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.
Sep 11 – 18
$250 per night
4.98 out of 5 average rating, 310 reviews
Guest favorite
Guest suite in Sag Harbor
Artists Sag Harbor Village Retreat
January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.
Nov 14 – 21
$213 per night
4.88 out of 5 average rating, 308 reviews
Guest favorite
Home in Southampton
Stunning 3 bed 2 bath home W Pool
Nestled on a serene an acre off a tranquil lane, this contemporary, designer-updated residence provides an idyllic Hamptons retreat. With 3 delightful bedrooms, 2 sleek bathrooms, and a seasonal heated pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. We maintain a strict policy against events, parties, and smoking. Please review the listing to ensure our home aligns with your preferences
May 16 – 23
$404 per night
4.97 out of 5 average rating, 234 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
Guest suite in Cutchogue
Walk to Vineyards, Beaches, Farms & Town
Sep 5 – 12
$141 per night
4.88 out of 5 average rating, 582 reviews
Guest favorite
Home in Sag Harbor
Sag Harbor Cottage, Walk to the Beach!
May 27 – Jun 3
$508 per night
4.96 out of 5 average rating, 253 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
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
Cottage in Riverhead
Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Apr 25 – May 2
$650 per night
4.98 out of 5 average rating, 126 reviews
Guest favorite
Guest suite in Hampton Bays
Beautiful, Bright 3 room suite w/private entrance
Nov 8 – 15
$220 per night
4.96 out of 5 average rating, 114 reviews
Guest favorite
Apartment in Hampton Bays
Vacation at the Beach: Entire Home
Sep 1 – 8
$428 per night
4.84 out of 5 average rating, 131 reviews
Guest favorite
Apartment in Hampton Bays
Charming Maritime Apartment Steps from the Beach
Nov 9 – 16
$201 per night
4.9 out of 5 average rating, 444 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 Sag Harbor
Cedar Haven In Sag Harbor
Nov 30 – Dec 7
$232 per night
4.95 out of 5 average rating, 188 reviews
Guest favorite
Guest suite in East Hampton
Be our guest! King ensuite private pool and entry
May 14 – 21
$400 per night
4.96 out of 5 average rating, 142 reviews
Guest favorite
Apartment in Hampton Bays
The House of the Mermaid aka La Casa della Sirena
May 27 – Jun 3
$175 per night
4.96 out of 5 average rating, 268 reviews

Southampton house rentals

Guest favorite
Home in Southampton
Waterview PoolOpen 3/22 DogsFree+Kayaks+PingPong
Sep 16 – 23
$899 per night
4.96 out of 5 average rating, 129 reviews
Guest favorite
Home in Sag Harbor
Luxury Private King Suite + 2 Floor Living Space
Nov 12 – 19
$369 per night
4.95 out of 5 average rating, 129 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 East Hampton
1800 Historical East Hampton Home, 1 Mile to Town!
Nov 16 – 23
$700 per night
4.93 out of 5 average rating, 137 reviews
Guest favorite
Home in East Hampton
Explore the Water & Woods at a Relaxing Retreat
Nov 22 – 29
$794 per night
4.97 out of 5 average rating, 116 reviews
Superhost
Home in Sag Harbor
Sag Harbor Gem, private, 4 Bedrooms, Pool w Summer
May 2 – 9
$261 per night
4.81 out of 5 average rating, 107 reviews
Guest favorite
Home in Southampton
Perfect Lake Cottage weekend Hamptons special
Jan 18 – 25
$696 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Southampton
Luxury Hamptons Poolside Paradise w/ Outdoor Sauna
Mar 28 – Apr 4
$701 per night
5.0 out of 5 average rating, 31 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
Tranquility at the Water’s Edge
Feb 15 – 22
$512 per night
5.0 out of 5 average rating, 20 reviews
Guest favorite
Home in Southampton
Village Charmer, 5 bedrooms with pool
Apr 5 – 12
$236 per night
4.94 out of 5 average rating, 63 reviews
Guest favorite
Home in Southampton
Beautiful Southampton Village Home with Pool
Nov 10 – 17
$599 per night
4.97 out of 5 average rating, 35 reviews

Beach house rentals in Southampton

Guest favorite
Home in Montauk
DITCH PLAINS SURF HOUSE
May 8 – 15
$492 per night
4.91 out of 5 average rating, 411 reviews
Superhost
Home in Hampton Bays
Nautical Cottage Near Beach, Wineries, Golf, Shops
Feb 19 – 26
$463 per night
4.88 out of 5 average rating, 216 reviews
Guest favorite
Home in East Hampton
Charming Quiet Cottage
Feb 4 – 11
$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 10 – 17
$700 per night
4.92 out of 5 average rating, 125 reviews
Superhost
Home in Greenport
Blue Bay Dream - Apt #2
Dec 21 – 28
$77 per night
4.94 out of 5 average rating, 136 reviews
Guest favorite
Home in Center Moriches
Walk to beach and playground. Outdoor hot tub.
Nov 21 – 28
$324 per night
4.98 out of 5 average rating, 185 reviews
Guest favorite
Home in Shirley
Luxurious Beachfront home on the Bay/Amazing views
Oct 27 – Nov 3
$450 per night
4.98 out of 5 average rating, 177 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
Guest favorite
Home in Southampton
Newly renovated Southampton home with heated pool
Jan 23 – 30
$739 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Home in Southampton
Charming Southampton Home
Apr 30 – May 7
$450 per night
4.94 out of 5 average rating, 50 reviews
Guest favorite
Home in Sag Harbor
Modern Residence in Sag Harbor
Apr 28 – May 5
$450 per night
4.94 out of 5 average rating, 18 reviews
Guest favorite
Home in Southampton
Spectacular Southampton Retreat!
May 5 – 12
$702 per night
4.89 out of 5 average rating, 19 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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