
House holiday rentals in Shirley
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Top-rated house rentals in Shirley
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Shirley
House rentals with a pool

4 BD w/ Heated Pool in E Hampton, Fully Furnished
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.

Southampton Escape, Heated Pool, hot tub, 3 bed,
The house was great! Our two infants loved the large deck and pool. So close to town and the beach. It was a perfect getaway!

Stunning Central E. Hampton Home w/ gunite pool.
Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!

Hope Haven
I was in Dion’s place with my family we really enjoyed the time we spent there,everything was perfect the pool was something that my kids enjoyed a lot, and hopefully we will come back again, for sure I totally recommend his house if you want to go and have a couple days of fun and relax thank you again Dion.

Modern Beach Area Vacation Home With Pool
We were all very happy with the check-in/check-out. Instructions were clear and host left helpful information. Beds were quite comfortable. More than enough space for all. Laundry room was a plus. Easy to access town & beach. Lovely place - quiet - clean. Would definitely book again.

Long Island home w/ large pool
My stay here was phenomenal! From the host’s response time, down to the amenities that were placed throughout the house. As soon as you walk in, it felt like home. The house is spacious and highly functional. The design of the house offers a perfect blend of modern mixed with nostalgic elements. The best stay by far. Would love to book again!

1940’s Westhampton renovated bungalow
Sarah was wonderful as a host and the home was very well maintained in a beautiful neighborhood. Thank you!

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes
We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.
Weekly house rentals

Private pool/walk to beach; farms/vineyards abound
Staying at Amy's place was perfect for my friends and I while we're out on the North Fork for a wedding. Amy was very responsive with any questions we had. We were all very comfortable in the main living area as well as our bedrooms. The house was conveniently located to the wedding venue and my friends were also very happy that it was located near some pickleball courts. Thank you Amy for a wonderful stay.

Indigo Inn III -A Retro Modern Cove White Plains
Great space. Wonderful communication with host regarding any questions we had. Host was quick to respond. Very happy with the stay, would rent again.

The Greenport Bungalow
My family and I stay in greenport quite a bit and all agreed that this was our favorite Airbnb to stay in! The house was comfortable and beautifully designed. The host was so helpful when we had questions. Also, the water pressure in the showers was awesome which is hard to come by! Thank you for a great stay - we will be back!!

Elegant, resort style, clean, north shore home
The inside and outside areas were meticulously maintained. The weather was great, so we were able to really enjoy the pool and deck. Michelle was extremely responsive and did a great job with instructions, recommendations, and communications. One member of our party needed to work a few days, and the office space in the basement was perfect.

3 bedroom cottage rental
My family and I had a very relaxing stay at this place. Cozy with plenty of amenities. PAPA, the neighborhood cat likes to visit in the morning on the front deck and he’s a very good boy. Bring him treats.

Historic Beachside Glamour
A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.

Comfortable Entire House for rent. 4 bed, 3 baths
Robert was a great host super friendly and a great house. My family enjoyed our stay and would recommend this house and location to anyone. Can’t wait to come back.

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens
This house was very good for me and my friends and we would love to go back!
Private house rentals

Peaceful and Private 3 bedroom home in the woods
Maura was an excellent host and the home was perfect! We enjoyed the weekend very much and cannot thank Maura enough for her kindness, responsiveness, warm hearted spirit, and for opening up her home to us. Will always keep this spot in mind for future SI adventures!

Restored farmhouse, walk to Carissa's, beach, town
We just spent an unforgettable weekend at J.P’s beautiful house, and we can't wait to be back! The house is absolutely beautiful, with impeccable taste and attention to detail. But what truly makes this property shine is its phenomenal location. Right in the middle of East Hampton and Amagansett and a 15 minute drive to Sag Harbor— couldn’t have asked for more. Also Carissa’s bakery is just a 6 minute walk. And, of course, no Hampton's experience is complete without a visit to Goldberg's for their classic lox and bagels - which is also a short walk away. The house itself is spacious, bright, and beautifully appointed, with everything you need to unwind and relax. Every room is nice and cozy and the kitchen is stunning with everything you need to cook with the amazing produce available at the so many farm stands around the area. (We loved Balsam and Amber Waves) J.P. was incredibly responsive and thoughtful, providing excellent recommendations and ensuring our stay was perfect.

The Perfect North Fork Escape
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

Welcome To Piper's Rest
Very beautiful house by the water nice neighborhood and very clean lovely home would love to stay here again

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend
Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back

Modern 2 bedroom — recently renovated in New York
It was an amazing experience. Wonderful Stay. Tomi was a gracious host. The place smelled amazing and very clean. I would love to stay here again and recommend it to everyone who is interested. 🙏🏽🙏🏽🙏🏽

Private Beach access along the Wine Trail
I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!

Beachfront paradise- come, stay, relax!
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Quick stats about house rentals in Shirley
Total rentals
70 properties
Total number of reviews
3.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
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- Beach
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Rye Beach
- Yale University
- Gilgo Beach
- Rye Playland Beach
- Napeague Beach
- Point Lookout Beach District Park
- Cooper's Beach, Southampton
- Dunewood
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Quotonset Beach
- Robert Moses State Park
- Rye Town Beach
- Giants Neck Beach
- Seaside Beach
- Amagansett Beach
- Sunken Meadow State Park
- Bethpage State Park
- Woodmont Beach
- Clinton Town Beach