Vacation rentals with a pool in Long Island Sound

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Long Island Sound

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Guilford

4.95 out of 5 average rating, 173 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)

Guest favorite

Home in Cutchogue

4.98 out of 5 average rating, 131 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!)

Guest favorite

Guesthouse in Southbury

4.94 out of 5 average rating, 309 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest favorite

Home in Stamford

4.95 out of 5 average rating, 240 reviews

Midcentury Modern ZenHouse Sculptor Studio

ZENHOUSE mission is rooted in the values of respect, creativity, and excellence. Inspired by the timeless principles of Zen, we offer a luxurious and exclusive experience where tranquility blends with art, spirituality, and nature. We provide a serene environment and personalized service to awaken your true nature and find Zen. Mid-century modern historic private estate surrounded by river @Zenhouse_satori and main house. Great for memorable romantic getaway, photoshoots and film locations!

Guest favorite

Home in Commack

4.99 out of 5 average rating, 125 reviews

GOOD VIBEZ HOUSE! HotTub~MiniGolf~GameRm~FirePit

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

Guest favorite

Rental unit in Deer Park

4.95 out of 5 average rating, 149 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)

Superhost

Home in Hampton Bays

4.94 out of 5 average rating, 121 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 favorite

Guest suite in Redding

4.91 out of 5 average rating, 141 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.

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 176 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Guest favorite

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.

Guest favorite

Condo in Norwich

4.95 out of 5 average rating, 130 reviews

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf

Guest favorite

Rental unit in Old Saybrook

4.96 out of 5 average rating, 120 reviews

Convenient and Cute in Downtown Old Saybrook

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you! **PETS: DOGS ALLOWED BY PRE-APPROVAL ONLY and ADDITIONAL $25 PET CLEANING FEE. Please see House Rules for more info.