Holiday rentals with a pool in Boston

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Guest favourite

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

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Guest favourite

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)

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Guest favourite

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.

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Guest favourite

Spacious quiet Newton Villa *Easy Boston Access!

Exclusive retreat in the heart of Boston's premier neighborhood. Minutes away from top Boston's attractions , our space offers the perfect blend of comfort and convenience. Spacious bedrooms, living room with king bed upon request, fully stocked kitchen with SS appliances, induction cooktop and double oven, whirlpool tub and bidet toilets, library for those family evening over the board games on main floor. Quiet space with massage chair and home theater TV seating on ground floor. STR-25-22

Lux 2BR Apt w/ Pool and Gym

Welcome to your perfect getaway! Our space combines the comforts of home with luxurious amenities to make your stay truly special. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • 24/7 access to a state-of-the-art fitness center • Modern yoga studio and high-tech training equipment • Experience the charm of Somerville while enjoying hotel-quality amenities at home.

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.

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.

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Guest favourite

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...

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.

The Weiss : Modern Gallery • Historic Property!

Stay inside a historic restored monastery in Brighton. This spacious studio blends preserved historic architecture with modern comfort and features an expandable room divider for a one-bedroom feel. Just a 5-minute walk to the T with easy access to Boston College, Harvard, hospitals, and downtown Boston. Amenities Include: → Blazing-fast WiFi → 65” Smart TV → Fully stocked kitchen → Washer & dryer → Comfortable queen bed

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Guest favourite

Steps from Harbor + Walk to Old Town + Restaurants

HIGHLIGHTS: • Marblehead Harbor - 4 houses away • The Barnacle Restaurant - 4 houses away • Private backyard pool • 0.2 Miles to Fort Sewall • 0.3 Miles to Gas House beach • 0.4 Miles to Old Town Marblehead • 300 Feet to The Barnacle Restaurant • Walkable to restaurants and shopping • Beautiful private garden • 1 King, 2 Twin and 1 Sofa Bed • 2-car off-street tandem parking spaces

Serenity - Harbor View

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.