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Vacation rentals in Southampton

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Top-rated vacation rentals in Southampton

Guests agree: these stays are highly rated for location, cleanliness, and more.

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A modern, sleek structure is surrounded by lush greenery, featuring a private pool and spacious patio area. Chaise lounges are positioned beside the clear water, while large glass doors provide a view of the interior, inviting natural light into the space.

Home in Water Mill

4.88 out of 5 average rating, 146 reviews

Modern House close to the beach

This modern home has all the amenities and comfort you would expect. You are 5 minutes from Southampton Village, 5 minutes from Flying Point Beach by car. Spacious back yard with beautiful patio furniture which gives onto beautiful pond. Fully equipped kitchen with Wolf stove. Lots of sun on this property. Quiet back patio area with barbecue and patio furniture. Fireplace available in the winter months. We use cotton linen and towels. Pool open in May. Pool heating is an additional cost.

A cozy living space features a brown leather sofa and a white coffee table on a geometric patterned rug. A large window allows natural light to fill the room, showcasing a wall-mounted fish decor and colorful accents. A decorative plant sits on the table.

Guesthouse in Southampton

4.95 out of 5 average rating, 443 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!

A charming cottage is framed by lush greenery and well-maintained landscaping. The light-colored exterior features large windows and a welcoming green door. A stone walkway leads to the entrance, while a gravel driveway curves around, enhancing the natural setting.

Cottage in Southampton

4.96 out of 5 average rating, 196 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Top guest favorite

A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.

Apartment in Sag Harbor

4.98 out of 5 average rating, 191 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Top guest favorite

A calm waterfront scene shows a serene body of water reflecting the sky. A sandy beach is visible, framed by natural vegetation, with a wooden barrier along the shoreline. The peaceful setting invites relaxation and enjoyment of the outdoors.

Apartment in Hampton Bays

4.97 out of 5 average rating, 402 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

A spacious living area features high ceilings and natural light streaming through large windows. A white sofa is paired with wooden chairs, while a glass coffee table sits on a woven rug. An elegant dining area is visible in the background with a large table.

Cottage in Southampton

4.96 out of 5 average rating, 154 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

A spacious living area features rustic wooden beams and light walls, creating a bright atmosphere. A comfortable white sectional sofa is adorned with neutral throw pillows, and a wooden coffee table holds a decorative bowl. Large windows allow natural light to fill the space.

Home in Water Mill

4.92 out of 5 average rating, 131 reviews

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

Dog friendly (upon request) Hampton Beach Barn with pool and infrared sauna. POOL OPEN - May 15th - October 20, 2025 US OPEN 2026 - 6 miles from Shinnecock Hills Golf Club This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic modern decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.

Top guest favorite

A sandy path leads through beach grass, flanked by wooden fencing, toward a tranquil ocean beyond. Clear blue skies complement the scene, where gentle waves are visible on the horizon.

Apartment in Hampton Bays

4.98 out of 5 average rating, 124 reviews

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.

A well-maintained outdoor pool area is surrounded by a wooden deck and lush greenery. Lounge chairs are positioned along the pool, with a shaded area provided by a large tree. The clear blue water of the pool reflects the sunlight, inviting relaxation.

Home in Water Mill

4.93 out of 5 average rating, 136 reviews

Astounding Watermill 5 Bedroom home with Pool

Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

A wide sandy beach stretches towards the horizon, where soft waves gently lap at the shore. Tall lifeguard stands are positioned along the beach, with a few distant figures walking. The sky features a gradient of muted colors as the sun sets, creating a serene atmosphere.

Apartment in Southampton

4.95 out of 5 average rating, 214 reviews

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

The exterior of a two-story home is visible, featuring large glass windows that promote natural light. A spacious wooden deck hosts a dining area with a white umbrella. Lush green grass and trees surround the area, creating a serene outdoor setting.

Home in Water Mill

4.91 out of 5 average rating, 113 reviews

Elegant Modern Artist's Residence

This simple and serene home is set against a farm preserve, exposed to beautiful light and views and biking distance to the beach. Very relaxing - a terrific, creative space for a couple or small group. A large vegetable garden is maintained on the property and is available for guests to harvest as they like. Fresh salad greens, herbs, vegetables for you to enjoy!

The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.

Guest suite in North Fork

4.88 out of 5 average rating, 683 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Southampton vacation rentals

Laptop-friendly workspace

Stay near Southampton's top sights

Cooper's Beach, Southampton220 locals recommend

Parrish Art Museum315 locals recommend

Duck Walk Vineyard125 locals recommend

Southampton house rentals

A contemporary home is depicted with a clear blue pool in the foreground, surrounded by a spacious wooden deck. Lush greenery and autumn foliage frame the property, while sliding glass doors provide views of the interior.

Home in Hampton Bays

4.94 out of 5 average rating, 137 reviews

Peaceful Retreat in Immaculate Architect’s House

Top guest favorite

A large outdoor pool is surrounded by lounge chairs and umbrellas, inviting relaxation. Well-maintained gardens and trees frame the area, with a spacious deck along one side. The bright blue sky enhances the tranquil atmosphere of this inviting outdoor retreat.

Home in Southampton

4.96 out of 5 average rating, 47 reviews

Spectacular Southampton Retreat!

