House holiday rentals in South Boston

4.97 out of 5 average rating, 329 reviews

A living room corner features a modern television on a wooden stand near a traditional fireplace, which includes a sleek black mantel. Art adorns the wall above the fireplace, while natural wood flooring creates a warm and inviting atmosphere.

Home in Somerville

Best House Cambridge/Somerville

spacious 1900's mansard Victorian. Bright cheerie & centrally located if you're looking for a pad in Cambridge/Somerville. A 10-12minute walk to Harvard Square & close to the Red Line. Great kitchen, living room & /cablewifi. Three bedrooms--one with a European Queen Bed, one double bed & one single. There is one full bathroom w/a large glass shower & a claw foot tub. There is a half bath on the first floor. There is a front porch to sit & sip wine on & a back deck where you can grill & eat out on. I've been living here 12 years--Its tastefully appointed, eclectic finds & a mid century modern touch--absolutely the best equipted kitchen. I've been a chef in Boston & Cambridge for quite some time!

4.86 out of 5 average rating, 345 reviews

The dining area features a wooden table with six chairs, complemented by a striped table runner. A stylish vase with dried stems is placed at the center. A cozy couch, adorned in rich upholstery, is located beside the table, with a cityscape wall art piece above a dark cabinet.

Home in Hyde Park

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

Relax in the Bostonian, a stylish, pet-friendly apartment on the semi-basement level of a charming multi-family house. The apartment is air conditioned & overlooks a beautiful patio and backyard. Located in quiet Hyde Park neighborhood, a 30 minute drive into downtown Boston. Plenty of free streetside parking. Private in unit laundry. Professionally cleaned. Room 1: Queen size bed Room 2: Queen size bed Room 3: Living room couch, TV, electric fireplace Dining room: includes two wall arcades

4.98 out of 5 average rating, 143 reviews

Home in Roxbury

Spacious & Comfy Retreat | 5* Location | Backyard!

Step into the spacious 3,000-square-foot 5BR 2.5BA getaway in the scenic Fort Hill neighborhood. It promises a relaxing retreat just a few mins from Fenway Park, the Longwood Medical Area, downtown Boston, universities, restaurants, shops, and much more. Families, leisure, and business guests will be left in awe of this lovely haven's unique design and rich amenity list. ✔ 5 Bedrooms ✔ Relaxing Living Area ✔ Chef's Kitchen ✔ Backyard ✔ Workspace ✔ Smart TVs ✔ Wi-Fi ✔ Parking See more below!

The kitchen features white cabinetry and stainless steel appliances, with a spacious layout for cooking. A game table is shown with a pool table in the background. A cozy living area includes a light blue accent wall and comfortable seating. The backyard displays a grassy area with a slide and a playset.

4.99 out of 5 average rating, 227 reviews

Family Friendly City Oasis! 2 Free Parking Spots!

Welcome to The Southie House! An epic private home for a family vacation or conference in the Heart of Boston! Close to the Red line T for access to downtown, Cambridge & local universities, and short ride to the BCEC. At the same time a short walk to the beach for relaxing. Enjoy the back yard oasis with the whole group! This home provides you with a private place to relax after a full day of exploring, ensuring you have all the comforts of home while traveling. COME SEE OUR NEW GAME-ROOM!

4.94 out of 5 average rating, 191 reviews

The exterior of a charming brick house is presented, featuring rounded corners and a dark front door. Large windows allow natural light to enter, while greenery adorns the adjacent wall. The inviting entrance is complemented by stone steps leading to the doorway.

Home in South End

Charming South End Farmhouse - Near Northeastern!

Charming 3-bedroom, 2.5-bathroom house located in Boston's vibrant South End! Our cozy and dog-friendly home has a private patio, dining area, a fully equipped kitchen, 1G Fiber wifi and sleeping accommodations for up to 7 guests. Perfect for families or larger groups! Featuring two TV's with streaming and essentials like fresh linens, towels, toiletries, extra pull out trundle couch. Just a short walk from Northeastern University, walkable to Fenway Park and a <5 minute walk to the T!

A modern living area features a light-colored sectional sofa and two patterned chairs arranged around a small table. A wall-mounted television is positioned above a sleek fireplace, surrounded by built-in shelving displaying decorative items. Natural light filters through sheer curtains.

4.87 out of 5 average rating, 257 reviews

Tribeca chic | 2 BR w/private patio

Welcome to our cozy, beautiful, newly renovated home! The house includes free wifi, washer/dryer, recently renovated kitchen along with a dedicated patio. A 2-minute walk to Shaws grocery store & shopping plaza (Marshalls, etc.). A 10-minute walk to the MBTA (silver/blue line). 4-minute drive to Logan Airport. Top-rated restaurants, waterfront, city views, & easy access to downtown Boston. Please note that hosts occupy the bottom floor and are available 24/7 for whatever you may need!

