Holiday rentals with a pool in Andover

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Andover

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

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Guest favourite

Home in Derry

4.9 out of 5 average rating, 143 reviews

Sanctum by the Lake

Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the large pool, hot tub, and lake access, The Sanctum by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

Guest favourite

Flat in Winthrop

4.96 out of 5 average rating, 301 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 favourite

Flat in Ipswich

5 out of 5 average rating, 31 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 favourite

Home in Kittery

4.95 out of 5 average rating, 37 reviews

Fantastic Kittery Home with Pool

Modern New Englander boasting a large, private backyard with pool (seasonal, from May to Oct, approx). Our comfortable, 3-bedroom home is a commuter's dream. Working from home? Use our separate dedicated office space with 1 gig WiFi. Playing hooky? So many options! Walk or bike to the fabulous eateries, shopping or breweries our area has to offer! Enjoy our pool or take a short drive to the beach! (Please note, our pool is normally unheated. For an additional $25 a day we'll heat it!)

Guest favourite

Flat in Winthrop

4.96 out of 5 average rating, 225 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. Stunning ocean views can be seen from our seasonal saltwater pool as well as from the year-round hot tub. We are 4 short miles from Boston and 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.

Guest favourite

Home in Hampton

5 out of 5 average rating, 37 reviews

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

⭐⭐⭐⭐⭐ Indulge in luxury in this 4-bedroom beach home in Hampton, NH, just a short walk to North Beach, boasting stunning water views of Mill Pond & Meadow Pond. Relax in the indoor heated pool and unwind in the NEW hot tub on the private deck, all while surrounded by the natural beauty of the marsh. Don't forget to check out previous guest reviews in the additional photos section. “Although we are a pet friendly property we do charge a pet fee of $100 for two pups under 50 pounds.”

Guest favourite

Cottage in Marblehead

4.98 out of 5 average rating, 107 reviews

Xmas Walk Central, 4 Houses from Harbor with Pool

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.

Guest favourite

Home in Hopkinton

4.95 out of 5 average rating, 147 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

This my home in which I am now an "empty-nester". I have 3 bedrooms available, each with a Queen bed, plus a room over the garage with 2 futons and a mattress. NOTE: I live here and will be home during your stay. You'll have access to a private bathroom and the rest of the house: kitchen, dining room, living room, etc. NO pets allowed. My place is close to Boston, Worcester, Providence, state parks, etc. Good for singles, couples, business travelers and families.

Guest favourite

Cottage in Newburyport

4.93 out of 5 average rating, 108 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 favourite

Flat in Holliston

4.96 out of 5 average rating, 119 reviews

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.

Guest favourite

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 favourite

Home in North Andover

4.94 out of 5 average rating, 152 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!