Apartment
10.0(48 Reviews)
1 Bedroom
2 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
CA $201/Night
7 Nights - CA $1,410
Smithtown Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Smithtown
10.0
House
8.0(1 Review)
4 Bedrooms
8 Guests
- Parking
Pool
View
Internet
CA $1,091/Night
7 Nights - CA $7,635
Hotel
8.8(431 Reviews)
Breakfast- Parking
- Kitchen
- Air Conditioner
CA $251/Night
7 Nights - CA $1,756
Apartment
10.0(27 Reviews)
1 Bedroom
2 Guests
Oceanfront- Parking
Ocean View- View
CA $253/Night
7 Nights - CA $1,773
Apartment
7.9(19 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
CA $138/Night
7 Nights - CA $963
Apartment
10.0(9 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $682/Night
7 Nights - CA $4,775
Cottage
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $438/Night
7 Nights - CA $3,066
Cabin
10.0(1 Review)
2 Bedrooms
6 Guests
Child Friendly
Security/Safety
CA $496/Night
7 Nights - CA $3,469
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
Hot Tub- Parking
- Pool
- Air Conditioner
CA $284/Night
7 Nights - CA $1,988
Luxury Holiday Rentals in Smithtown
Over 17+ Luxury Holiday Rentals in or Near Smithtown
House
10.0(15 Reviews)
4 Bedrooms
8 Guests
Private Pool- Oceanfront
- Parking
- Pool
CA $984/Night
7 Nights - CA $6,885
House
9.4(21 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $730/Night
7 Nights - CA $5,113
CA $531/Night
7 Nights - CA $3,719
Apartment
9.6(5 Reviews)
4 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $520/Night
7 Nights - CA $3,638
Apartment
9.4(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $333/Night
7 Nights - CA $2,334
Apartment
8.4(8 Reviews)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
CA $325/Night
7 Nights - CA $2,276
Hotel
8.6(51 Reviews)
- Private Pool
- Parking
- Pool
- Air Conditioner
CA $215/Night
7 Nights - CA $1,507
Hotel
6.3(122 Reviews)
- Air Conditioner
- Internet
- Child Friendly
CA $170/Night
7 Nights - CA $1,189
House
5 Bedrooms
10 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
CA $11,514/Night
7 Nights - CA $80,595
Top-Rated Holiday Rentals with a Pool in Smithtown
Over 4+ The Best Private Villas and Holiday Rentals in Smithtown with a Pool
Apartment
5.0(1 Review)
1 Bedroom
3 Guests
- Private Pool
- Pool
- Kitchen
- Internet
CA $225/Night
7 Nights - CA $1,576
House
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
CA $9,346/Night
7 Nights - CA $65,420
House
4 Bedrooms
8 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
CA $7,833/Night
7 Nights - CA $54,830
Apartment
1 Bedroom
2 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
CA $215/Night
7 Nights - CA $1,507
Smithtown Private Villas and Holiday Homes Under $200
Over 4+ Smithtown Private Villas and Holiday Homes Under $200
Apartment
5.0(1 Review)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Child Friendly
TV
CA $163/Night
7 Nights - CA $1,140
Hotel
5.6(480 Reviews)
- Kitchen
- Air Conditioner
- Child Friendly
- TV
CA $170/Night
7 Nights - CA $1,189
Apartment
1 Bedroom
2 Guests
- Oceanfront
- Ocean View
- View
- Kitchen
CA $169/Night
7 Nights - CA $1,180
Apartment
4.0(2 Reviews)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
Laundry
Bedding/Linens
CA $234/Night
7 Nights - CA $1,636
Book a Last Minute Place to Stay in Smithtown
About Casai's Private Villas and Holiday Rentals in Smithtown
Discover more than 26 vacation rentals available in Smithtown. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Smithtown.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Smithtown, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Smithtown. On average, places to stay near Smithtown offer 845.81 ft², with nightly prices averaging CA $1,443.
With Casai, finding and comparing holiday rentals in Smithtown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Smithtown, NY
There are 26 Smithtown, NY Holiday Rentals
- Prices for a holiday home in Smithtown start at CA $138
- Top rated vacation home in Smithtown is Snow Birds, Transitions, Temporary Work Assignments, This is it!
- Most popular short term in Smithtown is Residence Inn By Marriott Long Island Hauppauge
- Cheapest place to stay in Smithtown is Studio Apartment
- Most expensive holiday rental in Smithtown is Tranquil & Pet-Friendly Estate on Long Island!
Frequently Asked Questions About Smithtown?
What are the top holiday rentals in Smithtown?
With numerous options available in Smithtown, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Smithtown:
- Snow Birds, Transitions, Temporary Work Assignments, This is it!
- Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
- Tranquil & Pet-Friendly Estate on Long Island!
- Updated top level apartment - modern design with open floor plan
- Cozy Riverside Cottage
- Private Cabin in Multi Acre Park!
- Long Island Pool Getaway - Private apartment with shared pool/hot tub.
- Cozy 3BR Apartment in Peaceful Neighborhood With Kitchenette
- Lovely escape, home away from home 10 mins from all beaches.
- The Suite at North Shore Long Island, Prime Location, Unique and sophisticated
How many Casai.ca holiday rentals are available in Smithtown?
As of 2026, Casai boasts over 26 properties listed in the Smithtown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Smithtown.
