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Vacation rentals in Southampton

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Southampton

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

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A welcoming living area features a cozy leather sofa paired with a decorative coffee table atop a textured area rug. A skylight and large windows provide natural light, while a flat-screen TV is mounted on the wall. Steps lead to a bright bathroom space.

Guesthouse 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!

A private backyard space features a wooden gazebo with a seating area, surrounded by a gravel surface. Comfortable wicker furniture, including a sofa and chairs, invites relaxation. The fenced yard offers a sense of privacy, complemented by beach gear visible in the background.

Guesthouse in Milford

4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Top guest favorite

A well-lit wooden deck features comfortable seating arrangements with padded chairs, perfect for relaxation. Soft lights illuminate the space, creating a welcoming atmosphere. A protective railing borders the deck, with a view of a privacy fence in the background.

Home in Milford

5 out of 5 average rating, 102 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

An open kitchen space features modern appliances, including a stainless steel stove and ample counter space. Barstools are positioned at a breakfast bar, while natural light illuminates the area through several windows. Warm wood flooring complements the neutral-colored walls.

Home in North Fork

4.94 out of 5 average rating, 109 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

A covered outdoor seating area is furnished with a combination of turquoise and brown seating, complemented by decorative pillows. Soft lighting from string lights enhances the space. A swing seat is positioned against the wall, and a small table is centered on the tiled patio.

4.89 out of 5 average rating, 105 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

A view of the Peconic River is depicted from a wooden deck, featuring a small round table and two woven chairs. The water reflects clear blue skies, with boats visible in the distance and trees lining the shore.

Houseboat in North Fork

5 out of 5 average rating, 11 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

An outdoor deck area is seen featuring a large round table surrounded by several comfortable chairs. A sun umbrella provides shade, while a propane grill is positioned nearby. Lush trees create a natural backdrop, enhancing the serene atmosphere of the space.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Top guest favorite

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in North Fork

4.98 out of 5 average rating, 179 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Top guest favorite

A traditional New England house is set in the central village of the island, surrounded by lush green lawn. Tall trees provide shade, and the late afternoon sun creates elongated shadows across the grass, highlighting the inviting outdoor space.

Cottage in Shelter Island

4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

A serene pond is framed by lush greenery, reflecting the bright blue sky. Surrounding trees create a natural border, enhancing the peaceful atmosphere of this outdoor space.

Apartment in Montauk

4.94 out of 5 average rating, 205 reviews

Private paradise 3 min from town ice skating pond!

Located close to everything three minutes from town five minutes from the beaches you have your own pond to ice skate on in the winter months. Home is 2 minutes from Montauk Downs State Park and Golf Course. 5 minutes from Ditch Plains surfing, 8 minute walk to town.

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

Apartments

Convenient locations with everyday essentials

Popular amenities for Southampton vacation rentals

Laptop-friendly workspace

Stay near Southampton's top sights

Cooper's Beach, Southampton52 locals recommend

Parrish Art Museum48 locals recommend

Oakland's Restaurant & Marina40 locals recommend

Village of Southampton7 locals recommend

Duck Walk Vineyard26 locals recommend

Sant Ambroeus35 locals recommend

House rentals in Southampton

A charming Cape Cod cottage is showcased, featuring a light gray shingled exterior and blue door. The front yard is adorned with green grass and small shrubs, while steps lead to the entrance. Tall trees frame the property, providing a sense of privacy.

Home in Sag Harbor

4.85 out of 5 average rating, 160 reviews

Sag Harbor House for rent.

The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.

Home in East Haven

4.89 out of 5 average rating, 102 reviews

Welcome To Piper's Rest

Top guest favorite

A traditional two-story house is framed by well-maintained greenery and shrubs. A paved driveway leads to the entrance, while a detached garage is visible to the side. The exterior features white siding with red trim and multiple windows, creating a welcoming appearance.

Home in Southampton

4.96 out of 5 average rating, 120 reviews

4 Bed, 2 Bath, Southampton, L.I.

A spacious saltwater pool is surrounded by a well-manicured yard, featuring lounge chairs and large umbrellas. Water features create gentle splashes, enhancing the serene environment. The area is framed by trees, providing a natural backdrop for relaxation.

Home in Westhampton Beach

4.97 out of 5 average rating, 73 reviews

Brand new house with an all year round hot tub.

Top guest favorite

A charming single-story house features a classic shingle exterior with a brick chimney. A spacious front deck is bordered by white railings and overlooks a manicured lawn surrounded by trees. Soft sunlight filters through the leaves, enhancing the serene setting.

Home in East Hampton

4.95 out of 5 average rating, 230 reviews

Private beach, fully updated house, on 2 acres.

A neatly landscaped exterior features a charming entryway with a brick pathway leading to the front door. Flanked by mature shrubs and seasonal flowers, the home is designed with a textured façade, windowed accents, and a stairway that invites guests indoors.

Home in Lake Ronkonkoma

4.58 out of 5 average rating, 137 reviews

Spacious 3 Bdrm Bohemia Holbrook Stony Brook

A spacious living room features cathedral ceilings and a fireplace, surrounded by large windows that allow natural light to fill the space. Comfortable seating is arranged around a circular coffee table, complemented by decorative nautical elements on a cabinet.

Home in Hampton Bays

4.89 out of 5 average rating, 100 reviews

Hamptons Escape minutes from Beaches and Nightlife

A bright living area is illuminated by natural light through large windows. A decorative black wall with a welcome message adds character. A comfortable seating arrangement and dining space is featured. Art pieces are displayed, enhancing the creative ambiance of the space.

