Holiday rentals with a pool in Greenwich

4.89 out of 5 average rating, 448 reviews

Apartment in Union

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.

4.95 out of 5 average rating, 262 reviews

A spacious outdoor pool is surrounded by natural greenery, featuring a stone patio and a diving board. A covered lounge area with large windows overlooks the pool, providing a serene setting for relaxation and leisure.

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

Mid-century modern historic private estate surrounded by river @Zenhouse_satori and main house. Great for memorable romantic getaway, photoshoots and film locations! 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

4.98 out of 5 average rating, 135 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

4.84 out of 5 average rating, 618 reviews

A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.

Loft in Mountainville

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

4.98 out of 5 average rating, 126 reviews

The living area features a light-colored sofa and accent chair positioned around a glass coffee table. Large windows allow natural light to enter, while sheer curtains frame the view of the outdoor space. A television and elegant decor add comfort to the setting.

Apartment in New Haven

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

4.91 out of 5 average rating, 175 reviews

A spacious living area features large windows allowing natural light to fill the room. A stone fireplace is prominently placed against a wooden wall. Comfortable seating arrangements include a large sectional sofa, with decorative plants adding a touch of greenery.

Home in Yorktown Heights

Cozy getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook! Bedroom 1: King size bed, pack n play, toddler bed. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

4.95 out of 5 average rating, 177 reviews

A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.

Home in Cold Spring

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

4.92 out of 5 average rating, 153 reviews

A modern kitchenette is displayed, featuring white cabinetry and stainless-steel appliances. A comfortable brown sofa is positioned near a wooden coffee table. A dining area with a white table and chairs is also visible, alongside large windows allowing natural light into the space.

Apartment in Suffern

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

4.91 out of 5 average rating, 305 reviews

A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.

Apartment in Brookfield

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

4.95 out of 5 average rating, 112 reviews

An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.

Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

5 out of 5 average rating, 176 reviews

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

4.98 out of 5 average rating, 253 reviews

An aerial view showcases the antique farm property set within a spacious landscape. Surrounding areas feature a mix of treed land and open fields. The main house, along with additional structures and a large yard, is visible alongside winding roads, emphasizing the rural setting.

Barn in Bethel

Escape to a Restored New England Antique Milk Barn

A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Popular amenities for Greenwich rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 132 reviews

A spacious backyard features a rectangular pool surrounded by a wooden deck. Several lounge chairs are positioned along the deck, complemented by an umbrella for shade. Lush greenery lines the perimeter, creating a serene outdoor atmosphere.

Home in Massapequa

Great Family Times in this 5 Bedroom House

4.94 out of 5 average rating, 199 reviews

A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.

Home in Stormville

Private Hudson Valley Country Retreat

4.83 out of 5 average rating, 111 reviews

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

Entire Home (private pool), Event Friendly

5 out of 5 average rating, 33 reviews

An outdoor hot tub is surrounded by lush greenery and decorative lights, creating a serene atmosphere. A large screen displays a tropical scene, enhancing the retreat's relaxing vibe. The space is illuminated, emphasizing the tranquil setting ideal for unwinding.

Home in Commack

GoodVibezHouse1.0~The Ultimate Couples Retreat!

4.8 out of 5 average rating, 30 reviews

A rustic cabin with a distinctive thatched roof is set among lush greenery. The natural stone steps lead to the entrance, and a wooden gate adorned with climbing vines is slightly ajar, inviting guests to explore the serene surroundings.

Home in Ridgefield

Log House, sits on 3acres. A retired mini farm.

4.9 out of 5 average rating, 121 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

4.74 out of 5 average rating, 150 reviews

The outdoor pool area features a clear blue inground pool surrounded by a spacious stone patio. Two umbrella-covered seating areas with chairs and a table are visible, along with a large inflatable swan float resting on the water. Lush greenery and a white fence surround the space.

Home in Massapequa

Private 1br apt/private entrance/inground pool

4.94 out of 5 average rating, 174 reviews

An exterior view of the carriage house showcases a charming blue façade adorned with flower boxes under the windows. Lush greenery surrounds the property, while comfortable outdoor seating invites relaxation. The structure features multiple large windows that enhance the light and open feel.

