Holiday rentals in Shirley

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Top-rated holiday rentals in Shirley

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Guest favourite

Serviced apartment in Medford

4.88 out of 5 average rating, 139 reviews

Cozy Apartment with King Bed - Separate Entrance

Enjoy your stay in this private, clean and comfy environment. Space offers a bedroom with a king size bed and a desk for at-home work. Living room includes a smart TV and a sectional. Unleash your inner chef! Access to kitchen utensils, dinnerware, and pots/pans. Free parking on premises. Convenient location with many necessities nearby (mall/gas station/restaurants). We are located 2 mins from I-495 and 15 mins from Macarthur airport. Great for visiting family in Port Jefferson, Patchogue, etc!

Guest favourite

Home in Shirley

4.98 out of 5 average rating, 203 reviews

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

Guest favourite

Flat in Patchogue

4.88 out of 5 average rating, 219 reviews

Private 1br Apartment on Long Island

Bright & clean 1br apartment with private entrance on a quiet street. Refrigerator, microwave, keurig incl 2 miles to downtown restaurants, bars, breweries, shopping 10 miles to winery & vineyards 3 miles to beaches 3 miles to Fire Island Ferry 30miles to NYC 3 miles to Baseball Heaven 10 miles to Stonybrook University & hospital 1 mile to public horse farm & stable 3 miles to St Joseph's College .5 mile to Long Island Community Hospital 1 mile to hiking 45min to JFK 10min to McArthur airport

Superhost

Cabin in Shirley

4.87 out of 5 average rating, 161 reviews

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Top guest favourite

Flat in Patchogue

4.96 out of 5 average rating, 141 reviews

Charming 2 Bedroom apartment

Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

Top guest favourite

Home in Brookhaven

4.96 out of 5 average rating, 194 reviews

Beautiful & Independent Guest House near the water

Welcome to our beautiful yet very private guest house in Brookhaven. You are walking distance from the Deer Run Farm (fresh eggs every morning), Post-Morrow Nature Trails and a short drive to Bellport Village Historic District. We are also very close to Wine Country, The Hamptons & Fire Island. We offer all the accommodations you might need for longer stays Washer & Dryer; Dishwasher; High Speed internet and TVs with all the premium channels. EV Charger available (Tesla - Fees applies).

Guest favourite

Home in Mastic

4.95 out of 5 average rating, 148 reviews

Paradise Citadel hottub, Htd pool golf basketball

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 🏀 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 🚗 Free Parking 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

Superhost

Home in Shirley

4.94 out of 5 average rating, 236 reviews

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.

Guest favourite

Tiny home in Mastic

4.93 out of 5 average rating, 121 reviews

Cozy craftsman style home close to beaches

Feel refreshed when you stay in this rustic gem. 10 minutes from the fire island beaches this newly renovated home will take your breath away. 20 minutes from local wineries theres no shortage of things to do. This is a single dwelling home. There is a basement apartment with a separate entrance. The tenant does not have access to the house. Everything pictured is yours to use! Kick your feet up and enjoy the details of this handcrafted home. Tree house inside and out!

Guest favourite

Flat in Port Jefferson Station

4.9 out of 5 average rating, 119 reviews

The Elite Enclave

Welcome to our newly expanded and renovated Airbnb home! This elegant and modern space has been meticulously designed to provide travelers with a comfortable and unforgettable experience. Outfitted with state-of-the-art amenities and conveniences, every detail of this home has been carefully considered with your comfort in mind. Ideally located just an 8-minute drive from the Bridgeport & Port Jefferson Ferry. We are dedicated to making your stay with us truly exceptional.

Guest favourite

Flat in Shirley

4.94 out of 5 average rating, 108 reviews

Boho Beach Vibez Retreat! Private entrance

"Experience a different kind of stay with our unique Airbnb, the 'Boho Beach Vibez” This cozy 1-bedroom apartment , that’s approximately 500sqft is situated on the first level of our home with a separate entrance . Located in a prime area of our town, you'll find yourself just minutes away from all the stores, restaurants, highways, and within walking distance of hiking trails, the Carman’s river, and 5 miles from Smith Point beach. NOTE : hosts live on top level .

