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House vacation rentals in Shirley

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Top-rated house rentals in Shirley

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Top guest favorite

A cozy living area is highlighted by wooden paneling and stone columns. Comfortable seating is provided by a large couch adorned with colorful patterns. A dining table set for four sits beside a bright pink tablecloth. A subtle floral artwork adds an inviting touch to the space.

Home in North Fork

4.98 out of 5 average rating, 186 reviews

Quiet Canoe Lake Cottage getaway

Peaceful private home on lush green resort like compound with historical outbuildings plus an additional studio apartment available for larger groups.Ideal for couples or a small family looking to explore the North or South forks of Long Islands East End and a short drive to the Hamptons famous beaches, villages and restaurants.A true garden lovers getaway with extensive flowers, vegetable and fruits and even our own apiary providing local raw honey. Near lots of wineries, restaurants and 2 miles from Tanger outlet mall shopping & top 5 rated Splish Splash Water Park. .Adjacent to the Peconic River for canoeing, kayaking, fishing or birding. The quiet winding country roads on either side of the river are a favorite destination for walking/joggers, biking and motorcycle touring. Riverhead town is a great central location and an easy drive to bay and ocean beaches. The area is still very much a rural farming area and a foodies delight with many pick your own fields,farmers markets, farm stands, wineries, horse, buffalo, and goat farms and even a potato vodka distillery and tasting room! We have an awesome Aquarium in town and our newly reopened Suffolk Theater with nightly live music and shows. Riverhead has lots of inexpensive small cafe style eateries for those on a budget.

A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.

4.91 out of 5 average rating, 120 reviews

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.

Home in Shirley

4.98 out of 5 average rating, 212 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

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

4.96 out of 5 average rating, 230 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Top guest favorite

An aerial view captures a private guest house surrounded by lush green landscaping. Outdoor furniture is arranged around a small table, complemented by two sun beds. A barbeque grill is visible near the house, with vibrant flowers accentuating the backyard space.

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).

A well-lit bedroom features a spacious bed with decorative bedding, positioned against a soft blue wall. Natural light enters through large windows, adorned with sheer curtains. A compact dresser stands nearby, and an elegant table lamp adds functionality to the cozy space.

Home in Holbrook

4.9 out of 5 average rating, 289 reviews

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!

A well-maintained putting green lies in a spacious backyard, flanked by two shaded seating areas. Umbrellas provide shade over the chairs, while a swing set and a relaxing seating area with a tent can be seen in the background beyond the greenery.

4.95 out of 5 average rating, 152 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

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

4.93 out of 5 average rating, 128 reviews

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.

The open living area features a custom slate pool table with a vibrant arrangement of billiard balls. A modern kitchen is visible in the background, including sleek cabinetry and a refrigerator. A tasteful seating area includes a fireplace and a large wall-mounted television.

Home in Shirley

4.95 out of 5 average rating, 243 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.

A modern kitchen is showcased, featuring a large center island with four wooden bar stools. Stainless steel appliances and white cabinetry are complemented by granite countertops. Natural light filters in through a window above the sink, illuminating the inviting space.

Home in North Fork

4.95 out of 5 average rating, 135 reviews

⭐️Modern Farmhouse Long Island Wine Country🍷

Long Island’s North fork Long Island Wineries. Luxurious, clean , modern peaceful farmhouse. Top of the line fully stocked kitchen, stainless steel appliances, granite countertops. Keurig Coffee maker, Tea, Hot Coco. Coffee grinder . 2 fully stocked Spa like bathrooms w/ luxurious towels .4 Lg. Bedrooms. w/ luxurious linens .Cozy fireplace in Living room. Spacious dining room. Close to Farms, Wineries, Corn Mazes, Haunted Attractions, Sunflower Mazes. Pumpkin 🎃 Apple 🍎 Picking

A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.

4.89 out of 5 average rating, 120 reviews

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

A spacious outdoor patio features a large table surrounded by comfortable seating. A large umbrella provides shade, while the bright sunlight highlights the surrounding greenery. The area is bordered by a white fence and includes inviting lounge chairs.

