Holiday rentals in Southampton

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Top-rated holiday rentals in Southampton

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

Guest favourite
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.
18–25 Apr
$147 SGD per night
4.98 out of 5 average rating, 310 reviews
Guest favourite
Guest house 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.
13–20 Sep
$548 SGD per night
4.96 out of 5 average rating, 145 reviews
Guest favourite
Guest house 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!
8–15 May
$372 SGD per night
4.95 out of 5 average rating, 411 reviews

Popular amenities for Southampton holiday 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

Other great holiday rentals in Southampton

Guest favourite
Home in Southampton
Perfect Lake Cottage weekend Hamptons special
19–26 Jan
$932 SGD per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Southampton
Luxury Hamptons Poolside Paradise w/ Outdoor Sauna
12–19 Dec
$853 SGD per night
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Southampton
Spectacular Village Home: Close to Town and Ocean
11–18 May
$631 SGD per night
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Sag Harbor
Modern Home in Sag Harbor, NY
16–23 May
$912 SGD per night
4.84 out of 5 average rating, 45 reviews
Guest favourite
Guest house in Southampton
Southampton Modern Barn, Private Hot Tub and Pool
24–31 Jul
$1,118 SGD per night
4.98 out of 5 average rating, 45 reviews
Guest favourite
Home in Water Mill
WaterMill Oasis w/ Pool Close to Beach&Village!
24–31 Mar
$607 SGD per night
4.86 out of 5 average rating, 14 reviews
Guest favourite
Home in Southampton
Beautiful Southampton Village Home with Pool
25 May – 1 Jun
$1,262 SGD per night
4.97 out of 5 average rating, 35 reviews
Guest favourite
Cottage in Southampton
Towd Point Beach Treasure | 14 min walk to beach
25 Mar – 1 Apr
$390 SGD per night
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Southampton
"The Bungalow" Southampton Village
26 Aug – 2 Sep
$688 SGD per night
4.91 out of 5 average rating, 33 reviews
Guest favourite
Home in Southampton
Tranquility at the Water’s Edge
31 Dec – 7 Jan
$820 SGD per night
5.0 out of 5 average rating, 20 reviews
Guest favourite
Cottage in Southampton
Modern Southampton Cottage | Heated Pool & Peloton
19–26 Sep
$798 SGD per night
4.93 out of 5 average rating, 60 reviews
Guest favourite
Holiday home in Southampton
5BR, Luxury Home, Pool, Yard Close to Beach & Town
18–25 Nov
$889 SGD per night
5.0 out of 5 average rating, 39 reviews

Quick stats about holiday 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

$13 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Southampton