Vacation rentals with a pool in Boston

Private Suite• Pool • Sleeps 4 • Boston • Airport

Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

Value · Location · Wifi

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)

Location · Family · Comfort

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.

Location · Family · Laundry

Theatre | Arcade | Pool w. Free 3 Car Parking

Experience The Chelsea Retreat, your private escape with free parking for up to 3 cars and an average 15 minute drive to Boston’s top attractions! Enjoy a cinematic night with a 150” 4K theatre and immersive surround sound, challenge friends in the arcade with foosball, pinball, and classic arcade games, or unwind beneath the gazebo before floating the day away in the pool. Shoot hoops, fire up the BBQ, or retreat to a quiet, dedicated workspace. Luxury, fun, and convenience all in one place.

Location · Family · TV

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. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.

Value · Location · Cleanliness

Cozy Private Suite halfway between Cape & Boston

Large private room located in the Basement of a single family home. The home is conveniently located less than one minute from route 3 half way between Boston and Cape Cod. The room has a full size bed, and a euro lounger that can be used to relax and watch TV or reclyned for sleeping. There is a kitchenette located in the room which has a Fridge with top freezer, a microwave and a Keurig . The private bath is located inside the bedroom. Cool off in the pool during summer months.

Family · Location · Accuracy

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). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

Location · Value · Wifi

Private Pool Retreat w/Fire Pit Near Singing Beach

Relax in a private coastal retreat with a pool and fire pit, minutes from Singing Beach. This updated suite features a modern layout, fireplace, and two queen beds—one in a private sleeping area. Ideal for relaxing or remote work, with a secluded backyard, private entrance, free parking, and fast Wi-Fi. Near downtown Manchester-by-the-Sea, dining, and coastal views. Seasonal pool: 5/20–9/8. Walk to local shops, restaurants, and the harbor, all from this peaceful setting.

Family · Location · Amenities

The Drew : Vibrant • Comfortable • W/D • City View

Experience Boston in a beautiful luxe jr. 1 bedroom unit! Just a 5 min walk from the T and close to Boston College/Harvard. Unit Features -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed -> Game rooms across the property Air bed and single rolling cot available on request. Ideal for business travelers, couples, nurses, and anyone seeking comfort and peace in Boston.

Value · Family · Indoor spaces

“Luxury 2BR Cambridge | Pool + Parking”

Two blocks from Lechmere Station, with the Green Line running direct to Kendall Square, MIT, and Harvard, this residential 2BR/2BA operates on a different standard than corporate hotel rooms. On-site garage parking runs the elevator straight to your floor, unlimited in-and-out, versus $50-65/night at nearby garages that re-bill on every return. Two full bathrooms, in-unit laundry, a fully equipped kitchen, and shared pool access. Sleeps 5.

Value · Location · Hospitality

Luxury Grand Oasis | Pool · Gym · Parking · 2BR

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

Family · Location · Quiet

Brand New Luxury Retreat w/ Pool & Fitness Center

Experience modern South Boston living in this bright 2BR/1BA apartment! Enjoy a fully equipped kitchen with stainless steel appliances, in-unit washer/dryer, and spacious living areas with oversized windows. Relax by the seasonal pool, work out in the 24/7 fitness center, or unwind in the lush courtyard with grilling stations. Just minutes from Carson Beach, Downtown Boston, and the Red Line.

Family · Location · Getting around