Vacation rentals with a pool in Somerville

4.97 out of 5 average rating, 345 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

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

FamilyValueWalkability

4.97 out of 5 average rating, 445 reviews

A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.

Apartment in Waltham

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)

FamilyValueKitchen

4.96 out of 5 average rating, 282 reviews

A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.

Apartment in Winthrop

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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4.87 out of 5 average rating, 191 reviews

Apartment in Charlestown

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.

ValueFamilyEV charging

5.0 out of 5 average rating, 20 reviews

Home in Chelsea

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.

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4.96 out of 5 average rating, 159 reviews

A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.

Apartment in Brighton

The Murthy : Bright • Spotless • W/D

Enjoy Boston in this elegant suite 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 -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

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Guesthouse in West Roxbury

A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.

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.

ValueFamilyAccuracy

4.95 out of 5 average rating, 217 reviews

4.93 out of 5 average rating, 57 reviews

A well-maintained swimming pool is featured in the backyard, surrounded by a patio. Lush greenery and mature trees offer privacy. The two-story house is visible in the background, with large windows allowing light to enter. A basketball hoop is positioned adjacent to the pool area.

Home in Arlington

Beautiful Spacious 4BRM House!

A thoughtfully cared-for New England home best suited for a quiet, comfortable stay in a residential neighborhood. Enclosed back yard with pool during summer (June 21 - September 20) 4 bedrooms (2 ensuite), 3 full bathrooms, 1 half bath. Spread over 2 floors: - Floor 1: eat-in kitchen, 1/2 bath, living, dining, office - Floor 2: 4 bedrooms, 3 bathrooms, bonus room - Has STAIRS to bedrooms Outside: Yard, unheated swimming pool (summer 6/21-9/20), patio. 2 off-street parking.

FamilyLocationTV

4.97 out of 5 average rating, 120 reviews

The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.

Home in Weston

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...

ValueFamilyPool

4.67 out of 5 average rating, 12 reviews

Apartment in Somerville

Lux 2BR w Gym Pool sleep 7 in Assembly Square

Mass Living Dot Com Welcomes to your modern retreat in the heart of Assembly Square, where comfort meets luxury and convenience. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • Amazing Lounge on the 2ndfloor. • 24/7 fitness center, yoga studio, and artist space • Experience the charm of Somerville while enjoying hotel-quality amenities at home

LocationFamilyCleanliness

5.0 out of 5 average rating, 3 reviews

Apartment in Somerville

Central 2BR Condo in Assembly with Pool, Row Gym,

New England Stays Welcomes to your modern retreat in the heart of Assembly Square, where comfort meets luxury and convenience. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • Amazing Lounge on the 2ndfloor. • 24/7 fitness center, yoga studio, and artist space • Experience the charm of Somerville while enjoying hotel-quality amenities at home

LocationPoolAccuracy

4.93 out of 5 average rating, 27 reviews

Apartment in Cambridge

“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.

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Popular amenities for Somerville rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 84 reviews

Home in Waltham

Private/Quiet Single Family Home

LocationFamilyTV

5.0 out of 5 average rating, 42 reviews

Home in Newton

Spacious quiet Newton Villa *Easy Boston Access!

LocationValueAccuracy

4.95 out of 5 average rating, 91 reviews

An open-concept living space is highlighted by warm wood flooring and soft lighting. A modern kitchen with wooden cabinets and sleek countertops is visible in the background. Comfortable seating is arranged around a glass coffee table, inviting relaxation and conversation.

Home in Newton

Explore Boston in style! Dream home (STR-26-3)

LocationFamilyParks

4.83 out of 5 average rating, 71 reviews

Home in Somerville

Modern LUX| Yard • BBQ • Parking • Game Room • T

The image shows a hot tub situated on a shaded deck, overlooking a calm waterfront. The view includes a distant skyline with industrial buildings, framed by greenery. The clear water of the hot tub reflects the serene outdoor setting.

Home in Weymouth

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

FamilyLocationGetting around

The vibrant pool area features an in-ground pool surrounded by a spacious deck. Several lounge chairs are positioned along the poolside, with a patio umbrella providing shade. A charming house backdrop is visible, complemented by lush greenery.

Home in Revere

Boston 15 min away.

ValueFamilyDecor

4.82 out of 5 average rating, 62 reviews

Home in Salem

The Ideal Living Place in the NorthShore

New place to stay

Home in Reading

Well-Maintained House in a Quiet Neighborhood.

Other vacation rentals with a pool

4.88 out of 5 average rating, 8 reviews

Apartment in Dorchester

Brand New Luxury Retreat w/ Pool & Fitness Center

LocationFamilyAmenities

4.9 out of 5 average rating, 48 reviews

A motor yacht is docked at a marina, featuring a spacious upper deck with a canopy. The exterior showcases a cream-colored hull with large windows and a comfortable layout. A wooden walkway leads to the boat, surrounded by additional boats in the marina.

Boat in Charlestown

Serenity - 36’ Aft Cabin Carver

ValueLocationCondition

4.82 out of 5 average rating, 82 reviews

Apartment in Chelsea

Cozy 1BR Near Boston w/ Pool & Gym

ValueFamilyTV

4.93 out of 5 average rating, 73 reviews

Apartment in Chelsea

1 BDRM Retreat | King Bed, Pool, Gym, Parking+ Bus

ValueLocationQuiet

4.93 out of 5 average rating, 40 reviews

Apartment in Cambridge

Sunny Quiet 2 BR MIT Hrvrd BU Fenway Longwood

ValueLocationAmenities

5.0 out of 5 average rating, 8 reviews

Guest suite in Peabody

Luxury Modern Getaway (Near Salem/Boston)

ComfortAccuracyCheckout

4.89 out of 5 average rating, 9 reviews

A modern apartment building is illuminated at dusk, showcasing multiple stories with numerous windows. A well-lit parking area is visible in the foreground, filled with vehicles. The surrounding landscape includes greenery and a distant hill, enhancing the suburban setting.

Apartment in Chelsea

Entire one bedroom apartment

ValueLocationCheck-in