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.

Guest favorite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
Take a bike ride to Havens Beach and feel the sand in your toes. Walk to explore the shops, restaurants and bars on the quaint Main Street of Sag Harbor. Repair to your sun drenched home away from home to enjoy a relaxed meal alfresco on the deck. Unwind under the umbrellas on the expansive deck surveying the private fenced in backyard. Take in all the amenities of a newly renovated home situated in the Hampton - recent updates include a furnished basement, ping pong table, smart TVs and sound system. Extra touches include beach towels, beach chairs, bikes, cooler, games and more. This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4 skylights and large windows to bring the outdoors in. Brand new appliances, custom kitchen cabinets, large center island with bar stools are perfect for hosting friends & family. Central AC/forced air heating controlled by the Nest ensure your complete comfort. The master BR features a king bed and ensuite Bath with custom tile shower. The guest BRs have a queen bed and full bed respectively and share the hall bathroom with tub/shower. The large deck runs the length of the home and is perfect for al fresco dining & entertaining. Totally furnished with everything you need to enjoy yourself from the second you enter the home! We have four brand new adult bikes, helmets and locks for your enjoyment. Explore the village, bike to the beach or get some exercise while you're here. If you prefer to stay in, you'll find a games console / DVD player in the front room with a good selection of games and movies. Additionally, we provide 4 beach chairs, beach towels and a small cooler for your use. Enjoy! Guests have access to the entire house, backyard, deck, garage and driveway parking. We can be reached via cell or email and are very responsive. We will also have a friend who is local to the area who will be able to assist with any issues. Sag Harbor is the coolest, most authentic town in the Hamptons. Home to household names, the town retains its small-town charm and rustic maritime vibe. Browse the artsy, eclectic stores and strike up conversations in the coffee shops and local bars. Sag Harbor is a quaint, walkable town on the wharf with great restaurants and bars. The house is located less than a mile's walk into the main street. Beaches are accessible via bike or car. The Jitney stop from Manhattan is located on Main Street less than a mile from the house. There are taxis in the area available via phone for pick up. We provide four adult bikes, helmets and locks for your use.
Mar 16 – 23
$288 per night
4.97 out of 5 average rating, 120 reviews
Guest favorite
Guesthouse in Southampton
Tiny Home in Prime Spot in Southampton Village
Located in the heart of Southampton Village, this intimate, centrally-located cottage is the ideal 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!
Apr 29 – May 6
$278 per night
4.95 out of 5 average rating, 409 reviews
Guest favorite
Cottage in Southampton
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.
Oct 18 – 25
$384 per night
4.96 out of 5 average rating, 160 reviews

Popular amenities for Southampton vacation rentals

Stay near Southampton's top sights

Citarella Gourmet Market - Southampton66 locals recommend
Tate's Bake Shop76 locals recommend
75 Main36 locals recommend
Saaz19 locals recommend
Southampton Publick House37 locals recommend
Stony Brook Southampton Hospital13 locals recommend

Southampton beach vacation rentals

Guest favorite
Guesthouse in Hampton Bays
WELCOME TO THE LOVE SHACK BY THE SEA
Sep 30 – Oct 7
$500 per night
4.96 out of 5 average rating, 145 reviews
Guest favorite
Apartment in Sag Harbor
Sag Harbor Retreat
Jun 17 – 24
$750 per night
4.98 out of 5 average rating, 116 reviews
Guest favorite
Guest suite in Cutchogue
Walk to Vineyards, Beaches, Farms & Town
Mar 3 – 10
$141 per night
4.88 out of 5 average rating, 578 reviews
Guest favorite
Home in Hampton Bays
Beach House Feel - newly renovated backyard Oasis
Apr 24 – May 1
$360 per night
4.98 out of 5 average rating, 112 reviews
Guest favorite
Guest suite in Hampton Bays
CHARMING OCEAN BUNGALOW
Aug 10 – 17
$250 per night
4.98 out of 5 average rating, 308 reviews
Guest favorite
Apartment in Hampton Bays
Private & Cozy Cottage with short walk to beach!
Sep 19 – 26
$248 per night
4.97 out of 5 average rating, 340 reviews
Guest favorite
Home in Sag Harbor
Sag Harbor Cottage, Walk to the Beach!
Jun 6 – 13
$565 per night
4.96 out of 5 average rating, 253 reviews
Guest favorite
Cottage in Riverhead
Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Dec 7 – 14
$650 per night
4.98 out of 5 average rating, 126 reviews
Guest favorite
Guest suite in Sag Harbor
Artists Sag Harbor Village Retreat
Oct 22 – 29
$251 per night
4.88 out of 5 average rating, 307 reviews
Guest favorite
Apartment in Hampton Bays
Vacation at the Beach: Entire Home
May 17 – 24
$342 per night
4.84 out of 5 average rating, 131 reviews
Guest favorite
Home in East Hampton
Private beach Historical House with large property
Feb 24 – Mar 3
$475 per night
4.94 out of 5 average rating, 198 reviews
Guest favorite
Home in East Hampton
Silver House: 3BR Home with Private Beach Access
May 4 – 11
$299 per night
4.95 out of 5 average rating, 358 reviews

