House holiday rentals in South Boston

4.96 out of 5 average rating, 334 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!

ValueFamilyNearby

4.91 out of 5 average rating, 165 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

Welcome to our spacious urban retreat in the heart of Boston. This well maintained 4 bedroom unit is conveniently located near many city attractions. Enjoy quiet patio, backyard and free coffee bar. Great for a quick getaway or special gathering. 5 min walk to access bus and train 10 min drive to UMass Boston and JFK Library 20 min drive to Fenway Park and TD garden sports 10 min drive to the famous Franklin Park Zoo/Golf Course 20 min drive to Historical Downtown Boston and Prudential Shopping

ValueLocationAccess

4.93 out of 5 average rating, 153 reviews

A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.

Home in Stoughton

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and abundance on-street parking. Pet friendly!

ValueFamilyLayout

4.98 out of 5 average rating, 157 reviews

Home in Roxbury

Boston 5BR Home w/Free Parking & Yard-Sleep 12

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!

LocationFamilyKitchen

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, 235 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!

ValueFamilyBiking

4.94 out of 5 average rating, 196 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!

ValueFamilyGetting around

4.87 out of 5 average rating, 264 reviews

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.

Home in East Boston

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!

LocationFamilyOutdoor spaces

4.96 out of 5 average rating, 140 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.

FamilyLocationView

4.94 out of 5 average rating, 330 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

Charming apartment in a 19th century Victorian house conserves its period architectural details in recently renovated comfort. Light streams into this en-suite guest residence through gracious windows. Beautiful cabinetry and bookcases offer some evening reading. Enjoy the marble bathroom and hardware floors and well-appointed kitchenette. A stone's throw from Porter Square, where bars, cafes, boutiques, and transportation options abound. Minutes to Harvard, MIT and Boston.

LocationValueSolo travel

4.98 out of 5 average rating, 215 reviews

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.

Home in East Boston

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.

FamilyValueOutdoor spaces

4.85 out of 5 average rating, 138 reviews

Home in Medford

Queen Anne Victorian in Excellent Location

3BR/2FB Queen Anne Victorian in Medford Sq/Lawrence Estates. 3 fireplaces & hardwood throughout. Open kitchen, island w/hood, marble counters & SS chef’s kitchen appliances. Mahogany deck and professionally landscaped yard. Primary BR with fireplace, primary bath;marble flrs. Location location location. Steps away from Medford Square including the Chevalier Theater; Minutes away from downtown Boston, Tufts University, Davis Square and Cambridge.

ValueFamilyHiking

4.92 out of 5 average rating, 173 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

Creative loft style house that is home to a fashion designer and her family! Two floor loft like living very centrally located in Brookline MA. Very centrally located in Brookline Village. A few minutes walk to the T and very close to the hospital district. Whole house perfect for the whole family with fast Wifi and garage parking. Search for 'Everywhere Architecture' & click on 'White Place' to see more pictures!

ValueFamilyAccuracy

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

LocationFamilyCleanliness

5 out of 5 average rating, 39 reviews

Home in Newton

Spacious quiet Newton Villa *Easy Boston Access!

LocationFamilyHospitality

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

4.82 out of 5 average rating, 62 reviews

Boston 15 min away.

LocationValueCleanliness

4.95 out of 5 average rating, 55 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!

FamilyLocationAccuracy

4.97 out of 5 average rating, 78 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

LocationFamilyAccuracy

5 out of 5 average rating, 16 reviews

Home in Chelsea

Theatre | Arcade | Pool w. Free 3 Car Parking

FamilyLocationCleanliness

4.97 out of 5 average rating, 118 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

ValueFamilyBarbecue

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

4.87 out of 5 average rating, 70 reviews

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

FamilyLocationQuiet

Weekly house rentals

4.94 out of 5 average rating, 103 reviews

The modern two-story home features a blue exterior with white trim and three windows on the ground level, complemented by decorative planters. A bold red front door is centrally positioned, enhancing the welcoming entrance.

Home in Charlestown

Spacious & Pet-Friendly Modern Home in Charlestown

LocationValueDecor

4.93 out of 5 average rating, 378 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

LocationFamilyNearby

4.9 out of 5 average rating, 387 reviews

The living room features a comfortable couch adorned with a soft throw blanket. A large piece of artwork hangs on the wall, showcasing a vibrant floral design. Two stylish glass tables are positioned in front of the couch, accompanied by a decorative rug.

Home in Hyde Park

~*30min to Downtown*~ THE COSMOPOLITAN

ValueLocationOutdoor spaces

5 out of 5 average rating, 261 reviews

A charming house is nestled among trees, featuring a light-colored exterior with dark accents. An American flag is displayed outside. The front yard is landscaped with a stone wall and greenery, creating a serene setting. A gravel path leads to the entrance.

Home in Dedham

The Gatehouse, Cheerful 3 bedroom 3 bathroom house

LocationFamilyLaundry

4.95 out of 5 average rating, 184 reviews

Home in Woburn

Stone Cottage with meadow view

FamilyLocationLong stay

4.98 out of 5 average rating, 298 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!

ValueLocationKitchen

4.91 out of 5 average rating, 352 reviews

Home in Porter Square

Luxurious House-Harvard/PorterT 4BR/4Bath, Parking

ValueLocationQuiet

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, 64 reviews

Three level townhouse near South Boston's Best!

ValueFamilyBathroom

Private house rentals

4.65 out of 5 average rating, 34 reviews

The open-concept living and dining area features a cozy seating arrangement with a light-colored sofa and a colorful area rug. A wooden dining table with six chairs is positioned near a large window, and a wall-mounted TV is visible, enhancing the space's functionality.

Home in Dorchester

Bright & Spacious Boston Home, near T

FamilyValueCheck-in

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.

4.98 out of 5 average rating, 82 reviews

Cozy, comfortable and convenient

LocationFamilyHospitality

5 out of 5 average rating, 4 reviews

Spacious 3-Bedroom Home Near Convention Center

FamilyCleanlinessCheck-in

5 out of 5 average rating, 29 reviews

Home in Roslindale

Boston Buccaneer Retreat

LocationValueHospitality

5 out of 5 average rating, 8 reviews

S Boston | 5BD/2BA · Sky Deck | Downtown · Airport

FamilyLocationAccuracy

4.94 out of 5 average rating, 47 reviews

Home in Boston

Home in Boston/Milton

ValueLocationBackyard

4.98 out of 5 average rating, 55 reviews

A spacious living room features comfortable seating arranged around a central coffee table. A large television is mounted on a wooden cabinet, surrounded by shelves filled with books. Natural light filters through multiple windows, enhancing the bright and airy feel of the room.

Home in Roxbury

5-story Luxury Boston Brownstone

ValueFamilyIndoor spaces