Vacation rentals with a pool in Downtown, Boston

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Top-rated rentals with a pool in Downtown, Boston

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Guest favorite

Rental unit in Waltham

4.97 out of 5 average rating, 267 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

Guest favorite

Rental unit in Winthrop

4.96 out of 5 average rating, 297 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.

Superhost

Rental unit in Brighton

4.79 out of 5 average rating, 19 reviews

Cozy Boston studio with separate bedroom

Experience Boston in a beautiful luxe jr. 1 bedroom unit! Just a 5 min walk from the T and close to Boston College/Harvard, you can engage with all of Boston and tastefully long term. Unit Features -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed ->Game rooms all across the property Ideal for business travelers, couples, nurses, those in hospital treatment and everyone looking to experience Boston in comfort and peace.

Superhost

Rental unit in East Cambridge

4.65 out of 5 average rating, 23 reviews

City Skyline w/King Bed, Pool Gym Wi-Fi & Parking

**Ask About Monthly Rates!** Indulge in your next luxury apartment in Cambridge Crossing. The panoramic city skyline views from the open layout kitchen, dining, and living areas create a captivating atmosphere. Sink into comfort in king and queen sized bedrooms, both with en-suite bathrooms to add a touch of convenience. Building facilities, including a shared pool, rooftop oasis, gym, pool tables, fire pit. Gateway to the best of Boston/Cambridge! ✔ Pool ✔ City Skyline Views ✔ King Bed

Guest favorite

Cottage in Marblehead

4.98 out of 5 average rating, 107 reviews

4 Houses from Harbor | Old Town | Pool | Parking

Sitting a mere 4 houses down from the harbor in Old Town Marblehead, this home is a quaint antique cottage with a backyard pool that is surrounded by a beautiful garden — just steps away from The Barnacle Restaurant. Private backyard pool with indoor and outdoor seating. Close to attractions like Fort Sewall, Fort Beach, and local eateries. 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

Rental unit in Winthrop

4.95 out of 5 average rating, 222 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.

Guest favorite

Condo in East Cambridge

5 out of 5 average rating, 48 reviews

Modern New Lux Apt/ King bed close to MIT Harvard

1 Bed/ 1 Bath luxury condo conveniently located in a prime neighborhood in Cambridge, MA. Access to building gym, business center and outdoor gym in summer months. Luxurious KING size bed, 1 full size air mattress 1 couch, Washer/dryer. Convenient walk to cafes & restaurants, Markets, MBTA. Close to Freedom Trail, science museum, Cambridge side mall. NO smoking anywhere in the building. Suitable for children and pets. Street parking only or paid garage across the street.

Superhost

Rental unit in Malden

4.9 out of 5 average rating, 72 reviews

Luxe Serene 1BR 15 min from Boston with Gym & More

You will love this beautifully designed 1 Bedroom 1 Bath luxury unit that is in a central location between many great cities! You will be staying in a gorgeous private community with a gym, pool table, dog park, kids playground, tennis court, and tons of outdoor space. Have peace of mind knowing you’re in a safe space. Our luxury suite has a Queen Medium Firm bed along with a Queen Air Mattress for any additional guests. Check out more of our amenity spaces below!

Superhost

Rental unit in Waltham

4.73 out of 5 average rating, 108 reviews

King Room Suite in Waltham Hotel

Welcome to Suite in Waltham Hotel Located just seconds off of Interstate-95/Route128. The Hyatt House – Boston/Waltham is conveniently located near many attractions, companies, and educational institutes. Located just 2.5 miles away from Bentley University and 3.6 miles away from Brandeis University, the property is very conducive for those students/families visiting and attending these major colleges.

Guest favorite

Guest suite in Burlington

4.96 out of 5 average rating, 28 reviews

Stay a While, Studio Apartment-Pet Friendly

Welcome to our fabulous boho chic studio apartment, located 25 minutes North of Boston. We welcome all guests, including your beloved pets! 3/4 of a mile to the nearest MBTA bus stop, 3 miles to Lahey and 6 miles to Winchester Hospital. And best of all, Dunkin Donuts is a 5 minute walk from us ;)

Guest favorite

Guesthouse in West Roxbury

4.95 out of 5 average rating, 191 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.

Guest favorite

Rental unit in Back Bay

4.95 out of 5 average rating, 128 reviews

Rock Me Gently | Steps from Blues. Dive to Pool

Are you ready to rock? Prepare yourself for a hospitality experience like no other! Take a trip back in time with mid-century style, music and pop-culture details infused into your experience at The Verb Hotel. ▶ 2023 Travelers' Choice Best of the Best - Tripadvisor