Westport, Connecticut

Vacation Rentals in Westport, Connecticut

Discover 55 vacation rental properties in Westport. From 1 to 9 bedrooms. Average $1053/night. 100% have pools.

55 verified listings Book securely on VRBO Prices updated March 2026

55 properties available

Westport Paradise With Every Amenity!

Westport Paradise With Every Amenity!

1 bed 1 bath
PoolA/CWiFiBalcony
$561/night
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Your perfect Westport getaway is here!

Your perfect Westport getaway is here!

2 beds 1 bath
PoolA/CWiFiBalcony
$169/night
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Sunny Westport 2BR Retreat above historic Mill

Sunny Westport 2BR Retreat above historic Mill

2 beds 1 bath
PoolA/CWiFiBalcony
$263/night
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Sunny Studio APT above historic Westport Mill

Sunny Studio APT above historic Westport Mill

1 bed 1 bath
PoolA/CWiFiBalcony
$140/night
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Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants

Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants

2 beds 2 baths
PoolA/CWiFiBalcony
$359/night
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Historic Apartment in Downtown Westport

Historic Apartment in Downtown Westport

1 bed 1 bath
PoolA/CWiFiBalcony
$95/night
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Private Oasis in Westport with heated pool!

Private Oasis in Westport with heated pool!

4 beds 3 baths
PoolA/CWiFiBalcony
$914/night
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Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.

Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.

3 beds 2 baths
PoolA/CWiFiBalcony
$739/night
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Westport In-Town Stay

Westport In-Town Stay

3 beds 2 baths
PoolA/CWiFiBalcony
$458/night
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Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth

Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth

5 beds 4 baths
PoolA/CWiFiBalcony
$1,351/night
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Designer Modern Westport Estate

Designer Modern Westport Estate

5 beds 7 baths
PoolA/CWiFiBalcony
$2,911/night
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Waterfront Getaway - Saugatuck Shores, Westport

Waterfront Getaway - Saugatuck Shores, Westport

4 beds 3 baths
PoolA/CWiFiBalcony
$751/night
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Spacious Family Home

Spacious Family Home

4 beds 3 baths
PoolA/CWiFiBalcony
$519/night
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Ideal location-Compo Beach

Ideal location-Compo Beach

4 beds 2 baths
PoolA/CWiFiBalcony
$801/night
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Westport: Walk to Town (Really) Private Yard, One Floor

Westport: Walk to Town (Really) Private Yard, One Floor

4 beds 1 bath
PoolA/CWiFiBalcony
$538/night
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Your luxury dream villa! 😍<br><br>

Your luxury dream villa! 😍<br><br>

4 beds 4 baths
PoolA/CWiFiBalcony
$1,100/night
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Westport Mid-century Retreat

Westport Mid-century Retreat

2 beds 2 baths
PoolA/CWiFiBalcony
$494/night
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Otter Haven; an enchanting summer home in a perfect location

Otter Haven; an enchanting summer home in a perfect location

4 beds 1 bath
PoolA/CWiFiBalcony
$801/night
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Modern Waterfront Home <br>steps from the water in quiet beachside neighborhood

Modern Waterfront Home <br>steps from the water in quiet beachside neighborhood

3 beds 2 baths
PoolA/CWiFiBalcony
$500/night
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Luxury Coastal Estate, 7min to NYC train & beach. Heated pool & amazing gardens

Luxury Coastal Estate, 7min to NYC train & beach. Heated pool & amazing gardens

9 beds 8 baths
PoolA/CWiFiBalcony
$2,003/night
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Historic oyster shack.

Historic oyster shack.

1 bed 1 bath
PoolA/CWiFiBalcony
$3,604/night
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Westport Manor with 40 Foot Heated Pool/Spa

Westport Manor with 40 Foot Heated Pool/Spa

6 beds 5 baths
PoolA/CWiFiBalcony
$1,501/night
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Modern Farmhouse

Modern Farmhouse

4 beds 3 baths
PoolA/CWiFiBalcony
$650/night
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Fabulous private home on desirable street in Westport.

Fabulous private home on desirable street in Westport.

