Holiday rentals with a pool in Stamford

4.89 out of 5 average rating, 450 reviews

Flat 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.

4.98 out of 5 average rating, 132 reviews

Home in Newburgh

Fable Retreats: Hudson River House

Friends and family will be wowed when gathering at this spacious mid-century riverfront home. There’s a beautiful new gunite pool, hot tub, large patio, screened floating porch, and spacious decks for barbecuing and dining. Interiors feature 2 fireplaces, 2 living spaces with large TVs, fully-equipped kitchen, game room, exercise area, piano, home office, and lots of space to spread out both inside and outside. All of it looks out to the Hudson River where you may spy bald eagles nesting nearby.

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, 106 reviews

A spacious loft area features high ceilings with exposed beams and warm wooden accents. Two comfortable leather sofas face a central ottoman, surrounded by artwork and decor. Natural light floods in through large windows, highlighting the rich wooden floors and a decorative rug.

Cottage in Black Rock

Spacious Cottage Loft

Welcome to the Spacious Cottage Loft! Please enjoy a nice quiet relaxed atmosphere in this unique space. Its a little bit rustic with its shiplap pine and exposed beams. Its a little bit rock and roll with its little music space along with some favorite framed albums hanging on the walls. Very comfy queen size bed. 2 smart TVs (65" up & 55" down) for your entertainment pleasure. Roomy kitchen with brand new appliances. Bath-walk in shower. THIS SPACE IS DESIGNED TO ACCOMMODATE 1-2 GUESTS.

4.85 out of 5 average rating, 622 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.

4.93 out of 5 average rating, 140 reviews

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

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.

Guest house in Pound Ridge

The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.

4.94 out of 5 average rating, 114 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

4.91 out of 5 average rating, 307 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.

Flat 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, 115 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, 177 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.

Popular amenities for Stamford rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 32 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

4.91 out of 5 average rating, 133 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

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, 49 reviews

Home in Redding

Redding Retreat with Pool

5 out of 5 average rating, 34 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!

4.94 out of 5 average rating, 32 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

4.8 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

Apartment 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.

Apartment 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.

Apartment 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.

Apartment in Wallingford

4.35 out of 5 average rating, 17 reviews

Cozy, charming retreat in Wallingford.

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.

Apartment in Mount Sinai

1856 Trading House close to water

Apartment in Westport

New place to stay

Winter Break 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.

Apartment 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.

Apartment in West Orange

Cozy Stay

Other holiday rentals with a pool

5 out of 5 average rating, 24 reviews

Home in Croton-on-Hudson

Perfect NYC Getaway in the Hudson Valley

4.95 out of 5 average rating, 21 reviews

A cozy sleeping area features a wooden bed frame with a light-colored patterned comforter. A bedside lamp and dresser are present, along with a full-length mirror on one wall. A textured wall adds a subtle warmth, and warm lighting enhances the space.

Home in West Orange

Private studio; MSU/SHU/St. Barnabas

4.97 out of 5 average rating, 34 reviews

A sunlit living room features two soft blue armchairs positioned beside a glass coffee table. A lamp stands on a white side table, while sunlight filters through the large windows, illuminating the room. A sliding door leads to an outdoor deck, enhancing the spacious feel.

Flat in Ronkonkoma

New, spacious 1BR with a large deck close to train

4.63 out of 5 average rating, 41 reviews

A serene bedroom is presented with a spacious bed featuring a light-colored blanket. Windows with white blinds allow natural light to brighten the room. Two framed art pieces adorn the blue walls, and a small air conditioning unit is positioned beside the bed.

Home in Hauppauge

Teal oasis private guest house

Guest suite in Massapequa

A well-lit studio space features a Murphy bed with soft bedding, ready for use. A flat-screen TV is mounted on the wall opposite. A black dresser with woven baskets provides storage, complementing the simple, clean design of the room.

4.84 out of 5 average rating, 93 reviews

Private Murphy Bed Style Studio

4.92 out of 5 average rating, 63 reviews

A bright sleeping area features a spacious bed adorned with various pillows in shades of gray and white. Two table lamps flank the bed, providing soft illumination. The warm wall color enhances the cozy ambiance of the room.

Flat in Trumbull

Cozy studio unit

5 out of 5 average rating, 39 reviews

A spacious outdoor area features a flat-bottom gunite pool surrounded by a neatly landscaped yard. Comfortable seating is positioned on a patio beside the pool, enhanced by lush greenery. Two lounge chairs and a small table are visible, providing a serene space for relaxation.

Home in Bellport

Monkey Puzzle - Renovated Cottage in Bellport