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Vacation Home Rentals in Smithtown, New York

Vacation Home Rentals in Smithtown, New York

Smithtown Vacation Rentals - Lovely Long Island Home On 3 Acres, Near Beaches
Smithtown Vacation Rentals - Lovely Long Island Home on 3 Acres, Near Beaches
Vacation rental with 4 bedroom(s), 2 bathrooms(s)
2.9 miles to Smithtown
Smithtown, New York, 11780
Beautiful 4 bedroom 2 bath Long Island home nestled in the historic village of Saint James on the North Shore. This space is the main floor of a...

from 250 USD


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Vacation Home Rentals in the Smithtown, New York Area

Centerport Vacation Rentals - Centerport Harbor Bed & Breakfast
Centerport Vacation Rentals - Centerport Harbor Bed & Breakfast
Bed and breakfast
9.3 miles to Smithtown
Centerport, New York, 11721
Centerport Harbor is an unspoiled scenic inlet, extending southward from Northport Bay on Long Island's beautiful 'North Shore'. The Centerport...
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Port Jefferson Vacation Rentals - Holly Berry Bed And Breakfast
Port Jefferson Vacation Rentals - Holly Berry Bed and Breakfast
Bed and breakfast
9.6 miles to Smithtown
Port Jefferson, New York, 11777
Holly Berry Bed and Breakfast welcomes visitors to the harbor front village of Port Jefferson on Long Island, New York. Timeless spirit and warmth...
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Port Jefferson Vacation Rentals - The Ransome Inn
Bed and breakfast
9.6 miles to Smithtown
Port Jefferson, New York, 11777
Upon arriving at The Ransome Inn, you will be greeted by all the conveniences of your home and office while treating yourself to an abundance of...
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Port Jefferson Vacation Rentals - The White House On High Street
Bed and breakfast
9.6 miles to Smithtown
Port Jefferson, New York, 11777
Welcome to The White House On High Street, a truly elegant bed and breakfast set in the picturesque village of Port Jefferson, NY on Long Island’s...
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Lake George Vacation Rentals - Cottage Awesome Location For Families
Cabin with 3 bedroom(s), 3 bathrooms(s), sleeps 1
14.8 miles to Smithtown
Lake George, New York, 11713
The Kitchen is roomy and has a counter with bar stools for a quaint breakfast or snack. We include all the utensils you'll need to make ...

from 400 USD

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Ronkonkoma Vacation Rentals - North - Five Star Property
Apartment with 4 bedroom(s), 5 bathrooms(s), sleeps 15
4.7 miles to Smithtown
Ronkonkoma, New York, 11779
The house is located in the hills of Bridgehampton nestled on five wooded acres between the village of Bridgehampton and the town of Sag Harbor....
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Ronkonkoma Vacation Rentals - North - Five Star Property
Apartment with 4 bedroom(s), 5 bathrooms(s), sleeps 15
4.7 miles to Smithtown
Ronkonkoma, New York, 11779
The house is located in the hills of Bridgehampton nestled on five wooded acres between the village of Bridgehampton and the town of Sag Harbor....
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Fire Island Vacation Rentals - Great Family Beach House
Vacation rental with 4 bedroom(s), 2 bathrooms(s)
14.6 miles to Smithtown
Fire Island, New York, 11770
Four bedroom, 2 Bathroom house in Davis Park, Fire Island Great Location 2 houses from Ocean, 3 from bay, Full kitchen w/ dishwasher, living room...

from 400 USD


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Mastic Beach Vacation Rentals - Waterfront Home With Views Of Fire Island
Vacation rental with 3 bedroom(s), 2 bathrooms(s)
19.7 miles to Smithtown
Mastic Beach, New York, 11951
Serenity reigns in this modern, 3-bedroom home located in a 52 acre nature preserve overlooking Great South Bay and the eastern end of Fire...

from 429 USD


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Fire Island Vacation Rentals - Fire Island Pines Magnificent House On The Bay
Vacation rental with 3 bedroom(s), 3 bathrooms(s)
10.5 miles to Smithtown
Fire Island, New York, 11782
Two Story House Two Fireplaces Upstairs Master Suite Large heated swimming pool Central Air Conditioning & Heating Two bedrooms also have air...

