Vacation rentals in Southport, CT

Best vacation rentals and Airbnb offers in Southport, CT

Charming 2-bedroom apartment in delightful Bridgeport with WiFi

Apartment, Southport

Charming 2-bedroom apartment in delightful Bridgeport with WiFi is a apartment in Southport, with parking and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming 2-bedroom apartment in delightful Bridgeport with WiFi

Charming 2-bedroom apartment in delightful Bridgeport with WiFi is a apartment in Southport, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,151.

From$164/night

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Zen, Spacious & Comfy 2 bed, Lux beds

Apartment, Southport

Zen, Spacious & Comfy 2 bed, Lux beds is a apartment in Southport, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds is a apartment in Southport, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,204.

From$172/night

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Modern Apartment in Black Rock

Apartment, Southport

Modern Apartment in Black Rock is a apartment in Southport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Modern Apartment in Black Rock

Modern Apartment in Black Rock is a apartment in Southport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,270.

From$181/night

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Cozy 2 bedroom 2 bath house with in charming private house near Fairfield Border

Holiday Home, Southport

Cozy 2 bedroom 2 bath house with in charming private house near Fairfield Border is a holiday home in Southport, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Cozy 2 bedroom 2 bath house with in charming private house near Fairfield Border

Cozy 2 bedroom 2 bath house with in charming private house near Fairfield Border is a holiday home in Southport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,375.

From$196/night

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Vacation rentals with a pool in Southport, CT

Add a pool to the search when you want an easy place to cool off between outings.

Guest House at Norwalk Inn

Guest House, Southport

Guest House at Norwalk Inn is a guest house in Southport, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Guest House at Norwalk Inn

Guest House at Norwalk Inn is a guest house in Southport, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,292.

From$409/night

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Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

Holiday Home, Southport

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach is a holiday home in Southport, with pool access and easy beach access. This stay gives travelers a comfortable base for…

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About Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach is a holiday home in Southport, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,224.

From$1,461/night

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Designer Barn House • Hot Tub, Pool, Fire Pits & Entertainers Retreat

Country House, Southport

Designer Barn House · Hot Tub, Pool, Fire Pits & Entertainers Retreat is a country house in Southport, with pool access and a quieter setting. This stay gives travelers a comfortable base…

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About Designer Barn House • Hot Tub, Pool, Fire Pits & Entertainers Retreat

Designer Barn House · Hot Tub, Pool, Fire Pits & Entertainers Retreat is a country house in Southport, with pool access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $13,349.

From$1,907/night

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2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC

Holiday Home, Southport

2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC is a holiday home in Southport, with pool access, easy beach access, and a quieter setting. This stay gives…

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About 2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC

2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC is a holiday home in Southport, with pool access, easy beach access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $16,948.

From$2,421/night

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Vacation rentals with parking in Southport, CT

Find vacation rentals that make arriving by car easier.

Peaceful Hidden Gem Near The Beach Ideal For Longer Stays

Apartment, Southport

Peaceful Hidden Gem Near The Beach Ideal For Longer Stays is a apartment in Southport, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Peaceful Hidden Gem Near The Beach Ideal For Longer Stays

Peaceful Hidden Gem Near The Beach Ideal For Longer Stays is a apartment in Southport, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $885.

From$126/night

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Darien Home

Holiday Home, Southport

Darien Home is a holiday home in Southport, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Darien Home

Darien Home is a holiday home in Southport, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,826.

From$261/night

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Summer by the Shore, Washington Street nightlife, MetroNorth 60 minutes to GCT

Holiday Home, Southport

Summer by the Shore, Washington Street nightlife, MetroNorth 60 minutes to GCT is a holiday home in Southport, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Summer by the Shore, Washington Street nightlife, MetroNorth 60 minutes to GCT

Summer by the Shore, Washington Street nightlife, MetroNorth 60 minutes to GCT is a holiday home in Southport, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,125.

From$304/night

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4-bedroom house in delightful Bridgeport with all you need to call Home

Holiday Home, Southport

4-bedroom house in delightful Bridgeport with all you need to call Home is a holiday home in Southport, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 4-bedroom house in delightful Bridgeport with all you need to call Home

4-bedroom house in delightful Bridgeport with all you need to call Home is a holiday home in Southport, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,236.

From$319/night

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Pet-friendly vacation rentals in Southport, CT

Bring your pet along with stays that welcome four-legged travelers.

