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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Guest favorite

Guest suite in Hampton Bays

4.98 out of 5 average rating, 315 reviews

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.

Oct 27 – Nov 3

R5,452 ZAR per night

Guest favorite

Apartment in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Aug 28 – Sep 4

R7,236 ZAR per night

Guest favorite

Guesthouse in Hampton Bays

4.96 out of 5 average rating, 146 reviews

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.

May 5 – 12

R6,757 ZAR per night

Guest favorite

Guesthouse in Southampton

4.95 out of 5 average rating, 411 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!

Sep 21 – 28

R6,803 ZAR per night

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 100 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Dec 30 – Jan 6

R18,461 ZAR per night

Guest favorite

Home in Southampton

4.91 out of 5 average rating, 179 reviews

Peaceful Hamptons Cottage

Looking for a getaway? Nestled into one of the largest preserves in the Hamptons, this sunny newly renovated beachy cottage is the perfect retreat. The legendary Hamptons beaches, wineries, Southampton Village, and the world famous golf courses are less than a 10 minute drive away. There are many nearby essential shops, farm stands & restaurants. Set up for WFH with hi-speed wifi and a desk. Abuts a large nature preserve with hiking paths. Lots of deer will roam by your window!

Jul 14 – 21

R12,116 ZAR per night

Guest favorite

Home in Southampton

4.9 out of 5 average rating, 215 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

Sep 14 – 21

R10,957 ZAR per night

Guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

May 17 – 24

R15,457 ZAR per night

Guest favorite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Dec 5 – 12

R9,970 ZAR per night

Guest favorite

Apartment in Southampton

4.96 out of 5 average rating, 165 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

Jun 30 – Jul 7

R9,627 ZAR per night

Guest favorite

Home in Water Mill

4.91 out of 5 average rating, 109 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Dog friendly (upon request) Hampton Beach Barn with heated pool and infrared sauna. POOL OPEN - May 3, 2024 - October 28, 2024 This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic modern decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.

Dec 21 – 28

R16,388 ZAR per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 586 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Oct 15 – 22

R3,243 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Southampton vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Southampton

Guest favorite

Home in Sag Harbor

4.97 out of 5 average rating, 260 reviews

Sag Harbor Cottage, Walk to the Beach!

Sep 1 – 8

R15,710 ZAR per night

Guest favorite

Home in East Hampton

4.97 out of 5 average rating, 120 reviews

East Hampton (walking distance to village)

Oct 15 – 22

R13,384 ZAR per night

Guest favorite

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Dec 23 – 30

R8,048 ZAR per night

Guest favorite

Home in Southampton

4.95 out of 5 average rating, 246 reviews

Southampton Village Classic Summer Special!

Oct 25 – Nov 1

R20,145 ZAR per night

Guest favorite

Home in Sag Harbor

4.97 out of 5 average rating, 123 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

Nov 24 – Dec 1

R9,898 ZAR per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 21 reviews

Renovated Southampton Home+Pool

Nov 3 – 10

R6,912 ZAR per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 34 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Apr 18 – 25

R16,733 ZAR per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 41 reviews

Bay View Stunner, Modern 6 Bedroom w Heated Pool

May 18 – 25

R19,238 ZAR per night

Show all

Other great vacation rentals in Southampton

Guest favorite

Apartment in Hampton Bays

4.97 out of 5 average rating, 340 reviews

Private & Cozy Cottage with short walk to beach!

Sep 30 – Oct 7

R5,405 ZAR per night

Guest favorite

Apartment in Southampton

4.86 out of 5 average rating, 107 reviews

Southampton Village Studio

Mar 22 – 29

R6,158 ZAR per night

Guest favorite

Guesthouse in Southampton

5.0 out of 5 average rating, 58 reviews

Contemporary Cottage

Aug 29 – Sep 5

R8,277 ZAR per night

Guest favorite

Guesthouse in Southampton

4.98 out of 5 average rating, 45 reviews

Southampton Modern Barn, Private Hot Tub and Pool

Sep 21 – 28

R12,490 ZAR per night

Guest favorite

Cottage in East Hampton

5.0 out of 5 average rating, 30 reviews

Storybook Cottage Seconds to East Hampton Village

Oct 23 – 30

R10,376 ZAR per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 20 reviews

Modern Southampton home, heated pool, pickleball

Oct 26 – Nov 2

R16,949 ZAR per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 17 reviews

Perfect Lake Cottage weekend Hamptons special

Jun 14 – 21

R13,650 ZAR per night

Guest favorite

Vacation home in Southampton

4.98 out of 5 average rating, 41 reviews

5BR, Luxury Home, Pool, Yard Close to Beach & Town

Jan 22 – 29

R16,634 ZAR per night

Show all

Quick stats about vacation rentals in Southampton

Total rentals
630 properties
Rentals with a pool
340 properties have a pool
Pet-friendly rentals
250 properties allow pets
Family-friendly rentals
390 properties are a good fit for families
Total number of reviews
7.2K reviews
Nightly prices starting at
R190 ZAR 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 250 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 $90 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.
What are the most popular amenities for House Rentals in Southampton?
Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with self check-in, over 160 homes with a bbq area, over 70 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Southampton vacation rentals

Top-rated vacation rentals in Southampton

Vacation rentals for every style

Houses

Cottages

Apartments

Popular amenities for Southampton vacation rentals

Stay near Southampton's top sights

Other great vacation rentals in Southampton

Home in Sag Harbor

Home in East Hampton

Home in Sag Harbor

Home in Southampton

Home in Sag Harbor

Home in Southampton

Home in Southampton

Home in Southampton

Other great vacation rentals in Southampton

Apartment in Hampton Bays

Apartment in Southampton

Guesthouse in Southampton

Guesthouse in Southampton

Cottage in East Hampton

Home in Southampton

Home in Southampton

Vacation home in Southampton

Quick stats about vacation rentals in Southampton

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Southampton?

Are there pet-friendly vacation rentals in Southampton?

Are there Southampton vacation rentals on Airbnb with pools?

How much does it cost to stay in house rentals in Southampton?

Do house rentals in Southampton have a bbq area?

Do house rentals in Southampton have a gym?

Do house rentals in Southampton have self check-in?

What are the most popular amenities for House Rentals in Southampton?

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