from 1,143 USD


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Brookhaven Vacation Rentals - Newly Restored Traditional Home Classical Decor
Vacation rental with 3 bedroom(s), 2 bathrooms(s)
15.9 miles to Smithtown
Brookhaven, New York, 11719
Newly renovated, traditionally decorated/furnished house situated across from sprawling acres of Organic Farm and Post Morrow Preserve in...
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Sound Beach Vacation Rentals - Waterfront Beach House - Sound Beach
Vacation rental with 3 bedroom(s), 2 bathrooms(s)
13.4 miles to Smithtown
Sound Beach, New York, 11789
WATERFRONT BEACH HOUSE - SOUND BEACH - Long Island Located on the bluff with amazing views of the Long Island Sound around the year. 1:15 min...

from 390 USD


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Professionally Decorated Beach House W/Floating Dock For 60Ft Boat
House with 2 bedroom(s), 2 bathrooms(s), sleeps 4
5.5 miles to Smithtown
Beaver Island, 49782
This beach house on Beaver Island offers unspoiled views & dockage to accommodate boat of 60ft. This well-appointed 2 bedroom, 2 bath beach house...

from 2,100 USD

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Port Jefferson Vacation Rentals - Golden Pineapple Bed And Breakfast
Bed and breakfast
9.6 miles to Smithtown
Port Jefferson, New York, 11777
Step into the elegance and grace of the 1900's at The Golden Pineapple Bed and Breakfast. Your Hosts, Tom and Jennifer, have created a quiet...
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Seconds To Ocean And Bay
House with 4 bedroom(s), 2 bathrooms(s), sleeps 10
11.2 miles to Smithtown
Patchogue, 11772
Quiet, spacious, secluded newly renovated home.....steps to ocean. Large bedrooms with ceiling fans, great room downstairs, two large bathrooms,...
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Designer Luxury Home On The Beach-Minutes From Fire Island-Spectacular!!!
House with 3 bedroom(s), 2 bathrooms(s), sleeps 8
12 miles to Smithtown
Patchogue, 11772
Designer Home right on a sandy beach over looking Fire Island. 3 bedrooms, living room, dining room, kitchen, 2 full baths, full 50 foot deck on...

from 5,000 USD

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Oceanfront House In Davis Park
House with 4 bedroom(s), 2 bathrooms(s), sleeps 8
12 miles to Smithtown
Blue Point, 11715
This is the true sense of relaxing. Get on the ferry in Patchougue and enjoy a 20 minute ride to Davis Park. Once you arrive at Casa Meshugana...

from 6,500 USD

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Private Soiree Romantic Secluded Getaway
House with 3 bedroom(s), 3 bathrooms(s), sleeps 6
12.9 miles to Smithtown
Huntington, 11743
You can enjoy your trip to New York while staying in this wonderful, private, fully furnished home. It is located in West Hills which is a twenty...

from 4,000 USD

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Sound Beach Vacation Rentals - Waterfront Summer Getaway
Vacation rental with 2 bedroom(s), 2 bathrooms(s)
13.4 miles to Smithtown
Sound Beach, New York, 11789
Charming summer home with breathtaking water views. Steps from the beach; enjoy kayaking, windsurfing, fishing, swimming and long walks along the...

from 295 USD


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'14' Day Minimum' - Luxurious Beach House - Only Two Week Blocks Available
House with 4 bedroom(s), 3 bathrooms(s), sleeps 12
14.4 miles to Smithtown
Ocean Beach, 11770
Luxurious Beach House, Only steps to the beach Unique Mint 3300 sq ft recently built 4 bedroom home available form June to Sept 2011 4 bedroom,...

from 9,000 USD

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'Vintage' Fire Island Home
House with 5 bedroom(s), 3.5 bathrooms(s), sleeps 8
14.4 miles to Smithtown
Ocean Beach, 11770
This 'Vintage' Fire Island Home was built in 1938, and is located in the village of Ocean Beach, NY. This home was designed by the original owner...

from 4,000 USD

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Beautiful Newly Renovated Home, Very Close To Ocean
House with 5 bedroom(s), 2.5 bathrooms(s), sleeps 10
14.4 miles to Smithtown
Ocean Beach, 11770
This beautiful beach house has been totally renovated. When one walks into the house one automatically feels relaxed by the beach decor and sunny...

from 5,500 USD

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Bring Toothbrush, Toothpaste And Bathing Suits Only!
House with 3 bedroom(s), 1 bathrooms(s), sleeps 6
14.4 miles to Smithtown
Ocean Beach, 11770
This is a charming beach house with everything needed to provide a family with a fun-filled vacation. The master bedroom is air-conditioned with...

from 3,100 USD

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Castle In The Sky - Huge Discount Available While They Last!
House with 5 bedroom(s), 2 bathrooms(s), sleeps 14
14.4 miles to Smithtown
ocean beach, 11770
What is Fire Island? It is an island off Long Island that is visited by many people each summer. Isn't Fire Island a 'Gay Community'? This is...

