Vacation rentals in Smithtown

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Popular amenities for Smithtown vacation rentals

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

Superhost
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.
Apartment in Downtown Stamford
4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars3 months ago
Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit
Superhost
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
4.87 out of 5 average rating, 153 reviews

A-Frame cabin with private beach & epic sunsets

JenniferRating, 5 stars1 week ago
Amber’s place was immaculate and stunning. This was my 2nd time staying and it was just as magical! The place had plenty of space for a family of 3 and the washer/dryer was very convenient. We had a great time and would stay here again!
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

SheilaRating, 5 stars7 months ago
We had a wonderful stay at Olivia’s place. It is exactly as advertised, and the front porch and back patio are even bigger than pictured. There were a ton of beach accessories provided with the house- beach passes, chairs, bikes, towels. It’s a great location, short walk to both the beach and restaurants/shops. Olivia could not have been nicer, and was extremely communicative and responsive. Would definitely rent again!
Guest favorite
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
4.84 out of 5 average rating, 32 reviews

Home away your home

GeraldineRating, 5 stars4 days ago
Nice place exactly what the pictures show .. Super nice host.. but if you are looking for a quiet place. This place is definitely not it. You can hear every move and every sound from the people that live upstairs last night we spent a good few hours hearing a baby cry. Also they have the children’s toys such as a trampoline up against the window of the unityou do park on the street and the owner or tenants whoever lives upstairs parks in the driveways. it’s a very tight walk in between cars in the driveway because they do park a lot of cars in the driveway side-by-side.
Guest favorite
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
5 out of 5 average rating, 36 reviews

Villa Paraiso

SandraRating, 5 stars4 weeks ago
The house was great! Extremely spacious, well located. Communicating with Edwin both before and during the stay was always easy. He responds quickly and is very accommodating. It was an overall great experience!
Guest favorite
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
4.79 out of 5 average rating, 150 reviews

Bay's Edge Vacation Get a Way

BillRating, 5 stars1 week ago
Earl, was great to work with. We were only there for few hours. However I would recommend highly and will look to stay here again should work bring me back out that way.
Guest favorite
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
5 out of 5 average rating, 24 reviews

Nice getaway with your family.

Brittani and Chris Rating, 5 stars8 months ago
My group had a wonderful stay. We felt right at home. The property was private and the house was clean. The backyard is beautiful with a great pool. Erol was responsive throughout our stay. I would stay here again!
Top guest favorite
An outdoor space features a clear blue swimming pool surrounded by a stylish patio. Lounge chairs and umbrellas provide shaded seating areas, while lush green landscaping and decorative gravel enhance the serene environment.
Home in East Patchogue
5 out of 5 average rating, 20 reviews

Ho Hum Holiday In Bellport with Pool

GraceRating, 5 stars5 months ago
We needed a dog-friendly ranch style to home with three bedrooms and two bedrooms close to Sayville, where we would be celebrating Thanksgiving. I was lucky enough to find this rental which was clean, comfortable and ideal for our two-night stay. Adam was attentive and easily accessible via text. I would highly recommend this lovely home.

Quick stats about vacation rentals in Smithtown

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Self check-in, Gym, and BBQ grill

Frequently Asked Questions

  • How much does it cost to stay in house rentals in Smithtown?

    Experience the best of Smithtown with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Smithtown?

    Yes! Work meets play with ease at over 10 vacation rentals in Smithtown featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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  4. Suffolk County
  5. Smithtown