
House holiday rentals in Shirley
Find and book unique houses on Airbnb
Top-rated house rentals in Shirley
Guests agree: These houses are highly rated for location, cleanliness and more.

Luxurious Waterfront Beach House On The Bay
Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Amazing Home close to Everything -
Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

Gorgeous Waterfront and Indoor Pool Family Oasis!
Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

Cozy studio
We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

Paradise Citadel hottub, Htd pool, sauna, golf.
🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Cottage in the heart of Stony Brook Village
Totally renovated 100 year old charming but modern cottage steps from the Three Village Inn, Country House Restaurant, Stony Brook Village, Jazz Club, Sand St. Beach, Avalon Park, Carriage museum and the Long Island Music & Entertainment Hall of Fame. You will have the private upper floor of the cottage with a private entrance. There is a spacious porch and front yard with lounge chairs where you can watch the deer, chipmunks, birds, & rabbits. Short ride to Stony Brook University.

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy
Welcome to Coast to Coast - the perfect getaway from NYC! You may have heard about our new little secret - but you’ll have to come see it for yourself to believe it! Step back into prohibition era Long Island in our hidden speakeasy! Right by Smith Point Beach, we provide accommodations that go above and beyond- this is not your average AirBnB! Soak up the sun at one of LI's top beaches, then enjoy complimentary Netflix, Hulu, cable and more while you shoot pool or play games.

Cozy home. Comfy living
The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Modern Farmhouse Steps to Beach & Love Lane
Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Luxury Hamptons Home with Heated Saltwater Pool
Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

Beach Waterview, 3 KING Beds, Golf Putting Green
Take it easy at this 3 story waterview beach home with a putting green and fire pit. The Bellport Bay is across the street. Shirley Beach: 0.4 mile walk Smith Point Beach: 1.8 miles Featuring: 3 luxurious KING beds 👑 (and 2 fulls) Watch Netflix, Disney+ on the 70" living room TV and 3 50" bedroom TVs Fully equiped kitchen/dining room Enjoy BBQ Grill, fire pit on premium soft turf Highspeed mesh WiFi, keyless entry.
Popular amenities for Shirley house rentals
House rentals with a pool

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

Peaceful Retreat in Immaculate Architect’s House

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Beach Retreat - Heated Pool, Game Room & Bar

Classic Southampton Village Home w/ Pool

Stunning Farmhouse in NoFo I Heated Pool, Wineries

1800 Historical EH Home, 1 Mile to Town!

Private 1br apt/private entrance/inground pool
Weekly house rentals

Dahlia by the bay

A little getaway!

Stunning Guest Suite in Medford

Cottage with Seashells

Bellport Village Retreat

Sunset Cottage - Waterfront Getaway

New Beautiful, Relaxing Home !

Modern home with pool near beach
Private house rentals

Designer Home w/ Heated, Salt-Water Pool

Waterfront NoFo Cottage w/ public beach access

Peaceful and Bright 4 Bedroom Getaway Home

Charming Riverview Home*Firepit* Near Train & I-95

Hamptons Style Cottage close to everything!

Bellport Home: Pool, Hot Tub & Ping-Pong Oasis

RP modern cozy cabin

Trendy Ranch in Bellport Village
When is the best time to visit Shirley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $309 NZD | $282 NZD | $282 NZD | $309 NZD | $330 NZD | $436 NZD | $457 NZD | $494 NZD | $349 NZD | $402 NZD | $309 NZD | $309 NZD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 15°C | 21°C | 24°C | 23°C | 19°C | 13°C | 8°C | 3°C |
Quick stats about house rentals in Shirley

Total holiday rentals
Explore 70 holiday rentals in Shirley

Nightly prices starting at
Shirley holiday rentals start at $53 NZD per night before taxes and fees

Verified guest reviews
Over 4,050 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Shirley holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Shirley rentals

4.9 Average rating
Shirley stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Apartment rentals Shirley
- Pet-friendly rentals Shirley
- Rentals with beach access Shirley
- Rentals with pools Shirley
- Rentals with a washing machine and dryer Shirley
- Waterfront rentals Shirley
- Rentals with a fireplace Shirley
- Rentals with a patio Shirley
- Rentals with a fire pit Shirley
- Rentals with outdoor seating Shirley
- Family-friendly rentals Shirley
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- Yale University
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- Gilgo Beach
- Robert Moses State Park
- Walnut Public Beach
- Rowayton Community Beach
- Shinnecock Hills Golf Club
- Bethpage State Park
- Rye Playland Beach
- Cedar Beach
- Napeague Beach
- Jones Beach State Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Jennings Beach
- Sandy Beach
- Wildemere Beach
- Amagansett Beach
- Seaside Beach