Vacation rentals in Smithtown

5 out of 5 average rating, 8 reviews

The exterior view showcases a bright, newly constructed home with white siding and a stone accent at the lower level. A spacious porch with seating is visible, along with a well-maintained lawn and a fenced yard, creating a welcoming entrance.

Home in Fairfield

Newly built twin beach house within steps to beach

Keep it simple at this peaceful and centrally-located home. Newly built in 2019! Premier beach living at its finest. Steps to Fairfield’s beaches and less than a mile to downtown restaurants, shops, and bars. Fenced backyard. Central air throughout. Decks off the front and back with a Weber grill. Furnished with luxury furniture, sheets, comforters, and pillows. Smart TVs in every bedroom and living room. Tesla charging station at the house. Identical home next door available for larger bookings

Home in Fair Harbor, Fire Island

4.93 out of 5 average rating, 27 reviews

Chill Beachfront Cottage Amazing Bay/Sunset Views!

Charming, Classic Beach Cottage right on the BEACH! with Panoramic Views & Sunsets on the Great South Bay! Summer on Fire Island is truly paradise. The ocean is sensational, the weather is perfect, the sunrises & sunsets are spectacular, the residents are friendly & creative, & life is WONDERFUL. Our Cottage has 5 Bedrooms with 8 beds that sleep 11. Like Fair Harbor, it has a casual, laid back vibe that is comfortable & enjoyable for people of all ages. * KAYAKS are AVAILABLE! Ask Roberto

4.94 out of 5 average rating, 114 reviews

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

4.85 out of 5 average rating, 133 reviews

A cozy living area features a large sectional sofa with decorative cushions, complemented by a plush armchair. Natural light is invited through two front windows, while a coffee table sits at the center, surrounded by green plants and framed art on the walls.

Home in Baldwin

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

5 out of 5 average rating, 43 reviews

A wooden boardwalk leads toward the beach and ocean, bordered by vibrant umbrellas and beachgoers enjoying the sun. The clear blue sky reflects over the water, creating a serene coastal view. The structure allows for easy access to sandy shores.

Home in Ocean Beach

Sunny Spacious Pet Friendly Steps from the Beach

This ideally located four-bedroom home is the perfect spot for your family's vacation. The home features a spacious deck, central air conditioning, WiFi, 4 Smart TV's, a Sonos sound system and YouTube TV. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. There are 2 full bathrooms as well as an outdoor shower. Fully equipped including beach chairs, towels, 5 bikes, 2 wagons and beach toys for the kids. Sleeps 10.

4.88 out of 5 average rating, 102 reviews

A covered outdoor seating area is furnished with a combination of turquoise and brown seating, complemented by decorative pillows. Soft lighting from string lights enhances the space. A swing seat is positioned against the wall, and a small table is centered on the tiled patio.

Home in Mastic

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

5 out of 5 average rating, 11 reviews

A view of the Peconic River is depicted from a wooden deck, featuring a small round table and two woven chairs. The water reflects clear blue skies, with boats visible in the distance and trees lining the shore.

Houseboat in North Fork

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

4.99 out of 5 average rating, 174 reviews

A private outdoor deck featuring a wooden floor and a shaded area. Several seating options include four light-colored lounge chairs and a dining table surrounded by additional chairs, providing ample space for relaxation and dining while enjoying the ocean views.

Apartment in Long Beach

Incredible Long Beach Private Rental

True 5 star two bedroom rental. Newly renovated and professionally designed. Stunning ocean views from private second floor deck. You have your own barbecue and fully furnished outdoor space so you can enjoy the your stay on your terms. You are just a walk to the bars and restaurants of the West End. No car required! Walk or catch the bus from the train. Only 700 feet from the ocean. Due to allergies in the home we are unable to host any animals.

Guesthouse in Westhampton Beach

A charming guesthouse is illuminated by a warm light above the door, showcasing its well-maintained exterior. The inviting entrance features a single door and multiple small windows, framed by greenery and a pathway leading to the entrance.

5 out of 5 average rating, 3 reviews

Summer retreat cottage in WHB

Lovely guesthouse with private patio. Steps to Main Street and houses of worship. Enjoy walking or biking to the farmer's market, restaurants, marina, and beach. Bright kitchen and comfortable living room with wifi and smart tv. BBQ and outdoor shower for your use (located on the patio of the main house). Beach pass available for stays of 30+days; access to private village beaches before 10am and after 5pm as per village policy.

Apartment in Shippan Point

4.93 out of 5 average rating, 84 reviews

Seabreeze at the beach, west beach stamford, Ct

3 bedroom at the beach, free parking also free access to the beach, a cart with chairs, towels, and umbrella. and three adult bicycles, and boogie boards paddle boards. close to downtown and Harbor point, great for people coming to work in Stamford very close to all businesses. EV charging station. about 5 minutes to route 95. also a nice little Irish pub as you enter the beach. "GREAT FOOD AND DRINKS"

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What guests are saying

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

4.94 out of 5 average rating, 67 reviews6 days ago

We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!

Cottage in Norwalk

What guests are saying

Beach Vibes & Starry Skies

4.85 out of 5 average rating, 13 reviews2 months ago

My sisters and I had a wonderful stay at Tami's house. This place has sunrise AND sunset views which are absolutely beautiful in a crisp winter sky. The kitchen provided everything needed to cook a gourmet meal and there is no lack of places to eat if you prefer to go out. The location was perfect for relaxing, and the neighborhood felt safe. Tami was responsive and made sure everything went smoothly. I highly recommend this place to anyone visiting the East end and would love to stay there again in the future.

