Shirley holiday rentals

We found 347 holiday rentals — enter your dates for availability
Discover a selection of 14 homes and other holiday rentals in Shirley that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Shirley

Showing deals for:18 Dec - 25 Dec

Living area
Dining
Private kitchen
Interior
Exceptional
(6 reviews)

Shirley Bayfront Getaway – Kayak, Swim & Relax

Shirley

8% off
AU$11,544
for 7 nights, 1 home
AU$1,649 per night
includes taxes & fees
Shirley Bayfront Getaway – Kayak, Swim & Relax
Exterior
Bay facing side of house
Pool
Custom kitchen
Exceptional
(17 reviews)

Waterfront house next to Bellport golf course

Patchogue

8% off
AU$8,066
for 7 nights, 1 home
AU$1,152 per night
includes taxes & fees
Waterfront house next to Bellport golf course
Pool
Pool
Exterior detail
Room
Excellent
(36 reviews)

The Jahmtons Guest Room

Ridge

8% off
AU$1,421
for 7 nights, 1 room
AU$203 per night
includes taxes & fees
The Jahmtons Guest Room
Private kitchen
Property grounds
Interior
Interior
Very good
(34 reviews)

Waterfront Home With Recreational Dock! Great For Rafting, And Close To Beaches

Mastic Beach

8% off
AU$3,614
for 7 nights, 1 home
AU$516 per night
includes taxes & fees
Waterfront Home With Recreational Dock! Great For Rafting, And Close To Beaches
Dining
Outdoor dining
Private kitchen
Living area
Exceptional
(31 reviews)

“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath

Mastic Beach

9% off
AU$4,350
for 7 nights, 1 home
AU$621 per night
includes taxes & fees
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
Dining
Exterior
Room
Pool
Exceptional
(39 reviews)

11-Bedroom Mansion with a Seasonal Outdoor Pool open now plus 10.5 bathrooms

Eastport

8% off
AU$21,840
for 7 nights, 1 home
AU$3,120 per night
includes taxes & fees
11-Bedroom Mansion with a Seasonal Outdoor Pool open now plus 10.5 bathrooms
Terrace/patio
Exterior
Living area
Interior
Exceptional
(36 reviews)

40-Foot Pool Retreat Near the Hamptons — Easy NYC Access, Total Relaxation

Center Moriches

12% off
AU$5,633
for 7 nights, 1 home
AU$805 per night
includes taxes & fees
40-Foot Pool Retreat Near the Hamptons — Easy NYC Access, Total Relaxation
Private kitchen
Exterior detail
Living area
Interior
Exceptional
(14 reviews)

Farm and Wine Lovers’ Cottage Near the Hamptons

East Moriches

8% off
AU$5,109
for 7 nights, 1 home
AU$730 per night
includes taxes & fees
Farm and Wine Lovers’ Cottage Near the Hamptons
Exterior
Exterior detail
Interior
Living area
Exceptional
(14 reviews)

House of Peace

Mastic

11% off
AU$3,772
for 7 nights, 1 home
AU$539 per night
includes taxes & fees
House of Peace
Resort inspired backyard with heated pool, outdoor seating, and complete privacy
Dining
Interior
75 inch TV w/ Bose Soundbar
Exceptional
(16 reviews)

NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym

Westhampton

8% off
AU$8,984
for 7 nights, 1 home
AU$1,283 per night
includes taxes & fees
NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym
Exterior detail
Room
Private kitchen
Interior
Exceptional
(6 reviews)

South Shore Studio in Mastic

Mastic

8% off
AU$1,540
for 7 nights, 1 apartment
AU$220 per night
includes taxes & fees
South Shore Studio in Mastic
Terrace/patio
Marina
Living area
Exterior
Exceptional
(12 reviews)

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Mastic Beach

8% off
AU$3,624
for 7 nights, 1 home
AU$518 per night
includes taxes & fees
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Pool
Living area
Room
Property grounds
Exceptional
(5 reviews)

Hampton Retreat near the Beach

Remsenburg

16% off
AU$4,154
for 7 nights, 1 apartment
AU$593 per night
includes taxes & fees
Hampton Retreat near the Beach

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Shirley getaway

The parks and other outdoor surroundings create an inviting atmosphere in Shirley. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Shirley

