Holiday rentals with a pool in Greenwich

4.96 out of 5 average rating, 141 reviews

A scenic view from the steps leading down to the backyard, showcasing a heated pool surrounded by a fenced patio and a newly installed hot tub. Lush green lawn and vibrant flowers complement the serene lake visible in the background, providing a tranquil outdoor atmosphere.

Home in Monroe

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

ValueLocationTV

4.96 out of 5 average rating, 143 reviews

A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.

Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool (summer) and cedar soaking tub (winter). Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

LocationFamilyAir conditioning

4.96 out of 5 average rating, 269 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

LocationValueHiking

5.0 out of 5 average rating, 105 reviews

Home in New Windsor

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

Welcome to The Storm King Farmhouse! Experience the best of upstate living in this beautifully renovated 1800s farmhouse located 50 mi from NYC. The property features a heated pool, Finnish sauna, premium hot tub, pickleball & basketball court, fire pit, pond, and more! Located close to exciting Hudson Valley activities - Storm King Art Center (1 min), West Point (15 min), Legoland (25 min), hiking trails, breweries, etc. This is the perfect place to relax with family & friends! Pet friendly!

FamilyValueAccuracy

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.

FamilyValueHiking

4.93 out of 5 average rating, 157 reviews

A dining area is presented featuring a dark wooden table surrounded by four white chairs. A decorative potted plant is centered on the table, complementing the modern decor. A doorway leads to a softly lit bedroom in the background.

Home in Port Jefferson

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.

LocationFamilyDecor

4.95 out of 5 average rating, 135 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.

FamilyLocationSleep quality

5.0 out of 5 average rating, 187 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 salt pool/sauna

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, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

LocationValueCondition

4.82 out of 5 average rating, 107 reviews

An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.

Home in Philipstown

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

Escape the hustle and bustle of city life and unwind in the peaceful surroundings of this luxurious retreat. With a sauna, steam room, and pool, our home offers something for everyone. Whether you are enjoying the spa like amenities or cozying up by the wood-burning stove you will have an incredible time staying with us. Don't wait, book your perfect getaway now and recharge your mind, body, and soul at our idyllic oasis!

FamilyLocationCheckout

4.99 out of 5 average rating, 103 reviews

Home in Redding

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

ValueFamilyNearby

4.98 out of 5 average rating, 266 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.

LocationValueDecor

4.91 out of 5 average rating, 155 reviews

The home theater features a large screen and 15 electric recliner seats arranged in a semi-circle. Dark blue walls and patterned carpeting create a cozy movie-watching environment. Subtle lighting enhances the overall ambiance without overwhelming brightness.

Guest suite in Northport

Coastal Villa Suite pool•sauna•gym•theater•beach

Not many places can offer this many amenities: 15 seat movie theater🍿🎥🎞️, great for watching the World Cup!🌍🏆 , full gym 🏋️, sauna room🧖‍♀️, and pool table 🎱! Outdoors, you can enjoy the fire pit🔥, nearby beaches⛱, hot tub♨️, heated pool🏊🏾‍♂️, children’s playground🏞, a huge soccer/football field ⚽️🥅🏈, 2 off road go karts 🏁🏎️! NO PARTIES! NO MORE THAN 10 PEOPLE!

FamilyLocationView

Popular amenities for Greenwich rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 71 reviews

Home in Greenwich

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

ValueLocationOutdoor spaces

4.98 out of 5 average rating, 98 reviews

A spacious fenced backyard is showcased, featuring a grassy area and a wooden picnic table. The house stands in the background with a stone accent wall. An above-ground pool is visible, surrounded by a paved area, offering a tranquil outdoor setting.

Home in Stamford

Gameroom, backyard + pool! 5m to train + downtown

ValueLocationOutdoor spaces

5.0 out of 5 average rating, 28 reviews

Home in Weston

3‑Acre Weston Retreat w/ Pool & Basketball Court

LocationValueSleep quality

4.88 out of 5 average rating, 50 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

FamilyLocationRiver

5.0 out of 5 average rating, 9 reviews

Home in Carmel Hamlet

Highland Colonial - Spacious Home w/ Pool

FamilyLocationSleep quality

4.91 out of 5 average rating, 54 reviews

Home in Suffern

Group Retreat | Pool, Hot Tub & Gourmet Kitchen

ValueFamilyParking

4.94 out of 5 average rating, 94 reviews

A well-maintained pool is surrounded by lush green grass, offering a relaxing outdoor space. Several lounge chairs are positioned around the pool area, and a light stone bench adds a comfortable seating option. Sunlight filters through the trees, enhancing the serene atmosphere.

Home in Redding

Lovely Country Retreat:

LocationFamilyHiking

5.0 out of 5 average rating, 12 reviews

A spacious outdoor area features a glistening pool surrounded by multiple lounge chairs and large umbrellas. A wooden deck leads to a relaxing seating area with comfortable couches, providing ample space for gatherings. Lush greenery is visible in the background, adding a sense of privacy.

Home in Norwalk

Casa la Lazy | 3 BDRM | 1.5 Bth | Pool | BBQ

LocationFamilyOutdoor spaces

Condo rentals with a pool

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 Midtown Manhattan

5.0 out of 5 average rating, 3 reviews

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

LocationHospitality

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

Amazing Entire Home. Minutes To Time Square NYC

ValueBathroomCondition

A lively entertainment area features a vintage arcade machine beside a soft rug. Two bar stools are positioned at a glass-top table. Natural light streams in from large windows, illuminating the modern space furnished with a comfortable sofa.

Condo in Yonkers

Beautiful 1 BR 1 BR in the heart of yonkers

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

4.0 out of 5 average rating, 12 reviews

Lovely 2 bedroom Entire Home Across Time Square

ValueFamilySleep quality

Other holiday rentals with a pool

5.0 out of 5 average rating, 3 reviews

Apartment in Stamford

Spacious Harbor Apt with Balcony, Gym and Pool

LocationNearbyPets

4.96 out of 5 average rating, 79 reviews

Apartment in Stamford

Stamford Grand Apartment

ValueFamilyWi-Fi

Guesthouse in Bedford Hills

The cottage is tucked amidst vibrant autumn foliage, framed by trees. A large front deck, furnished with two chairs, provides a serene entry, while the three expansive windows invite natural light. The wooden exterior blends harmoniously with the surrounding woodland.

5.0 out of 5 average rating, 95 reviews

The Perch: Saltwater Pool Woodland Cottage Retreat

LocationFamilyAmenities

5.0 out of 5 average rating, 7 reviews

Barn in Mount Kisco

Idyllic Retreat

FamilyLocationDecor

Apartment in White Plains

5.0 out of 5 average rating, 5 reviews

Designer 1BR | Luxe Amenities, Gym, Parking

LocationNearbyAmenities

Guesthouse in Tomkins Cove

A tranquil outdoor space features a modern pool area surrounded by lounge chairs and potted plants. Soft lighting highlights the inviting seating beneath a covered patio. The backdrop includes a dark-colored cottage, with warm lights illuminating the entrance.

4.89 out of 5 average rating, 36 reviews

The cottage at Oasis Cove

FamilyLocationAccuracy

4.98 out of 5 average rating, 101 reviews

A warm wooden interior is featured, with wall art depicting horses and rural scenes. A rustic wooden table is positioned near the window, and a candle sits at its center. A potted plant adds a touch of greenery beside a cozy armchair.

Farm stay in Redding

Charming Historic Cottage in the Redwoods

LocationFamilySleep quality