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
Guest suite in Hampton Bays
CHARMING OCEAN BUNGALOW
My ocean Bungalow is super well located in Hampton Bays. You will be 10 minutes away from the center of town where the Hampton Bays train station is. You also have Starbucks, Ride Aid, king Kullen, and great eateries at your fingertips. You will also have another two great supermarkets; Stop&Shop and Wild by Nature natural food store. You will be staying in a room with a feeling of a Junior Suite with approximately 400sq feet, a much larger area than a standard room. It has an attached small full bathroom, a living space that I call “home theater” with a 75” smart TV, a wet Bar with Coffee, Expresso and Tea, your own refrigerator. No heavy cooking is allowed indoors but I will offer a grill outside, for the most gastronomically inclined guests ... there’s no dining area but you are more welcome to use the dining table at the outdoor stone patio. One of the nicest thing about our location is that we are 5 minutes from Ponquogue Beach with excellent near by restaurants such as Oklands, Sundays on the Bay, on Beach Road and Dockers waterside on Dune Road. Meschutt beach is also a great location with live music throughout the summer, not a beach for surfers or adventure swimmers, since it’s on Peconic Bay, but on a plus side, there’s a full outdoor bar for adults, I love their Rum punch, and a full service snack bar, and a gift shop that sells beach gear... etc.
Apr 18 – 25
$110 per night
4.98 out of 5 average rating, 310 reviews
Guest favorite
Guesthouse in Hampton Bays
WELCOME TO THE LOVE SHACK BY THE SEA
Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.
Sep 13 – 20
$409 per night
4.96 out of 5 average rating, 145 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 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!
May 8 – 15
$278 per night
4.95 out of 5 average rating, 411 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
Stony Brook Southampton Hospital13 locals recommend
75 Main36 locals recommend
Saaz19 locals recommend
Southampton Publick House37 locals recommend

Southampton beach vacation rentals

Guest favorite
Home in East Hampton
Ritz-East Hampton Cottage- 5 stars
Sep 2 – 9
$629 per night
4.96 out of 5 average rating, 187 reviews
Guest favorite
Home in Sag Harbor
Sag Harbor Cottage, Walk to the Beach!
Jul 11 – 18
$791 per night
4.96 out of 5 average rating, 253 reviews
Guest favorite
Guest suite in Sag Harbor
Artists Sag Harbor Village Retreat
Apr 18 – 25
$213 per night
4.88 out of 5 average rating, 308 reviews
Guest favorite
Home in Hampton Bays
Beach House Feel - newly renovated backyard Oasis
Apr 30 – May 7
$360 per night
4.98 out of 5 average rating, 112 reviews
Guest favorite
Cottage in Riverhead
Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Apr 26 – May 3
$650 per night
4.98 out of 5 average rating, 126 reviews
Guest favorite
Guest suite in Sag Harbor
Old World Charm Private Suite with Own Entrance
Mar 28 – Apr 2
$209 per night
4.89 out of 5 average rating, 126 reviews
Guest favorite
Apartment in Hampton Bays
The House of the Mermaid aka La Casa della Sirena
May 13 – 20
$171 per night
4.96 out of 5 average rating, 268 reviews
Guest favorite
Guest suite in Hampton Bays
Beautiful, Bright 3 room suite w/private entrance
Oct 21 – 28
$220 per night
4.96 out of 5 average rating, 114 reviews
Guest favorite
Apartment in Hampton Bays
Vacation at the Beach: Entire Home
Dec 21 – 28
$271 per night
4.84 out of 5 average rating, 131 reviews
Guest favorite
Home in East Hampton
Silver House: 3BR Home with Private Beach Access
May 16 – 23
$372 per night
4.95 out of 5 average rating, 363 reviews
Guest favorite
Guest suite in Wading River
Beachy En Suite /Gateway to The North Fork
Sep 6 – 13
$101 per night
4.9 out of 5 average rating, 226 reviews
Guest favorite
Bungalow in Hampton Bays
Hamptons Waterfront- Great Location!
Aug 5 – 12
$641 per night
5.0 out of 5 average rating, 110 reviews

