House holiday rentals in South Boston

4.96 out of 5 average rating, 336 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!

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.

4.91 out of 5 average rating, 171 reviews

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

4.98 out of 5 average rating, 164 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!

5.0 out of 5 average rating, 228 reviews

Home in Cambridge

Cozy, Spacious Home in the Heart of Cambridge

Welcome to your home away from home in the heart of Cambridge! This spacious 4bd/2ba home is perfect for family visits, getaways with friends, and long-term stays. House-trained pets are welcome! We are very conveniently located in Central Square: <5 min walk from H Mart, Target, CVS, restaurants, cafes <5 min walk from the Central T station and bus stop 1 stop/15 min walk from MIT/Kendall Square 1 stop/20 min walk from Harvard University 3 stops/15 min ride from Boston Common/Downtown Boston

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, 239 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!

4.95 out of 5 average rating, 200 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!

4.87 out of 5 average rating, 266 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!

4.94 out of 5 average rating, 105 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

Bring the whole family — pets included — to this bright and modern 1,500+ sq ft (2 bedroom) home, perfectly located on Main Street in the heart of Charlestown. Start your mornings with a stroll to nearby coffee shops, then head to iconic sites like the Bunker Hill Monument or the USS Constitution at the Navy Yard. In the evening, take a short walk over the bridge to explore Boston’s famous North End, and cap off your day with fine dining or waterfront drinks back at the Navy Yard.

4.85 out of 5 average rating, 130 reviews

A well-lit dining area features a wooden table surrounded by chairs, complemented by a decorative chandelier overhead. The open layout allows for a view into the comfortable living area, where soft seating and natural light create a relaxed ambiance.

Home in Winthrop

Sunny 3 bedroom on beach

Welcome to our beautiful 3 bedroom apartment on the beach! Enjoy stunning ocean views and easy access to Winthrop Beach, only 2 minutes away. Accommodations for up to six guests, making it perfect for families or groups of friends. Bright and airy living area with plenty of natural light and a cozy seating area, perfect for relaxing after a long day at the beach. The dining area offers ample seating, and the fully equipped kitchen, private deck with breathtaking views of the ocean.

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.

4.96 out of 5 average rating, 141 reviews

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 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, 100 reviews

Beautiful Southie Single Family

Your whole family can enjoy this single-family rental in the heart of Southie. Five bedrooms with lots of room for families of all ages! This house is situated in a picture-perfect, calm, and quiet part of Boston but is centrally located a short walk from beaches, parks, shopping, and top-rated restaurants. Easy public transit connects you directly to the Back Bay, Seaport, or Downtown. Plus you can bring your car and park in our garage spot a 10 min walk from the front door.

4.98 out of 5 average rating, 219 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.

Popular amenities for South Boston house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

5.0 out of 5 average rating, 20 reviews

Home in Chelsea

Theatre | Arcade | Pool w. Free 3 Car Parking

4.98 out of 5 average rating, 80 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

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!

5.0 out of 5 average rating, 42 reviews

Home in Newton

Spacious quiet Newton Villa *Easy Boston Access!

4.94 out of 5 average rating, 84 reviews

Home in Waltham

Private/Quiet Single Family Home

4.76 out of 5 average rating, 38 reviews

Home in Canton

Luxury lake retreat- pool, fire pit, trails

4.91 out of 5 average rating, 53 reviews

Home in Marblehead

Pool is Open in Sept.+Walking Trails+Dead End St.

Weekly house rentals

4.94 out of 5 average rating, 191 reviews

The living area features a glass dining table surrounded by wooden chairs. A comfortable gray sofa is positioned nearby, complemented by decorative cushions. Natural light floods in through multiple large windows, enhancing the airy and bright ambiance of the space.

Home in Revere

Modern 2-bedroom w/parking near Encore and Logan

4.91 out of 5 average rating, 173 reviews

The living room features a cozy arrangement of soft gray sofas adorned with decorative pillows. A rustic brick fireplace is framed by a wooden mantel, above which a large flat-screen TV is mounted. A round coffee table sits at the center, complemented by a light-colored area rug.

Home in Revere

Spacious and Luxurious House

4.87 out of 5 average rating, 301 reviews

A comfortable sleeping area is equipped with a spacious bed layered with plush bedding and decorative pillows. A cozy seating area features a light-colored couch beside a bedside table with a lamp. Soft natural light streams through windows dressed in sheer and dark curtains.

Home in Revere

Rio Stays

4.89 out of 5 average rating, 181 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

4.9 out of 5 average rating, 389 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

4.85 out of 5 average rating, 139 reviews

Home in Medford

Queen Anne Victorian in Excellent Location

4.98 out of 5 average rating, 114 reviews

A spacious kitchen features modern appliances and wooden cabinetry, creating a functional cooking area. In another section, a cozy living room showcases a comfortable sofa, floor-to-ceiling windows, and soft lighting. The brightly lit bedroom displays a large bed with simple decor. An inviting outdoor patio has several Adirondack chairs surrounding a propane fire pit.

Home in Somerville

E2 Huge New Home Harvard Boston MIT 1 Free Parking

4.98 out of 5 average rating, 302 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!

Private house rentals

5.0 out of 5 average rating, 4 reviews

Spacious 3-Bedroom Home Near Convention Center

4.97 out of 5 average rating, 30 reviews

Modern 5B3B in Boston | Steps to the T

5.0 out of 5 average rating, 9 reviews

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

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, 85 reviews

Cozy, comfortable and convenient

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.

4.86 out of 5 average rating, 36 reviews

Private Parking! 4BR Family Home in South Boston

5.0 out of 5 average rating, 16 reviews

Brand New 3BR | Walk to Transit | Near Boston 85c

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.

4.67 out of 5 average rating, 36 reviews

Bright & Spacious Boston Home, near T