Holiday rentals in Southampton

4.95 out of 5 average rating, 87 reviews

Modern Southampton Cottage | Heated Pool & Peloton

Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

5 out of 5 average rating, 14 reviews

Flat in Southampton

Southampton Village Near Ocean & Shops - Suite "A"

Our suite "A" features location, location, location! You are so close to everything, you can leave your car behind! Just two blocks from historic Main Street. Ocean beach is less than a mile at the end of the road. Brand new lower level apartment. Private entrance. Enjoy sipping wine outdoors in a private sitting area. Off street parking for one car available. Level 2 EV charger w/J1772 plug available for overnight charging. On the premises for use is a heated gunite pool & outside shower.

Guest house in Southampton

4.95 out of 5 average rating, 440 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

4.91 out of 5 average rating, 45 reviews

Summer in the Hamptons! SH Gem mins from the Beach

Welcome to your perfect Hamptons getaway! This sun-filled, architecturally unique home is ideal for a summer retreat or a cozy weekend escape. Offering modern furnishings, and an open floor plan, this space is perfect for small groups. Whether you're enjoying the crisp evenings of early spring, sun-drenched summer days, or the vibrant fall season, this home is a serene escape year-round. Cozy up by the fire, relax on the sun-soaked balconies, or unwind in the beautifully renovated pool house.

Guest house in Southampton

4.98 out of 5 average rating, 60 reviews

Southampton Modern Barn, Private Hot Tub and Pool

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

Superhost

4.89 out of 5 average rating, 273 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

4.93 out of 5 average rating, 30 reviews

Charming Village home in the heart of Southampton

Designer decorated home in the heart of Southampton Village. Conveniently located minutes to town and ocean beaches, this sun-drenched gem offers a primary ensuite and two guest rooms with shared bathroom. Eat-in kitchen features Viking and Sub-Zero appliances. Dining room is adjacent to the open concept living room. Separate TV room is furnished with a sofa that converts to a double-sized bed. Outdoor oasis is surrounded by mature landscaping and gunite pool with waterfall.

4.97 out of 5 average rating, 31 reviews

Newly Renovated Towd Point Beach Treasure

This stylish modern chic beach home is situated by the waters edge and one of the most idyllic beaches in the Hamptons. Make this home your summer escape and enjoy the cozy interior with brand new furniture throughout, hand selected by a renowned Hamptons interior designer. Outside, relax in the gunite pool or take the scenic walk to the shore. Along Towd Point, you'll find gorgeous beach homes, friendly neighbors, summer vibes and sunsets that will create lifelong memories!

4.83 out of 5 average rating, 24 reviews

Enchanting Cottage in the Heart of Southampton Vil

Enchanting Cottage in the Heart of Southampton Village Escape to this delightful cottage nestled in the heart of Southampton Village, offering a perfect blend of charm, comfort, and convenience. Situated just moments away from the beach, restaurants, and entertainment, this retreat boasts private gardens and access to a refreshing pool. 🛏️ Bedrooms: Studio 🛁 Bathrooms: 1 🌳 Outdoor Space: Private gardens 🏊 Pool Access: Available (open MDW -LDW) 🚘 Two Parking Spaces

Superhost

4.83 out of 5 average rating, 210 reviews

Chic Southampton Retreat – Near Beaches & Village

Chic & cozy Hamptons retreat just minutes from Southampton Village and beaches! Enjoy a private backyard with sundeck, hot tub, fire pit, outdoor shower, and indoor fireplace. Next door to world-famous Shinnecock Hills Golf Club and 15 mins to Poxabogue public course. Close to Wölffer Estate, Duck Walk, and Channing Daughters wineries. Walk the nearby Scallop Pond Preserve or Elizabeth Morton Wildlife Refuge. Perfect year-round getaway!

4.97 out of 5 average rating, 109 reviews

Flat in Hampton Bays

Walk to Bay and Ocean-Newly Renovated

Newly renovated! Walking distance to beautiful bays , ocean beaches, restaurants and bars. Perfect Hamptons vacation getaway. Wine Country and Montauk are great day trips from this centrally located spot. Easily access Hampton Bays with public transportation via LIRR or Hampton Jitney, than a 3-5 minute Uber to apartment. Monthly stays will have cleaning service provided every two weeks.

4.96 out of 5 average rating, 208 reviews

Flat in Southampton

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

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Convenient locations with everyday essentials

Popular amenities for Southampton holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Southampton's top sights

Cooper's Beach, Southampton56 locals recommend

Parrish Art Museum50 locals recommend

Duck Walk Vineyard26 locals recommend

Other great holiday rentals in Southampton

5 out of 5 average rating, 32 reviews

Perfect So. Hampton Home on pond Enjoy July 4 now

LucreciaRating, 5 stars9 months ago

We had a great time at Denise's house. The house is lovely , the garden and the pond are super relaxing and very nice , it gives the house a different touch. It is 5 min drive from Southampton Main Street

4.94 out of 5 average rating, 71 reviews

5BR, Luxury Home, Perfect Getaway, Close to Beach

KristinaRating, 5 stars2 weeks ago

We absolutely loved our stay! The house was beautiful and Tracie was always responsive. Will definitely stay again!

5 out of 5 average rating, 10 reviews

Home in Water Mill

Waterfront home next to the beach in Southampton !

ManuelaRating, 5 stars3 weeks ago

Our family of five just spent Memorial Day weekend at this house. The views and location are amazing. Rohit is very responsive and friendly. The house is very practical, super clean, very nice kitchen, everything is new. Hope to go back soon!

Superhost

4.9 out of 5 average rating, 60 reviews

Bay View Cottage- Short Walk to Private Beaches

RichelleRating, 5 stars4 days ago

We brought our dog and enjoyed the fenced in yard. There was a beach that was dog friendly about a 15 minute walk away. The living room was very comfortable and we enjoyed our stay. There is a major road right next to the home which was a little loud at times but nothing crazy. I’d recommend it to others.

4.97 out of 5 average rating, 106 reviews

Southampton beach cottage with pool- open in May

SunnyRating, 5 stars1 month ago

Thank you for the stay! We had a wonderful time the location is great!!! We hope to come back and stay again in the future.

5 out of 5 average rating, 8 reviews

Flat in Southampton

Southampton apt walk to village

RoshniRating, 5 stars1 week ago

Had a lovely stay! Beautiful apartment with private entrance. The living spaces, bathroom, kitchen and bedroom were modern, very clean and had all the necessary amenities for a comfortable stay. The place is within walking distance of the train station and village. Would absolutely stay here again.

5 out of 5 average rating, 17 reviews

Villa in Hampton Bays

Hamptons Bungalow With Pool

RalphRating, 5 stars3 weeks ago

My family and I were lucky enough to stay at Jenna’s over Memorial Day Weekend. The house was even better than the pictures, if that’s possible. Very clean, and beautifully presentable. Everything was clean and ready for us, and Jenna had genuinely everything we could have possibly needed. Jenna was extremely communicative even leading up to our stay. Hope to stay again sometime soon!