4 beds 3 baths
PoolA/CWiFiBalcony
$801/night
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Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse

Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse

4 beds 4 baths
PoolA/CWiFiBalcony
$354/night
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3 Bedroom Luxury Cape - Walk To Train & Beach

3 Bedroom Luxury Cape - Walk To Train & Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$451/night
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Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach

Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$1,001/night
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Summer rental House Westport

Summer rental House Westport

3 beds 2 baths
PoolA/CWiFiBalcony
$334/night
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Mill Pond Retreat

Mill Pond Retreat

4 beds 2 baths
PoolA/CWiFiBalcony
$554/night
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Upscale custom home minutes from NYC

Upscale custom home minutes from NYC

3 beds 3 baths
PoolA/CWiFiBalcony
$451/night
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Luxurious 5-Bedroom Estate with Saltwater Pool, Spa, Game Room, 2 Offices

Luxurious 5-Bedroom Estate with Saltwater Pool, Spa, Game Room, 2 Offices

5 beds 7 baths
PoolA/CWiFiBalcony
$3,000/night
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ESCAPE to Westport Direct WATERFRONT Beachouse w/Rooftop Deck

ESCAPE to Westport Direct WATERFRONT Beachouse w/Rooftop Deck

2 beds 2 baths
PoolA/CWiFiBalcony
$400/night
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Amazing New Construction Home with Large Yard. 5 Minutes to EVERYTHING!

Amazing New Construction Home with Large Yard. 5 Minutes to EVERYTHING!

3 beds 2 baths
PoolA/CWiFiBalcony
$676/night
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Exquisite Waterfront Villa

Exquisite Waterfront Villa

4 beds 4 baths
PoolA/CWiFiBalcony
$1,530/night
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Monthly Rental-4 Bedroom Colonial in Westport, CT

Monthly Rental-4 Bedroom Colonial in Westport, CT

4 beds 3 baths
PoolA/CWiFiBalcony
$420/night
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Walk-To-Town Cozy Colonial with Fireplace!

Walk-To-Town Cozy Colonial with Fireplace!

4 beds 2 baths
PoolA/CWiFiBalcony
$596/night
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June Rental, Spectacular Views, INFINITY Pool, Perfect Location

June Rental, Spectacular Views, INFINITY Pool, Perfect Location

5 beds 5 baths
PoolA/CWiFiBalcony
$1,993/night
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Luxury beach home at Compo Beach, Westport CT

Luxury beach home at Compo Beach, Westport CT

4 beds 4 baths
PoolA/CWiFiBalcony
$986/night
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Dramatic family home directly on the Saugatuck River in Westport, CT

Dramatic family home directly on the Saugatuck River in Westport, CT

5 beds 3 baths
PoolA/CWiFiBalcony
$338/night
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Heated Pool on Quiet Lane in Charming Westport 3 miles To Beach

Heated Pool on Quiet Lane in Charming Westport 3 miles To Beach

5 beds 4 baths
PoolA/CWiFiBalcony
$1,251/night
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Westport Wonder Summer Rental with Pool!

Westport Wonder Summer Rental with Pool!

5 beds 4 baths
PoolA/CWiFiBalcony
$1,702/night
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Westport, CT - Walk To The Beach - NYC Getaway

Westport, CT - Walk To The Beach - NYC Getaway

4 beds 2 baths
PoolA/CWiFiBalcony
$1,001/night
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Beautiful Summer Escape

Beautiful Summer Escape

5 beds 6 baths
PoolA/CWiFiBalcony
$1,501/night
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Walk-to-Town New home w/new furnishings, Grill Center & Playset

Walk-to-Town New home w/new furnishings, Grill Center & Playset

5 beds 5 baths
PoolA/CWiFiBalcony
$808/night
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Vacation Home away from home with private pool-mins away from beach

Vacation Home away from home with private pool-mins away from beach

6 beds 4 baths
PoolA/CWiFiBalcony
$1,501/night
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Summer in Westport, CT! - Renovated, Private, Close to everything!

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

5 beds 3 baths
PoolA/CWiFiBalcony
$1,501/night
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Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport.

Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport.

6 beds 3 baths
PoolA/CWiFiBalcony
$1,753/night
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Westport summer 5 bed home on quiet street 6 mins to the beach!

Westport summer 5 bed home on quiet street 6 mins to the beach!

5 beds 5 baths
PoolA/CWiFiBalcony
$800/night
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More destinations in Connecticut

New Haven (158) Stonington (135) Milford (100) Mystic (93) Stamford (84) Old Saybrook (82) Westbrook (74) Old Lyme (71) Fairfield (57) Madison (56) Branford (53) Norwich (52) Greenwich (52) Groton (51) Bridgeport (47) East Lyme (43) Clinton (42) Hartford (40) Guilford (38) New Fairfield (37)