from 1,000 USD

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Classic Fire Island Cottage
Cottage with 3 bedroom(s), 1.5 bathrooms(s), sleeps 6
14.4 miles to Smithtown
Ocean Beach, 11770
This 100 year old cottage is a “true Fire Island classic”. This private home is located in the village of Ocean Beach, NY, and is a two minute...

from 4,000 USD

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Cool Summer Beach House On Fire Island, New York-7 Night Minimum Stay
House with 5 bedroom(s), 2 bathrooms(s), sleeps 10
14.4 miles to Smithtown
Ocean beach, 11770
This home is in a unique summer beach community on fire island in New York. The area is accessible by passenger ferry or boat. Motor vehicles are...

from 6,000 USD

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Fire Island Ocean Beach -Huge Discount, Available While They Last!
House with 6 bedroom(s), 1.5 bathrooms(s), sleeps 14
14.4 miles to Smithtown
ocean beach, 11770
What is Fire Island? • It is an island off Long Island that is visited by many people each summer. Isn't Fire Island a 'Gay Community'? • This is...
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Fire Island Ocean Beach -Huge Discount, Available While They Last!
House with 6 bedroom(s), 1.5 bathrooms(s), sleeps 12
14.4 miles to Smithtown
Ocean Beach, 11770
What is Fire Island? • It is an island off Long Island that is visited by many people each summer.Isn't Fire Island a 'Gay Community'? • This is...

from 1,000 USD

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Great Family Beach House, Steps To Beach, Beautiful Deck, New Kitchen, Bicycles
House with 3 bedroom(s), 1 bathrooms(s), sleeps 6
14.4 miles to Smithtown
Ocean Beach, 11770
Leave your car, your shoes and the noise of the city behind. Ocean Beach on Fire Island is a charming community without cars, where the residents...

from 3,100 USD

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Lovely Fire Island Home Very Close To Ocean
House with 3 bedroom(s), 1.5 bathrooms(s), sleeps 6
14.4 miles to Smithtown
Ocean Beach, 11770
This house shows the love that it has been given. It is country style with modern amenities. Each bedroom is charming and unique. The loft...

from 3,800 USD

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Luxury Home With Views Galore
House with 5 bedroom(s), 2.5 bathrooms(s), sleeps 14
14.4 miles to Smithtown
Ocean Beach, 11770
What is Fire Island? It is an island off Long Island that is visited by many people each summer. Isn't Fire Island a 'Gay Community'? This is...

from 1,000 USD

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Open For Business 2012! Prices Below Market!
House with 4 bedroom(s), 1 bathrooms(s), sleeps 7
14.4 miles to Smithtown
Ocean Beach, 11770
Thank you for your interest. We rent to families only, sorry. This one-level house includes four bedrooms and one bathroom. It is for families...
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The Pirate House
Chalet with 4 bedroom(s), 1 bathrooms(s), sleeps 8
14.4 miles to Smithtown
ocean beach, 11770
SIX HOUSES TO THE BEACH, THREE DECKS, OUTDOOR SHOWER, LOFT OVERLOOKING LIVING ROOM AND DINING AREA, LOADED WITH NAUTICAL ITEMS, AND PIRATE...

from 2,750 USD

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Waterfront Beach House - Amazing Water Views, Natural & Calm, Wineries & Farms
House with 3 bedroom(s), 2 bathrooms(s), sleeps 10
14.4 miles to Smithtown
Sound Beach, 11789
Located on the bluff with amazing views of the Long Island Sound around the year - This is our Waterfront Heaven. Set in a quiet neighborhood, the...

from 2,700 USD

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Where The Sidewalk Ends - A Spacious, Private Family Retreat
House with 4 bedroom(s), 2 bathrooms(s), sleeps 10
14.4 miles to Smithtown
ocean beach, 11770
2wk MINIMUM STAY REQUIRED! No shares, only SINGLE FAMILY occupancy! Family-friendly home in the FI Summer Club with the ultimate private back...

from 5,000 USD

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Charming, Peaceful Beach Home Steps From Ocean
House with 5 bedroom(s), 2.5 bathrooms(s), sleeps 10
14.5 miles to Smithtown
Seaview, 11770
Steps to the ocean. Only one hour to the ferry from NYC. Beautiful and relaxing both during Peak and Off-Peak seasons

from 4,000 USD

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Classic 5 Br Bayfront, Seaview Fire Island
House with 5 bedroom(s), 1 bathrooms(s), sleeps 14
14.5 miles to Smithtown
Ocean Beach, 11770
Gorgeous view of Bay, sunrise and sunset, 5 minute walk from Ocean Beach and Seaview ferries and shops, 2 blocks from beach, large 5 BR old style...

