Shirley holiday lettings

We found 370 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.

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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)
  • Roanoke Vineyards (14.6 mi / 23.6 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.
How much does it cost to rent a holiday home in Shirley?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Shirley to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Shirley holiday house rentals?
You can find great discounts on house rentals in Shirley on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Shirley?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Shirley holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Shirley holiday rental?
Book your Shirley holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Shirley home rental booking on Vrbo?
To find Shirley holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Shirley holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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