Are you searching for attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Shirley a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Long Island Game Farm (5.2 mi / 8.4 km)
  • Swan Lake Golf Club (7.6 mi / 12.2 km)
  • Splish Splash Water Park (10.9 mi / 17.6 km)
  • Safari Adventure (12.8 mi / 20.5 km)
  • Jamesport Vineyards (17.4 mi / 28 km)
  • Bellport Country Club (5.4 mi / 8.7 km)

Exploring the natural landscape of Shirley

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Shirley is a great place to spend some time outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Smith Point County Park (5 mi / 8 km)
  • Cupsoque Beach (7.1 mi / 11.5 km)
  • Shorefront Park (8.1 mi / 13.1 km)
  • Fire Island National Seashore (8.4 mi / 13.6 km)
  • Cedar Beach (12.2 mi / 19.7 km)
  • Lake Ronkonkoma (13.3 mi / 21.4 km)

Transport to and around Shirley

The nearest airport is in Shirley, NY (WSH-Brookhaven Calabro), located 1.7 mi (2.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Islip, NY (ISP-MacArthur), which is 12.1 mi (19.4 km) away.

If you'd prefer to travel by train, you can make your way to Mastic Shirley Station.

Frequently asked questions

What is the best area to stay in Shirley when booking a holiday rental?
When considering a holiday rental in Shirley, New York, a great area to stay is the charming neighbourhood of Mastic Beach. This community offers a lovely coastal vibe, with easy access to the beautiful beaches along the Atlantic Ocean. You can enjoy plenty of outdoor activities, including swimming, fishing, and hiking in nearby nature reserves. The area is known for its scenic landscapes, making it a superb spot for those looking to relax and unwind.Another appealing option is the Shirley area itself, which features a mix of residential charm and local conveniences. Here, visitors can explore local parks, such as the expansive Southaven Park, which offers trails and picnic spots, ideal for a leisurely day out. The proximity to attractions like the Fire Island National Seashore makes it an excellent base for exploring the natural beauty of Long Island.While exact property numbers can fluctuate, Shirley and its surrounding neighbourhoods typically boast a diverse range of holiday rentals, suiting various preferences and budgets.
Where are the best areas for renting a beach house in Shirley?
For renting a beach house in Shirley, the area adjacent to the picturesque Smith Point County Park is an excellent choice. This stretch of coastline offers easy access to sandy beaches and the scenic beauty of the Atlantic Ocean. Many rental properties here come with amenities that enhance the beach experience, such as outdoor decks for sunbathing, private yards great for barbecues, and spacious living areas designed for relaxation after a day in the sun.Additionally, the nearby Fire Island National Seashore provides a great experience with its pristine beaches and nature trails. Rentals in this vicinity often feature outdoor showers, allowing guests to rinse off after a day at the beach, and some may even provide bicycles for exploring the local area.For those looking for a lively option, the Shirley area has access to local shops, restaurants, and entertainment options. Properties here may include modern kitchens for cooking meals and comfortable gathering spaces, making them ideal for families or groups looking to enjoy a beach getaway.
What is the most popular type of holiday rental accomodation in Shirley?
In Shirley, holiday houses are the most popular choice for holiday rentals, with around 40 available throughout the area. These properties typically offer spacious living arrangements, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy a comfortable stay. Additionally, there are about 20 apartments in Shirley, which provide a more compact option for travellers. These apartments usually feature essential amenities such as kitchen facilities, living areas, and convenient access to local attractions.
Are there any family house rentals in Shirley?
In Shirley, New York, there are numerous family-friendly house rentals available, with about twelve options to choose from. This charming area is close to beautiful beaches and nature reserves, making it an ideal spot for families looking to enjoy some outdoor activities.Properties in Shirley typically feature spacious living areas, fully equipped kitchens for preparing family meals, and comfortable bedrooms to accommodate everyone. Many homes also offer outdoor spaces where children can play and adults can relax, along with amenities such as Wi-Fi and air conditioning to ensure a pleasant stay.Visitors will find that the local beaches are just a short drive away, great for a day of sun and sand, while nearby parks provide opportunities for picnics and recreational activities.
Can I rent a holiday home with a pool or hot tub in Shirley?
In Shirley, New York, there are several holiday homes available for rent that feature pools and hot tubs. This charming area offers a peaceful retreat with convenient access to nearby beaches and local attractions. Many of these rentals come equipped with amenities such as private swimming pools, relaxing hot tubs, spacious outdoor decks, and fully functional kitchens, making them ideal for families or groups seeking both relaxation and entertainment. Additionally, some properties may include features like barbecue facilities and gardens, enhancing the outdoor experience.