Home in Fairfield

4.96 out of 5 average rating, 157 reviews

Top Rated Gem | Fire Pit | BBQ | FFU | Near Beach

Welcome to Fairfield Cottage, a cozy retreat that beautifully combines comfort and stylish design for you and your guests. With thoughtful decor and essential amenities, you'll feel right at home. Conveniently located just 90 minutes to NYC, you can easily visit attractions like the Norwalk Aquarium, Beardsley Zoo, and local farms. Unwind at nearby Jennings and Penfield beaches located just 3 miles away, or explore the charming village of Southport.

Vacation rentals for every style

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Popular amenities for Shirley house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A contemporary home is depicted with a clear blue pool in the foreground, surrounded by a spacious wooden deck. Lush greenery and autumn foliage frame the property, while sliding glass doors provide views of the interior.

Home in Hampton Bays

4.94 out of 5 average rating, 136 reviews

Peaceful Retreat in Immaculate Architect’s House

A contemporary two-story wooden house is nestled among lush greenery. A gravel driveway leads to the front entrance, flanked by trees and shrubs. Soft sunlight filters through the foliage, creating a serene and inviting atmosphere.

Home in Westhampton Beach

4.93 out of 5 average rating, 111 reviews

Hamptons Oasis: pool, grill, lush landscape

A modern home is set in a lush green environment, showcasing a spacious heated saltwater pool surrounded by a stone patio. Relaxing lounge chairs are placed alongside the pool, and the house features large windows that reflect the tranquility of the yard.

Home in East Hampton

4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

4.96 out of 5 average rating, 113 reviews

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

A spacious outdoor pool is surrounded by a stone patio, nestled within a serene environment of tall trees. The pool features a diving board and is complemented by nearby planters. A main house can be seen in the background, enhancing the tranquil setting.

Home in Stamford

4.95 out of 5 average rating, 256 reviews

Midcentury Modern ZenHouse Sculptor Studio

Home in Southampton

4.93 out of 5 average rating, 111 reviews

Classic Southampton Village Home w/ Pool

A solar heated pool is surrounded by spacious lounge chairs and a stone patio, offering a relaxing outdoor space. Nearby, a dining area with an umbrella invites al fresco meals, while the cottage can be seen through the lush greenery in the background.

Home in East Hampton

4.94 out of 5 average rating, 165 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

A private heated pool is surrounded by a wooden deck, featuring two red lounge chairs. Volleyball nets are set up across the pool, which is framed by lush greenery and a large umbrella providing shade. Clear blue water reflects the bright sky.

Home in Commack

4.99 out of 5 average rating, 148 reviews

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

Weekly house rentals

A two-story blue house is set in a well-maintained yard with green grass and neatly trimmed hedges. A double garage doors are visible on the left, and a front porch with steps leads to the main entrance, framed by decorative shrubs.

Home in Center Moriches

4.95 out of 5 average rating, 37 reviews

Peaceful and Bright 4 Bedroom Getaway Home

A quaint cottage exterior is framed by lush greenery, including ornamental grasses and shrubs. A wooden path leads to the entry, highlighting a welcoming entrance set under a tree. The soft colors of the cottage blend harmoniously with the natural surroundings.

Home in Mastic Beach

4.53 out of 5 average rating, 164 reviews

Cottage with Seashells

Top guest favorite

The exterior of a charming cottage displays a white facade with dark blue trim and a welcoming front door. A well-manicured lawn featuring stepping stones leads up to the porch, surrounded by colorful flower beds and greenery.

Home in Patchogue

4.99 out of 5 average rating, 85 reviews

Hamptons Style Cottage close to everything!

A panoramic view captures the lush greenery of a residential area, bordered by a vibrant blue body of water. The azure expanse of the sound contrasts against the treetops, while scattered homes can be seen nestled among the trees, creating a serene landscape.

Home in Rocky Point

4.95 out of 5 average rating, 20 reviews

RP modern cozy cabin

The exterior of a two-story home is showcased, featuring a light-colored facade and a welcoming front porch. An inviting turquoise door is centered, flanked by large windows. Lush greenery and landscaped gardens surround the entrance, enhancing the peaceful ambiance of the property.

