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Darien Vacation Rentals

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50 rentals in Darien.
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Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC, vacation rental in Darien
Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC, vacation rental in Darien
Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC, vacation rental in Darien

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Home for Your Family Vacation, vacation rental in Darien
Beautiful Home for Your Family Vacation, vacation rental in Darien
Beautiful Home for Your Family Vacation, vacation rental in Darien

Beautiful Home for Your Family Vacation

Rental Home
7 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Space, expansive property with views and pool, vacation rental in Darien
Space, expansive property with views and pool, vacation rental in Darien
Space, expansive property with views and pool, vacation rental in Darien

Space, expansive property with views and pool

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Darien Family Home, vacation rental in Darien
Beautiful Darien Family Home, vacation rental in Darien
Beautiful Darien Family Home, vacation rental in Darien

Beautiful Darien Family Home

Rental Home
6 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Charming 4 bedroom that backs up to a park; 1 mile from the beach!, vacation rental in Darien
Charming 4 bedroom that backs up to a park; 1 mile from the beach!, vacation rental in Darien
Charming 4 bedroom that backs up to a park; 1 mile from the beach!, vacation rental in Darien

Charming 4 bedroom that backs up to a park; 1 mile from the beach!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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New Stylish Beach Home near Stamford Downtown/Cove Beach/ 40 min to NYC �, vacation rental in Darien
New Stylish Beach Home near Stamford Downtown/Cove Beach/ 40 min to NYC �, vacation rental in Darien
New Stylish Beach Home near Stamford Downtown/Cove Beach/ 40 min to NYC �, vacation rental in Darien

New Stylish Beach Home near Stamford Downtown/Cove Beach/ 40 min to NYC �

Rental Home
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Bright Stylish Chic 4BR 4BA Home Close to Greenwich CT Beach and Shops, vacation rental in Darien
Bright Stylish Chic 4BR 4BA Home Close to Greenwich CT Beach and Shops, vacation rental in Darien
Bright Stylish Chic 4BR 4BA Home Close to Greenwich CT Beach and Shops, vacation rental in Darien

Bright Stylish Chic 4BR 4BA Home Close to Greenwich CT Beach and Shops

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Rowayton House Close To Town, vacation rental in Darien
Rowayton House Close To Town, vacation rental in Darien
Rowayton House Close To Town, vacation rental in Darien

Rowayton House Close To Town

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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SHORELINE HOLIDAY GETAWAY BIG YARD FIREPLACE, vacation rental in Darien
SHORELINE HOLIDAY GETAWAY BIG YARD FIREPLACE, vacation rental in Darien
SHORELINE HOLIDAY GETAWAY BIG YARD FIREPLACE, vacation rental in Darien

SHORELINE HOLIDAY GETAWAY BIG YARD FIREPLACE

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Ocean Coast Luxury Beach House (ACROSS THE ROAD FROM THE BEACH, 45 MIN TO NYC), vacation rental in Darien
Ocean Coast Luxury Beach House (ACROSS THE ROAD FROM THE BEACH, 45 MIN TO NYC), vacation rental in Darien
Ocean Coast Luxury Beach House (ACROSS THE ROAD FROM THE BEACH, 45 MIN TO NYC), vacation rental in Darien

Ocean Coast Luxury Beach House (ACROSS THE ROAD FROM THE BEACH, 45 MIN TO NYC)

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Private 3.5 acre estate  Zen House /Historic mid century modern  / lap pool, vacation rental in Darien
Private 3.5 acre estate  Zen House /Historic mid century modern  / lap pool, vacation rental in Darien
Private 3.5 acre estate  Zen House /Historic mid century modern  / lap pool, vacation rental in Darien

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

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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NAUTICAL FAIRYTALE BEACH HOUSE (ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC), vacation rental in Darien
NAUTICAL FAIRYTALE BEACH HOUSE (ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC), vacation rental in Darien
NAUTICAL FAIRYTALE BEACH HOUSE (ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC), vacation rental in Darien

NAUTICAL FAIRYTALE BEACH HOUSE (ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Private beach/tennis community. $8k October thru December. ONE MONTH MINIMUM., vacation rental in Darien
Private beach/tennis community. $8k October thru December. ONE MONTH MINIMUM., vacation rental in Darien
Private beach/tennis community. $8k October thru December. ONE MONTH MINIMUM., vacation rental in Darien

Private beach/tennis community. $8k October thru December. ONE MONTH MINIMUM.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Mid  Century Modern ZEN  House  with Pool. 50 min from New York City, vacation rental in Darien
Mid  Century Modern ZEN  House  with Pool. 50 min from New York City, vacation rental in Darien
Mid  Century Modern ZEN  House  with Pool. 50 min from New York City, vacation rental in Darien

Mid Century Modern ZEN House with Pool. 50 min from New York City

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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3-LEVEL LARGE HOUSE/CLOSE TO NYC, STAMFORD, WESTPORT, BEACH, GR-WICH, vacation rental in Darien
3-LEVEL LARGE HOUSE/CLOSE TO NYC, STAMFORD, WESTPORT, BEACH, GR-WICH, vacation rental in Darien
3-LEVEL LARGE HOUSE/CLOSE TO NYC, STAMFORD, WESTPORT, BEACH, GR-WICH, vacation rental in Darien

