
Vacation rentals with a pool in Stamford
Find and book unique homes with a pool on Airbnb
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 €43 per night before taxes and fees

Verified guest reviews
Over 900 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 60 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!
Top-rated rentals with a pool in Stamford
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Modern 3 Bedroom Apartment Oasis PRIME Location
Stunning modern 3 bedroom / 2 bathroom space in PRIME location! JFK only 20 mins away - LaGuardia 30 mins away! Guests would enjoy a fully stocked kitchen including Keurig coffee machine w/ all the coffee you desire, spacious space (all of 2nd floor), tranquil/peaceful backyard w/ in ground pool! Located in tranquil serene family friendly neighborhood with beautiful parks nearby, beautiful park across street and Hempstead State Park 5 mins drive! Guests will feel right at home away from home!

Entire Home, Private Indoor Pool
This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

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

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.

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!

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.

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.

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Welcome to Hudson Valley Hideaway — a Modern stylish family friendly home in Beacon, NY, just 1.5 miles from downtown and the train. Bright, stylish home with 4 bedrooms, w/ 1 King bedroom, 2 queens and a Twin XL, stocked kitchen, and cozy living spaces. Enjoy a private fenced backyard retreat with pool, hot tub, fire pit, and grill. Perfect for relaxing or exploring the Hudson Valley, with easy access to Route 84 and local attractions.

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.

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!

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.

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 Stamford rentals with a pool
House rentals with a pool

Luxury modern farmhouse with heated pool & hot tub

Port Jefferson Convenient, Cozy and Chic!

Great Family Times in this 5 Bedroom House

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

Joyful Beach House, viewing The Great South Bay

Gorgeous Waterfront and Indoor Pool Family Oasis!

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

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC
Condo rentals with a pool

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

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

Amazing Entire Home. Minutes To Time Square NYC

Beautiful 1 BR 1 BR in the heart of yonkers

Lovely 2 bedroom Entire Home Across Time Square
Other vacation rentals with a pool

Spacious Cottage Loft

The Cottage by the Lake: Hudson Valley Indulgence

Spacious Harbor Apt with Balcony, Gym and Pool

Stamford Grand Apartment

Designer 1BR | Luxe Amenities, Gym, Parking

The Perch: Saltwater Pool Woodland Cottage Retreat

Idyllic Retreat

The cottage at Oasis Cove
When is the best time to visit Stamford?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €214 | €224 | €230 | €257 | €280 | €317 | €287 | €289 | €294 | €323 | €266 | €264 |
| 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 |
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