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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.

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Guesthouse in Hempstead

4.84 out of 5 average rating, 122 reviews

Private Guest house with pool access.

Warning‼️this listing price is for 1 adult only. A $50 daily fee will apply for additional guest. Unapproved guest will result in cancellation no refund. Clean, stylist, peaceful, private space. Seasonal Pool access from July until 1st of September . ⛔️ Do not flush toilet paper on the toilet it will overflow, garbage disposal and trash bags are available. For pets a fee will apply. No smoking 🚭, No parties, 2 guest Max. Security Cameras. No parking on premises. Street parkings are available 24/7

Home in Cutchogue

4.98 out of 5 average rating, 128 reviews

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 available (inquire!)

Home in Commack

4.99 out of 5 average rating, 124 reviews

GOOD VIBEZ HOUSE! GolfCourse~GameRm~AngelWingMural

STAY. SOMEWHERE. DIFFERENT. Definitely not your average Airbnb. Located literally right in the Heart of Long Island, in a very super SAFE & QUIET neighborhood, THE GOOD VIBEZ HOUSE will make you feel like you are away on vacation, at a unique, smart, fun, modern, cozy, luxury 5 star Tropical Resort. As Superhosts, we strive to provide every guest with top level hospitality, luxury, amenities and 5 star experience that you deserve. *HEATED* POOL OPENS APRIL 30TH *Hot tub is open year-round

Rental unit in Deer Park

4.95 out of 5 average rating, 146 reviews

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)

Home in Hampton Bays

4.94 out of 5 average rating, 120 reviews

Peaceful Retreat in Immaculate Architect’s House

This "like new" contemporary three-bedroom, three-and-one-half bath home is the perfect winter and summer gateway. Located in a quiet and secluded area of the West Tiana shores community. It is situated near bay & ocean beaches, East Quogue & Hampton Bays Village. The main level features soaring ceilings, and windows on all sides, large open living and dining areas, and a contemporary kitchen. The living room directly faces the pool, cedar deck, and a manicured garden and outdoor shower

Guest suite in Redding

4.91 out of 5 average rating, 139 reviews

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.

Home in Mastic Beach

4.93 out of 5 average rating, 118 reviews

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.

Home in Manorville

4.98 out of 5 average rating, 241 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Ultimate house with 4 Bds, 3 Baths, finished basement with entertainment area and gym. Minutes from the Hamptons and North Fork. Everything for your rest in any weather and season. Yamaha piano, Japanese massage chair, karaoke, drum set, electric guitars, ping pong, fossball and pool tables,board games. Fully landscaped backyard with flowering plants, outdoor lights. 2 BBQ areas, Gazebo with fireplace and projector. Easy access to beaches, restaurants, farms, vineyards and shopping.

Home in Westhampton Beach

4.98 out of 5 average rating, 112 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.

Home in Sag Harbor

4.85 out of 5 average rating, 258 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Home in Southampton

4.97 out of 5 average rating, 150 reviews

Dream Home with a wonderful heated pool in SH

Situated on a half-acre of land, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 4 wonderful bedrooms 3 modern bathrooms and a solar heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

Rental unit in Rocky Point

4.94 out of 5 average rating, 143 reviews

North shore Guest Room.

This apartment is our guest room with outside private entrance and off street parking. Apartment has a refrigerator, microwave, coffee maker, and toaster oven. Queen bed and a twin pullout couch bed is provided. The place is appropriate for a short stay as an affordable alternative to hotel stay.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Bungalows

Intimate homes. inviting architecture

Popular amenities for Long Island rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Fire Island Pines

4.92 out of 5 average rating, 73 reviews

The Legendary Pyramid House

Home in Bellport

4.93 out of 5 average rating, 15 reviews

Bellport Abode

Home in Syosset

4.92 out of 5 average rating, 49 reviews

Elegant, resort style, clean, north shore home

Home in East Hampton

4.94 out of 5 average rating, 155 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Home in Greenwich

4.97 out of 5 average rating, 34 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

Home in Pound Ridge

5 out of 5 average rating, 145 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Home in Southampton

5 out of 5 average rating, 35 reviews

Renovated Southampton Home+Pool

Home in East Hampton

4.93 out of 5 average rating, 139 reviews

Heated pool, games room, near beach, kid-friendly

Condo rentals with a pool

Condo in Montauk

4.91 out of 5 average rating, 23 reviews

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Condo in Montauk

5 out of 5 average rating, 20 reviews

Sun N Sound Resort, Montauk, NY

Condo in Montauk

5 out of 5 average rating, 208 reviews

Montauk Waterfront Condo w/ Sunset Views

Condo in Greenport

4.89 out of 5 average rating, 145 reviews

Beautiful Waterview Condo on the North Fork of LI

Condo in Greenport

5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

Condo in Hampton Bays

4.95 out of 5 average rating, 42 reviews

A Unique Piece of Paradise, Water Front pool

Condo in Greenport

4.9 out of 5 average rating, 110 reviews

Seaside Escape w Pool, Private Beach & Patio

Condo in Greenport

4.92 out of 5 average rating, 137 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Home rentals with a private pool

Bungalow in East Hampton

4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

Home in East Hampton

4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

Home in East Hampton

4.88 out of 5 average rating, 33 reviews

Chic Poolside Hideaway in East Hampton

Home in Southampton

5 out of 5 average rating, 81 reviews

Best of Country and Beach Living

Home in East Hampton

4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

Home in Southampton

4.93 out of 5 average rating, 61 reviews

Southampton Quiet Private Home/Pool 6min to Villag

Home in Southampton

4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

Home in East Hampton

5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

Destinations to explore