4.96 out of 5 average rating, 137 reviews

A bright living area features a plush blue sofa adorned with a light throw blanket, complemented by a glass coffee table. Natural light filters through sheer curtains, illuminating the space. A stylish armchair and a dining area with a wooden table are visible in the background.

Home in Dorchester

LargeDuplex10Beds w/prkg near Downton

Blending modern conveniences with historic charm, this newly renovated duplex features 5 bedrooms/2 bathrooms. Open space kitchen-living room, 55"Roku TV. Free Wifi. Free Laundry 8mns to Beach Free Street Parking 4.6 miles to Downtown, Convention. Perfect for large groups Close to major Universities. 8 Minutes walk to train Free coffee/tea, toaster, blender. Free linens, towels. 10 mns to Dorchester brewing, South Bay center & beach. We love and look forward to hosting you.

The living room features a crimson couch paired with patterned armchairs, arranged around a central coffee table. The space is enhanced by natural light from large windows with shutters. Decorative plants are positioned nearby, contributing to a cozy and welcoming environment.

4.98 out of 5 average rating, 208 reviews

Boston Best with Parking - GREAT reviews

**READ our reviews :) - 10min walk to Airport Blue line subway T-stop - 10min drive to Downtown Boston - Local dining options in walking distance - 1 parking spot available upon request - Spacious and comfortable house Welcome to your Best Boston experience. I am Rafael and I will ensure that you get any attention needed with a text, call, or email. We hope that you enjoy our recommendations for activities and meals - we based them on our lifelong East Boston experiences.

4.81 out of 5 average rating, 204 reviews

A living room area features a striped couch in shades of green and cream, positioned in front of a wooden coffee table with a television atop it. A framed painting of a ship hangs above a decorative fireplace, while built-in shelves add a touch of storage and display.

Home in Charlestown

Getaway in Historic Charlestown

**PLEASE NOTE REGARDING PARKING" Resident sticker parking 8 am to 8 pm Monday thru Friday. Weekends and holidays, no restrictions. The automobile has to be registered in Charlestown to get a parking sticker. The first floor of a three-story wooden framed home, built-in 1875. A totally private space. There is a good-sized living room, a bedroom with a queen size sleigh bed, and a full kitchen. The 'cozy' bathroom was added in 2012. Maximum of TWO people.

4.87 out of 5 average rating, 179 reviews

A spacious family room is presented with a large television mounted on the wall. Two comfortable sofas are arranged around a coffee table. Natural light filters through multiple windows adorned with wooden blinds, enhancing the room's welcoming ambiance.

Home in Quincy

Spacious, Cozy Home in Greater Boston - 4 Beds

Modern, spacious, and family friendly home in lovely North Quincy neighborhood of historic Quincy. Thoughtfully designed with large family room, 55 inch TV, Large parking lot, and porch. Comfortably sleeps at least 8! 10 Minute walk to Red Line Subway , only a 20 minute ride to downtown Boston! Easy access to South Station, Logan Airport, North End, Faneuil Hall, Government Center, Boston Common, Harvard Square, Back Bay, Fenway Park, and Beacon Hill.

4.98 out of 5 average rating, 292 reviews

A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.

Home in Dedham

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.

4.9 out of 5 average rating, 176 reviews

An airy living space features high ceilings with slanted angles and large windows allowing natural light to filter in. Wooden floors are complemented by simple furnishings, including a dining table with chairs and a bright arrangement of flowers. Nearby, cabinets provide ample storage.

Home in Jamaica Plain

Now availJamaica Plain & Arboretum 20min toBoston

Bright and sunny 2-bedroom retreat with a fully equipped kitchen, spacious bath with rain shower and tub, and TVs in each room. Enjoy fresh coffee daily with espresso maker, milk steamer, and grinder provided. Including a blender..A selection of teas .WiFi and off-street parking included. Private, peaceful, and filled with natural light—perfect for relaxing mornings and cozy evenings!

Popular amenities for South Boston house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 23 reviews

A welcoming living area features a large yellow sectional sofa, paired with woven chairs. A colorful area rug anchors the space, complemented by a light wood floor. The walls are adorned with a tropical mural, and a kitchen area is visible in the background.

Home in Hull

NEW! Walk To Beach! Sunshine House

5 out of 5 average rating, 35 reviews

A vibrant pool glistens under sunlight, surrounded by dense greenery. Two cushioned lounge chairs sit under a shaded structure, offering a relaxing spot for guests. The sparkling water reflects the natural surroundings, creating an inviting atmosphere for leisure.

Home in Newton

Private heated Pool *Easy Boston Access! STR-25-22

4.93 out of 5 average rating, 44 reviews

Home in Marblehead

Pool Is Open! 4-Bed Home w/Pool + Walking Trails

4.94 out of 5 average rating, 53 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!

4.97 out of 5 average rating, 71 reviews

An inviting bedroom features wood-paneled ceilings and soft lighting. A spacious bed is situated near a window with light filtering through. A vintage-style chair and a wooden bench add to the room's charm, complemented by a decorative area rug underfoot.

