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Compare 54 Villas in Shelter Island Heights with updated reviews, rates, and availability.

Spacious Oceanview Villa (Sleeps 22)

10.0 out of 10, Exceptional, (34)
"Absolutely loved staying here. Katie was super helpful and my group had an amazing time. The house is plenty big for big groups. While my group was supposed to be 16, we only had 8 but it felt even more special! Everyone had their own rooms & thoroughly enjoyed their time. Thank you for being an incredible host, Katie! "
Spacious Oceanview Villa (Sleeps 22)

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

10.0 out of 10, Exceptional, (1)
"Very nice house In great shape and outstanding pool area."
1.5 Acre Luxury Escape - Saltwater Pool with Water Views

Waterfront Holiday Vacation Villa New England - 2 min from Ocean W/ fireplace

10.0 out of 10, Exceptional, (13)
"This is a gorgeous, comfortable, well-maintained property and everything was perfect. We all agreed we would love to stay here again! Check-out was listed as 10 AM but we pre-arranged to check-out at noon for no additional charge. "
Waterfront Holiday Vacation Villa New England - 2 min from Ocean W/ fireplace

New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

10.0 out of 10, Exceptional, (17)
"This is a large and extremely comfortable house. The owner is attentive to any questions you might have. LOVED spending time there. "
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Hampton Private Retreat - last minute offer June 23-

10.0 out of 10, Exceptional, (19)
"My family and I could not have picked a more beautiful home to celebrate my mom’s 80th birthday! We had a few rainy days and two 18 year olds, who were more than happy to stay at home and take advantage of the pool table, ping pong table, full gym…everything! Conny was so warm and welcoming in all of her communications. Her home is absolutely stunning! It was beautifully decorated and had many spaces to gather as a family. We spent every morning having coffee on the front porch and afternoons in...
Hampton Private Retreat - last minute offer June 23-

Villa Flasses

3.0 star property
Villa Flasses

Villa Direen Modern East Hampton Villa

3.5 star property
Villa Direen Modern East Hampton Villa

Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach

Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach

Villa Spectrum

3.5 star property
Villa Spectrum

Villa Coastal Bliss

Villa Coastal Bliss

Luxurious beach house on the Long Island sound

Luxurious beach house on the Long Island sound

Villa Victoria: Your Exquisite Luxury Retreat in Bridgehampton

2.0 star property
Villa Victoria: Your Exquisite Luxury Retreat in Bridgehampton

Live on the Water: Dock, Beach, Boat, Kayak & Fish

10.0 out of 10, Exceptional, (1)
"I have rented many houses in the Hamptons and this was the best by far! Family friendly, great hosts and magical spot!"
Live on the Water: Dock, Beach, Boat, Kayak & Fish

Villa Keylime

2.0 star property
Villa Keylime

Villa Emery

2.0 star property
Villa Emery

MODERN 5 BEDROOM MONTAUK BEACH HOME

MODERN 5 BEDROOM MONTAUK BEACH HOME

Villa Gally

2.0 star property
Villa Gally

Villa Spectrum

2.0 star property
Villa Spectrum

Villa Sofia: Luxurious Retreat in East Hampton North

2.0 star property
Villa Sofia: Luxurious Retreat in East Hampton North
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.
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Other property types in Shelter Island Heights

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1140)
"Beautiful place to stay, friendly and profesional staff, great room with nice balcony very comfortable suite. Will go back for sure. "
The price is SAR 491
SAR 634 total
includes taxes & fees
19 Mar - 20 Mar
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (366)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk . "
The price is SAR 510
SAR 624 total
includes taxes & fees
19 Mar - 20 Mar
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"Great cozy place"
The price is SAR 494
SAR 646 total
includes taxes & fees
20 Mar - 21 Mar
Windward Shores Ocean Resort
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

How much do villas in Shelter Island Heights cost?
Villas in Shelter Island Heights range between and per night. These stays provide the privacy of your own space at a price that’s easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Shelter Island Heights?
Take your pick of multiple villas in Shelter Island Heights with a total average guest review rating of 10.0. Villa Machis comes highly recommended by travelers. This 3.5-star property offers a dock and a firepit. Villa Lavender is another popular option. It has a 3.5-star rating and amenities including a terrace and a yard.
How many villas are there in Shelter Island Heights?
Shelter Island Heights has 54 villas to choose from. Find your perfect stay quickly and easily by clicking the “Villa” checkbox under the “Property type” tab in our filter tool.
Why book your villa in Shelter Island Heights with Expedia?
Reserving a villa in Shelter Island Heights is as simple as deciding on your travel dates and choosing the option that checks your boxes. Searching for something inexpensive or upscale, or a stay that also offers a kitchen and laundry? Use Expedia’s search filters to narrow your results and find your ideal pad.
How can I find cheap villas in Shelter Island Heights?
An excellent way to track down cheap villas in Shelter Island Heights is with Expedia’s convenient filter tool. Narrow down your search by star rating, amenities and budget to land awesome deals in only a couple of clicks.