Holiday Rentals in Town of Southampton

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Top Cities in Town of Southampton

Southampton
Holiday RentalsHoliday Rentals

Southampton

Southampton

Featured Holiday Rentals in Town of Southampton

10 Bedroom Hampton House with a regulation size Pickleball
Pool

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball
Unique location fenced in private beach
Terrace/patio

Unique location fenced in private beach

10.0 out of 10, Exceptional, (6)
"In town for a funeral. Provided everything we needed for this unforeseen situation. Very clean. "
The price is €731
includes taxes & fees
23 Feb - 24 Feb
Unique location fenced in private beach
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (168)
"We had a wonderful stay. The house was great and check in and check out were both easy. We definition would love to stay again."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Outdoor dining

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

10.0 out of 10, Exceptional, (98)
"Pam was very communicative prior to our stay and a welcoming host. The house was clean, centrally located, and spacious. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms
A heated pool

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

10.0 out of 10, Exceptional, (29)
"We enjoyed a year end visit at Jean Marc's beautiful home. There were incredible water views from the floor to ceiling windows in the living room and the master bedroom. The house was clean, comfortable and well furnished. In particular, the kitchen was stocked with everything you need for preparing family meals. Jean Marc was a very responsive and accommodative host!"
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
On the beach, sun-loungers, beach towels

Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

9.8 out of 10, Exceptional, (57)
"My friends, partner and I stayed over Columbus day weekend and were pleasantly surprised with the heated pool still being open, which was a huge highlight. The house was super clean and had everything you would need. We did have a minor issue with the hot water not working in the cottage, but other than that everything was great and we would defintely stay again!"
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
Summer 2025 Now Available! Wolffer Vineyard Close!
Outdoor pool, a heated pool

Summer 2025 Now Available! Wolffer Vineyard Close!

10.0 out of 10, Exceptional, (83)
"Our stay was amazing! The house was fabulous, beautifully appointed, very clean, private and secluded. Lots to do in the area. Jay was very responsive and helpful when we had questions. Would definitely stay again. "
Summer 2025 Now Available! Wolffer Vineyard Close!
Hampton Bays Beach Oasis
Outdoor pool, a heated pool

Hampton Bays Beach Oasis

9.6 out of 10, Exceptional, (10)
"We had a wonderful experience absolutely perfect for entertaining family and friends our first time renti g through VRBO. The accommodations were spectacular as well as comfortable. The owners were very accessible and we look forward to renting here again"
Hampton Bays Beach Oasis
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (127)
"Wonderful throw back beach house..nothing fancy but very comfortable and the views are amazing! Loved spending our Christmas Holiday relaxing by the bay..and the year round hot tub was up and running when we got there! Perfect spot..will definitely go back next year! "
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Terrace/patio

Watermill Retreat, minutes from Southampton Town Ctr and Beaches!

9.6 out of 10, Exceptional, (12)
"We loved this house and Margaux was a great host! Communication was easy and excellent. We loved every minute! Thanks!"
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Beautiful Hamptons home close to beaches, shopping, & restaurants!
Fridge, microwave, oven, stovetop

Beautiful Hamptons home close to beaches, shopping, & restaurants!

10.0 out of 10, Exceptional, (8)
"Had a great stay! Everything about the stay was perfect. Place was all that we expected and more. Host was easy to reach and very responsive. "
Beautiful Hamptons home close to beaches, shopping, & restaurants!
Beautiful resort style backyard with newly added professional PICKLEBALL COURT.
Terrace/patio

Beautiful resort style backyard with newly added professional PICKLEBALL COURT.

9.8 out of 10, Exceptional, (54)
"The house was exactly as described. Excellent stay and the house was super friendly! Highly recommend for any group of friends looking to stay in the Hamptons! Pool was very nice and pickleball courts in excellent condition! Host was super friendly and helped with any questions. Bedrooms were nice and spacious! Nothing But good things to say about my stay "
Beautiful resort style backyard with newly added professional PICKLEBALL COURT.
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger
Fridge, microwave, oven, stovetop

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger

9.6 out of 10, Exceptional, (96)
"House was ideal for our extended family for thanksgiving weekend."
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger
Charming Village home in the heart of Southampton
Smart TV

Charming Village home in the heart of Southampton

10.0 out of 10, Exceptional, (20)
"We loved our stay! The location was perfect for our family, so easy to walk to town, close to the beach and easy to get to other towns. House was perfect as well, we didn’t get to enjoy the outdoors due to rain but loved the indoor space. Plenty of places to hang and enjoy/relax. Hoping to visit again soo!"
Charming Village home in the heart of Southampton
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road
Outdoor dining

Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road

10.0 out of 10, Exceptional, (78)
"We loved our stay in this home! It was the perfect size for our extended family. It was well appointed. The kids loved playing in both levels of the garage. The kitchen had everything we needed. The beds were all comfy. We even took a dip in the cold pool! The owner was responsive to our requests and met all of our needs. I highly recommend this home!"
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (18)
"My friends and I stayed at this house for a few days around New Year's. The house is very spacious, and the grounds are lovely. We had a group of 5 and had lots of room to congregate and disappear if we needed alone time. The hot tub was exactly what some of us needed, while the kitchen provided others with much comfort. The one bummer was when we arrived; it looked like someone had just had a party outside so that first made for a bit of cleanup. That little bump shouldn't stop you from...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
New Fully Remodeled Post Modern Home, Perfect getaway for a family!
Fridge, microwave, oven, stovetop

New Fully Remodeled Post Modern Home, Perfect getaway for a family!

10.0 out of 10, Exceptional, (14)
"House was very very nice. It was 8 people in my group and we all fit comfortably. Perfect wooded quiet location. House was very very clean with a supply of toilet paper, paper towels and trash bags. Beds and linen were very comfortable. House host was wonderful to communicate with quick responses. Everything in the house was functional, nothing was broken. We loved The Hamptons and the experience to stay here ! and "
New Fully Remodeled Post Modern Home, Perfect getaway for a family!
Home page of Southampton Village
Fridge, microwave, oven, stovetop

Home page of Southampton Village

9.4 out of 10, Exceptional, (18)
"Mike is a delightful person. He was very communicative and helpful with any questions we had. He spent a good 15 minutes on the phone with me offering recommendations! You rarely get such responsive hosts. The house was everything we could have asked for and we would definitely visit this lovely home again!"
Home page of Southampton Village
Beautiful Southampton Village home, new reno, Heated pool!
Outdoor pool, a heated pool

Beautiful Southampton Village home, new reno, Heated pool!

10.0 out of 10, Exceptional, (33)
"an amazing experience and stay. i booked the house in proximity to the half marathon i was running in. It served well and also a safe haven for my family. looking forward to next year!"
Beautiful Southampton Village home, new reno, Heated pool!
Minutes from the beach, brand new 4 bedroom
Fridge, microwave, oven, stovetop

Minutes from the beach, brand new 4 bedroom

The price is €1,456
includes taxes & fees
23 Feb - 24 Feb
Minutes from the beach, brand new 4 bedroom
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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