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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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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!

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.

Apartment in Southampton

4.96 out of 5 average rating, 27 reviews

Beautiful Sunny one bedroom apt in SH. NY.

Enjoy a stylish experience at this centrally-located place. This stunningly-beautiful sunny apartment is located in the heart of Southampton New York, where the sea and the earth elements create the most peaceful setting. The apartment has a private entrance and private bathroom, is located at a short walking distance to Main Street, library, grocery stores, restaurants, shopping stores and pharmacies. PLEASE NOTE: PETS ARE NOT ALLOWED. QUITE TIME 10 PM -9AM

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.

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!

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$.

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.

Home in Hampton Bays

5 out of 5 average rating, 25 reviews

Convenient 2 Bedroom Hampton’s Getaway

Your family will be close to everything when you stay at this centrally-located beach house . Close to beaches, restaurants and shopping. Biking and walking distance to Town and Ocean. You can also take advantage of our close proximity to the North Fork and the wineries. Montauk is about 35 miles east.

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...

Apartment in Montauk

4.93 out of 5 average rating, 193 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

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

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

Cottage in North Fork

4.97 out of 5 average rating, 150 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Apartment in North Fork

4.86 out of 5 average rating, 7 reviews

Beach House - Apt 2

Cabin in Shirley

4.86 out of 5 average rating, 141 reviews

A-Frame cabin with private beach & epic sunsets

Home in Madison

5 out of 5 average rating, 14 reviews

Beach Home & Garden Paradise

Apartment in Montauk

4.89 out of 5 average rating, 66 reviews

Ocean View Studio with King Bed

Home in Shirley

4.9 out of 5 average rating, 135 reviews

Cope near the beach

Home in Clinton

4.95 out of 5 average rating, 118 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

Home in East Patchogue

4.79 out of 5 average rating, 149 reviews

Bay's Edge Vacation Get a Way

Southampton house rentals

Home in Hampton Bays

4.96 out of 5 average rating, 25 reviews

4BR Gem in Hampton Bays, Near the beach

Home in Hampton Bays

4.76 out of 5 average rating, 80 reviews

Cozy 4-bedroom home close to the beach & town

Home in Sag Harbor

4.85 out of 5 average rating, 160 reviews

Sag Harbor House for rent.

Home in Southampton

4.96 out of 5 average rating, 119 reviews

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

Home in Westhampton Beach

4.97 out of 5 average rating, 64 reviews

Brand new house with an all year round hot tub.

Home in Manorville

4.98 out of 5 average rating, 246 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Home in Sag Harbor

5 out of 5 average rating, 13 reviews

Near Beach & Sag Harbor in the Heart of Hamptons!

Home in North Fork

4.93 out of 5 average rating, 258 reviews

Dream Get Away

Beach house rentals in Southampton

Home in Montauk

4.97 out of 5 average rating, 37 reviews

Beach Front House

Home in Old Saybrook

5 out of 5 average rating, 15 reviews

Cornfield Point Beach House View

Home in West Haven

4.75 out of 5 average rating, 32 reviews

Coastal Cottage.

Home in Westhampton Beach

4.96 out of 5 average rating, 26 reviews

Dune Rd Village Waterfront Private Beach Access

Home in Woodmont

4.94 out of 5 average rating, 18 reviews

Bohemian Beach Oasis- Private Beach

Home in Fenwick

5 out of 5 average rating, 3 reviews

Fenwood Coastal Getaway Private Beach Access

Home in Montauk

4.71 out of 5 average rating, 21 reviews

The Raffle Beach House

Home in East Hampton

5 out of 5 average rating, 3 reviews

The beach house.

Quick stats about vacation rentals in Southampton

Total rentals
670 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
7.5K reviews
Family-friendly rentals
420 properties are a good fit for families
Pet-friendly rentals
260 properties allow pets
Rentals with a pool
380 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 cottage rentals in Southampton?
Experience the best of Southampton with our cottage rentals, starting at about $130 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