Villa vacation rentals in The Hamptons

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Top-rated villa rentals in The Hamptons

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Guest favorite

Villa in Water Mill

5.0 out of 5 average rating, 16 reviews

Incredible 9+ Bedroom Watermill Home w Heated Pool

This newly renovated 9000 SF Southampton villa with a heated gunite pool & hot tub, 9-bedroom, 8.5-bathroom, nestled on a quiet cul-de-sac in Watermill. Bright & airy with large windows, blackout shades in bedrooms, indoor/outdoor sound system, W/D on every floor (3 sets). Formal dining/living area, chefs kitchen, kids TV room, Media room, gym, fire pit, outdoor kitchen, sauna, kids arcade, pool table. Please read our disclosures & house manual. Not a party house, nor are any events permitted.

May 12 – 19

G$227,839 GYD per night

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 11 – 18

G$138,472 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$157,626 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.

Mar 10 – 17

G$181,780 GYD per night

Guest favorite

Villa in Guilford

5.0 out of 5 average rating, 11 reviews

TREETOPS! An upscale, unique 5 bdrm home with POOL

TREETOPS is a 4850 square ft 5 bedroom Mid century Modern perched on an outcropping of granite cliffs, surrounded by 2 acres of beautiful forest. *Property not suitable for children under 8 years old* Stroll along the loop trail in our woods, sit in the garden, have a fire in the fire pit, or relax and get some sun by the marine-blue, stone-decked pool! Birdwatching, breakfast, and evening cocktails are best on the spacious wrap-around deck. Hiking is just steps away at "Westwoods Trailhead".

Oct 21 – 28

G$109,009 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.

May 1 – 8

G$232,037 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.

Oct 15 – 22

G$239,187 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.

Sep 21 – 28

G$136,207 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!

Nov 4 – 11

G$152,190 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

Dec 19 – 26

G$104,035 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.

Jul 21 – 28

G$216,383 GYD per night

Superhost

Villa in Southampton

4.92 out of 5 average rating, 13 reviews

Heavenly SH Village Escape W Heated Pool

Nestled in the core of Southampton Village, this fully revamped 3 bed/2.5 bath residence is a stone's throw from Main St and renowned ocean beaches. The home boasts contemporary upgrades, including central heat/AC and a newly installed 20 x 40-foot heated gunite pool set on spacious grounds. Beaches and Town are easily accessible by bike, and car. Experience luxury with top-tier furnishings, elegant décor, and marble-finished bathrooms.

Jun 3 – 10

G$201,839 GYD per night