House holiday rentals in South Boston

4.97 out of 5 average rating, 326 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!

4.99 out of 5 average rating, 226 reviews

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.

Home in South Boston

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 & GYM

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.

4.9 out of 5 average rating, 154 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

4.94 out of 5 average rating, 151 reviews

A cozy living area features two comfortable sofas flanking a light wood coffee table, with a decorative plant positioned atop it. A flat-screen television is displayed across from the seating. Large windows allow natural light to illuminate the space, complemented by soft lighting from a nearby lamp.

Home in Medford

Cozy & Modern 2 Bedroom House - Free Parking !

Welcome to our charming, renovated bungalow near Tufts University has been meticulously cared by owner and is ready to welcome new guests. Enjoy 2 beds/1 bath, private parking, and walkable access to Medford's attractions including; banks, shopping centers, local restaurants/cafes, Encore casino, public transportation, Middlesex Fells Reservation and much more. Tastefully furnished with new queen beds, remote work setup, a relaxing living area, and a fully equipped kitchen for your comfort.

4.94 out of 5 average rating, 194 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

This is a 1st floor private unit nestled in a serene urban enclave. Conveniently surrounded by public transit, shops, and dining options within a 0.6-mile radius. Originally a charming Victorian abode, meticulously renovated in 2016 to seamlessly blend historic elegance with contemporary comforts. Revel in a fully-equipped kitchen, private rear porch, and a tranquil bedroom boasting a plush queen-size bed. Tailored for your short or extended stay needs, with central air for optimal comfort.

4.95 out of 5 average rating, 189 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!

4.85 out of 5 average rating, 117 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, 137 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.

4.98 out of 5 average rating, 205 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.

4.91 out of 5 average rating, 201 reviews

Home in Malden

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

Stay in our elegant Boho-Modern Home Only 15min from Boston's Major Attractions. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dinning and Large Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Laundry Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

4.85 out of 5 average rating, 163 reviews

A comfortable living area features a light-colored sectional sofa adorned with textured throw blankets and pillows. A wooden coffee table sits in front, and a rattan chair is positioned beside a window. Natural light streams in, highlighting the woven wall decor.

Home in Somerville

Cozy Stylish 4br3ba 3mins to Somerville Subway

Experience classic Boston charm in this beautifully maintained 100+ year-old home, perfectly located in a quiet residential neighborhood. • Professionally cleaned after each stay • Comfy queen beds in all quiet rooms • 3-min walk to Green Line + 15-min subway ride to downtown • 14 mins to Boston Logan Airport • Free coffee & tea • 2 onsite parking spots The ideal base for your Boston business trip or vacation — historic character, modern comfort, unbeatable convenience.

4.81 out of 5 average rating, 203 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.

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

5 out of 5 average rating, 17 reviews

Home in Bedford

Bauhaus Retreat in Nature Preserve w/ Pool

4.94 out of 5 average rating, 52 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, 70 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

4.97 out of 5 average rating, 114 reviews

Home in Weston

Spacious vacation unit in premium suburban town

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, 67 reviews

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

Weekly house rentals

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.

4.72 out of 5 average rating, 29 reviews

Bright & Spacious Boston Home, near T

4.99 out of 5 average rating, 95 reviews

A spacious living room is shown, featuring comfortable grey sofas adorned with orange cushions. A round coffee table sits centrally, surrounded by a natural wood floor. A large television is mounted on the wall, with soft lighting from recessed ceiling fixtures enhancing the space.

Home in Boston

Brand New 4BR 2.5Bath House 20Min Downtown Boston

4.97 out of 5 average rating, 33 reviews

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.

Home in South Boston

Private Parking! 4BR Family Home in South Boston

4.97 out of 5 average rating, 32 reviews

Home in Swampscott

Oceanfront Master Suite: Jacuzzi & Private Deck

5 out of 5 average rating, 24 reviews

Home in Roslindale

Boston Buccaneer Retreat

4.9 out of 5 average rating, 86 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 ❤️

4.96 out of 5 average rating, 23 reviews

Central, Stylish Home in Quiet Boston Neighborhood

4.94 out of 5 average rating, 35 reviews

Home in Back Bay

Private loft style townhouse.

Private house rentals

5 out of 5 average rating, 3 reviews

Home in Revere

Beach walk

5 out of 5 average rating, 10 reviews

Home in Revere

Modern 2BR Getaway Near Revere Beach

4.96 out of 5 average rating, 25 reviews

A classic two-family residence features a white exterior and a welcoming entrance. The property showcases a front porch with white railings and steps leading to the door. Lush greenery surrounds the home, including well-maintained shrubs and flowering plants along the walkway.

Home in Winchester

3 Bedroom Boston-area Gem

4.93 out of 5 average rating, 40 reviews

Home in Boston

Home in Boston/Milton

4.97 out of 5 average rating, 97 reviews

Home in Cambridge

Pvt Bedrm/Bathrm/Kitch'ette on Quiet Tree Lined St

4.97 out of 5 average rating, 34 reviews

An open concept sitting area and kitchen is displayed, featuring a dining table set for four. A plush area rug complements the hardwood flooring, while large windows allow natural light to fill the space. Colorful seating is arranged nearby, creating a welcoming gathering environment.

Home in Cambridge

3bed, 2bath house, walk to Harvard/MIT+parking

4.93 out of 5 average rating, 76 reviews

A modern kitchen is seen, featuring sleek white cabinets and a gray stone island with seating for three. Stainless steel appliances, including a refrigerator and microwave, are positioned thoughtfully. Natural light pours in through large windows, illuminating the warm wooden flooring.

Home in Somerville

Beautiful appartement - quiet location - downtown