Are there pet-friendly house rentals in Shirley?
In Shirley, New York, there are several pet-friendly house rentals available that cater to travellers looking to enjoy a getaway with their furry companions. Many of these properties are equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can roam freely.The area itself is close to various parks and recreational spaces that welcome pets, making it appealing for those who enjoy outdoor activities with their animals. For instance, the nearby Wertheim National Wildlife Refuge offers walking trails and scenic views, great for leisurely strolls with pets. Additionally, the proximity to the coastline allows for delightful beach outings, where pets can enjoy the sand and surf.
Are there any remote work holiday rentals in Shirley?
In Shirley, New York, there are numerous options for remote work holiday rentals, with around 60 available in the area. Many of these properties are well-equipped to accommodate remote workers, featuring amenities such as free Wi-Fi, dedicated workspaces, and comfortable living areas. Travellers can expect to find modern conveniences, including fully equipped kitchens, which allow for easy meal preparation, and often outdoor spaces for relaxation during breaks.The neighbourhood is conveniently located near local attractions, including beautiful beaches and parks, providing a superb balance between work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Shirley?
In Shirley, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals also feature a blender for convenient smoothie-making or meal prep. Outdoor spaces such as decks or patios are common, providing a lovely area to relax and enjoy the fresh air. Additionally, rentals typically offer coffee and tea makers for those who enjoy a warm beverage upon waking up. Onsite parking is another amenity that travellers can expect, making it easier for those with vehicles to access the area comfortably.
When is the best time to visit Shirley for a holiday rental?
The best time to visit Shirley for a holiday rental is during the peak season from June to August. This vibrant period attracts families and outdoor enthusiasts looking to enjoy the beautiful summer weather. With warm temperatures averaging around 20 to 30 degrees Celsius, visitors can indulge in a variety of outdoor activities, from relaxing on the nearby beaches to exploring the scenic trails of the region.July stands out as the most popular month, offering a lively option filled with community events and local festivals. It's an ideal time for those who love to soak up the sun, participate in water sports, or simply enjoy the local cuisine at outdoor eateries. The long daylight hours provide ample opportunity for sightseeing and enjoying scenic walks along the shoreline.For travellers seeking a more budget-friendly option, December is a great choice. This month sees fewer tourists, allowing for a quieter experience while still enjoying the charm of Shirley during the winter season. It's a wonderful time for those who appreciate a peaceful getaway, perhaps indulging in off-season rates for holiday rentals while enjoying the festive spirit of the area.Ultimately, the best time to visit Shirley hinges on your preferences for either the bustling summer energy or the tranquil winter charm.
What are the top attractions in Shirley?
In Shirley, New York, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The nearby Fire Island National Seashore offers stunning beaches, walking trails, and opportunities for wildlife observation, making it a superb spot for outdoor enthusiasts. Holiday rentals in this area often provide easy access to the beach, allowing guests to enjoy the sun and surf.For those interested in local history and culture, the Long Island Museum in nearby Stony Brook is a fantastic destination, showcasing art, history, and the heritage of Long Island. The quaint village of Patchogue, just a short drive away, features a vibrant arts scene, with galleries, theatres, and diverse dining options along its picturesque waterfront.Additionally, the scenic Wertheim National Wildlife Refuge offers walking trails and birdwatching opportunities, enriching the experience for nature lovers.
Are all fees included in the Shirley holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Shirley holiday homes with parking?
Stayz offers a wide selection of holiday homes in Shirley with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Shirley holiday homes?
You can find great discounts on holiday homes in Shirley on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Shirley holiday home booking on Stayz?
To find Shirley holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Shirley?
A long-stay holiday home in Shirley is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Shirley holiday home?
Book your Shirley holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Shirley?
Prices for holiday homes in Shirley vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Shirley to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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