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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

4.87 out of 5 average rating, 117 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

Guest suite in Redding

4.91 out of 5 average rating, 137 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, kitchen, a dedicated 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.

Cottage in Guilford

4.95 out of 5 average rating, 170 reviews

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)

Home in Cutchogue

4.98 out of 5 average rating, 120 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, 123 reviews

GOOD VIBEZ HOUSE! Angel Wing Mural~HotTub~Pool!

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 IS NOW OPEN! *Hot tub is open year-round

Condo in Greenport

4.92 out of 5 average rating, 133 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Rental unit in Deer Park

4.94 out of 5 average rating, 139 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, 117 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

Home in Manorville

4.98 out of 5 average rating, 234 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 Stamford

4.96 out of 5 average rating, 235 reviews

Midcentury Modern ZenHouse Sculptor Studio

Zenhouse mission to inspire creativity, art, spirituality and rejuvenate.Experience complete tranquility in the Zen-like environment .Please read house rules before booking . Zen House Satori consists of an architecturally significant mid-century modern 3.5 acre private estate -main house @ Zenhouse in CT. This is the ideal setting for a memorable romantic getaway, solo adventures and business travelers – not to mention photoshoots and film locations! Inside Sculptor studio

Home in Westhampton Beach

4.98 out of 5 average rating, 107 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, 256 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.

Vacation rentals for every style

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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 Cutchogue

4.96 out of 5 average rating, 197 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Home in Massapequa

4.92 out of 5 average rating, 113 reviews

Great Family Times in this 5 Bedroom House

Home in Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

Home in East Hampton

4.94 out of 5 average rating, 155 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Home in Pound Ridge

5 out of 5 average rating, 142 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Home in Mastic Beach

4.93 out of 5 average rating, 117 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Home in Sag Harbor

4.95 out of 5 average rating, 111 reviews

Sag Harbor Village Cottage with Pool

Home in Bellport

5 out of 5 average rating, 21 reviews

Trendy Ranch in Bellport Village

Condo rentals with a pool

Condo in Montauk

5 out of 5 average rating, 11 reviews

Second Floor Corner Unit Overlooking the Ocean

Condo in Montauk

4.9 out of 5 average rating, 21 reviews

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

Condo in Montauk

5 out of 5 average rating, 19 reviews

Sun N Sound Resort, Montauk, NY

Condo in Montauk

5 out of 5 average rating, 206 reviews

Montauk Waterfront Condo w/ Sunset Views

Condo in Greenport

4.89 out of 5 average rating, 143 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, 107 reviews

Seaside Escape w Pool, Private Beach & Patio

Home rentals with a private pool

Home in East Hampton

4.73 out of 5 average rating, 15 reviews

Historical Estate Home with Backyard Pool

Bungalow in East Hampton

4.93 out of 5 average rating, 105 reviews

East Hampton Ranch with Access to Clearwater Private Beach

Home in East Hampton

4.88 out of 5 average rating, 33 reviews

Chic Poolside Hideaway in East Hampton

Home in East Hampton

4.82 out of 5 average rating, 44 reviews

Enchanting Home with Large Decks and Heated Pool

Home in Southampton

4.95 out of 5 average rating, 19 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

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