3-LEVEL LARGE HOUSE/CLOSE TO NYC, STAMFORD, WESTPORT, BEACH, GR-WICH

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Newly listed Property, Home away from Home, Close to restaurants and local beach, vacation rental in Darien
Newly listed Property, Home away from Home, Close to restaurants and local beach, vacation rental in Darien
Newly listed Property, Home away from Home, Close to restaurants and local beach, vacation rental in Darien

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Secluded cottage on cul de sac in Rowayton., vacation rental in Darien
Secluded cottage on cul de sac in Rowayton., vacation rental in Darien
Secluded cottage on cul de sac in Rowayton., vacation rental in Darien

Secluded cottage on cul de sac in Rowayton.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean Dream Beach Home, vacation rental in Darien
Ocean Dream Beach Home, vacation rental in Darien
Ocean Dream Beach Home, vacation rental in Darien

Ocean Dream Beach Home

Rental Home
6 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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North Stamford Guest House, vacation rental in Darien
North Stamford Guest House, vacation rental in Darien
North Stamford Guest House, vacation rental in Darien

North Stamford Guest House

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Modern Waterfront Home  * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY, vacation rental in Darien
Modern Waterfront Home  * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY, vacation rental in Darien
Modern Waterfront Home  * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY, vacation rental in Darien

Modern Waterfront Home * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Seaside Village of Rowayton Summer Rental, vacation rental in Darien
Seaside Village of Rowayton Summer Rental, vacation rental in Darien
Seaside Village of Rowayton Summer Rental, vacation rental in Darien

Seaside Village of Rowayton Summer Rental

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stylish Contemporary Home  in Secluded Beach Community, vacation rental in Darien
Stylish Contemporary Home  in Secluded Beach Community, vacation rental in Darien
Stylish Contemporary Home  in Secluded Beach Community, vacation rental in Darien

Stylish Contemporary Home in Secluded Beach Community

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Canaan-Great Fairfield County Location. Walk to Town. Walk to Train, vacation rental in Darien
New Canaan-Great Fairfield County Location. Walk to Town. Walk to Train, vacation rental in Darien
New Canaan-Great Fairfield County Location. Walk to Town. Walk to Train, vacation rental in Darien

New Canaan-Great Fairfield County Location. Walk to Town. Walk to Train

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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6BR /6Bth Luxury retreat near NYC & nature, vacation rental in Darien
6BR /6Bth Luxury retreat near NYC & nature, vacation rental in Darien
6BR /6Bth Luxury retreat near NYC & nature, vacation rental in Darien

6BR /6Bth Luxury retreat near NYC & nature

Rental Home
6 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
More info
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New modern house near the water (WESTPORT RESIDENTS ONLY), vacation rental in Darien
New modern house near the water (WESTPORT RESIDENTS ONLY), vacation rental in Darien
New modern house near the water (WESTPORT RESIDENTS ONLY), vacation rental in Darien

New modern house near the water (WESTPORT RESIDENTS ONLY)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Antique House on Private Island in Long Island Sound, vacation rental in Darien
Antique House on Private Island in Long Island Sound, vacation rental in Darien
Antique House on Private Island in Long Island Sound, vacation rental in Darien

Antique House on Private Island in Long Island Sound

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Old Greenwich Summer Perfection near Beach and Town!, vacation rental in Darien
Old Greenwich Summer Perfection near Beach and Town!, vacation rental in Darien
Old Greenwich Summer Perfection near Beach and Town!, vacation rental in Darien

Old Greenwich Summer Perfection near Beach and Town!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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The most convenient location in Norwalk to all locations and destinations., vacation rental in Darien
The most convenient location in Norwalk to all locations and destinations., vacation rental in Darien
The most convenient location in Norwalk to all locations and destinations., vacation rental in Darien

The most convenient location in Norwalk to all locations and destinations.

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Modern & clean - 5 min from train station to NYC, vacation rental in Darien
Modern & clean - 5 min from train station to NYC, vacation rental in Darien
Modern & clean - 5 min from train station to NYC, vacation rental in Darien

Modern & clean - 5 min from train station to NYC

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Historic Summer cottage, close to private beach for rent by the month or week, vacation rental in Darien
Historic Summer cottage, close to private beach for rent by the month or week, vacation rental in Darien
Historic Summer cottage, close to private beach for rent by the month or week, vacation rental in Darien

Historic Summer cottage, close to private beach for rent by the month or week

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Waterfront Old Greenwich House, Ct, vacation rental in Darien
Waterfront Old Greenwich House, Ct, vacation rental in Darien
Waterfront Old Greenwich House, Ct, vacation rental in Darien

Waterfront Old Greenwich House, Ct

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Home in Downtown Stamford CT!, vacation rental in Darien
Beautiful Home in Downtown Stamford CT!, vacation rental in Darien
Beautiful Home in Downtown Stamford CT!, vacation rental in Darien

