Tuckahoe Vacation Rentals

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Check prices for these dates

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
This weekend
Oct 24 - Oct 26
Next weekend
Oct 31 - Nov 2

Vacation Rentals in Tuckahoe

Outdoor pool, a heated pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"Wonderful outdoor space and great pool. Host was responsive and property was close to all things needed and wanted! Great rental for families."
United States
Patricia Fox M.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Beach nearby
Cliffside Resort Condominiums
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (244)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
United States
dean
The price is ￥34,160
￥45,658 total
includes taxes & fees
Nov 2 - Nov 3
Cliffside Resort Condominiums
Outdoor pool, a heated pool
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
United States
James S.
The price is ￥23,926
￥56,842 total
includes taxes & fees
Oct 29 - Oct 30
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Terrace/patio
The SandPiper
The SandPiper
9.8 out of 10, Exceptional, (27)
"My wife and I stayed at the Sandpiper for a long weekend. The property was very clean with a warm welcoming feeling. It is within walking distance to the beach and downtown shopping. Great location. I would recommend it to everyone."
United States
steve
The SandPiper
Property grounds
Fairy Tale Guest Cottage in Magic Garden by Pool
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (76)
"It was a beautiful cottage on a gorgeous property with gracious hosts. I recommend it!!!!"
United States
Lisa
Fairy Tale Guest Cottage in Magic Garden by Pool
Outdoor pool, a heated pool
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
10.0 out of 10, Exceptional, (192)
"House was more then I can imagine , host was great , house literally have anything you forgot at home . "
United States
Isiah L.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Property grounds
Work and Play Special! Extended Stay Discount
Work and Play Special! Extended Stay Discount
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is ￥109,375
￥202,195 total
includes taxes & fees
Nov 5 - Nov 6
Work and Play Special! Extended Stay Discount
Terrace/patio
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (141)
"Perfect property to hangout and stay entertained for hours"
United States
Ryder I.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Outdoor pool, a heated pool
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
United States
Kilee B.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Fridge, microwave, oven, stovetop
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
United States
Gina G.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Smart TV, fireplace, stereo
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
10.0 out of 10, Exceptional, (95)
"We loved our stay - it was nice to be a short walk away from the bay and the pool was great. The home was very clean and comfortable."
United States
Katie C.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Oven, stovetop, dishwasher
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
8.4 out of 10, Very Good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
United States
Riyao
The price is ￥75,803
￥138,674 total
includes taxes & fees
Oct 26 - Oct 27
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Outdoor pool, a heated pool
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
9.4 out of 10, Exceptional, (74)
"As always everything was excellent, This is our third stay at this property and we are booked for 2026"
United States
Michael R.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
TV, fireplace, video library, stereo
Stunning Hampton Holiday Family Fantasy for your Team
Stunning Hampton Holiday Family Fantasy for your Team
9.8 out of 10, Exceptional, (74)
"Everything was great!!!"
Mexico
Mauricio E.
Stunning Hampton Holiday Family Fantasy for your Team
Exterior
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
8.0 out of 10, Very Good, (3)
"Great location and comfortable stay, amazing sheets.Ended up buying for my home. "
United States
David Y.
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
A heated pool
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
10.0 out of 10, Exceptional, (90)
"Beautiful house , with pool and amazing backyard, perfect to chill with your friends and family ! "
United States
Priya B.
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
Outdoor dining
Summer getaway
Summer getaway
9.0 out of 10, Wonderful, (14)
"Perfect location for a family holiday "
Germany
Olaf U.
Summer getaway
Terrace/patio
Private beach on a fenced in property sunset views
Private beach on a fenced in property sunset views
10.0 out of 10, Exceptional, (12)
"We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay."
United States
Hanna M.
The price is ￥45,421
￥222,849 total
includes taxes & fees
Oct 26 - Oct 27
Private beach on a fenced in property sunset views
Fridge, microwave, oven, stovetop
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
9.6 out of 10, Exceptional, (26)
"Ken was great and easy to work with. The house was nice and perfect for our stay!"
United States
Graham J.
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Pool
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
9.0 out of 10, Wonderful, (10)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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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Top Tuckahoe Hotel Reviews

Greenporter Hotel

Greenporter Hotel

10/10 Excellent
"Great place. Would come again"
Helmut 2-night trip
Posted 4 days ago
Greenporter Hotel

Find out more about Tuckahoe

Search for holiday rentals in Tuckahoe on Expedia! You can easily find your home rentals, villas, holiday apartments in Tuckahoe using one of the methods below:

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Look no further and take a look at our great range of rental properties in Tuckahoe!

Frequently asked questions

Are there vacation rentals in Tuckahoe?

Yes, you can find vacation rentals close to top points of interest in Tuckahoe, or you can go with a more secluded option if you're looking for a relaxing stay. Visitors to Tuckahoe speak positively about the beaches and coffeehouses 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 vacation rentals in Tuckahoe?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: Visitors like this Tuckahoe vacation home rental. It offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Tuckahoe?

Expedia has 56 vacation 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 Sebonack Golf Course.

What are vacation rentals like in Tuckahoe?

Vacation rentals are private properties you can stay in for several days or more in Tuckahoe. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family gatherings.