
Vacation rentals with a pool in Long Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Long Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Union 2BR Resort-Style Apt – Easy NYC Transit
✨ Urban Luxury next to Union Station ✨ Welcome to AVE Union, where premium living meets 24/7 service with an award-winning team.🏆 Community has a resort-style pool, outdoor kitchen, fire pit lounges, and outdoor gaming areas. 🚆 Perfect for Commuters - Easy NYC access via Secaucus or PATH - Minutes to Newark Airport & Short Hills Mall - Minutes from Newark Liberty International Airport 🛋️ Private Balconies. 💼 Productivity Center 💪 Performance & Wellness 🏡 Professional Environment.

Luxury cottage by the sea with hot tub and pool
We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

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)

East Hampton Village Fringe, Renovated with Pool
This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Artist Retreat in Beautiful Country Setting
Stay at this unique property, owned and designed by a Eu artist, and enjoy the quiet countryside and natural beauty that rural CT has to offer. A large one bedroom studio with an modern fireplace, is equipped with a comfortable king size bed, full bathroom, sauna, indoor resistance pool- available at an extra charge, kitchenette, a workspace, and high-speed internet for seamless remote work. Relax in the evening at your own private outdoor seating area surrounded by the property's charm.

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.

King 1BR Apt with Cozy Den and Luxury Amenities
This gorgeous apt, located in a brand-new luxury building at the center of New Haven’s historic downtown, offers unparalleled comfort, service, and amenities. You can watch a movie on a 65" HDTV, work in one of 5 co-working spaces, or relax at the pool w/ grills and cabanas. Highlights: • Walkable access to Yale • Deep-clean prior to every guest • Coffee, fresh linens, and bathroom essentials • 24/7 fitness center • Rooftop sun terrace + grills • Entertainment lounge w/ bowling alley

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.

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

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.

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.
Popular amenities for Long Island rentals with a pool
House rentals with a pool

Private Oasis W/Stunning Vinyard and Pool Views

Chic Hamptons Retreat | Fireplace, Hot Tub, Beach

Hamptons Oasis: pool, grill, lush landscape

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Bellport Village Retreat

Light-filled Retreat by the Bay

1800 Historical EH Home, 1 Mile to Town!

Secluded Farmhouse - Studio Apartment Style Unit
Condo rentals with a pool

Beautiful condo on Long Islands Northfork

Montauk Waterfront Condo w/ Sunset Views

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

1856 Trading House close to water

Waterfront Autumn Escape in Wine Country: 2BR

Beachside Waterview 2Br Condo w/ Pool in Greenport

Montauk Oceanfront Condo
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach

Explore the Water & Woods at a Relaxing Retreat
Enchanting Home with Large Decks and Heated Pool

Southampton Quiet Private Home/Pool 6min to Villag
Perfect Getaway at Sunny Modern Shampton LakeHouse
Saltbox with Separate Poolhouse in Northwest Woods
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Mount Pocono Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Rentals with an EV charger Long Island
- Loft rentals Long Island
- Tent rentals Long Island
- Serviced apartment rentals Long Island
- Rentals with a fireplace Long Island
- Hotel rentals Long Island
- Rentals with lake access Long Island
- Rentals with a hot tub Long Island
- Private suite rentals Long Island
- Chalet rentals Long Island
- Mansion rentals Long Island
- Pet-friendly rentals Long Island
- House rentals Long Island
- Waterfront rentals Long Island
- Beachfront rentals Long Island
- Rentals with a fire pit Long Island
- Rentals with a home theater Long Island
- Farmstay rentals Long Island
- Cottage rentals Long Island
- Bed and breakfasts Long Island
- Rentals with an accessible height toilet Long Island
- Rentals with outdoor seating Long Island
- Ski-in/ski-out rentals Long Island
- Beach house rentals Long Island
- Rentals with beach access Long Island
- Rentals with a kayak Long Island
- Rentals with an accessible height bed Long Island
- Condo rentals Long Island
- Guesthouse rentals Long Island
- Apartment rentals Long Island
- Family-friendly rentals Long Island
- Fitness-friendly rentals Long Island
- Vacation home rentals Long Island
- Boutique hotel rentals Long Island
- Aparthotel rentals Long Island
- Rentals with a sauna Long Island
- Resort rentals Long Island
- Luxury rentals Long Island
- Rentals with breakfast Long Island
- Bungalow rentals Long Island
- Tiny house rentals Long Island
- Rentals with a washer and dryer Long Island
- Rentals with a patio Long Island
- Smoking-friendly rentals Long Island
- Townhouse rentals Long Island
- Villa rentals Long Island
- Rentals with pools New York
- Rentals with pools United States
- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- Yale University
- MetLife Stadium
- Central Park Zoo
- Jones Beach
- Yankee Stadium
- Fairfield Beach
- Citi Field
- United Nations Headquarters
- Southampton Beach
- Grand Central Terminal
- Rye Beach
- Statue of Liberty
- Cooper's Beach, Southampton
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- Gilgo Beach
- The Metropolitan Museum of Art
- Things to do Long Island
- Nature and outdoors Long Island
- Art and culture Long Island
- Entertainment Long Island
- Sightseeing Long Island
- Tours Long Island
- Food and drink Long Island
- Sports activities Long Island
- Wellness Long Island
- Things to do New York
- Entertainment New York
- Art and culture New York
- Food and drink New York
- Nature and outdoors New York
- Sports activities New York
- Wellness New York
- Tours New York
- Sightseeing New York
- Things to do United States
- Sports activities United States
- Tours United States
- Food and drink United States
- Entertainment United States
- Wellness United States
- Nature and outdoors United States
- Art and culture United States
- Sightseeing United States