Vacation rentals with a pool in Fairfield County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Fairfield County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 307 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest favorite

Home in Stamford

4.95 out of 5 average rating, 239 reviews

Midcentury Modern ZenHouse Sculptor Studio

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

Guest favorite

Home in Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

Guest favorite

Rental unit in Milford

4.99 out of 5 average rating, 84 reviews

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.

Guest favorite

Guest suite in Redding

4.91 out of 5 average rating, 141 reviews

Artist Retreat in Beautiful Country Setting

Stay at this unique property, owned and designed by a Eu artist, and enjoy the quiet countryside and natural beauty that rural CT has to offer. A large one bedroom studio with an modern fireplace, is equipped with a comfortable king size bed, full bathroom, sauna, indoor resistance pool- available at an extra charge, kitchenette, a workspace, and high-speed internet for seamless remote work. Relax in the evening at your own private outdoor seating area surrounded by the property's charm.

Guest favorite

Guesthouse in Easton

4.84 out of 5 average rating, 101 reviews

Entire Guest House at Fox Pond Farm.

Recently renovated private guest house with access to swimming pool offers sleeping for eleven in four bedrooms. Tastefully decorated with all amenities. Close to Merritt Parkway and train to Manhattan. This is a natural refuge on eleven very private acres. Large private terrace faces westerly for amazing sunsets and offers a "Plein Air" environment for alfresco meals, cocktails and relaxation. An attached vegetable and flower garden with fountain offer a quiet space to relax and reflect.

Guest favorite

Home in Weston

5 out of 5 average rating, 9 reviews

Amazing Home & Private Court on Quiet 3 Acres

The way Airbnb was meant to be - a home away from home. Enjoy complete privacy on this immaculate property - bring the family for a getaway in one of the most beautiful areas of Connecticut. This newly renovated home has high-end South African interior design and fully equipped with thoughtful touches. Come and create memories you will never forget. —— No parties, events, or commercial activity. Firm on 8 adults total. If there is anything we can do for you please ask :)

Guest favorite

Guesthouse in Bedford Hills

5 out of 5 average rating, 24 reviews

The Perch, a luxe cottage in the woods 1h from NYC

"The Perch is a peaceful, thoughtfully appointed woodland haven." - Elyssa The Perch, our luxe cottage nestled in the woods in Bedford, NY is the perfect country getaway. Surrounded by nature, this charming retreat offers a perfect getaway for those seeking peace and quiet, in the heart of Bedford with all the surrounding amenities just 1 hour from NYC. The newly renovated cottage is thoughtfully designed to provide a cozy and inviting atmosphere.

Guest favorite

Home in Fairfield

5 out of 5 average rating, 36 reviews

Fairfield! 5 bedroom, 3.5 bath on cul-de-sac

Spacious, renovated & furnished, contemporary home w/fenced in yard. Relax by the heated Gunite Pool, or 1 of the 5 nearby beaches. Pool is opened mid-May to mid-Sept (weather permitted). 5 bedrooms (8 beds), sleeps 10/12, 3.5 baths, walk out basement, outdoor deck. Near town, universities so prebook for tours, parent & Alumni weekends. Near many kid friendly activities, Fairchild Wheeler Public golf course and transportation into NYC Grand Central!

Guest favorite

Home in Redding

4.93 out of 5 average rating, 84 reviews

Private * Hiking * Swimming * Pool * Steam-room

Escape to our spacious midcentury home set against a park in the charming town of Redding. Enjoy the luxury of a private heated pool open from Memorial Day to Sept 30th or snug up in the living room and enjoy the forest views as your backdrop. Our five-bedroom house is the perfect retreat for large families or groups of friends looking to relax and explore the area. The house is about an hour and a half drive from NYC.

Guest favorite

Farm stay in Redding

5 out of 5 average rating, 49 reviews

Charming Historic Cottage in the Redwoods

Travel back in time to Marchant Farm and enjoy an authentic farm life experience in the historic, newly restored Sunflower Cottage. Whether you need a place to recharge or to reconnect with nature, you will find it here. Relax and unwind in the stunning floor to ceiling cedar living area. With 2 air conditioned bedrooms, each with full beds, and the children's magical loft space with two twin beds and play area.

Guest favorite

Home in Pound Ridge

5 out of 5 average rating, 147 reviews

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.