modern Waterfront Home * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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#2 - Your own place on the Beach near Silver Sands Park, vacation rental in Southport

#2 - Your own place on the Beach near Silver Sands Park

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded cottage on cul de sac in Rowayton., vacation rental in Southport

Secluded cottage on cul de sac in Rowayton.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular Modern Home Near NYC, vacation rental in Southport

Spectacular Modern Home Near NYC

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Executive Estate 1 Hr from New York City, vacation rental in Southport

Luxury Executive Estate 1 Hr from New York City

6 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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#1 - A beach place by Silver Sands Park, vacation rental in Southport

#1 - A beach place by Silver Sands Park

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New modern house near the water (WESTPORT RESIDENTS ONLY), vacation rental in Southport

New modern house near the water (WESTPORT RESIDENTS ONLY)

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront Cottage w/Porch on Long Island Sound, vacation rental in Southport

Beachfront Cottage w/Porch on Long Island Sound

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Interior Designer's Enchanting And Bucolic Home, vacation rental in Southport

Interior Designer's Enchanting And Bucolic Home

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Updated Farmhouse Retreat, vacation rental in Southport

Updated Farmhouse Retreat

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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A Beautiful Nature Retreat, vacation rental in Southport

A Beautiful Nature Retreat

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Cozy Little Cottage, vacation rental in Southport

The Cozy Little Cottage

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Suburban Getaway. Heated Pool. NO PARTIES., vacation rental in Southport

Suburban Getaway. Heated Pool. NO PARTIES.

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Nature Lovers Perfect Location, an hour from Manhattan, vacation rental in Southport

Nature Lovers Perfect Location, an hour from Manhattan

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Mill Pond Retreat, vacation rental in Southport

Mill Pond Retreat

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A Fine Waterfront Private Home, In Park-like seaing, vacation rental in Southport

A Fine Waterfront Private Home, In Park-like seaing

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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See Beautiful Fall Foliage - Lovely CT country home sleeps 10 + heated  pool!, vacation rental in Southport

See Beautiful Fall Foliage - Lovely CT country home sleeps 10 + heated pool!

3 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate, vacation rental in Southport

Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Large Studio by the Beach w/private entrance, vacation rental in Southport

Large Studio by the Beach w/private entrance

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fitz Haven Lovely 2-Bed Apartment in Bridgeport, vacation rental in Southport

Fitz Haven Lovely 2-Bed Apartment in Bridgeport

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfy and Stylish Harbor Point Studio, vacation rental in Southport

Comfy and Stylish Harbor Point Studio

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Newly listed Property, Home Away from Home, Close to restaurants and local beach, vacation rental in Southport

Newly listed Property, Home Away from Home, Close to restaurants and local beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The West Lane Inn - Queen Room, vacation rental in Southport

The West Lane Inn - Queen Room

1 bedroom
1 bathroom
Sleeps 1
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