Villa vacation rentals in Water Mill

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Top-rated villa rentals in Water Mill

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Guest favorite

Villa in Hampton Bays

4.9 out of 5 average rating, 30 reviews

Enjoy the Summer in your own private Oasis!

Your whole group will enjoy easy access to everything from this centrally located relaxed and private home. Grab a book and sit by the Koi Pond in the Meditation Garden, fish food provided. Feeling energetic? Take a walk to the public Bay Beach, or a very short drive to Meschutt Beach and Tikki Joe’s Bar & Grill. You are a 3 minute drive to Cowfish and Rumba Restaurants. 5 minutes to Hampton Bays village with Southampton’s Main Street and World Famous Coopers Beach only an 8 minute drive away.

Nov 8 – 15

ﺩ.ﺇ2,483 per night

Villa in Southampton

Villa South

A sun drenched home with modern + minimalist decor - gated / deer fence property. An easy few mile drive to the sought after Coopers Beach and Southampton Village and under 2 hours from NYC. Heated saltwater pool , grill, seating and lounge area accessible from the dining, living and master bedroom - seamless indoor - outdoor experience. Surround sound system and equipped with beach accessories. Brand new Kitchen appliances, High Speed Internet, Smart Home technology + a Sonos surround system.

Sep 13 – 20

ﺩ.ﺇ2,782 per night

Guest favorite

Room in Orient

4.89 out of 5 average rating, 9 reviews

Spend the weekend at the beach in my studio grd fl

Take it easy at this unique and tranquil getaway. wake up to the sound of the waves and birds signing. 12 minutes from quaint town of Greenport. your private studio is in the back of my house facing the ocean. your only neighbors are the seagulls. park in the driveway or pull you car right up on the lawn in front of your studio. sliding glass door onto deck, lawn, sandy dune and steps down to my private beachfront. ok to bring dogs to beach, running on lawn, off the lease. I do not mind barking

May 19 – 26

ﺩ.ﺇ2,811 per night

Guest favorite

Villa in Southampton

5.0 out of 5 average rating, 76 reviews

NEW Hamptons Water Living: Dock Beach Kayak & Fish

One mile from the beach, this child-friendly waterfront Southampton home is a perfect family destination. Ready for watersports: kayaking, paddleboarding, boating, or jet skiing. Walk down to the beach for a swim in the bay. Return home to a backyard that has it all: a large private dock, fire pit, swing/playset, hammock, Weber grill, and oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village and Sag Harbor.

Jun 5 – 12

ﺩ.ﺇ2,767 per night

Guest favorite

Villa in Southampton

4.93 out of 5 average rating, 44 reviews

Retreat in Southampton with heated pool

INQUIRE ABOUT MONTHLY RENTALS! Newly renovated second floor. Come and enjoy with family and friends your own beautiful house in Southampton. 5-minute drive to Cooper’s Beach and to Southampton Village. Enjoy beautiful ocean beaches, have brunch in the Village, swim in your 32’ heated pool, enjoy a BBQ on your patio under the shadow of a Japanese Maple, indulge in a quiet evening with a book by the fireplace, or take advantage of the home office while your family & friends enjoy the property.

Dec 23 – 30

ﺩ.ﺇ2,884 per night

Guest favorite

Villa in Southampton

4.94 out of 5 average rating, 16 reviews

Chic 4 Bed, 3 Bath Home w/ Pool - Walk to Beach

Enjoy a serene Hamptons summer in this bright renovated home. Take a quiet tree lined walk (7 min) to the local beach, kayak the calm blue waters of Peconic Bay to Clam Island or hike back trails to Elizabeth Morton Park. Within 15 mins: Sag Harbor, Southampton & Bridgehampton present many options to join the summer festivities. Shop local farms and vineyards for a true farm to table cookout or enjoy the myriad local restaurants and bars. Welcome to the summer of endless possibilities.

Mar 25 – Apr 1

ﺩ.ﺇ4,286 per night

Villa in Sag Harbor

Sag Village Farmhouse walking to town

Charming village cottage on fenced 1/2 acre with large gunite heated pool and bluestone patio -- - walking distance from jitney and town (7 min)-- close to playground (5 min) and school. Fits the whole family plus with four bedrooms (each with queen bed) , 3 1/2 bathrooms. Pool house w/ TV, Internet, kitchenette and full bathroom can fit extra guest. Fun and tastefully appointed as un upscale, but not stuffy family rental. Useful amenities include outdoor shower, bikes, Come Enjoy!

May 13 – 20

ﺩ.ﺇ2,726 per night

Guest favorite

Villa in Hampton Bays

5.0 out of 5 average rating, 11 reviews

Picturesque 5-bedroom Hamptons villa with pool

Relax with the whole family at this peaceful place to stay. Go for a swim in the 20’ x 40’ heated pool or enjoy the scenic garden and woods while lounging in the outdoor living room. Grill some burgers or make s’mores over the fire pit. Centrally located. 6 min. drive to LIRR and Hampton Jitney and minutes to I-495. 2 mins. to bay beaches and 10 mins. to ocean beaches. 10 mins. to Southampton Village. 20 mins. to the wineries. Explore all the Hamptons have to offer and more!

Jan 11 – 18

ﺩ.ﺇ1,781 per night

Villa in Sag Harbor

Gorgeous Sag Harbor Oasis ~ ♛Royal Beds ~ Backyard

Experience the breathtaking Sag Harbor by staying at this charming 5BR 2.5 Bath house. It offers a perfect escape from the everyday hustle and bustle just two miles from the booming village full of top restaurants, boutiques, attractions, and historical landmarks. The charming design, dreamy backyard, and rich amenity list will satisfy your every need. ✔ 5 Comfy BRs ✔ 2 Living Rooms ✔ Full Kitchen ✔ Office ✔ Outdoor Dining & BBQ ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking

Feb 8 – 15

ﺩ.ﺇ3,279 per night

Guest favorite

Villa in East Quogue

5.0 out of 5 average rating, 12 reviews

Farm reserve sunset views

Beautiful villa in beginning part of the Hamptons for a more convenient commute. A private hideaway surrounded by nature where you can relax. It’s perfect for families and friends who love nature, horses and beautiful sunsets. Since our property is spread out over an acre (and surrounded by greater than acre properties), we have the space to allow our guests the ability to maintain a safe distance while still being able to relax comfortably during their stay.

Oct 2 – 9

ﺩ.ﺇ1,876 per night

Room in Orient

balcony entrance to ensuite room with king bed +

Take it easy at this private beachfront. wake up to the sound of the waves and birds signing. 12 min from quaint town of Greenport. your room is in the back of my house, up the stairs to balcony entrance facing the ocean. your only neighbors are the seagulls. park in the driveway or pull you car right up on the lawn + sandy dune, stairs down to my private pebble beachfront. lots of waterfront dining.

Jul 28 – Aug 4

ﺩ.ﺇ3,154 per night

Guest favorite

Villa in Southold

4.97 out of 5 average rating, 29 reviews

North Fork Hideaway

Our North Fork home is an escape from the real world. We are parked on 3 private acres. There's a heated pool and plenty of space inside. Near us are beaches, wineries, organic farms and some of the best restaurants on Long Island. Our home is perfect for families with kids, but also works great for couples and friends.

May 11 – 18

ﺩ.ﺇ3,694 per night