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.

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Guest favorite

Rental unit in Winthrop

4.96 out of 5 average rating, 298 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favorite

Home in Lynn

4.93 out of 5 average rating, 42 reviews

Classic New England 3BR Charmer

Step into a meticulously designed space that combines modern comforts with touches of New England character. Our home features 3 inviting bedrooms, 1.5 bathrooms, spacious common areas and outside space, offering ample room for your group. Our location is a gateway to exploring New England's rich history, including Historic Salem, Downtown Boston, the North Shore beaches and the Lynn Woods Reservation which is just steps away from our home. Feel free to reach out with questions ahead of booking!

Guest favorite

Dome in Methuen

4.93 out of 5 average rating, 69 reviews

Stunning Geodesic Dome Farmhouse @ Melita Farms

Welcome to our Geodesic Dome Farmhouse! Discover exceptional comfort & peaceful serenity on our 56 acre farm. Renovated in 2021, the house features unique architectural designs, an airy open floor plan, and a variety of amenities to ensure your stay is a one of a kind experience! Master Suite & Full Bath - 1st Floor 4 Bedrooms & Full Bath - 2nd Floor Fully Equipped Kitchen Spacious Living & Dining Area Swimming Pool (Open May) Wrap Around Porch Grill & Patio Seating Half Bath + Washer/Dryer

Guest favorite

Rental unit in Ipswich

5 out of 5 average rating, 30 reviews

Dunover Farm. One bedroom apartment.

Welcome to our fully renovated apartment on our charming farm retreat near breathtaking Cranes Beach! 1-Bedroom, 1-bath private apartment Outside, you'll find a spacious patio and pool area where you can soak up the tranquility of the farm. Sip your morning coffee with the sheep, or savor a glass of wine in the evening as you enjoy the view of the horses. We are close to the quaint town of Ipswich, minutes to Cranes Beach, minutes to MBTA commuter rail train, and only 40 minutes to Boston.

Guest favorite

Rental unit in Winthrop

4.96 out of 5 average rating, 224 reviews

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. Our saltwater pool is nicely terraced and overlooks stunning ocean views. We are 4 short miles from the city and public transportation is easily accessible; a convenient option into Boston. 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.

Superhost

Home in Rockport

5 out of 5 average rating, 4 reviews

Rockport Pool House|4BR/3BA Walk to Bearskin Neck

KEY FEATURES: → Perfect Rockport getaway only 5 minute walk to scenic Downtown Rockport → Backyard oasis - sprawling lawn, deck and inground pool available May to September. Please note that pool is not heated. →Lots of board games and books to enjoy → Generous sized and fully stocked eat-in kitchen → Hi-speed WiFi and Smart TV to stream your favorites → Avoid Rockport parking headaches with 3 driveway parking spots → Primary bedroom w/ ensuite bath and French doors with balcony

Guest favorite

Cottage in Marblehead

4.98 out of 5 average rating, 107 reviews

4 Houses from Harbor | Old Town | Pool | Parking

Marblehead Harbor is just 4 houses away from this beautiful home with a backyard pool in Old Town Marblehead. This quaint antique cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

Guest favorite

Home in North Andover

4.92 out of 5 average rating, 12 reviews

Peaceful New England Retreat Close to It All

Have fun with the whole family at this relaxing, stylish haven in a prime location with easy access to countless New England destinations. Just down the road from Philips Academy, Brooks School, and Merrimack College; within a 30 minute drive of Boston, Salem, MA, several beautiful North Shore beaches, and Portsmouth, NH, just to name a few. There are restaurants and shops as well as a network of hiking trails leading to Lake Cochicewick, all within a short walk.

Guest favorite

Cottage in Newburyport

4.93 out of 5 average rating, 107 reviews

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

Guest favorite

Home in Gloucester

5 out of 5 average rating, 10 reviews

Twin Shores Poolside Haven

Be the first to stay at the newly renovated Twin Shores Poolside Haven! Escape to this charming 3-bedroom, 2-bath home that sleeps 8. Nestled just short walks away from the pristine shores of Good Harbor Beach in Gloucester and Long Beach in Rockport, this vacation rental promises sun-soaked days and tranquil evenings by the pool. Book today and start making unforgettable memories on the beautiful shores of Rockport and Gloucester, MA!

Guest favorite

Home in North Andover

4.94 out of 5 average rating, 150 reviews

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!

Superhost

Rental unit in Methuen

4.68 out of 5 average rating, 50 reviews

Lovely Studio renovated-pool

Enjoy our studio, will be a pleasure host you. The studio is on the basement, same level as the garage, not too down, renovated recently. We have tenants who lives upstairs. No Parties at the place. No smoking inside the place🚭 $250 violation fee. Dog is allowed 🐶 dog fee is $200 each dog. We have a beautiful pool area, the guests can enjoy.