Home in Montauk

4.99 out of 5 average rating, 101 reviews

6 minute walk to Ditch Plains Beach

Beach house rentals in Southampton

A stunning view of the beach and water extends from a balcony. The calm sea reflects the sky's hues, while a sandy shore and a low wooden dock are visible. Bright sunlight illuminates the scene from a hanging light fixture above.

Home in Milford

4.84 out of 5 average rating, 56 reviews

Newly Built Beach House Getaway

A spacious living room features a high ceiling with large windows allowing natural light. A staircase leads to an upper level. Comfortable seating is arranged around a coffee table, with art displayed on the walls, including framed pieces and a large stone accent.

Home in East Patchogue

4.79 out of 5 average rating, 150 reviews

Bay's Edge Vacation Get a Way

A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.

Home in West Haven

4.95 out of 5 average rating, 19 reviews

Beach House steps from sand & Amazing Views

An aerial view captures a series of beach cottages along a sandy shoreline. The highlighted cottage sits prominently, showcasing its close proximity to the water. The surrounding area features expansive beaches and residential structures, with a backdrop of distant grassy land.

Home in Milford

4.91 out of 5 average rating, 43 reviews

The Seashell House

Home in Woodmont

4.9 out of 5 average rating, 20 reviews

Bohemian Beach Oasis- Private Beach

A staircase leading from the second floor descends towards the beach, providing a view of the calm ocean. The sandy shore is visible, along with distant boats on the water. Lush greenery borders the lower area, enhancing the coastal scenery.

Home in Milford

5 out of 5 average rating, 9 reviews

Renovated House on Private Cedar Beach

A modern living space features a mounted flat-screen TV on a white wall, complemented by a sleek black cabinet. A small white desk with a chair is positioned nearby, and natural light floods the area from a light fixture above. Stairs lead to the upper level.

Home in Milford

4.92 out of 5 average rating, 25 reviews

Modern Beach Mood 2!

A charming beachside home is showcased, featuring a wrap-around porch with seating. The sandy beachfront extends along the water's edge, and a clear blue sky overhead enhances the coastal atmosphere. Nearby houses are visible, offering a sense of community along the shore.

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

Lakefront house rentals in Southampton

The bedroom features a patterned bedspread and cozy pillows, with two windows providing natural light. Glass doors lead to a private deck overlooking the lake, framed by a simple rug and an outdoor seating area, enhancing the connection to the serene waterfront.

Home in North Fork

4.94 out of 5 average rating, 31 reviews

Waterfront NoFo Cottage w/ public beach access

Large glass doors create a connection to the outdoors, allowing views of greenery and water. A hammock hangs outside, emphasizing relaxation. A spacious seating area is faintly visible, complemented by a wooden table and white chairs. Decorative hats are placed on the shelf above the doorway.

Home in Montauk

4.95 out of 5 average rating, 62 reviews

Waterfront Home with Private Beach

A spacious two-story house is depicted, featuring a wooden exterior and a wraparound deck on the upper level. Large windows allow natural light to illuminate the interior. Surrounding greenery enhances the serene outdoor environment, providing ample space for relaxation and outdoor activities.

Home in Montauk

4.94 out of 5 average rating, 35 reviews

Lake View & Access, Newly Renovated Montauk Oasis

A modern kitchen features sleek white cabinetry and a large island with bar seating for four. Two woven pendant lights hang above, illuminating the space. Large windows allow natural light to fill the room, enhancing the open and airy atmosphere.

Home in Westhampton

5 out of 5 average rating, 13 reviews

1940’s Westhampton renovated bungalow

The entrance of a coastal cottage is framed by natural wood shingles. A light blue door stands out under a covered porch, surrounded by potted flowers in white and purple. Lanterns add gentle illumination, while a decorative pumpkin and a blue pumpkin provide seasonal accents.

Home in North Fork

4.91 out of 5 average rating, 23 reviews

Coastal Cottage on the Water

A charming cottage-style home is set amid lush greenery, featuring a covered porch with white railings. A gravel pathway leads to the entrance, surrounded by manicured shrubs and a well-kept lawn. The exterior is finished with natural wood siding and a sloped gray roof.

Home in Hampton Bays

5 out of 5 average rating, 3 reviews

Hamptons Waterview Cottage

A sunset casts golden hues over the water from a waterfront deck, showcasing the tranquil bay. Two images feature a sandy beach with gentle waves and a spacious patio adorned with green grass and seating for relaxation.

Home in North Fork

4.75 out of 5 average rating, 4 reviews

Beachfront Retreat - 5BR Home with Stunning Views

A well-maintained exterior showcases a multi-level stone pathway leading to a beautifully designed house, surrounded by lush foliage. A peaceful water feature is visible in the foreground, along with ornamental grass and various plants that enhance the natural setting.

Home in Bayport

4.83 out of 5 average rating, 164 reviews

Luxury Waterfront Oasis • Modern Retreat for 8

Quick stats about vacation rentals in Southampton

Total rentals
640 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
7.8K reviews
Family-friendly rentals
400 properties are a good fit for families
Pet-friendly rentals
250 properties allow pets
Rentals with a pool
370 properties have a pool

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Southampton?
Yes! Work meets play with ease at over 280 vacation rentals in Southampton featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Southampton?
Experience the best of Southampton with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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 250 vacation rentals for guests traveling with pets.
Are there Southampton house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 300 house 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.
Are there family-friendly house rentals in Southampton?
Southampton has more than 340 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore