Villa vacation rentals in Boston

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Top-rated villa rentals in Boston

Guests agree: these villas are highly rated for location, cleanliness, and more.

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The two-story home features a wraparound porch with multiple seating areas and outdoor railings. Lush green lawns and well-maintained hedges surround the property, which showcases a symmetrical façade and ample windows for natural light.

Villa in Gloucester

Over By Good Harbor: Phenomenal views and just

AdhwaRating, 5 stars60 months ago

Simply beautiful! We had a couple of issues accessing the house because of a wrong code, and issues with hot water but the host was really quick to respond and was extremely accommodating. One thing I'd say is, the neighbouring houses are closer than they appear so it wasn't as private as we expected.

A charming Victorian home is set on a grassy hillside, showcasing white siding and large windows. The front porch features a welcoming entrance, surrounded by well-maintained landscaping, including trees and shrubs. Clear blue skies create a bright backdrop for this inviting property.

Villa in Rockport

4.67 out of 5 average rating, 3 reviews

Pleasant House in Rockport: Old-world charm and

RebeccaRating, 5 stars35 months ago

This house is gigantic! Four full bathrooms (two upstairs, two downstairs). One of the upstairs bathrooms has a shower/tub and the rest have shower stalls. The kitchen and the grill were well-equipped and everything was in working order. The decor has a lot of personality -- clearly someone really loves pop music. One thing worth mentioning, a few of the bedrooms have an unexpected step up or down when you leave the room, including the one bedroom that's on the ground floor. This might be an issue for people who are older or less confident on stairs? But it wasn't a problem for my family.

A charming Queen Anne-style house is presented in a serene outdoor setting. Lush greenery and colorful flowers surround the entrance, enhancing the inviting appearance. A balcony can be seen on the second floor, offering a view of the tranquil surroundings.

Villa in Annisquam

4.67 out of 5 average rating, 3 reviews

Helena House: European flair, close to Plum Cove

EmmanuelRating, 5 stars23 months ago

We immediately felt at home at Helena’s House. The bedrooms are large and comfortable, the living rooms are welcoming and the kitchen is well equipped. Add an excellent location and all the ingredients of a great stay were in place. All in all, the house is larger than what the pictures suggest and will comfortably house a group of eight. We would definitely come back.

Guest favorite

A cozy bedroom features a spacious bed adorned with decorative pillows and a textured blanket. Soft lighting is provided by a lamp on a nightstand. A tissue box is placed on the bedside table, while a floral curtain gently frames a window.

Private room in Brighton

5 out of 5 average rating, 8 reviews

Lakefront villa near Boston College, free parking

Our house is a villa with a yard and free parking. The house is quiet and safe, surrounded by mountains and rivers. We are a few steps away from Boston University and a 10-minute drive from Boston College, Northeastern University, and Harvard University. 15 mins walk to chestnut hill station, the tram can go anywhere, very convenient. 15 min walk to the business district, surrounded by 711 supermarkets, pizzerias, Chinese restaurants, bars, hotels, etc. 5 min drive to chestnut hill business district, supermarkets, shopping malls, furniture shops, bakery shops, restaurants. The reservoir is just opposite, surrounded by trees, and the water surface is sparkling and beautiful. Suitable for morning and evening walks, jogs and workouts. You are welcome to use our dining room, kitchen, living room, and lounge. Our kitchen provides you with disposable cutlery and reusable cutlery, pots, kitchenware, condiments, etc.

Top guest favorite

A bright and spacious room features two wooden beds dressed in blue quilts, complemented by wooden nightstands. Soft natural light enters through two large windows with sheer curtains. A comfortable armchair sits in the corner, alongside a decorative area rug.

Private room in West Roxbury

5 out of 5 average rating, 32 reviews

Charming & Cozy Large Room with 2 Single Beds & TV

Welcome to our century-old home. Just a 5-minute walk away is Reservation Park for morning exercises or relaxation. Our serene neighborhood boasts tall evergreen trees. Our historic house was featured in the movie Spotlight, earning recognition with the 2016 Academy Award. Convenience is key with nearby bus routes (35, 36, 37, 38, 34, 34E, 40) to the Orange Line subway. Major amenities are a 15-minute walk away. Parking is available. Boston College is a 15-minute drive away. Warmly welcome!

A charming historic home is framed by lush green trees, with vibrant red foliage accentuating the entrance. A covered porch with decorative railings invites relaxation, while the turreted roof adds architectural interest. Sunlight filters through the leaves, creating a serene and inviting exterior.

Private room in Watertown

4.73 out of 5 average rating, 11 reviews

Historic 1893 Queen Anne Victorian Home

If you’re staying in the Greater Boston Area, don’t subject yourself to modern buildings from the 20th & 21st centuries. Instead, treat yourself to a home that’s stood tall for over half of America’s history. A history that of course began in our great Commonwealth of Massachusetts. Stay in style in scenic Watertown with great transit access to Cambridge (especially Harvard) & Boston. The room has a queen bed, among other amenities all awaiting your patronage.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Boston villa rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Family-friendly villa rentals

A charming waterfront home is displayed, featuring a light-colored facade and a welcoming front door. A well-maintained lawn surrounds the house, with a brick pathway leading to the entrance. Nearby structures are visible in the background under a clear sky.

Villa in Gloucester

Perrywinkle: Waterfront on Gloucester’s Rocky Neck

JimRating, 5 stars23 months ago

Great area. Great place.

Villa in Rockport

4.67 out of 5 average rating, 3 reviews

Pleasant House in Rockport: Old-world charm and

RebeccaRating, 5 stars35 months ago

This house is gigantic! Four full bathrooms (two upstairs, two downstairs). One of the upstairs bathrooms has a shower/tub and the rest have shower stalls. The kitchen and the grill were well-equipped and everything was in working order. The decor has a lot of personality -- clearly someone really loves pop music. One thing worth mentioning, a few of the bedrooms have an unexpected step up or down when you leave the room, including the one bedroom that's on the ground floor. This might be an issue for people who are older or less confident on stairs? But it wasn't a problem for my family.

A view of the serene Annisquam River is framed by blooming lilac flowers. A gazebo is positioned to the left, overlooking the water. A round table and chairs are set on a deck, providing a perfect spot to enjoy the tranquil scenery.

Villa in Gloucester

4.6 out of 5 average rating, 5 reviews

Sunset Cove: Waterfront home in the Goose Cove

JasonRating, 5 stars23 months ago

The Cape Ann area was lovely for a family vacation. The house has tremendous views. Spacious and well-appointed. Great spot to soak in the water views. Very comfortable.

A spacious living area features a classic billiards table with a green felt surface, positioned prominently under natural light from large windows. A sectional sofa is visible in the background, complemented by minimalistic decor.

Villa in Gloucester

Plaisance: Enjoy the best of Gloucester living.

BarryRating, 5 stars35 months ago

The house was beautiful. Just as we expected! Thanks for making our stay a great memory.

Top guest favorite

The kitchen features modern appliances, including a stainless steel refrigerator and stove. A white countertop extends into a pass-through bar, with a bowl of snacks displayed. Natural light filters through the window, illuminating the sleek cabinetry and grey tile backsplash.

Villa in Cambridge

4.98 out of 5 average rating, 262 reviews

Phil's Harvard & MIT Home

BayleyRating, 5 stars3 days ago

Wonderful experience! Phil and Joyce were amazing - highly recommend staying here if you are in the Cambridge area !

Villa in Gloucester

Over By Good Harbor: Phenomenal views and just

AdhwaRating, 5 stars60 months ago

Simply beautiful! We had a couple of issues accessing the house because of a wrong code, and issues with hot water but the host was really quick to respond and was extremely accommodating. One thing I'd say is, the neighbouring houses are closer than they appear so it wasn't as private as we expected.

Villa in Annisquam

4.67 out of 5 average rating, 3 reviews

Helena House: European flair, close to Plum Cove

EmmanuelRating, 5 stars23 months ago

We immediately felt at home at Helena’s House. The bedrooms are large and comfortable, the living rooms are welcoming and the kitchen is well equipped. Add an excellent location and all the ingredients of a great stay were in place. All in all, the house is larger than what the pictures suggest and will comfortably house a group of eight. We would definitely come back.

A spacious deck is shown with multiple lounge chairs positioned for sunbathing. The view extends toward the ocean, with distant houses visible along the shoreline and greenery interspersed throughout the landscape.

Villa in Gloucester

Salt Island Views: Walking distance to both Good

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Private villa rentals

A charming three-bedroom house is presented, featuring a large front porch. The property is surrounded by vibrant autumn foliage, creating a welcoming facade. A prominent sign displays the home's amenities, highlighting its proximity to Harvard Yard and available parking.

Villa in Cambridge

4.67 out of 5 average rating, 3 reviews

Harvard Sq 3BR House w/ parking

TimRating, 5 stars4 weeks ago

fantastic location and a great place for groups. highly recommended

Villa in Gloucester

4.6 out of 5 average rating, 5 reviews

Sunset Cove: Waterfront home in the Goose Cove

JasonRating, 5 stars23 months ago

The Cape Ann area was lovely for a family vacation. The house has tremendous views. Spacious and well-appointed. Great spot to soak in the water views. Very comfortable.

Top guest favorite

Villa in Cambridge

4.98 out of 5 average rating, 262 reviews

Phil's Harvard & MIT Home

BayleyRating, 5 stars3 days ago

Wonderful experience! Phil and Joyce were amazing - highly recommend staying here if you are in the Cambridge area !

Villa in Gloucester

Over By Good Harbor: Phenomenal views and just

AdhwaRating, 5 stars60 months ago

Simply beautiful! We had a couple of issues accessing the house because of a wrong code, and issues with hot water but the host was really quick to respond and was extremely accommodating. One thing I'd say is, the neighbouring houses are closer than they appear so it wasn't as private as we expected.

Guest favorite

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.

Villa in Newton

4.93 out of 5 average rating, 70 reviews

Explore Boston in style! Dream home, pool, sauna.

ChristopherRating, 5 stars1 week ago

Great location, well stocked, and just as advertised. Would definitely stay again!

Villa in Gloucester

Perrywinkle: Waterfront on Gloucester’s Rocky Neck

JimRating, 5 stars23 months ago

Great area. Great place.

Villa in Rockport

4.67 out of 5 average rating, 3 reviews

Pleasant House in Rockport: Old-world charm and

RebeccaRating, 5 stars35 months ago

This house is gigantic! Four full bathrooms (two upstairs, two downstairs). One of the upstairs bathrooms has a shower/tub and the rest have shower stalls. The kitchen and the grill were well-equipped and everything was in working order. The decor has a lot of personality -- clearly someone really loves pop music. One thing worth mentioning, a few of the bedrooms have an unexpected step up or down when you leave the room, including the one bedroom that's on the ground floor. This might be an issue for people who are older or less confident on stairs? But it wasn't a problem for my family.

Villa in Gloucester

Plaisance: Enjoy the best of Gloucester living.

BarryRating, 5 stars35 months ago