from 2,000 USD

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Comfortable A-Frame House Steps From Ocean
House with 7 bedroom(s), 1.5 bathrooms(s), sleeps 10
14.5 miles to Smithtown
Seaview, 11770
Welcome to our home in Seaview, Fire Island. Seaview is one of the most sought-after communities on the island. Our home is 4 blocks from the...

from 4,000 USD

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Great 3Br Beach House- Perfect For A Family With Young Children
House with 3 bedroom(s), 1 bathrooms(s), sleeps 6
14.5 miles to Smithtown
Fire Island, 11770
SEAVIEW JULY RENTAL: 3BR, 1 1/2 bath 2 story upside-down beach house. The bedrooms (with ceiling fans) and bathrooms are downstairs and open...

from 3,000 USD

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Great Family Friendly House Steps Away From Bay And Beach
House with 5 bedroom(s), 2 bathrooms(s), sleeps 10
14.5 miles to Smithtown
Seaview, 11770
Large open and bright beach house in family friendly community with views of the bay and sunset. Just steps away from the beach, store and 5 min...

from 2,500 USD

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Huge Beautiful Beach House, Near Ocean
House with 5 bedroom(s), 2.5 bathrooms(s), sleeps 13
14.5 miles to Smithtown
Ocean Bay Park, Fire Island, 11770
Modern, comfortable, bright, and breezy. Perfect for several families or friends to enjoy the beach and each other. Open common area includes...

from 5,500 USD

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Lovely 2-Story Family Home With Large Sunny And Shady Decks
House with 3 bedroom(s), 2 bathrooms(s), sleeps 6
14.5 miles to Smithtown
Fire Island, 11770
Comfortable, tastefully decorated family home with a high, dramatically slanted ceiling in the living room, architectural wood open staircase and...

from 4,000 USD

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Ocean Beach, Fire Island Bayfront, Your Own Private Swimming Dock
House with 4 bedroom(s), 2 bathrooms(s), sleeps 8
14.5 miles to Smithtown
Ocean Beach, 11770
Fans over every bed, and lots of windows keep those bay breezes blowing. Set in the deck, a large hottub, facing the sunset. It's really an...

from 3,600 USD

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Ocean Front Home With Great Roof Deck
House with 4 bedroom(s), 1.5 bathrooms(s), sleeps 8
14.5 miles to Smithtown
Ocean Bay Park, 11770
Location, Location, Location. Listen to the ocean sounds all day and night. 4 bedroom Ocean Front home. 2 Great Ocean Front decks....

from 4,900 USD

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Bright And Breezy Beach House In Ocean Bay Park
House with 3 bedroom(s), 2 bathrooms(s), sleeps 9
14.6 miles to Smithtown
Ocean Bay Park, 11770
Air Conditioned, light, bright, and breezy beach house. Great for entertaining and family friendly. Trex Decking no splinters. Cathedral ceilings...

from 3,200 USD

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Charming Ocean Bay Park Studio With Spectacular Bay View
Studio with 0 bedroom(s), 1 bathrooms(s), sleeps 2
14.6 miles to Smithtown
Ocean Bay Park, 11795
Welcome to paradise! You can be here in less than 2 hours from NYC or a scenic 1/2 hr. ferry ride from Bay Shore, Long Island. Here you will find...

from 1,000 USD

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Distinct Architectural House Overlooking Ocean & Bay
House with 5 bedroom(s), 2.5 bathrooms(s), sleeps 10
14.6 miles to Smithtown
Ocean Bay Park, 11770
Architecturally designed house draws in light, air and waterviews. It surrounds a small pond, nestled into a sand-dune.The house brings the...

from 5,000 USD

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Distinct Architectural House Overlooking Ocean And Bay
House with 5 bedroom(s), 3 bathrooms(s), sleeps 10
14.6 miles to Smithtown
Ocean Bay Park, 11770
Architecturally designed house draws in light, air and water views. It surrounds a small pond nestled into a sand dune. The house brings the...

from 4,000 USD

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Fire Island Cottage - Your Own Private 1 Bedroom Oasis
Cottage with 1 bedroom(s), 1 bathrooms(s), sleeps 4
14.6 miles to Smithtown
Ocean Bay Park, 11770
Private 1-BR (One Bedroom) cottage rental. Roof deck. Steps to the beach. Unit 2 is a fantastic one-bedroom rental with new pine floors in the...

from 1,350 USD

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