Home in East Patchogue

4.96 out of 5 average rating, 25 reviews

Bayside Breeze

A spacious backyard is visible, featuring a newly installed heated pool surrounded by lush landscaping. Deck furniture invites relaxation, while tall grasses and flowering plants frame the scene. The exterior of the home highlights modern design elements against a backdrop of overcast skies.

Home in Bellport

5 out of 5 average rating, 33 reviews

Trendy Ranch in Bellport Village

Top guest favorite

A spacious outdoor area features a flat-bottom gunite pool surrounded by a neatly landscaped yard. Comfortable seating is positioned on a patio beside the pool, enhanced by lush greenery. Two lounge chairs and a small table are visible, providing a serene space for relaxation.

Home in Bellport

5 out of 5 average rating, 31 reviews

Monkey Puzzle - Renovated Cottage in Bellport

A sparkling blue swimming pool is framed by lush greenery. A charming white cart decorated with yellow accents stands nearby, complemented by a floral arch. A bistro set with light blue chairs and a small table offers a cozy outdoor seating area.

Home in Eastport

4.94 out of 5 average rating, 17 reviews

Midsummer Nights in Eastport

Private house rentals

A charming two-story house with wooden siding is set within a landscaped yard featuring lush green grass. Sunlight reflects off the windows, and a small balcony is visible on the upper level. A patio area with outdoor seating is located to the side.

Home in Westhampton Beach

4.98 out of 5 average rating, 40 reviews

Walk to the village! Modern beach house

A wooden dock extends into calm waters, surrounded by lush green reeds and grasses. A boat can be seen gliding across the water, with trees lining the background, creating a serene natural setting.

Home in Mastic Beach

4.97 out of 5 average rating, 34 reviews

Mastic Beach Waterfront Designer Retreat

The exterior of a renovated home is displayed with a spacious backyard, featuring a heated pool and sun beds arranged on a gravel surface. Lush trees surround the property, and a small seating area is visible on the deck, enhancing the outdoor space.

Home in Bellport

5 out of 5 average rating, 17 reviews

Home in Bellport Village w Pool

A two-story summer house is framed by a well-maintained lawn and vibrant red maple tree. The front porch features classic white railings, while a covered grill sits on the paved driveway. A wooden fence encloses the yard, creating a private outdoor space.

Home in Mastic Beach

4.94 out of 5 average rating, 17 reviews

Gateway to the Hamptons in Mastic Beach

Top guest favorite

The outdoor patio features a hot tub surrounded by lounge chairs and umbrellas. A dining table is positioned near a barbecue, offering ample space for relaxation and dining. Lush greenery lines the perimeter, enhancing the tranquil outdoor setting.

Home in Bellport

4.93 out of 5 average rating, 74 reviews

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

Top guest favorite

A spacious living area features a white sectional sofa and leather armchairs, arranged to face large glass doors that provide views of the beach. Natural light fills the room, highlighting warm wood paneling and a cozy, inviting atmosphere. A dining table is visible in the background.

Home in North Fork

5 out of 5 average rating, 14 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

A tranquil view of calm waters stretching to the horizon, framed by soft pastel hues of pink and blue in the evening sky. A wooden walkway leads to the water's edge, providing access to the peaceful atmosphere of the surrounding landscape.

Home in Center Moriches

4.85 out of 5 average rating, 13 reviews

Beach Vibes & Starry Skies

A modern living area is displayed with light-colored furniture, including two patterned armchairs, a round leather ottoman, and a cozy seating arrangement. A fireplace is framed by built-in shelves showcasing decorative items and a large framed photograph hangs above, complementing the bright ambiance.

Home in East Quogue

5 out of 5 average rating, 10 reviews

Charming, Modern Hamptons Gem

Quick stats about house rentals in Shirley

Total rentals
70 properties
Total number of reviews
3.7K reviews
Family-friendly rentals
30 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
40 properties have a dedicated workspace

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