Home in Englewood

Englewood NJ Country Carriage House (15 min NYC)

Condo rentals with a pool

The living area is furnished with a light-colored sofa and a contemporary coffee table, creating a comfortable space for relaxation. A flat-screen TV is mounted on the wall, with decorative accents like a large metallic flower piece and vibrant wall art. Shelves and a kitchenette are visible in the background.

Condo in Weehawken Township

4 out of 5 average rating, 12 reviews

Lovely 2 bedroom Entire Home Across Time Square

The building exterior features an elegant facade with arched windows and a covered entrance. The marquee displays 'The Manhattan Club.' Soft lighting highlights architectural details, while potted plants are placed at either side of the entrance, adding to the welcoming appearance.

Condo in Theater District - Times Square

5 out of 5 average rating, 3 reviews

The Manhattan Club in the heart of midtown!!!!

A stylish living room features a dark accent wall with a large TV displaying floral imagery. A low, wooden sideboard adds texture, complemented by decorative items. A cozy, light-coloured couch is paired with a patterned area rug, creating an inviting atmosphere.

Condo in Wallingford

4.35 out of 5 average rating, 17 reviews

Cozy, charming retreat in Wallingford.

Condo in Harrison

New place to stay

Private 1 BedRm EntireApartment ~ dm for flat rate

4.95 out of 5 average rating, 41 reviews

Two people are seen swimming in a calm body of water, surrounded by gentle ripples reflecting sunlight. Lush greenery lines the distant shoreline, creating a serene backdrop against the shimmering surface.

Condo in Mount Sinai

1856 Trading House close to water

Condo in Westport

New place to stay

Peaceful condo available in Westport

A cozy bedroom features a spacious bed draped with a dark green blanket. Emerald green accents adorn the walls, while natural light filters through sheer curtains. A large mirror reflects the vibrant decor, complementing a patterned area rug underfoot.

Condo in Weehawken Township

Amazing Entire Home. Minutes To Time Square NYC

A two-car garage is visible with a light-colored vehicle parked in front. The entrance features a set of stairs leading to the upper level, framed by wooden balconies. Natural stone accents complement the exterior design of the building in a secure, residential area.

Condo in West Orange

Cozy Stay

Other holiday rentals with a pool

4.94 out of 5 average rating, 31 reviews

A sparkling pool is set on a wooden deck, surrounded by lush greenery. Views of rolling hills and trees stretch into the distance under a clear blue sky, creating a serene and inviting outdoor space.

Home in East Fishkill

Hudson Valley Retreat | Hot Tub, Pool & Gym

5 out of 5 average rating, 17 reviews

Home in Weston

Dream Home w/ Pool & Basketball Court on 3 Acres

5 out of 5 average rating, 31 reviews

A newly renovated two-story house is showcased, featuring a light-colored exterior with large windows. A neatly landscaped yard surrounds the home, with a pathway leading to the entrance steps. A garage is visible to the right, complementing the charming residential setting.

Home in Bellport

South Bay Holiday

4.94 out of 5 average rating, 31 reviews

A serene outdoor setting features a sparkling swimming pool surrounded by lush greenery. Comfortable seating areas, including deck chairs, are positioned nearby. Hammocks hang between trees, providing a relaxing retreat. Scenic views of the Hudson River and mountains enhance the tranquil atmosphere.

Home in Philipstown

Arkadia House Mid-century retreat with pool & view

4.89 out of 5 average rating, 19 reviews

Home in Redding

Meeker Hill House - Country Escape w/ Heated Pool

5 out of 5 average rating, 13 reviews

A comfortable living area features a striped sofa adorned with patterned cushions, positioned beside a wooden coffee table. A vase of fresh flowers sits atop the table. Light filters through a large window with divided panes, illuminating the space and connecting to the kitchen area visible in the background.

Home in Sherman

Designers Historic Connecticut Home

5 out of 5 average rating, 27 reviews

A serene backyard scene features a sparkling pool adjacent to a stone patio. Colorful chairs surround a fire pit, framed by lush greenery and blooming flowers. The tranquil pond adds to the peaceful atmosphere, creating a relaxing outdoor space for guests.

Tiny home in Halesite

Cozy Cottage