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, 317 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.

May 30 – Jun 6

€ 260 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.

Oct 3 – 10

€ 303 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 7 – 14

€ 306 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 22 – 29

€ 340 per night

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 164 reviews

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.

Jan 21 – 28

€ 400 per night

Guest favorite

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence for pool area. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

May 7 – 14

€ 614 per night

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 101 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!

Aug 28 – Sep 4

€ 937 per night

Guest favorite

Home in Southampton

4.91 out of 5 average rating, 180 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!

Aug 5 – 12

€ 617 per night

Guest favorite

Guest suite in Sag Harbor

4.95 out of 5 average rating, 189 reviews

Cedar Haven In Sag Harbor

This is a large one room studio apartment with private entrance and ensuite bathroom. The unit is private and closed off from the host’s house. The large main room has a queen bed, and a spacious seating area that includes chairs as well as a comfy leather couch. PLEASE NOTE: One night stays are welcomed but there is a higher rate: IN season, (June 1 - Oct 31) the ONE NIGHT RATE is $375 OFF season, (mid Oct - end of May) the ONE NIGHT RATE is $300

Nov 8 – 15

€ 188 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.

Sep 19 – 26

€ 734 per night

Guest favorite

Home in Sag Harbor

4.97 out of 5 average rating, 260 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Aug 29 – Sep 5

€ 933 per night

Guest favorite

Apartment in Southampton

4.96 out of 5 average rating, 166 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

Aug 16 – 23

€ 607 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

Stony Brook Southampton Hospital13 locals recommend

Tate's Bake Shop76 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

4.94 out of 5 average rating, 102 reviews

Sag Harbor Village Cottage with Pool

Jun 11 – 18

€ 857 per night

Guest favorite

Home in East Hampton

4.97 out of 5 average rating, 120 reviews

East Hampton (walking distance to village)

Nov 20 – 27

€ 681 per night

Guest favorite

Home in Southampton

4.98 out of 5 average rating, 111 reviews

Contemporary house in the woods.

Jan 18 – 25

€ 502 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

Oct 9 – 16

€ 423 per night

Guest favorite

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Dec 5 – 12

€ 727 per night

Guest favorite

Home in Sag Harbor

4.97 out of 5 average rating, 124 reviews

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

Nov 24 – Dec 1

€ 508 per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 57 reviews

Dream home in SH with Heated Pool OPEN from May 4

Feb 1 – 8

€ 526 per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 34 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Feb 10 – 17

€ 729 per night

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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!

May 9 – 16

€ 277 per night

Guest favorite

Guesthouse in Southampton

5.0 out of 5 average rating, 58 reviews

Contemporary Cottage

Aug 9 – 16

€ 416 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 25 – Oct 2

€ 601 per night

Guest favorite

Cottage in East Hampton

5.0 out of 5 average rating, 31 reviews

Storybook Cottage Seconds to East Hampton Village

Oct 23 – 30

€ 532 per night

Guest favorite

Cottage in Water Mill

4.98 out of 5 average rating, 56 reviews

Head of Pond House - Waterfront Cottage

Oct 14 – 21

€ 556 per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 21 reviews

Modern Southampton home, heated pool, pickleball

Sep 23 – 30

€ 1,055 per night

Guest favorite

Home in Southampton

4.97 out of 5 average rating, 35 reviews

Beautiful Southampton Village Home with Pool

Oct 3 – 10

€ 803 per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 45 reviews

Perfect Family Escape with Heated Pool

May 15 – 22

€ 788 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
€ 9 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!
What are the most popular amenities for House Rentals in Southampton?
Enhance your stay in our House Rentals with the most popular amenities: over 330 homes with wifi, over 80 homes with self check-in, over 70 homes with a gym, over 160 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 apartment rentals in Southampton have self check-in?
Absolutely! We offer over 10 apartment rentals with self check-in in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Southampton have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Southampton. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Southampton?
Southampton has more than 390 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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 Southampton

Home in Sag Harbor

Home in East Hampton

Home in Sag Harbor

Home in Southampton

Home in Southampton

Other great vacation rentals in Southampton

Apartment in Hampton Bays

Guesthouse in Southampton

Guesthouse in Southampton

Cottage in East Hampton

Cottage in Water Mill

Home in Southampton

Home in Southampton

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?

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

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 apartment rentals in Southampton have self check-in?

Do apartment rentals in Southampton have wifi?

Are there family-friendly vacation rentals in Southampton?

Destinations to explore