Photo by Doug Kerr

Search Villas in Smithtown

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 5 Villas in Smithtown with updated reviews, rates, and availability.

Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

10.0 out of 10, Exceptional, (15)
"We recently had the joy of staying here with family meeting from different parts of New York and New Jersey. House is beautiful, location is quiet and peaceful with a great view of the bay. Nearby to some great Long Island beaches. Loved the pool and amenities of the home. Faraz was an excellent host and extremely responsive to our needs "
The price is AED 2,291
AED 5,649 total
includes taxes & fees
13 Mar - 14 Mar
Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

Beachfront Mega Mansion

Beachfront Mega Mansion

Exquisite Waterfront Villa

Exquisite Waterfront Villa

Medieval-Themed Castle < 10 Mi to Shirley Beach!

Medieval-Themed Castle < 10 Mi to Shirley Beach!

Medieval-themed Castle < 10 Mi to Shirley Beach!

3.0 star property
Medieval-themed Castle < 10 Mi to Shirley Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Smithtown
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Smithtown

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (49)
"Really liked Dune. I had a great room that was on the other side from Sea Grape - bar that could be loud. I heard noting from room 31. Could walk to Post Rd and the beach. Ocean view from room. "
The price is AED 894
AED 1,230 total
includes taxes & fees
18 Mar - 19 Mar
DUNE Fairfield Beach

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very Good, (44)
"This house was very nice, as pictured or better. Clean, no issues checking in or out. Wagon was there as promised, more bikes than promised, lots of beach towels and chairs provided. The house had two wonderful outdoor second story decks with great views of the water and the ferry dock. Location was perfect, so convenient to ferry and market. Two things not great. Although it had an AC unit in every bedroom that all worked fine which made ground floor cool and comfortable, the main living...
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

🌞New Listing!! Ocean View Retreat!🌞

9.4 out of 10, Exceptional, (21)
"Quick 2-night stay, couldn’t have been more comfortable. Ocean Beach (town) has everything (one would need for a Fire Island stay), yet the house is beautifully secluded away from it all. The house is well-cared for with delightful details. The view is wonderful. We had everything we needed. Would stay here again in a heartbeat. Thank you!"
🌞New Listing!! Ocean View Retreat!🌞
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your villa in Smithtown with Expedia?
We think vacation time shouldn’t be complicated, so if you’re in search of villas at a nice price, Expedia can help. Save those pennies and pick an all-inclusive stay, or splurge on a 5-star villa to spoil your loved ones. Our handy filters make it simple to find a retreat in Smithtown that you’ll adore.
How can I find cheap villas in Smithtown?
With Expedia’s user-friendly filter tool, locating cheap villas in Smithtown is a cinch. To find accommodations that are easy on the wallet, refine your search results by budget, star rating and amenities.