Tuckahoe Holiday Rentals

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Holiday Rentals in Tuckahoe

Newly Renovated Southampton Home with Heated Pool
Newly Renovated Southampton Home with Heated Pool
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, 183 reviews
"Wonderful stay and super clean! Can’t wait to come back. "
The price is NZ$588
includes taxes & fees
27 Jun - 28 Jun
Cliffside Resort Condominiums
Airstream Art Studio Sculpture/Nature Preserve
10.0 out of 10, Exceptional, 2 reviews
"This place was one of the best parts of my stay on LI. It is tucked away on a beautiful stretch of property but still close to central locations making it easy to go out for provisions. I "gifted" myself a stay here as a single-mother and former art maker. This was the first time I painted in 10+ years, the environment and the energy filled my cup to overflowing! Thank you so much for having this space available. I will return."
The price is NZ$386
includes taxes & fees
17 Jun - 18 Jun
Airstream Art Studio Sculpture/Nature Preserve
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Summer in the Hamptons! Beautiful home with pool, hot tub, pirate ship and more!
10.0 out of 10, Exceptional, 68 reviews
"We had a great time at this house. Kids loved the toys and the pool. Host was very helpful."
Summer in the Hamptons! Beautiful home with pool, hot tub, pirate ship and more!
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, 18 reviews
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, 49 reviews
"Close to the restaurants and beaches. We enjoyed exploring the nearby areas within 15 to 30 mins drive"
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, 12 reviews
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, 25 reviews
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
10.0 out of 10, Exceptional, 1 review
"Our overall expertise was great. Home was very clean and had all the essentials you need for a nice comfortable stay. The beds were very comfy, equipped with great linens and pillows. Home was cozy and comfortable. Can’t wait to stay again."
The price is NZ$3,252
includes taxes & fees
5 Jun - 6 Jun
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, 73 reviews
"This place exceeded all expectations, offering a perfect blend of convenience and serenity. Situated just moments from downtown, the location provided easy access to the vibrant community, while still offering a peaceful retreat. The highlight of our stay was undoubtedly the private beach access. Tucked away in a tranquil neighborhood, it boasted unparalleled beauty and tranquility. Simply being in the vicinity was a getaway in itself, with breathtaking views that soothed the soul. The...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, 7 reviews
"This place was nice and roomy for our family of 8 plus 3 littles kiddos. Pretty clean as well. I gave listing accuracy a 5 because it is accurate but that may be because it doesn't tell you much. We were a little short on towels, many light bulbs were burnt out or just missing. We replaced some (they were there) and moved others to balance out the light. No kitchen linens, short on bath towels, short on paper towels and definitely not enough TP. 3 partial rolls and 1 bathroom had none so we had...
Gorgeous private Hamptons house with pool and volleyball court
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, 12 reviews
"Incredible property, incredible people to work with! We this is our second year in a row renting this house for a holiday weekend, and we look forward to renting every year forward! The house itself is stunning, clean and full of activities from the pool, to the tennis court, to the movie room. Rebecca and Shaun are truly a pleasure, and reply immediately to any questions, requests or needs. They even left us a welcome present for returning this year! Thank you for allowing us to have an annual...
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, 147 reviews
"In town for a wedding - a large, convenient location that fulfilled the needs we had for that stay."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, 23 reviews
"It was a great weekend"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
10.0 out of 10, Exceptional, 47 reviews
"Beautiful property right on Dune road. Stunning beach views, clean, great communication. Overall a wonderful stay!"
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, 28 reviews
"The house was beautiful and comfortable. We enjoyed the property and watching the wildlife. The fire pit was great for a group gathering. We didn't cook but the kitchen appeared well stocked. The house was short on paper products. We left a note for the house manager when we left."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Contemporary home, newly built, heated pool and hot tub, large deck and...
10.0 out of 10, Exceptional, 4 reviews
"The property manager was incredibly helpful in providing check-in and check-out information, and was readily available to answer any questions during our stay. The house perfectly matched what we saw in the photos and was ideal for our getaway. We're already looking forward to returning in the summertime to fully enjoy the pool."
Contemporary home, newly built, heated pool and hot tub, large deck and...
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
10.0 out of 10, Exceptional, 75 reviews
"Great location. Pristine beach with hardly anyone else on the beach (mid May). No shampoo or conditioner in bathrooms as reported. The house needs a bit of TLC. Could be a bit cleaner. There was sand on the floor in the master bedroom upon our arrival. It seemed like there was white dog hair on the bedspread. I dont have a dog. The dishwasher seemed like it was working but was not getting the dishes clean. I think it is time for a new dishwasher."
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
Recently renovated private 2.1 acre gated home with heated pool and tennis court
10.0 out of 10, Exceptional, 13 reviews
"Great for a large group!"
Recently renovated private 2.1 acre gated home with heated pool and tennis court
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
10.0 out of 10, Exceptional, 9 reviews
"This is a beautiful, comfortable and recently renovated home in a lovely neighborhood. The yard is also very nice, it was too cold for the pool but we enjoyed the hot tub and outdoor seating areas. We had a wonderful stay!"
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Don't see what you're looking for?
See all available properties in Tuckahoe
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.

Other types of properties in Tuckahoe you may be interested in

The Atlantic Hotel
2.5 star property
7.0 out of 10, Good, 776 reviews
"We enjoyed our stay and felt it was good value for the area. "
The price is NZ$525
includes taxes & fees
5 Jun - 6 Jun
The Atlantic Hotel
Newly Renovated Southampton Home with Heated Pool
Newly Renovated Southampton Home with Heated Pool
The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, 76 reviews
"Large room recently updated, didn’t hear other guests "
The price is NZ$444
includes taxes & fees
5 Jun - 6 Jun
The Bentley Hotel Southampton
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Tuckahoe holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Tuckahoe. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Tuckahoe. Seeing all the best attractions is bound to make you fall in love with Tuckahoe. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Tuckahoe short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Tuckahoe?

Yes, there are holiday rentals close to the most popular sights in Tuckahoe, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Tuckahoe speak positively about the beaches and coffee shops in this destination. Make sure you have time to check out the golf courses and monuments during your trip.

What are some of the best holiday rentals that Tuckahoe has to offer?

Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool: This holiday home rental outside of Tuckahoe offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Tuckahoe?

Expedia has 59 holiday rentals for your stay in Tuckahoe.

What can I see and do in Tuckahoe?

While exploring the area, visit family-friendly sights like Railroad Museum of Long Island, or get outside and enjoy nature at The Hamptons Beaches. Other places in town to visit include Shinnecock Hills Golf Course and Southampton Golf Range.

What are holiday rentals like in Tuckahoe?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Tuckahoe. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family getaway.

Recent reviews of Tuckahoe properties
Expedia verified reviews