Southampton house rentals

Guest favorite
Home in Southampton
4 Bed, 2 Bath, Southampton, L.I.
Jan 16 – 23
$350 per night
4.95 out of 5 average rating, 109 reviews
Guest favorite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
Sep 14 – 21
$533 per night
4.97 out of 5 average rating, 121 reviews
Guest favorite
Home in Sag Harbor
Luxury Private King Suite + 2 Floor Living Space
Nov 5 – 12
$369 per night
4.95 out of 5 average rating, 129 reviews
Guest favorite
Home in East Hampton
Explore the Water & Woods at a Relaxing Retreat
Oct 27 – Nov 3
$794 per night
4.97 out of 5 average rating, 116 reviews
Guest favorite
Home in East Hampton
East Hampton (walking distance to village)
Nov 28 – Dec 5
$607 per night
4.97 out of 5 average rating, 118 reviews
Guest favorite
Home in East Hampton
1800 Historical East Hampton Home, 1 Mile to Town!
Dec 5 – 12
$650 per night
4.93 out of 5 average rating, 137 reviews
Guest favorite
Home in East Hampton
Private beach Historical House with large property
Jan 15 – 22
$475 per night
4.94 out of 5 average rating, 200 reviews
Guest favorite
Home in Southampton
Bay View Stunner, Modern 6 Bedroom w Heated Pool
Apr 10 – 17
$293 per night
5.0 out of 5 average rating, 36 reviews
Guest favorite
Home in Southampton
Perfect Lake Cottage weekend Hamptons special
Jan 19 – 26
$696 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Southampton
Scandinavian Cottage
Apr 30 – May 7
$296 per night
4.91 out of 5 average rating, 33 reviews
Guest favorite
Home in Southampton
Luxury Hamptons Poolside Paradise w/ Outdoor Sauna
Dec 12 – 19
$638 per night
5.0 out of 5 average rating, 31 reviews
Guest favorite
Home in Sag Harbor
Modern Home in Sag Harbor, NY
May 16 – 23
$681 per night
4.84 out of 5 average rating, 45 reviews

Beach house rentals in Southampton

Guest favorite
Home in Greenport
The Sandpiper- Apt #1
Feb 6 – 13
$120 per night
4.96 out of 5 average rating, 297 reviews
Guest favorite
Home in Montauk
DITCH PLAINS SURF HOUSE
Nov 19 – 26
$244 per night
4.91 out of 5 average rating, 411 reviews
Superhost
Home in Hampton Bays
Nautical Cottage Near Beach, Wineries, Golf, Shops
Feb 20 – 27
$479 per night
4.88 out of 5 average rating, 216 reviews
Guest favorite
Home in East Hampton
Charming Quiet Cottage
Feb 5 – 12
$250 per night
4.91 out of 5 average rating, 142 reviews
Guest favorite
Home in East Hampton
Kid-friendly, heated pool, games room, near beach
May 29 – Jun 5
$950 per night
4.92 out of 5 average rating, 125 reviews
Guest favorite
Home in Center Moriches
Walk to beach and playground. Outdoor hot tub.
Oct 19 – 26
$313 per night
4.98 out of 5 average rating, 185 reviews
Guest favorite
Home in Greenport
The Greenport Bungalow
Aug 15 – 22
$496 per night
4.97 out of 5 average rating, 217 reviews
Guest favorite
Home in Shelter Island
Shelter island retreat
Mar 31 – Apr 7
$405 per night
4.97 out of 5 average rating, 156 reviews
Guest favorite
Home in Greenport
Nofo Bungalow-In The Heart of Greenport Village
Jul 14 – 21
$499 per night
4.98 out of 5 average rating, 162 reviews
Guest favorite
Home in Southampton
Tranquility at the Water’s Edge
Dec 31 – Jan 7
$613 per night
5.0 out of 5 average rating, 20 reviews
Guest favorite
Home in Southampton
Spectacular Southampton Retreat!
Jan 10 – 17
$467 per night
4.89 out of 5 average rating, 19 reviews
Guest favorite
Home in Southampton
Breezy Waterfront Home With private Dock
Apr 17 – 24
$491 per night
4.98 out of 5 average rating, 90 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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