
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

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

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!

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!

The Cozy Little Cottage
Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

Family Retreat with Heated Pool, Hot Tub, Sauna.
🛏 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

Joyful Beach House, viewing The Great South Bay
Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

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.

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

The Sandpiper
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

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

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.
Popular amenities for house rentals in Shirley
House rentals with a pool

Chic Hamptons Retreat | Fireplace, Hot Tub, Beach

Peaceful Retreat in Immaculate Architect’s House

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

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

Brand new house with an all year round hot tub.

Classic Southampton Village Home w/ Pool

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room
Weekly house rentals

Close to Beach | With Pool | Hampton Bays

Stunning Guest Suite in Medford

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

RP modern cozy cabin

Cozy & private getaway beach view house

Sunset Cottage - Waterfront Getaway

Cozy Studio in Bridgeport

Waterfront Designer Retreat | Fire Pit & Sunsets
Private house rentals

Dahlia by the bay

A little getaway!

Historic East Hampton Home - Private Beach Access

Newly done basement apartment Great location

Lakehouse Getaway North Fork

Contemporary East Hampton 4 Bedroom, Pool

Stunning sunset charming waterfront home 4 seasons

1 King Bed/1 Bath 750 SF Cottage Loft Style Home
When is the best time to visit Shirley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £130 | £119 | £119 | £130 | £139 | £184 | £193 | £209 | £148 | £170 | £130 | £130 |
| 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 60 holiday rentals in Shirley

Nightly prices starting at
Shirley holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 3,820 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Shirley holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shirley rentals

4.9 Average rating
Shirley stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with outdoor seating Shirley
- Family-friendly rentals Shirley
- Rentals with a fireplace Shirley
- Rentals with beach access Shirley
- Waterfront rentals Shirley
- Rentals with a firepit Shirley
- Rentals with pools Shirley
- Pet-friendly rentals Shirley
- Rentals with a patio Shirley
- Rentals with a washing machine and dryer Shirley
- Flat rentals Shirley
- House rentals Suffolk County
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- Yale University
- Ohel Chabad-Lubavitch
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Robert Moses State Park Beach
- Sunken Meadow State Park
- Jones Beach State Park
- Long Island Aquarium
- Sherwood Island State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Yale University Art Gallery
- Dunewood
- Compo Beach
- Orient Beach State Park
- Meschutt Beach
- East Hampton Main Beach
- Wölffer Estate Vineyard
- Gouveia Vineyards
- Silver Sands State Park
- Atlantic Avenue Beach




