
Vacation rentals with a pool in Stamford
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Stamford
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

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.

Lakeview with Pool + Dry Sauna, 30+ day stays only
Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. UNHEATED cold pool open after 6/10 with a hot cedar sauna next to it for hot/cold therapy. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Nearby hikes include Fahenstock Park or walk up the hill to trails of Volz park!

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

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.

The Magic Red Barn with Heated Salt Pool
Experience countryside magic just one hour from NYC! Enjoy nature’s wonderland, nearby farmers’ markets, and scenic trails. Indulge in our heated saltwater pool for a perfect retreat. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn featuring: 1 king, 2 queen, 1 toddler bed, full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests seeking escape. Enjoy complete privacy—no other guests. Fiber optic Wi-Fi.

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.

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.

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Welcome to Hudson Valley Hideaway — a stylish, family-friendly 4BR/2BA home tucked in the corner of Beacon just 1.5 miles from downtown & the Hudson River. Enjoy a chic living room w/ 85” TV, stocked kitchen, dining room, 1Gb WiFi, workspace & A/C. Sleep soundly in 1 King, 2 Queens & 1 Twin XL. Outside, unwind in the fenced oasis w/ pool, slide, hot tub, grill & fire pit. Modern comfort meets cozy Hudson Valley charm. SPECIAL: 20% OFF all winter stays!

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.

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.

The Cottage by the Lake: Hudson Valley Indulgence
The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.
Popular amenities for Stamford rentals with a pool
House rentals with a pool

Dream Home w/ Pool & Basketball Court on 3 Acres

The Barger Wixon House

Nice getaway with your family.

Arkadia House Mid-century retreat with pool & view

Riverfront Cottage-Pool-Hot Tub-Fireplace 35m>NYC

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

Englewood NJ Country Carriage House (15 min NYC)

Bellport Park | Pool, Fire Pit & Balcony
Condo rentals with a pool

Lovely 2 bedroom Entire Home Across Time Square

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

Cozy, charming retreat in Wallingford.

Beautiful 1 BR 1 BR in the heart of yonkers

1856 Trading House close to water

Weekend Condo in Westport

Casa Monteverde® Designer 1BR w/ 15 min to NYC

Amazing Entire Home. Minutes To Time Square NYC
Other vacation rentals with a pool

Winter Retreat: Private Jacuzzi, Game room & more

The Suite Life in Dix Hills

Cozy studio unit

Prime Locale: Ideal Guesthouse

The Perch: Saltwater Pool Woodland Cottage Retreat

The cottage at Oasis Cove

Designer King 1BR Near NYC | Parking, Pool & Gym

Charming Historic Cottage in the Redwoods
When is the best time to visit Stamford?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ911 | ﺩ.ﺇ922 | ﺩ.ﺇ812 | ﺩ.ﺇ845 | ﺩ.ﺇ951 | ﺩ.ﺇ1,300 | ﺩ.ﺇ1,230 | ﺩ.ﺇ1,238 | ﺩ.ﺇ1,260 | ﺩ.ﺇ1,385 | ﺩ.ﺇ1,138 | ﺩ.ﺇ1,131 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about vacation rentals with a pool in Stamford

Total vacation rentals
Explore 100 vacation rentals in Stamford

Nightly prices starting at
Stamford vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 860 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
100 of Stamford vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Stamford rentals

4.8 Average rating
Stamford stays are highly rated by guests—averaging 4.8 out of 5!
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- Times Square
- Madison Square Garden
- New York City Center
- Brooklyn Bridge
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Bronx Zoo
- Yale University
- Rockefeller Center
- Grand Central Terminal
- Yankee Stadium
- Ohel Chabad-Lubavitch
- United Nations Headquarters
- Jones Beach
- Bryant Park
- Empire State Building
- Citi Field
- Statue of Liberty
- Radio City Music Hall
- Old Glory Park
- USTA Billie Jean King National Tennis Center
- Fairfield Beach
- Thunder Ridge Ski Area




