Vacation rentals with a pool in Essex County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Essex County

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

1 of 1 pages1 / 1

Guest favorite

Cottage in Plum Island

Sunset Waterfront Retreat | Private Beach, Pool &

Waterfront retreat with private beach access, panoramic marsh views, and unforgettable sunsets. Designed for families and groups looking to relax, reconnect, and enjoy the best of Plum Island living. Enjoy the private pool (open seasonally), expansive outdoor living spaces, firepit lounge, and peaceful wildlife views directly from the property. Spend your days walking the island, to local beaches and restaurants, or simply unwinding by the water. Inside, the home features a modern kitchen, was

4.93 out of 5 average rating, 141 reviews

Top guest favorite

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

Private Suite• Pool • Sleeps 4 • Boston • Airport

Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

4.97 out of 5 average rating, 348 reviews

Top guest favorite

A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.

Apartment in Winthrop

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

4.96 out of 5 average rating, 286 reviews

Top guest favorite

Home in Chelsea

Theatre | Arcade | Pool w. Free 3 Car Parking

Experience The Chelsea Retreat, your private escape with free parking for up to 3 cars and an average 15 minute drive to Boston’s top attractions! Enjoy a cinematic night with a 150” 4K theatre and immersive surround sound, challenge friends in the arcade with foosball, pinball, and classic arcade games, or unwind beneath the gazebo before floating the day away in the pool. Shoot hoops, fire up the BBQ, or retreat to a quiet, dedicated workspace. Luxury, fun, and convenience all in one place.

5.0 out of 5 average rating, 20 reviews

Top guest favorite

Guest suite in Marblehead

Headers’ Haven

Your family will be close to everything when you stay at this centrally-located in-law suite. Walking distance to beaches, shops, and restaurants. Steps from Steer Swamp Conservation Area. 13 miles from Boston, and an easy 10 min drive to Salem. Cool off in the pool during the summer heat, or relax in the hot tub on a chilly evening. There’s room for everyone on the pull out sectional to snuggle up for a movie night, complete with popcorn and candy machines. Sure to be a fun and cozy stay!

5.0 out of 5 average rating, 90 reviews

Guest favorite

A well-maintained swimming pool is featured in the backyard, surrounded by a patio. Lush greenery and mature trees offer privacy. The two-story house is visible in the background, with large windows allowing light to enter. A basketball hoop is positioned adjacent to the pool area.

Home in Arlington

Beautiful Spacious 4BRM House!

A thoughtfully cared-for New England home best suited for a quiet, comfortable stay in a residential neighborhood. Enclosed back yard with pool during summer (June 21 - September 20) 4 bedrooms (2 ensuite), 3 full bathrooms, 1 half bath. Spread over 2 floors: - Floor 1: eat-in kitchen, 1/2 bath, living, dining, office - Floor 2: 4 bedrooms, 3 bathrooms, bonus room - Has STAIRS to bedrooms Outside: Yard, unheated swimming pool (summer 6/21-9/20), patio. 2 off-street parking.

4.93 out of 5 average rating, 59 reviews

Superhost

Home in Methuen

The Stunning Melita Farms Geodesic Dome Farmhouse

Your next stay awaits at the Melita Farms Geodesic Dome Farmhouse. The farmhouse is nestled off the beaten path (yet minutes from local gems) and is the perfect balance of retreat and convenience. Fall in love the moment you arrive on this 56 acre non-profit working farm to the moment you enter the front door. The farmhouse comfortably hosts up to 10 guests. Features 5 bedrooms, 2.5 bathrooms, hardwood floors, soaring cathedral ceilings, pool, and stunning farm views.

4.92 out of 5 average rating, 12 reviews

Guest favorite

Apartment in Manchester-by-the-Sea

Private Pool Retreat w/Fire Pit Near Singing Beach

Relax in a private coastal retreat with a pool and fire pit, minutes from Singing Beach. This updated suite features a modern layout, fireplace, and two queen beds—one in a private sleeping area. Ideal for relaxing or remote work, with a secluded backyard, private entrance, free parking, and fast Wi-Fi. Near downtown Manchester-by-the-Sea, dining, and coastal views. Seasonal pool: 5/20–9/8. Walk to local shops, restaurants, and the harbor, all from this peaceful setting.

4.91 out of 5 average rating, 203 reviews

Top guest favorite

A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.

Home in North Andover

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

4.95 out of 5 average rating, 184 reviews

Superhost

Apartment in Chelsea

Cozy 1BR Near Boston w/ Pool & Gym

🌟 Features You’ll Love • 1BR w/ king bed • Fast Wi-Fi + workspace • Smart TVs • Full kitchen • Washer/dryer • Private patio • Private parking • Pool, gym, game room & business lounge 📍 Prime Location • Chelsea, minutes from Boston ✨ Perfect For • Business travelers, travel nurses & city stays 💫 Good To Know • Strictly non-smoking Dont miss out- reserve your stay today and enjoy a memorable Boston experience.

4.8 out of 5 average rating, 86 reviews

Top guest favorite

Home in Marblehead

Exclusive Lifestyle on Marblehead Neck

Located on Marblehead Neck, just a short walk to the harbor and Chandler Hovey Tower park, you'll find all you need to enjoy a luxurious stay. All the comforts you need are provided in a beautifully designed, clean and functional home. Well-equipped kitchen, enclosed backyard with a firepit and plunge pool, billiard room. Lots of light and space. Plenty of separate rooms for everyone to have the space they need.

5.0 out of 5 average rating, 38 reviews

Superhost

A classic red-shingled house is depicted, featuring multiple gabled roofs and a welcoming front porch. A paved pathway leads to the entrance, bordered by landscaped greenery. The parking area is visible alongside the building, with a mix of outdoor lighting and natural shade from nearby trees.

Apartment in Haverhill

Bradford 2BR Retreat | Pool, Fire Pit & Parking

🏡 Peaceful 2BR Bradford, MA stay with a King bed, Queen bed, private fire pit, shared fenced backyard, seasonal pool access, fast WiFi, Smart TV, fully equipped kitchen, dining for six, and free parking. Conveniently located near Haverhill, the MBTA Commuter Rail, scenic trails, Merrimack River waterfront, and Boston day-trip routes. Ideal for families, couples, business travelers, and extended stays.

4.74 out of 5 average rating, 53 reviews