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Southampton vacation rentals

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Top-rated vacation rentals in Southampton

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

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A spacious living room is furnished with a light gray sectional sofa and a wooden coffee table featuring a multi-colored pattern. Large windows allow natural light to fill the area, and framed photographs adorn the walls, enhancing the cozy setting.

Home in Mastic

4.88 out of 5 average rating, 99 reviews

Cozy home. Comfy living

The whole group will enjoy easy access to everything from this centrally located home. three comfortable bedroom and two bathrooms with a 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. Grace period of 15 mins after check is given after that fees will incur at the nightly rate.

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

The exterior of a multi-story building is presented, featuring a combination of gray siding and a gabled roof. Natural landscaping surrounds the entrance, including ornamental grasses and bushes. Sunlight filters through the trees, creating a serene atmosphere in the outdoor space.

Guest suite in Branford

4.9 out of 5 average rating, 100 reviews

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

The spacious patio is shaded by a vine-covered pergola, featuring a round dining table surrounded by black chairs. Lounge chairs are positioned nearby, and the yard extends beyond, showcasing green grass and a variety of plants, contributing to an inviting outdoor space.

Home in North Fork

4.93 out of 5 average rating, 107 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.

Home in Westhampton Beach

5 out of 5 average rating, 4 reviews

Summer Main Home plus cottage close to Main Street

Come relax and enjoy! Beautifully updated Main home with separate cottage. Perfect for in-laws and guests. Each home has its own kitchen, living space, washer/dryer, and outdoor seating. Main house: 4 Br, 3 ba Cottage: 2 Br, 1 ba Outdoor shower for an after beach rinse, 2 patios, pergola, hammock, bbq. A two person kayak available for use; beach passes included. Games, internet, tv... Walk to coffee shops, restaurants, worship, and marina. Bike to beach.

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, 10 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 aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.

Home in Milford

5 out of 5 average rating, 100 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌟 Special Discounts on Early Birds, Last-Minute Stays & 7+ Nights! 🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

A rocky shoreline is framed by a silhouetted tree against a colorful sunset. Clouds display shades of pink and orange as the sun sets over the water, creating a serene atmosphere. The beach area offers a peaceful view of nature.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay 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$.

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, 175 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.

A spacious outdoor deck features a hot tub and comfortable seating area, surrounded by lush greenery. The inviting hot tub offers a relaxing retreat, while the seating includes a large sofa and a coffee table, creating an ideal space for outdoor gatherings.

Home in Montauk

4.91 out of 5 average rating, 46 reviews

Montauk Family Gem: HotTub, Pro Kitchen, Fireplace

Escape to your perfect Montauk getaway! Nestled on a secluded, beautifully landscaped lot at the end of a quiet dead-end street, this recently renovated 4-bedroom, 3.5-bathroom beach house offers the ultimate combination of luxury, comfort, and privacy. We are also pet friendly!

A traditional New England-style house features a front porch supported by white columns. Two white chairs and a small table are arranged on the porch, complemented by a dark front door. Large windows allow natural light to fill the space, surrounded by green landscaped areas.

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...

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, Southampton112 locals recommend

Parrish Art Museum262 locals recommend

Oakland's Restaurant & Marina104 locals recommend

Village of Southampton98 locals recommend

Duck Walk Vineyards94 locals recommend

Sant Ambroeus83 locals recommend

Southampton beach vacation rentals

Outdoor seating is arranged on a wooden deck, featuring sleek loungers. Surrounding planters add greenery, while the view stretches to the calm water and distant horizon. Sunlight brightens the area, enhancing the serene ambiance of the beachfront setting.

Cottage in North Fork

4.97 out of 5 average rating, 150 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

A wide-angle view captures the beach and waterfront community, showcasing houses lined along the shore. A sandy beach meets calm waters, with a jetty extending into the sea. Fluffy clouds float in a clear blue sky above the scenic landscape.

Guesthouse in Milford

4.92 out of 5 average rating, 204 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.

