House holiday rentals in South Boston

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!

Family · Location · Comfort

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!

Family · Value · Checkout

Top 10% Stay | Sleeps 6 | Easy Boston Access

Beautifully renovated 2-bedroom retreat designed for a more elevated, comfortable stay just outside Boston. Recognized as a top 10% home, this space combines thoughtful design, a standout kitchen, and a calm, modern feel—perfect for groups, families, or longer stays. Getting into Boston is simple: the bus stops right outside and connects to Sullivan Square (Orange Line) in about 10 minutes. From your front door, downtown Boston is typically about 35–40 minutes door-to-door—no car required.

Family · Value · Nearby

~*30min to Downtown*~ THE COSMOPOLITAN

Stylish contemporary kid-friendly apartment on the first floor of a multi-family. Bright and roomy bedrooms with a large eat-in kitchen. Central air conditioning. Plenty of free street parking. Access to shared laundry room. Located in Hyde Park neighborhood, 30 minute drive into downtown Boston. Professionally cleaned and disinfected. Room 1: Queen size bed, closet, TV Room 2: Queen size bed, closet Room 3: Living room couch bed, closet, TV Entryway: Includes Mrs. Pac Man wall arcade

Family · Location · Comfort

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!

Location · Family · Air conditioning

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!

Value · Family · Parking

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.

Value · Family · Breakfast

Bright Family Oasis Near Boston w/ Parking

Bright, plant-filled oasis in a quiet Medford neighborhood just minutes from Boston, with easy access to transit and free parking. Guests return again and again for the spotless cleanliness, curated art, and true “home away from home” feel. Enjoy a fully equipped chef’s kitchen and private backyard. Perfect for exploring the city, then relaxing in a peaceful, beautifully designed space. Or working from home. Conveniently located for day trips to Salem, Cambridge and downtown Boston.

Family · Location · Parks

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.

Location · Value · Amenities

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!

Family · Location · Indoor spaces

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.

Family · Value · Air conditioning

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!

Location · Family · Accuracy