Guest favourite

Home in Shirley

4.95 out of 5 average rating, 129 reviews

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.

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Popular amenities for Shirley holiday rentals

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Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Shirley

Guest favourite

Flat in Mastic

5 out of 5 average rating, 6 reviews

1 Bed room Apartment in Manorville.

AyajRating, 5 stars2 weeks ago

We absolutely loved our stay at C & S – it truly felt like a home away from home. The hosts were incredibly friendly and responsive, going above and beyond to make us feel welcome. We were especially touched by the thoughtful toy corner they set up for our 2-year-old daughter—she walked in and exclaimed, “Wow, this is so amazing!” It was a wonderful experience from start to finish. Thank you so much for hosting us—we’d love to return if we’re ever in the area again!

Home in Shirley

4.87 out of 5 average rating, 140 reviews

Cope near the beach

ClarkRating, 5 stars2 days ago

Great cozy place for 6 people to fit in for a weekend trip and the beach is a 5 min drive away along with other commodities that are close by and the rooms and space was cozy would definitely recommending booking here and I would go again

Home in Bellport

5 out of 5 average rating, 4 reviews

Bellport Village Retreat

Dean And AnneRating, 5 stars2 months ago

Karen’s home was so beautiful, well decorated and comfortable. The home was very well equipped with everything we needed including high end amenities all throughout the home and a chefs kitchens dream. We have stayed in Airbnb’s in many parts of the country and the home far exceeded our expectations. On top of that Karen was a kind and responsive host. We really would give this host and home 10 stars if that was possible. Highly recommend that you book the home of you have the opportunity.

Guest favourite

Home in Mastic Beach

5 out of 5 average rating, 10 reviews

Newly Renovated Home in Mastic Beach!

GregRating, 5 stars2 days ago

Great stay! Very homey and affordable. Was exactly what we need for a our brief stay in the area

Guest favourite

Home in Coram

4.9 out of 5 average rating, 10 reviews

Luxe Home Escape

BayleeRating, 5 stars3 days ago

Nerlly’s place was absolutely beautiful and cozy! The location is super quiet and you feel incredibly safe and content during your stay. The bed and couch were so comfortable which definitely helped after two nights in a row of concerts! The space was absolutely perfect for my sister, friend, and I. We were completely comfortable and felt so safe during our stay. I definitely recommend staying here!

Guest favourite

Guest house in Mastic Beach

4.91 out of 5 average rating, 22 reviews

Cozy Guesthouse 10 min to Ocean

LucilleRating, 5 stars1 week ago

Good amenities in a private, cozy spot. The place was very clean and well-maintained. Liz was great. She met us upon arrival and walked us through everything we needed to know to enjoy our stay. We would definitely stay there again. Excellent experience overall.

Top guest favourite

Home in Mastic

5 out of 5 average rating, 12 reviews

Beautiful Home

AudreyRating, 5 stars2 weeks ago

We had a lovely stay at Christian’s home. The beautiful design, decor and layout of the home were perfect for our group of seven. The outdoor space was very inviting. We wished that our stay was longer so we could fully enjoy both the indoor and outdoor space. We will certainly rebook with Christian the next time we visit Long Island.

Guest favourite

Guest suite in Patchogue

4.87 out of 5 average rating, 82 reviews

Studio in Cool Patchogue Village

JennaRating, 5 stars1 week ago

Lori is a great host and highly responsive. Very cozy place! It has everything you need. Bed was also extremely comfortable. Felt very safe and private. An added bonus is it’s super close to the Main Street of Patchogue. Highly recommend!

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Quick stats about holiday rentals in Shirley

Total rentals
90 properties
Total number of reviews
5K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Holiday rentals in Shirley

Top-rated holiday rentals in Shirley

Holiday rentals for every style

Popular amenities for Shirley holiday rentals

Other great holiday rentals in Shirley

Quick stats about holiday rentals in Shirley

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Rentals with dedicated workspaces

Destinations to explore