Home in Norwood

the house of id; vintage shop, accessible space

5 out of 5 average rating, 7 reviews

Home in Chelsea

Free Parking Close to All Major Boston Attractions

4.97 out of 5 average rating, 115 reviews

Home in Weston

Spacious vacation unit in premium suburban town

4.94 out of 5 average rating, 88 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)

Weekly house rentals

4.93 out of 5 average rating, 369 reviews

A cozy living room is highlighted by wood paneling and exposed beams. Plush seating includes a sofa and two armchairs. A coffee table is centered in the space, with a television displaying programming. Natural light fills the room through multiple windows adorned with soft curtains.

Home in Brighton

All the comforts of home, quiet city neighborhood

4.92 out of 5 average rating, 167 reviews

A spacious living area features a mix of comfortable seating, including a large sofa and a cozy armchair. Natural light streams through multiple windows covered with woven shades. Shelves filled with books and decorative items line one wall, while a light-colored rug adds warmth to the concrete floor.

Home in Brookline

Pretzel Factory Loft w/Peloton

4.94 out of 5 average rating, 324 reviews

A spacious bedroom is illuminated by natural light from large windows, featuring a comfortable bed with soft linens. Two plush armchairs are positioned across from a cozy sofa. A modern glass coffee table holds a magazine, while decorative elements add charm to the setting.

Home in Cambridge

Stunning urban hideaway nearby Harvard Square

4.99 out of 5 average rating, 273 reviews

A warm living area features a brown leather sofa accompanied by two striped chairs. A rustic table stands in the center, while a colorful area rug covers the floor. An artwork hangs on the wall, and a 'Boston' sign adds character to the space.

Home in West Roxbury

The Red Door Carriage House

A stone sign marked 'BEACHMONT' stands prominently at the entrance of a landscaped area. Surrounding features include a stone-paved pathway, a bench, and several tables. Lush greenery lines the background, providing a natural backdrop to the welcoming space.

4.78 out of 5 average rating, 234 reviews

Renovated Cozy City Getaway

4.91 out of 5 average rating, 203 reviews

Home in Malden

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free

4.9 out of 5 average rating, 156 reviews

An inviting entryway is adorned with a decorative mirror and a houseplant next to a console table. The living area is visible in the background, featuring a comfortable black sofa, a patterned area rug, and a mounted television on the wall.

Home in Dorchester

New Spacious Home in Boston

4.94 out of 5 average rating, 195 reviews

A cozy living room features a dark sofa adorned with decorative pillows, positioned beside a glass coffee table. Light fixtures cast a warm glow, while elegant artwork and a decorative chest add character. Natural light filters in through large windows, enhancing the tranquil ambiance.

Home in Jamaica Plain

Fully-Equipped, Private 1st Floor 1-Bed/1-Bath Apt

Private house rentals

A welcoming living room features brown leather sofas arranged around a circular wooden table. A patterned area rug adds warmth to the hardwood floor. Natural light enters through multiple windows, with plants positioned near the corners. Decorative artwork is displayed on the walls.

4.97 out of 5 average rating, 79 reviews

Cozy, comfortable and convenient

5 out of 5 average rating, 4 reviews

Spacious 3-Bedroom Home Near Convention Center

A spacious living room is furnished with a leather sectional couch adorned with various throw pillows. Light enters through large windows dressed with sheer curtains. A square coffee table is centered in the room, featuring decorative items and artworks displayed on the walls.

4.97 out of 5 average rating, 34 reviews

Private Parking! 4BR Family Home in South Boston

A bright living area features floor-to-ceiling glass doors that frame scenic waterfront views. A cozy sofa is positioned alongside a wooden table with a potted plant. Sunlight streams in, highlighting the wood-paneled ceiling and warm oak flooring.

5 out of 5 average rating, 51 reviews

Waterfront Escape - Close to Airport & Downtown

The living room features a leather sofa and an armchair with light upholstery, arranged around a central ottoman. Natural light enters through the large windows, adorned with curtains. A small wooden table and a plant add to the inviting atmosphere, alongside a mounted television.

4.97 out of 5 average rating, 94 reviews

Beautiful Southie Single Family

4.9 out of 5 average rating, 87 reviews

A well-furnished living area features a light-colored sofa adorned with patterned cushions, complemented by a blue ottoman. A large area rug in soft tones enhances the warmth of the hardwood floor. Natural light enters through multiple windows, while a decorative chandelier hangs from the ceiling.

Home in Winthrop

Cozy & Modern Entire Residential Home ❤️

A cozy lounge area features a large flat-screen TV displaying a streaming service. Soft seating is provided with gray sofas and blue armchairs. A light-colored coffee table is centered on a blue and cream patterned rug, complementing the room's neutral walls and bright window treatments.

4.91 out of 5 average rating, 54 reviews

Three level townhouse near South Boston's Best!