Villa vacation rentals in Suffolk County

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Top-rated villa rentals in Suffolk County

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Guest favorite

Villa in Shelter Island

5 out of 5 average rating, 17 reviews

The Lord‘s Villa & Estate

This stunning waterfront Estate House is a quiet paradise set in 7 private acres on the Menantic Peninsula. Newly renovated with panoramic sea views from every room. Cathedral ceiling and copious skylights create sun-filled, spacious living and dining areas. Enjoy strolls along the water’s edge or use the private, sandy beach area for sunning, soaking, kayaking, and clamming. Watch sunsets from the seaside jacuzzi or commune with nature in this peaceful sanctuary. Concierge services available.

Guest favorite

Villa in Southampton

5 out of 5 average rating, 92 reviews

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

*Follow Us: Insta @29watersedge* 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. Return home to a backyard that has it all: a large dock, fire pit, swing/playset, hammock, 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.

Guest favorite

Villa in Southport ( Fairfield)

5 out of 5 average rating, 15 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.

Guest favorite

Villa in Guilford

5 out of 5 average rating, 24 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".

Guest favorite

Villa in Water Mill

4.96 out of 5 average rating, 23 reviews

Incredible 9+ Bedroom Watermill Home w Heated Pool

Luxury 9000 SF Southampton villa with a heated gunite pool & hot tub, steam shower, 9-bedroom, 8.5-bathroom, nestled on a quiet cul-de-sac in Watermill. Bright with large windows, e-shades in bedrooms, indoor/outdoor sound system, W/D on every floor (3 sets). Formal dining/living area, chefs' kitchen, TV room, movie room, gym, fire pit, outdoor kitchen, sauna, arcade, pool table, air hockey and foosball. Please read our disclosures & house manual. Not a party house and no events permitted.

Guest favorite

Villa in Southampton

4.95 out of 5 average rating, 55 reviews

Just renovated - Southampton retreat

JUST RENOVATED! INQUIRE ABOUT MONTHLY RENTALS! 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 salt water 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.

Guest favorite

Villa in East Hampton

4.99 out of 5 average rating, 75 reviews

East Hampton Village Fringe, Renovated with Pool

This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Guest favorite

Villa in Deer Park

4.88 out of 5 average rating, 66 reviews

A Modern Getaway Perfect for Families & Business

Discover the perfect blend of style and functionality in this modern two-story home, ideal for both family retreats and business gatherings. It boasts 4 bedrooms, 3 bathrooms, 2 fully-equipped kitchens, and 3 spacious living rooms. With 6 comfortable beds, an authentic wood-burning fireplace, and 4 smart TVs, you’ll find all the comforts of home. Enjoy the private balcony, 2 outdoor furnished patios, BBQ grill for entertaining, 3 bicycles and 6 private parking spots for you and your guests.

Guest favorite

Villa in East Hampton

4.94 out of 5 average rating, 17 reviews

Modern Farmhouse in East Hampton with beach access

Modern farmhouse is a short walk from Sammy's Beach. Perfect for WFH w/ strong wifi and built in Sonos speakers throughout. Guest wing has 2 bedrooms with queen size beds that share a spacious bathroom as well as a separate workspace. 2 living rooms, one w/ a working fireplace. Master bedroom is perfectly set up with an en-suite bathroom & tub. Rear yard has a heated pool, hot tub & gas fire pit. Billiard room can be used as a 4th bedroom. House sleeps 8. Weekly rentals in summer only.

Guest favorite

Villa in Hampton Bays

4.94 out of 5 average rating, 16 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!

Guest favorite

Villa in East Quogue

4.91 out of 5 average rating, 22 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.

Villa in Medford

4.68 out of 5 average rating, 25 reviews

Tranquil Escape: 4BR Retreat with Pool Bliss!

Experience the perfect blend of comfort and convenience at our charming retreat! With four cozy bedrooms, indoor and outdoor entertainment spaces, a fully stocked kitchen, and modern amenities like free WiFi and a private pool, your stay promises relaxation and enjoyment. Book now for an unforgettable getaway!