
Vacation rentals with a pool in Downtown
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Downtown
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Boston Modern Apt: Luxe Stay w/ Gym, Parking
Discover Boston from a contemporary luxury apartment with exceptional ambiance and amenities. STRICT NONSMOKING!!! The Unit: → Lightning Fast Wi-Fi → Comfortable King Bed → Dedicated Corporate Office Workspace → 65" Living Room Smart TV → 55" Bedroom Smart TV → Fully Stocked Kitchen → Washer & Dryer → Private Parking The Amenities: → Business Lounge → Pool → Full Size Gym → Gameroom Ideal for business travelers, travel nurses and corporate clients looking to experience Boston in style.

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)

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.

Peaceful suite in Boston with city views
Enjoy Boston in an elegant 2 bedroom/bath with sleek interior furnishing for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

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! ✔ City Skyline Views ✔ King Bed ✔ Gym

Spacious vacation unit in premium suburban town
Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2K Sqft of space. There are chickens in the backyard...the host can provide some fresh eggs too if desired.

Stylish and Cozy at Revere Beach
Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Monthly Skyline Apartment
Welcome to your next retreat, a waterfront haven of fully furnished corporate housing that blends luxury with urban ease. Highlights: • Exceptional location 5-min to the center of downtown • Direct Harborwalk access near Lo Presti Park • Rooftop lounge with skyline vistas, and cozy seating • Pool terrace with grills and herb garden • Chef’s kitchen, billiards, and stylish social spaces • 24/7 fitness center with Peloton and harbor views • Private work rooms and a creative music studio

Condo in Kendall Square MIT/Harvard
Stunning apartment in Kendall Square with all amenities: gym, pool, social room, business center, grills, courtyard. Just a 5-minute walk to MIT, the subway, the Charles River, and a short walk to Beacon Hill and other Boston highlights. Experience vibrant executive and family life with nearby restaurants and cafes. This luxurious, safe complex offers a quiet apartment with high-speed WiFi, HVAC, a sofa bed, a cozy living area, and an open kitchen. Perfect for business or leisure.

Elegant Oasis with Pool and Gym - 2Bath
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

Serenity - 36’ Aft Cabin Carver
At Constitution Marina's Bed & Breakfast Afloat you can enjoy the ambiance, the comfort, the romance of staying ON THE WATER with all the amenities of a modern hotel, at rates as low as you'll find anywhere in Boston! For boats with 2 staterooms, there is an additional fee of $100.00 plus tax/night if the 2nd room is rented. The 2nd room is booked directly through the host.
Popular amenities for Downtown rentals with a pool
House rentals with a pool

Nana-tucket Inn

Hopkinton Mass 3+ Bedrooms - Great location!

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

Bauhaus Retreat in Nature Preserve

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Ocean Side, Amazing View, close to town/beach, Spa

Seaview Summit | Ocean Views, Indoor Pool, Beach
Other vacation rentals with a pool

The Attia

Seaport 2BR 2BA Apartment with beautiful views

15 min from boston airport/pets welcome/6 guest

Luxurious 2BR w/ Pool, Gym & W/D, nr Blue Line,

Ideal for long stays | Spacious suite in Boston

Stylish StudioLux in Vibrant East Boston

2bed Condo in Cambridge w/balcony Garage Parking

The Harvey: Large • Near T • Gym • Kitchen • W/D
Quick stats about vacation rentals with a pool in Downtown
Total rentals
40 properties
Nightly prices starting at
€ 9 before taxes and fees
Total number of reviews
140 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Rentals with a fireplace Downtown
- Fitness-friendly rentals Downtown
- Rentals with a washer and dryer Downtown
- House rentals Downtown
- Rentals with outdoor seating Downtown
- Rentals with an EV charger Downtown
- Rentals with breakfast Downtown
- Rentals with a patio Downtown
- Pet-friendly rentals Downtown
- Apartment rentals Downtown
- Serviced apartment rentals Downtown
- Condo rentals Downtown
- Rentals with pools Boston
- Rentals with pools Suffolk County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Hampton Beach
- Fenway Park
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- Duxbury Beach
- New England Aquarium
- Good Harbor Beach
- Canobie Lake Park
- MIT Museum
- Freedom Trail
- Crane Beach
- Faneuil Hall Marketplace
- Onset Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- North Hampton Beach
- Rye North Beach
- Oakland Beach
- Quincy Market
- Prudential Center
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