Beautiful Home in Downtown Stamford CT!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Getaway - Saugatuck Shores, Westport, vacation rental in Darien
Waterfront Getaway - Saugatuck Shores, Westport, vacation rental in Darien
Waterfront Getaway - Saugatuck Shores, Westport, vacation rental in Darien

Waterfront Getaway - Saugatuck Shores, Westport

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Nature refuge 5min from train to NYC, vacation rental in Darien
Nature refuge 5min from train to NYC, vacation rental in Darien
Nature refuge 5min from train to NYC, vacation rental in Darien

Nature refuge 5min from train to NYC

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Apt in downtown Stamford CT, vacation rental in Darien
Cozy Apt in downtown Stamford CT, vacation rental in Darien
Cozy Apt in downtown Stamford CT, vacation rental in Darien

Cozy Apt in downtown Stamford CT

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated 1BR APT, walk to train and more!, vacation rental in Darien
Renovated 1BR APT, walk to train and more!, vacation rental in Darien
Renovated 1BR APT, walk to train and more!, vacation rental in Darien

Renovated 1BR APT, walk to train and more!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront home in heart of Rowayton with dock and beach access, vacation rental in Darien
Waterfront home in heart of Rowayton with dock and beach access, vacation rental in Darien
Waterfront home in heart of Rowayton with dock and beach access, vacation rental in Darien

Waterfront home in heart of Rowayton with dock and beach access

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Rowayton Home, vacation rental in Darien
Waterfront Rowayton Home, vacation rental in Darien
Waterfront Rowayton Home, vacation rental in Darien

Waterfront Rowayton Home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Greenwich home - perfect NYC getaway, vacation rental in Darien
Greenwich home - perfect NYC getaway, vacation rental in Darien
Greenwich home - perfect NYC getaway, vacation rental in Darien

Greenwich home - perfect NYC getaway

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Pretty Farmhouse with Pool in Historic Silvermine, vacation rental in Darien
Pretty Farmhouse with Pool in Historic Silvermine, vacation rental in Darien
Pretty Farmhouse with Pool in Historic Silvermine, vacation rental in Darien

Pretty Farmhouse with Pool in Historic Silvermine

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Charming 3 BD/2.5 BA with Fenced Yard and Solarium, 2 Mi to Calf Pasture Beach!, vacation rental in Darien
Charming 3 BD/2.5 BA with Fenced Yard and Solarium, 2 Mi to Calf Pasture Beach!, vacation rental in Darien
Charming 3 BD/2.5 BA with Fenced Yard and Solarium, 2 Mi to Calf Pasture Beach!, vacation rental in Darien

Charming 3 BD/2.5 BA with Fenced Yard and Solarium, 2 Mi to Calf Pasture Beach!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Comfy and Stylish Harbor Point Studio, vacation rental in Darien
Comfy and Stylish Harbor Point Studio, vacation rental in Darien
Comfy and Stylish Harbor Point Studio, vacation rental in Darien

Comfy and Stylish Harbor Point Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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1 Yr Rental Min. Feel the spray of the sea and warm sand between your toes..., vacation rental in Darien
1 Yr Rental Min. Feel the spray of the sea and warm sand between your toes..., vacation rental in Darien
1 Yr Rental Min. Feel the spray of the sea and warm sand between your toes..., vacation rental in Darien

1 Yr Rental Min. Feel the spray of the sea and warm sand between your toes...

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Modern Greenwich house with water view., vacation rental in Darien
Modern Greenwich house with water view., vacation rental in Darien
Modern Greenwich house with water view., vacation rental in Darien

Modern Greenwich house with water view.

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Perfect Home Away from Home - Close to restaurants, local beaches, theaters, sle, vacation rental in Darien
Perfect Home Away from Home - Close to restaurants, local beaches, theaters, sle, vacation rental in Darien
Perfect Home Away from Home - Close to restaurants, local beaches, theaters, sle, vacation rental in Darien

Perfect Home Away from Home - Close to restaurants, local beaches, theaters, sle

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stylish Private Studio Near Downtown Stamford!, vacation rental in Darien
Stylish Private Studio Near Downtown Stamford!, vacation rental in Darien
Stylish Private Studio Near Downtown Stamford!, vacation rental in Darien

Stylish Private Studio Near Downtown Stamford!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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MY HAPPY PLACE, vacation rental in Darien
MY HAPPY PLACE, vacation rental in Darien
MY HAPPY PLACE, vacation rental in Darien

MY HAPPY PLACE

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Condo / Entire Apartment, vacation rental in Darien
Condo / Entire Apartment, vacation rental in Darien
Condo / Entire Apartment, vacation rental in Darien

Condo / Entire Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Waterfront, vacation rental in Darien
Waterfront, vacation rental in Darien
Waterfront, vacation rental in Darien

Waterfront

Rental Home
0 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Modern 1-bedroom apartment in Harbor Point, vacation rental in Darien
Modern 1-bedroom apartment in Harbor Point, vacation rental in Darien
Modern 1-bedroom apartment in Harbor Point, vacation rental in Darien

Modern 1-bedroom apartment in Harbor Point

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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