Holiday rentals with a pool in Shirley

4.94 out of 5 average rating, 311 reviews

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

4.98 out of 5 average rating, 102 reviews

Cottage in Black Rock

Spacious Cottage Loft

Welcome to the Spacious Cottage Loft! Please enjoy a nice quiet relaxed atmosphere in this unique space. Its a little bit rustic with its shiplap pine and exposed beams. Its a little bit rock and roll with its little music space along with some favorite framed albums hanging on the walls. Very comfy queen size bed. 2 smart TVs (65" up & 55" down) for your entertainment pleasure. Roomy kitchen with brand new appliances. Bath-walk in shower. THIS SPACE IS DESIGNED TO ACCOMMODATE 1-2 GUESTS.

4.94 out of 5 average rating, 192 reviews

Apartment in Deer Park

Best Studio-Private Entrance+Parking-Close To All

Make yourself at home! This Deer Park Den is your perfect suburban getaway in the heart of Long Island, close to everything and right in the middle of all the fun. Walking distance to lots of great restaurants that give you plenty of great options for ordering in or dining out. Other local destinations include: - Tanger outlets (1 Mile) - Heartland Golf Park (1.5 Miles) - Edgewood Oak Brush Plains Preserve (0.5 Mile) - Robert Moses state park (12 Miles) - Sunken Meadow state park (12 miles)

4.98 out of 5 average rating, 176 reviews

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

4.93 out of 5 average rating, 130 reviews

Home in Patchogue

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.

4.94 out of 5 average rating, 133 reviews

Sag Harbor Village Cottage with 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, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Superhost

4.85 out of 5 average rating, 112 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

Superhost

Home in Massapequa

4.73 out of 5 average rating, 146 reviews

Private 1br apt/private entrance/inground pool

Fully private apartment ...private bathroom, private bedroom with queen size bed, private living room with 2 couches & 1 futon with a separate private entrance, private kitchen (please note dishwasher is inoperative & not listed as an added amenity). Equipped with modern decor, ROKU smart TV, wifi, backyard patio & inground pool. Pool is seasonal & open from Memorial Day until end of September. Pool is limited to Airbnb guests listed on reservation only. Pool hours are 8am-8pm.

Apartment in The Hamptons

4.93 out of 5 average rating, 131 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

4.99 out of 5 average rating, 145 reviews

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.

4.9 out of 5 average rating, 221 reviews

Home in North Fork

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).