Lovely 1-bedroom Basement apartment in Stamford

Apartment, Southport

Lovely 1-bedroom Basement apartment in Stamford is a apartment in Southport, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Lovely 1-bedroom Basement apartment in Stamford

Lovely 1-bedroom Basement apartment in Stamford is a apartment in Southport, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,071.

From$153/night

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Charming Home in Seaside

Holiday Home, Southport

Charming Home in Seaside is a holiday home in Southport, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Charming Home in Seaside

Charming Home in Seaside is a holiday home in Southport, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,223.

From$318/night

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Quintessential Cozy Haven, Brooklawn Beauty

Holiday Home, Southport

Quintessential Cozy Haven, Brooklawn Beauty is a holiday home in Southport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Quintessential Cozy Haven, Brooklawn Beauty

Quintessential Cozy Haven, Brooklawn Beauty is a holiday home in Southport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,419.

From$346/night

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Southport Shoreline Charm: Elegant Coastal Escape

Holiday Home, Southport

Southport Shoreline Charm: Elegant Coastal Escape is a holiday home in Southport, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Southport Shoreline Charm: Elegant Coastal Escape

Southport Shoreline Charm: Elegant Coastal Escape is a holiday home in Southport, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,679.

From$526/night

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Vacation rentals with a kitchen in Southport, CT

Compare stays with kitchen access for longer trips and easier meals.

Charming 1 bedroom by the Beach!

Holiday Home, Southport

Charming 1 bedroom by the Beach! is a holiday home in Southport, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Charming 1 bedroom by the Beach!

Charming 1 bedroom by the Beach! is a holiday home in Southport, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,882.

From$269/night

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The B&W Haven 5BR Home with yard theater + Office

Holiday Home, Southport

The B&W Haven 5BR Home with yard theater + Office is a holiday home in Southport, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About The B&W Haven 5BR Home with yard theater + Office

The B&W Haven 5BR Home with yard theater + Office is a holiday home in Southport, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,861.

From$409/night

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Modern + Spacious 5BR/2BA Home, Renovated Backyard

Holiday Home, Southport

Modern + Spacious 5BR/2BA Home, Renovated Backyard is a holiday home in Southport, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Modern + Spacious 5BR/2BA Home, Renovated Backyard

Modern + Spacious 5BR/2BA Home, Renovated Backyard is a holiday home in Southport, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,872.

From$410/night

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Bright and cheery summer retreat. Close to Compo, Saugatuck dining, and town.

Holiday Home, Southport

Bright and cheery summer retreat. Close to Compo, Saugatuck dining, and town. is a holiday home in Southport, with pet-friendly space, kitchen access, and a quieter setting. This stay gives…

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About Bright and cheery summer retreat. Close to Compo, Saugatuck dining, and town.

Bright and cheery summer retreat. Close to Compo, Saugatuck dining, and town. is a holiday home in Southport, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,632.

From$519/night

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Family-friendly vacation rentals in Southport, CT

Plan a trip with stays that give families more room to spread out.

Cozy country cottage in horse country ,private 1 hour toNYC

Cottage, Southport

Cozy country cottage in horse country ,private 1 hour toNYC is a cottage in Southport, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Cozy country cottage in horse country ,private 1 hour toNYC

Cozy country cottage in horse country ,private 1 hour toNYC is a cottage in Southport, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,780.

From$254/night

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Family Home Near Roosevelt Forest & Historic Sites

Cottage, Southport

Family Home Near Roosevelt Forest & Historic Sites is a cottage in Southport, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Family Home Near Roosevelt Forest & Historic Sites

Family Home Near Roosevelt Forest & Historic Sites is a cottage in Southport, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,921.

From$297/night

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Seaside Serenity: 2B 1B, Patio,Near Beach

Cottage, Southport

Seaside Serenity: 2B 1B, Patio,Near Beach is a cottage in Southport, with pet-friendly space, easy beach access, and outdoor space. This stay gives travelers a comfortable base for…

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About Seaside Serenity: 2B 1B, Patio,Near Beach

Seaside Serenity: 2B 1B, Patio,Near Beach is a cottage in Southport, with pet-friendly space, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,651.

From$379/night

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Dreamy Beachfront Cottage with NYC views

Holiday Home, Southport

Dreamy Beachfront Cottage with NYC views is a holiday home in Southport, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About Dreamy Beachfront Cottage with NYC views

Dreamy Beachfront Cottage with NYC views is a holiday home in Southport, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,783.

From$826/night

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