Cabin in Shirley

4.86 out of 5 average rating, 142 reviews

A-Frame cabin with private beach & epic sunsets

Home in Westbrook

4.82 out of 5 average rating, 11 reviews

Beachside @ 455 Seaside

A patio area features a round table surrounded by multiple chairs, positioned on a stone pathway. A few lounge chairs are placed nearby, with low shrubs and neatly trimmed grass framing the scene. A set of stairs leads to the entrance of the house.

Home in Shirley

4.9 out of 5 average rating, 136 reviews

Cope near the beach

Home in Old Saybrook

4.97 out of 5 average rating, 120 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

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, 149 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

4.94 out of 5 average rating, 18 reviews

Beach House steps from sand & Amazing Views

Southampton house rentals

The living area features a blend of comfortable seating options, including a sofa and armchairs. Large windows allow natural light to flow in, and a cozy stove is positioned prominently. A dining table with chairs is visible, along with decorative accents, such as mirrors and art pieces.

Home in Ocean Bay Park

4.96 out of 5 average rating, 27 reviews

Ocean Bay Park - Now booking 2025 Season.

A cozy living area features a light-colored sofa adorned with blue and white throw pillows. Woven armchairs flank a wooden coffee table, while a stone fireplace adds warmth. Two large windows allow natural light to fill the space, complemented by greenery and decorative accents.

Home in Montauk

4.98 out of 5 average rating, 90 reviews

Sea Roost

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.

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, 119 reviews

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

An outdoor area features a large saltwater pool with a colorful float in the center. Adjacent to the pool, a spa is integrated into the stone patio. Lush greenery surrounds the space, providing privacy, with sun loungers arranged neatly along the edge.

Home in Southampton

5 out of 5 average rating, 14 reviews

Pool&Spa open till December

Home in Westhampton Beach

4.97 out of 5 average rating, 67 reviews

Brand new house with an all year round hot tub.

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, 228 reviews

Private beach Historical House with large property

A serene backyard scene features a spacious, well-maintained pool surrounded by a manicured lawn. The two-story home with a red exterior is situated behind the pool, framed by lush greenery and trees. Comfortable lounge chairs are positioned around the pool for relaxation.

Home in Hampton Bays

4.89 out of 5 average rating, 85 reviews

Perfect Hamptons Summer Rental with Pool

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

4.83 out of 5 average rating, 54 reviews

Newly Built Beach House Getaway

An aerial view showcases the beach house's location amidst lush marshland and distant water. The neighborhood features a mix of homes, green spaces, and winding roads, with access to scenic coastal views just beyond.

Home in Old Saybrook

5 out of 5 average rating, 15 reviews

Cornfield Point Beach House View

Home in Old Saybrook

4.84 out of 5 average rating, 44 reviews

Chalker Beach House Steps to the Water

A spacious dining area features a large wooden table surrounded by wooden chairs, accommodating numerous guests. Natural light floods in through large windows with light-filtering shades, enhancing the inviting atmosphere. The room's design emphasizes simplicity and functionality, ideal for shared meals and gatherings.

Home in East Lyme

5 out of 5 average rating, 10 reviews

Black Point Retreat - Entertain & Enjoy the Beach!

A bright living room features a spacious white sofa, complemented by two blue armchairs, and a round coffee table centered on a patterned area rug. Natural light fills the space through large windows, highlighting a cozy fireplace and decorative elements on a console.

Home in Milford

5 out of 5 average rating, 5 reviews

Seaside Paradise

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 light green two-story house is surrounded by lush greenery and young trees. A stone pathway is visible leading up to the entrance, framed by ferns and a gravel area, creating a serene outdoor space.

Home in East Hampton

5 out of 5 average rating, 3 reviews

The beach house.

Quick stats about vacation rentals in Southampton

Total rentals
650 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
7.7K reviews
Family-friendly rentals
410 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 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 260 vacation rentals for guests traveling with pets.
Are there Southampton vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 380 vacation homes with pools in Southampton, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in villa rentals in Southampton?
Experience the best of Southampton with our villa rentals, starting at about $260 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Southampton have a bbq area?
Absolutely! We offer over 160 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 80 house rentals with a gym in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Southampton have self check-in?
Absolutely! We offer over 10 apartment rentals with self check-in in Southampton. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Southampton?
Southampton has more than 420 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore