Fairfield, Connecticut

Vacation Rentals in Fairfield, Connecticut

Discover 57 vacation rental properties in Fairfield. From 1 to 6 bedrooms. Average $700/night. 100% have pools.

57 verified listings Book securely on VRBO Prices updated March 2026

57 properties available

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

3 beds 1 bath
PoolA/CWiFiBalcony
$446/night
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Westport "Gold Coast" across from Southport beach

Westport "Gold Coast" across from Southport beach

1 bed 1 bath
PoolA/CWiFiBalcony
$226/night
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Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

3 beds 2 baths
PoolA/CWiFiBalcony
$389/night
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Family Friendly: Renovated, Bright Home near Beach, with a Firepit

Family Friendly: Renovated, Bright Home near Beach, with a Firepit

3 beds 2 baths
PoolA/CWiFiBalcony
$323/night
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Amazing Direct Beachfront Home close to golf, tennis, restaurants and shopping

Amazing Direct Beachfront Home close to golf, tennis, restaurants and shopping

4 beds 3 baths
PoolA/CWiFiBalcony
$851/night
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Beachy Kind of Life

Beachy Kind of Life

3 beds 3 baths
PoolA/CWiFiBalcony
$325/night
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Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!

Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!

6 beds 4 baths
PoolA/CWiFiBalcony
$1,251/night
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Steps away from the beach -updated 4bd/2 bath beach house with guest house

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

3 beds 2 baths
PoolA/CWiFiBalcony
$351/night
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Stunning direct waterfront beach house!

Stunning direct waterfront beach house!

3 beds 3 baths
PoolA/CWiFiBalcony
$751/night
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Fairfield Beach House

Fairfield Beach House

4 beds 2 baths
PoolA/CWiFiBalcony
$414/night
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Large waterfront beach house at the Point ! Bring your family and friends

Large waterfront beach house at the Point ! Bring your family and friends

5 beds 3 baths
PoolA/CWiFiBalcony
$1,367/night
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Spacious&Gracious- 5BR Fam-Friendly near I95&Shops

Spacious&Gracious- 5BR Fam-Friendly near I95&Shops

5 beds 2 baths
PoolA/CWiFiBalcony
$728/night
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Beach cottage steps from the sand and surf!!

Beach cottage steps from the sand and surf!!

4 beds 2 baths
PoolA/CWiFiBalcony
$451/night
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Beach house - perfect location next to beach and town!

Beach house - perfect location next to beach and town!

4 beds 1 bath
PoolA/CWiFiBalcony
$337/night
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Elegant Beachfront, beautiful views. Come enjoy!

Elegant Beachfront, beautiful views. Come enjoy!

5 beds 3 baths
PoolA/CWiFiBalcony
$1,251/night
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Summer Rental. Beachfront family home on Long Island Sound.

Summer Rental. Beachfront family home on Long Island Sound.

3 beds 2 baths
PoolA/CWiFiBalcony
$781/night
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Fairfield Beach Modern Colonial

Fairfield Beach Modern Colonial

4 beds 3 baths
PoolA/CWiFiBalcony
$2,003/night
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Sophisticated Country Ranch Home

Sophisticated Country Ranch Home

3 beds 2 baths
PoolA/CWiFiBalcony
$1,176/night
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Dreamy Beachfront Cottage with NYC views

Dreamy Beachfront Cottage with NYC views

4 beds 1 bath
PoolA/CWiFiBalcony
$951/night
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Connecticut Estate - Now available July 9-23rd 2023

Connecticut Estate - Now available July 9-23rd 2023

5 beds 3 baths
PoolA/CWiFiBalcony
$1,237/night
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Fairfield beach area cozy retreat

Fairfield beach area cozy retreat

4 beds 2 baths
PoolA/CWiFiBalcony
$532/night
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Fairfield Historic Street. Private Heated Pool. Walk to Town Restaurants & Beach

Fairfield Historic Street. Private Heated Pool. Walk to Town Restaurants & Beach

4 beds 3 baths
PoolA/CWiFiBalcony
$630/night
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Summer estate close to NY, NJ, MA w heated pool sleeps 16

Summer estate close to NY, NJ, MA w heated pool sleeps 16

6 beds 7 baths
PoolA/CWiFiBalcony
$2,840/night
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4 BR Classic Country House in CT

4 BR Classic Country House in CT

4 beds 4 baths
PoolA/CWiFiBalcony
$1,251/night
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Chilax with family in modern colonial Cul de sac near university

Chilax with family in modern colonial Cul de sac near university

4 beds 2 baths
PoolA/CWiFiBalcony
$583/night
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Quiet suburban home close to Fairfield beaches and universities

Quiet suburban home close to Fairfield beaches and universities

3 beds 1 bath
PoolA/CWiFiBalcony
$239/night
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ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM

ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM

4 beds 4 baths
PoolA/CWiFiBalcony
$1,331/night
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Lovely 5 Bedroom Beach House with Large Backyard - Walk to Beach, Town or Train

Lovely 5 Bedroom Beach House with Large Backyard - Walk to Beach, Town or Train

5 beds 3 baths
PoolA/CWiFiBalcony
$1,001/night
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Quintessential Waterfront Beach House Dripping Over the Long Island Sound

Quintessential Waterfront Beach House Dripping Over the Long Island Sound

5 beds 2 baths
PoolA/CWiFiBalcony
$826/night
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Lake House this Vacation rental is an a privet Neighborhood association lake.

Lake House this Vacation rental is an a privet Neighborhood association lake.

4 beds 3 baths
PoolA/CWiFiBalcony
$293/night
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Luxury Beachfront living with amazing views

Luxury Beachfront living with amazing views

4 beds 4 baths
PoolA/CWiFiBalcony
$900/night
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Southport Charm! Steps away from town!

Southport Charm! Steps away from town!

4 beds 3 baths
PoolA/CWiFiBalcony
$977/night
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Design features being prepped and curated. Don’t miss out our costal discount

Design features being prepped and curated. Don’t miss out our costal discount

4 beds 2 baths
PoolA/CWiFiBalcony
$366/night
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Cheerful 6-Bedroom Villa with Pool and Tennis Courts near the beach!

Cheerful 6-Bedroom Villa with Pool and Tennis Courts near the beach!

6 beds 4 baths
PoolA/CWiFiBalcony
$693/night
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Cozy beach retreat with stunning views of Long Island Sound

Cozy beach retreat with stunning views of Long Island Sound

3 beds 2 baths
PoolA/CWiFiBalcony
$701/night
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Spectacular direct waterfront with rooftop hot tub 360 degree views.

Spectacular direct waterfront with rooftop hot tub 360 degree views.

3 beds 1 bath
PoolA/CWiFiBalcony
$1,251/night
View Details → Book on VRBO
Spacious 5-bedroom, house in Southport with WiFi, AC, near train, harbor, town.

Spacious 5-bedroom, house in Southport with WiFi, AC, near train, harbor, town.

5 beds 4 baths
PoolA/CWiFiBalcony
$761/night
View Details → Book on VRBO
Beautiful home on private beach, sleeps 11! Bring your family and friends!

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

6 beds 4 baths
PoolA/CWiFiBalcony
$977/night
View Details → Book on VRBO
Beachfront cottage located in the heart of Fairfield Beach!!

Beachfront cottage located in the heart of Fairfield Beach!!

3 beds 1 bath
PoolA/CWiFiBalcony
$500/night
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Sun and Fun on the beach!!

Sun and Fun on the beach!!

4 beds 2 baths
PoolA/CWiFiBalcony
$676/night
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Charming Cottage By The Sea on Fairfield Beach

Charming Cottage By The Sea on Fairfield Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$324/night
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Cozy summer house 4 bed & 2 baths - Weekly rental

Cozy summer house 4 bed & 2 baths - Weekly rental

4 beds 2 baths
PoolA/CWiFiBalcony
$215/night
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Steps to the Sand & Surf!

Steps to the Sand & Surf!

4 beds 2 baths
PoolA/CWiFiBalcony
$451/night
View Details → Book on VRBO
Steps from the beach with water views!

Steps from the beach with water views!

4 beds 2 baths
PoolA/CWiFiBalcony
$451/night
View Details → Book on VRBO
Exceptional August rental one block from beach!

Exceptional August rental one block from beach!

3 beds 2 baths
PoolA/CWiFiBalcony
$217/night
View Details → Book on VRBO
Charming Summer House (newly remodeled). 4 min from the beach

Charming Summer House (newly remodeled). 4 min from the beach

4 beds 2 baths
PoolA/CWiFiBalcony
$500/night
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Gem by the Sound - Fairfield Beachside Rental

Gem by the Sound - Fairfield Beachside Rental

2 beds 2 baths
PoolA/CWiFiBalcony
$395/night
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479 South Benson Road

479 South Benson Road

2 beds 2 baths
PoolA/CWiFiBalcony
$253/night
View Details → Book on VRBO

More destinations in Connecticut

New Haven (158) Stonington (135) Milford (100) Mystic (93) Stamford (84) Old Saybrook (82) Westbrook (74) Old Lyme (71) Madison (56) Westport (55) Branford (53) Norwich (52) Greenwich (52) Groton (51) Bridgeport (47) East Lyme (43) Clinton (42) Hartford (40) Guilford (38) New Fairfield (37)