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

4.97 out of 5 average rating, 117 reviews

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

Top guest favorite

A welcoming living area features a comfortable sofa adorned with coral-patterned pillows. A rustic coffee table sits at the center, surrounded by natural light from large windows. A view of the open space and kitchen area can be seen in the background.

Home in Sag Harbor

4.97 out of 5 average rating, 149 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

Top guest favorite

A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.

Home in Southampton

5 out of 5 average rating, 47 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

Home in North Fork

4.93 out of 5 average rating, 140 reviews

Modern Farmhouse Steps to Beach & Love Lane

A charming cottage exterior is framed by lush greenery and well-maintained landscaping. A brick pathway leads to the welcoming entrance, which features double doors and several windows. Solar lanterns hang gracefully on either side, adding a subtle touch of warmth to the inviting approach.

Home in East Hampton

4.94 out of 5 average rating, 165 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

Home in Sag Harbor

4.95 out of 5 average rating, 296 reviews

Sag Harbor Cottage, Walk to the Beach!

Other great vacation rentals in Southampton

An outdoor seating area features a round black table accompanied by a chair with a cushion. The tiny house is visible in the background, showcasing its modern black exterior and large windows, surrounded by trees and a gravel landscape.

Tiny home in Southampton

5 out of 5 average rating, 9 reviews

Hamptons Tiny House!

An aerial view of the Mid Century Modern home is showcased, surrounded by lush greenery. The spacious yard features a heated pool, deck chairs, and a large checkered game board. A shaded seating area is positioned nearby, offering a perfect gathering spot amidst the natural landscape.

Villa in East Hampton

4.97 out of 5 average rating, 36 reviews

Luxe| Pool|BeachCar Beach Pass|GameRm|Movie|HotTub

A trellised patio, adorned with soft curtains, overlooks the heated outdoor pool. Outdoor dining furniture is arranged under the structure, surrounded by well-manicured greenery. The serene atmosphere invites relaxation and enjoyment in this private outdoor space.

Home in Southampton

5 out of 5 average rating, 4 reviews

4BR/3.5BA: Southampton, Heated Pool, Near to beach

Flower gardens feature vibrant hydrangeas in shades of blue and pink, surrounded by lush green foliage. The garden is set against a backdrop of gravel pathways and dense shrubbery, contributing to the tranquil and natural ambiance of the property.

Home in Southampton

4.88 out of 5 average rating, 8 reviews

Southampton Village Studio Queen Bed Kitchenette

Top guest favorite

The image showcases a spacious outdoor area featuring a heated gunite pool surrounded by manicured grass. Four loungers with umbrellas are positioned near the pool, while a cozy seating arrangement is visible on the patio. A charming cottage is seen in the background.

Cottage in Southampton

4.96 out of 5 average rating, 94 reviews

Modern Southampton Cottage | Heated Pool & Peloton

A charming garage is seen with a vintage vehicle parked inside. The weathered wood exterior complements the surrounding greenery. Bright sunlight filters through, illuminating the space. A colorful flower pot adds a touch of vibrancy to the gravel driveway.

Cottage in Southampton

4.91 out of 5 average rating, 11 reviews

Steps to Train, Dining & Beach ( Southampton Vill)

A cozy living area features a comfortable sofa adorned with neutral-toned cushions. A large television is mounted on the wall. Natural light filters through multiple windows, brightening the space. A small side table and an armchair complement the seating arrangement, creating an inviting atmosphere.

Apartment in Southampton

5 out of 5 average rating, 16 reviews

Southampton apt walk to village

A heated salt water pool is surrounded by a stone patio, reflecting sunlight on its clear surface. A Japanese Maple tree provides shade along one edge, enhancing the serene outdoor space. Lush green grass and a white fence enclose the area, creating a private setting.

Villa in Southampton

4.94 out of 5 average rating, 69 reviews

Just renovated Southampton retreat w/ heated pool

Quick stats about vacation rentals in Southampton

Total rentals
650 properties
Nightly prices starting at
R177 ZAR before taxes and fees
Total number of reviews
8.1K reviews
Family-friendly rentals
420 properties are a good fit for families
Pet-friendly rentals
270 properties allow pets
Rentals with a pool
380 properties have a pool

Frequently Asked Questions

Where should I stay in Southampton?
Make yourself at home in Southampton by choosing from our most frequently booked neighborhoods. We have over 1,390 vacation rentals in Shinnecock, and over 1,390 vacation rentals in Shinnecock Hills.
Are there vacation rentals with a dedicated workspace in Southampton?
Yes! Work meets play with ease at over 290 vacation rentals in Southampton featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Southampton?
Four-legged friends are welcome in Southampton. Choose from more than 270 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Southampton?
Experience the best of Southampton with our cottage rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Southampton apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 apartment rentals with pools in Southampton, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Southampton have a bbq area?
Absolutely! We offer over 150 house rentals with a bbq area in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southampton have a gym?
Absolutely! We offer over 70 house rentals with a gym in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southampton have self check-in?
Absolutely! We offer over 80 house rentals with self check-in in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do guesthouse rentals in Southampton have wifi?
Absolutely! We offer over 10 guesthouse rentals with wifi in Southampton. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Southampton?
Southampton has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore