Vacation rentals with a pool in Essex County

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.

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.

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.

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

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint 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.

Twin Shores Poolside Haven

Pool open for the season! Welcome to Twin Shores Poolside Haven, steps from the North Shore’s best beaches! 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!

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (open 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.

Elegant Oasis with Pool and Gym

Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa

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!