Home in Center Moriches

What guests are saying

The Barefoot Bungalow

4.88 out of 5 average rating, 40 reviews7 months ago

This house was a lovely place for our family trip! Our party of 4 had plenty of room to spread out, beach is just a few min away, along with restaurants, shops etc. There is plenty of room in the backyard, but my family really enjoyed sitting on the front porch and playing cards. Everything we needed was there, and all questions answered quickly! I would definitely book again!!

Bungalow in Long Beach

What guests are saying

Private Beach access along the Wine Trail

4.92 out of 5 average rating, 12 reviews1 month ago

I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!

Home in North Fork

What guests are saying

Waterfront Getaway Just 20 Min from Bethpage Park!

4.97 out of 5 average rating, 38 reviews5 months ago

What can you say that hasn't been already said by previous reviewers. John's house in Freeport is a gem. Perfect getway for weekend for our family. We were greeted by a nice bottle of wine and a generous basket of snacks (always a nice touch). The house was spacious and super clean. The beds were extremely comfy and the kitchen was well equipped for anything you may need. So many fun things we really didn't get to take advantage of (Tiki Room, fire pit etc..). But the crowning jewel is the location on the water. If you just want a place to sit and relax as the sun rises or sets (yes you get to see both from the back deck) this is your place. John was a gracious and responsive host. We hope to be back next year.

Home in Freeport

What guests are saying

Exquisite Spacious Waterfront Modern-Sleeps 8

4.83 out of 5 average rating, 163 reviews6 months ago

We spent a week at Joe‘s house and couldn’t be happier. The house, property, and surrounding area was amazing. Everything was super clean, and you won’t find a spot like this anywhere else. The master bathroom is incredible. Already trying to figure out how I can replicate that shower in my own house lol. would recommend this place 100%

Home in Bayport

What guests are saying

Cheerful and beautifully remodeled Beach cottage

4.78 out of 5 average rating, 23 reviews2 months ago

Definitely is the best place that we have been , nice location ,super clean, kitchen is beautiful, the cottage is extremely private, bathroom super clean, in summer would be great to come back ,in other words absolutely fantastic!!! 100% recommended

Cottage in East Quogue

What guests are saying

2BR Apartment with Terrace

4.8 out of 5 average rating, 5 reviews8 months ago

Mathew was very accommodating and very responsive. His location on the board walk was very centrally located. Walking distance to everything. He allowed late check out which was nice. It was my first time on the island so was not aware of many rules and regulations. I suggest researching before booking.

Apartment in Ocean Beach

What guests are saying

Berry Farm House - Apt 2

4.93 out of 5 average rating, 27 reviews3 months ago

Perfect space to celebrate Christmas this year. The house is private (set back from the main road) and the views were beautiful. We had a question at check-in, the property management company was quick to respond and resolve the issue. Perfect location for a home base when visiting the Long Island wineries!

Apartment in North Fork

What guests are saying

Harbor Water Views

4.9 out of 5 average rating, 21 reviews2 weeks ago

this spot was a great home base for three adults and a baby while we were in town for a week. we were able to get to nearby places quickly from this location and it was so nice to stay in this comfortable and functional (we cooked a lot) home. the weather wasn't on our side for sitting outside but that would have been the cherry on top. Derek was a great host - very responsive and helpful.

Home in Copiague

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Popular amenities for Smithtown vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Smithtown's top sights

Stop & Shop8 locals recommend

Caleb Smith State Park7 locals recommend

Mannino's7 locals recommend

Uncle Giuseppe's Marketplace7 locals recommend

Whisper Vineyards7 locals recommend

Maureen's Kitchen6 locals recommend

Other great vacation rentals in Smithtown

Apartment in Downtown Stamford

An expansive outdoor area showcases a heated pool surrounded by wooden decking. Sun loungers and umbrellas are arranged around the pool, with colorful seating accents visible. Pathways meander through lush greenery, integrating seating and recreational spaces within the tranquil courtyard.

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

4.87 out of 5 average rating, 153 reviews

Large windows allow natural light to fill the open living space, showcasing the stunning view of the Great South Bay. A comfortable sofa with decorative pillows faces the water, complemented by a dining area nearby. Warm wood tones enhance the cozy atmosphere of the room.

Cabin in Shirley

A-Frame cabin with private beach & epic sunsets

A wide wooden boardwalk stretches into the distance, illuminated by evenly spaced street lamps. The calm evening atmosphere is enhanced by gentle lighting from nearby buildings. An individual can be seen walking along the boardwalk, adding a sense of scale to the expansive path.

Home in Long Beach

5 out of 5 average rating, 7 reviews

Vacation Rental - Long Beach - NY 3 Bedroom 2 Bath

4.84 out of 5 average rating, 32 reviews

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and an oven. Gray cabinetry contrasts with a mosaic backsplash. A sink is positioned beneath a window, while a clean mat lies on the floor near the countertop.

Apartment in Brentwood

Home away your home

5 out of 5 average rating, 36 reviews

An open and airy living space is highlighted by large windows that fill the room with natural light. A modern chandelier hangs overhead, and a plush, light blue sofa is positioned next to a wooden dining table with black chairs, enhancing the inviting ambiance.

Home in Long Beach

Villa Paraiso

4.79 out of 5 average rating, 150 reviews

A modern bathroom features a dual sink vanity with sleek fixtures and a large mirror above. Neutral-toned tile lines the walls and floor. Natural light filters through a window, and two white towels are neatly arranged on a towel rack beside the toilet.

Home in East Patchogue

Bay's Edge Vacation Get a Way

5 out of 5 average rating, 24 reviews

A large outdoor pool is surrounded by a stone patio, equipped with several lounge chairs. Lush greenery lines the perimeter, providing a natural backdrop. Soft sunlight reflects off the water, enhancing the inviting atmosphere of the spacious area.

Home in Dix Hills

Nice getaway with your family.