Villa vacation rentals in Brookhaven

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Top-rated villa rentals in Brookhaven

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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 9 – 16

G$138,396 GYD 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

G$157,540 GYD per night

Superhost

Villa in Greenport

4.84 out of 5 average rating, 32 reviews

Year-Round Heated Pool Villa - 3 blocks from town

Pool heated to hot tub temperatures & open year round! This brand new construction house is perfect for large groups. Gather with friends and family in the double height ceiling open concept living room/dining room/kitchen area. Soak up the sun lounging by the pool. Take a super short walk to town to enjoy the incredible local shops, restaurants, and bars. Then end with a nightcap relaxing in the heated hot tub seating section of the pool. There's no better place to stay in Greenport Village.

Feb 4 – 11

G$175,900 GYD per night

Guest favorite

Villa in Southport ( Fairfield)

5.0 out of 5 average rating, 12 reviews

Designer Villa bordering Westport

This designer cottage is built from the framework of a 300 year old New England farmhouse. The house is next to a forest and a small river, which can be accessed on the property. During the summer guests can enjoy a pool, hot tub, and a quaint natural getaway from city life. During the winter enjoy a cozy setting with a large fire place and a host of games and activities. Located minutes from the beach, Westport's town center, the historic sailing town of Southport and the train station.

Oct 24 – 31

G$218,967 GYD 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.

Jan 22 – 29

G$160,672 GYD 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 26 – Apr 2

G$239,057 GYD per night

Villa in Norwalk

4.78 out of 5 average rating, 9 reviews

Cottage in Silvermine: Norwalk New Canaan Wilton

Nestled in a leafy Norwalk neighborhood filled with historic houses, this newly remodeled charming guest cottage/Barndominum on 1 acres in opposite the Silvermine river (where New Canaan, Wilton, and Norwalk meet). The guest cottage is separate from the main house. It is a quaint, quiet and cozy. 1 bedroom 1 bathroom new kitchen including range, dishwasher, Keurig and washer and dryer. The bedroom has a queen bed and the living room has a sofa and chairs. Twin cots can be brought in.

Aug 13 – 20

G$66,886 GYD per night

Guest favorite

Villa in Milford

4.88 out of 5 average rating, 65 reviews

Bohemian Beach Oasis. Steps from beach!

Designer beach house 120 steps to Burwell Beach! Embrace the Bohemian life - a Girls Getaway weekend or a weeklong Family escape. With an open floor plan, spacious kitchen + granite counters & patio access, you'll be living your best Boho life. Bedrooms include a spectacular master suite offering a spa bathroom & walk in closet. 2 more bright rooms upstairs. The third-floor loft leads out to a rooftop deck with spectacular water views! Backyard setup ideal for a post beach recharge.

Jul 3 – 10

G$145,980 GYD 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!

Dec 14 – 21

G$101,405 GYD per night

Villa in Bridgeport

5.0 out of 5 average rating, 4 reviews

Indulge in Prime Luxury 3BR 3-7 Guest

Experience luxury and convenience at our stunning villa! Whether you're planning a group retreat or a family escape, our exquisite property is your ideal haven. Located just moments away from major hospitals, universities, and transportation hubs, our villa provides unmatched accessibility to all your needs. Note: lower level unit listing it might be someone staying/living on the lower unit. They will not be able to disturb or enter the listing separately entrance

Aug 29 – Sep 5

G$100,643 GYD per night

Guest favorite

Villa in Weston

5.0 out of 5 average rating, 11 reviews

Great 4 bed 4.5 bath home w hot tub & heated pool

One of a kind modern 4-bedroom plus office 4.5 bath home is perfectly outfitted for your valuable r & r. This mid-century modern home comes with a hot tub (year round) and heated in ground pool with outdoor heated shower (seasonal). The home has extensive southern exposure and ton of windows; hence it gets great light. House sits on a 2-acre leveled lot. And is professionally furnished with designer furniture and accessories. TVs (75 & 65 inch) and propane BBQ grill.

Oct 18 – 25

G$214,601 GYD 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

G$104,478 GYD per night