Southampton house rentals

Guest favorite
Home in East Hampton
Ritz-East Hampton Cottage- 5 stars
Jul 4 – 11
$700 per night
4.96 out of 5 average rating, 187 reviews
Guest favorite
Home in Southampton
Peaceful Hamptons Cottage
May 30 – Jun 6
$382 per night
4.9 out of 5 average rating, 178 reviews
Guest favorite
Home in Sag Harbor
Sag Harbor home away from home
Dec 23 – 30
$381 per night
4.97 out of 5 average rating, 169 reviews
Guest favorite
Home in Southampton
Southampton Village Classic Summer Special!
Mar 23 – 30
$677 per night
4.95 out of 5 average rating, 246 reviews
Guest favorite
Home in Southampton
Waterview DogsStayFree! Kayaks Fireplace Ping-Pong
Oct 31 – Nov 7
$643 per night
4.96 out of 5 average rating, 127 reviews
Guest favorite
Home in Sag Harbor
Luxury Private King Suite + 2 Floor Living Space
Feb 11 – 18
$369 per night
4.95 out of 5 average rating, 129 reviews
Guest favorite
Home in Southampton
Spacious House in Southampton Village
Mar 14 – 21
$853 per night
4.96 out of 5 average rating, 157 reviews
Guest favorite
Home in Southampton
Contemporary house in the woods.
Apr 4 – 11
$411 per night
4.98 out of 5 average rating, 111 reviews
Guest favorite
Home in Southampton
4 Bed, 2 Bath, Southampton, L.I.
Oct 31 – Nov 7
$364 per night
4.95 out of 5 average rating, 109 reviews
Guest favorite
Home in East Hampton
1800 Historical East Hampton Home, 1 Mile to Town!
Apr 29 – May 6
$614 per night
4.93 out of 5 average rating, 137 reviews
Guest favorite
Home in Shelter Island
Huge Island Getaway Pool HotTub Walk To Beach
Nov 21 – 28
$687 per night
4.97 out of 5 average rating, 182 reviews
Guest favorite
Home in East Hampton
Explore the Water & Woods at a Relaxing Retreat
Jun 3 – 10
$888 per night
4.97 out of 5 average rating, 112 reviews

Beach house rentals in Southampton

Guest favorite
Home in Montauk
DITCH PLAINS SURF HOUSE
Nov 21 – 28
$294 per night
4.9 out of 5 average rating, 407 reviews
Guest favorite
Home in Greenport
The Greenport Bungalow
Aug 23 – 30
$495 per night
4.97 out of 5 average rating, 214 reviews
Guest favorite
Home in Shelter Island
Shelter island retreat
Feb 4 – 11
$405 per night
4.97 out of 5 average rating, 156 reviews
Guest favorite
Home in Center Moriches
Walk to beach and playground. Outdoor hot tub.
Jun 18 – 25
$329 per night
4.98 out of 5 average rating, 185 reviews
Guest favorite
Home in East Hampton
HeatedSaltWaterPool-Walk2Beach-Fireplace-Yard4Pup
Mar 27 – Apr 3
$331 per night
4.87 out of 5 average rating, 188 reviews
Guest favorite
Home in Hampton Bays
Nautical Cottage Near Beach, Wineries, Golf, Shops
Jul 19 – 26
$775 per night
4.88 out of 5 average rating, 216 reviews
Guest favorite
Home in East Hampton
Kid-friendly, heated pool, games room, near beach
Jun 9 – 16
$950 per night
4.92 out of 5 average rating, 124 reviews
Guest favorite
Home in Shirley
Luxurious Beachfront home on the Bay/Amazing views
Jan 13 – 20
$450 per night
4.99 out of 5 average rating, 175 reviews
Guest favorite
Home in Greenport
Nofo Bungalow-In The Heart of Greenport Village
Aug 9 – 16
$499 per night
4.98 out of 5 average rating, 160 reviews
Guest favorite
Home in Rocky Point
The Katalpa House -by the beach
Dec 14 – 21
$136 per night
4.92 out of 5 average rating, 173 reviews
Guest favorite
Home in East Hampton
Charming Quiet Cottage
Nov 19 – 26
$300 per night
4.91 out of 5 average rating, 142 reviews
Guest favorite
Home in Southampton
Beautiful Southampton Home
Mar 12 – 19
$450 per night
5.0 out of 5 average rating, 18 reviews

Quick stats about vacation rentals in Southampton

Total rentals

640 properties

Rentals with a pool

340 properties have a pool

Pet-friendly rentals

260 properties allow pets

Family-friendly rentals

390 properties are a good fit for families

Total number of reviews

7.3K reviews

Nightly prices starting at

$10 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Southampton?

    Yes! Work meets play with ease at over 260 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 340 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 house rentals in Southampton?

    Experience the best of Southampton with our house rentals, starting at about $80 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 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 320 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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