
Holiday rentals with a pool in Shirley
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Shirley

Total holiday rentals
Explore 20 holiday rentals in Shirley

Nightly prices starting at
Shirley holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Shirley holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shirley rentals

4.9 Average rating
Shirley stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with a pool in Shirley
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Modern home with pool near beach
Our home is located in Shirley, Long Island. It is two miles away from oceanfront Smith Point Beach. This listing is to book the entire home when we are out of town. Please check our reviews on the other listing of the same room and home. The guest bedroom is on the main level of our home, with a bathroom adjacent to the room. The room is equipped with a comfortable queen size bed, table with two chairs, closet, two nightstands, an armchair, and Apple TV with various streaming apps to use

Gorgeous Waterfront and Indoor Pool Family Oasis!
Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

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.

Brand new house with an all year round hot tub.
Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

Beach House Feel - Newly renovated Backyard Oasis
You will love this sunny, completely renovated three bedroom ranch. It's beautifully decorated with beach and nautical themes throughout the house. You can cook or barbeque at home on your private deck or go out and enjoy the many award winning restaurants in the area. Come home from the beach or shopping and lounge by the pool. At night, gather around the fire pit while making smores or just admiring the stars. This house is perfect for families, couples, or a girls/guys getaway.

Port Jefferson Convenient, Cozy and Chic!
Bright, modern, newly renovated and landscaped space can sleep up to 6! Countless amenities including a kitchen with dishwasher, full size refrigerator. 3 bedrooms, 2 full baths, and common living space. Great for boaters or attending events in Port Jefferson, Stony Brook or anywhere on Long Island. We are a 1 minute drive or 10 minute walk from Port Jefferson Harbor and Ferry Dock. Centrally located on LI for easy access to LI rail road and bus routes.

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach
Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

Private Oasis W/Stunning Vinyard and Pool Views
Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

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.

Guest House retreat with amazing pool !!!
Slice of Heaven #2 Bellport Village, a destination town overlooking the great south bay as seen in Coatal Living's top places to vacation. Written by Coastal Living: a gorgeously unassuming little seaport on long Island's South Shore, this village holds a royal flush of pleasures- A small town community feel, colonial style architecture, and even its own performing arts center, all 90mins from NYC.

"NORTH APT." Renovated 1 Br Apt. In Great Location
The 1 Bedroom "North Apartment" is located in our newly renovated beach house, perfectly located just seconds away from the ocean and only three blocks from the harbor in Fire Island Pines. The house has 2 outdoor decks with a pool and a hot tub, both with ocean views. The apartment has a queen size bed, Heat & A/C units in every room, internet, TV and much more amenities!

The Unhampton
This Brookhaven Hamlet detached space (totally separate) is for people who love nature and preserved quiet spaces. Fire Island is a ferry ride away, Manhattan is one hour by train and the Hamptons are a 25 minute ride.15 minutes from the restaurants and coffee shops in Patchogue and just a couple of minutes from Bellport Village. Centrally located and truly peaceful!
Popular amenities for Shirley rentals with a pool
House rentals with a pool

Splendid private cottage

Designer Home w/ Heated, Salt-Water Pool

Summer Retreat: Private Jacuzzi, Game room & more

Sag Harbor Hamptons hideaway

Hamptons Getaway/ Backyard OASIS/EV charger

Relax Villa ,Hot tub /New pool,7min from the beach

Bayside paradise w/ huge yard

Cozy Home with Pool - Near Beach and Restaurants
Apartment rentals with a pool

Greenport Getaway at Cliffside Condos

Beautiful condo on Long Islands Northfork

Waterfront Escape | Private Beach, Pool & Views

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

Newly Renovated Modern Townhouse w/Pool & Tennis

1856 Trading House close to water

A Unique Piece of Paradise, Water Front pool
Home rentals with a private pool
Enchanting Home with Large Decks and Heated Pool
East Hampton Villa | Heated Saltwater Pool & Beach
Perfect Getaway at Sunny Modern Shampton LakeHouse
Saltbox with Separate Poolhouse in Northwest Woods
Destinations to explore
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- Pet-friendly rentals Shirley
- Flat rentals Shirley
- Rentals with a patio Shirley
- Family-friendly rentals Shirley
- Rentals with outdoor seating Shirley
- House rentals Shirley
- Rentals with beach access Shirley
- Rentals with a fireplace Shirley
- Rentals with a washing machine and dryer Shirley
- Waterfront rentals Shirley
- Rentals with a firepit Shirley
- Rentals with pools Suffolk County
- Rentals with pools New York
- Rentals with pools United States
- Beach
- Yale University
- Jones Beach
- Cooper's Beach, Southampton
- Fairfield Beach
- Robert Moses State Park Beach
- Sunken Meadow State Park
- Jones Beach State Park
- Hammonasset Beach State Park
- UBS Arena
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Long Island Aquarium
- Sherwood Island State Park
- Orient Beach State Park
- Amagansett Beach
- Compo Beach
- Wölffer Estate Vineyard
- Ohel Chabad-Lubavitch
- Meschutt Beach
- Jennings Beach
- Hofstra University
- Soundview Beach





