Family-friendly vacation rentals in Medford

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Popular amenities for Medford family-friendly rentals

Family-friendly home rentals with a hot tub

A spacious living room features a comfortable sectional sofa in a neutral color, paired with a coffee table positioned on a patterned area rug. Natural light fills the room through a large window, complemented by soft drapes. A flat-screen TV and elegant lighting complete the inviting space.
Apartment in Fenway-Kenmore
4.73 out of 5 average rating, 83 reviews

Renovated 2Bed, 0.5 mile to Longwood Med Hospital

AmyRating, 5 stars1 month ago
This condo was perfect for what we needed. Just two bedrooms, a kitchen and living room, so we could relax in between walking adventures. I wish I had come across this back in the fall when my daughter was playing soccer for Northeastern because the soccer field is literally across the street. There is a nice walking trail about a quarter of a mile away. We really liked Coolidge Corners. Easy to get Ubers. The place was perfect and comfortable and easy to get in/out.
A charming house is framed by colorful flowers and lush greenery, with steps leading up to the entrance. The exterior features a mix of stone and wood, complemented by red accents. Umbrellas provide shade over outdoor seating areas.
Home in Gloucester
4.9 out of 5 average rating, 10 reviews

Steps to Good Harbor Beach

MichaelRating, 5 stars71 months ago
Kate's house in Gloucester is an ideal place to experience one of the best beaches on the North Shore. Kate's home accommodated the eight of us very comfortably; the proximity to the beach was second to none and Kate and Michelle's response to a couple of minor issues we had was expeditious and friendly. There aren't enough superlatives I could use to recommend Kate's place.
Guest favorite
The kitchen features modern cabinetry and high-end stainless steel appliances, including a refrigerator and microwave. A dark countertop extends to a breakfast bar with two white stools. Warm hardwood floors and soft overhead lighting create an inviting cooking space.
Apartment in South Boston
4.91 out of 5 average rating, 66 reviews

South Boston. Minutes away from Convention Center

LeeRating, 5 stars2 weeks ago
The apartment was exactly like described in an amazing location. I was attending a conference at the EXPO center, and it was an easy 25 minute walk there and back. Area is safe and clean. The best feature is the is less than a minute walk from a beautiful park and beach. Multiple Restaurants within walking distance and had no trouble getting items delivered. Would definitely stay again. Thank you so much Tanya!
Top guest favorite
The exterior of a fully remodeled three-bedroom house showcases a stylish design with multiple levels. A spacious rooftop deck is visible atop the structure, while an inviting front entrance leads into the well-maintained property. The surroundings include a paved driveway and landscaped areas.
Home in Newbury
4.98 out of 5 average rating, 51 reviews

Plum Island - Luxury Beach House

TracyRating, 5 stars9 months ago
We rent a house on PI every year and this house was perfect for us. We could walk to the basin with our SUP’s, easy walk to beach and stores and ice cream! We loved the double outdoor shower option for the kids after a long sandy day at the beach and they supplied all the beach toys, umbrellas and chairs! The rooftop deck was our favorite part we watched the sunset every night. We would rent this house again if the dates line up!
Guest favorite
A spacious living room features a comfortable white sofa paired with an accent chair. Natural light floods in through multiple windows, creating a bright atmosphere. A large area rug lies on the hardwood floor, and a decorative painting adds a touch of color above the fireplace.
Home in Brighton
4.96 out of 5 average rating, 266 reviews

Spacious 3 bed, in unit laundry, central Air

BillRating, 5 stars3 weeks ago
We had a great stay! This house was in a great location, and very nice/spacious. We also appreciated the very thorough and clear communication regarding check-in etc, before the stay. I highly recommend Joel as a host!
Superhost
The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.
Apartment in Roxbury
4.78 out of 5 average rating, 329 reviews

Modern, Spacious 1BR for 4 - Easy Marathon Access!

YsamarRating, 5 stars2 weeks ago
Very quiet area. Close to the orange Line and multiple busses. Check In/out was easy. Apt room temp was good. Hot water was extra hot, so also a plus. Cable TV was nice.

Family- and pet-friendly home rentals

Guest favorite
A wooden deck is situated in the foreground, featuring a small seating area and an umbrella. Lush greenery, including tall evergreen trees and colorful shrubs, creates a natural backdrop. A stone pathway leads into the garden area, enhancing the tranquil outdoor space.
Apartment in Lakeside Marblehead
4.94 out of 5 average rating, 196 reviews

Two bedroom Apt with a deck

EmilyRating, 5 stars1 week ago
We had a great stay here! Very flexible check in, the comfiest beds and a variety of incredible books to choose from if you’re staying in!! The host was very sweet and even gave us a recommendation for a great spot to watch the full moon that evening. Gorgeous gardens in the back. Highly recommend this stay!
Top guest favorite
A well-equipped kitchen presents stainless steel appliances and an island with seating for four. Natural light floods the space through large windows, creating a bright and inviting atmosphere. The adjacent sunroom is visible through an open entryway, enhancing the home’s spacious feel.
Home in Wakefield
4.96 out of 5 average rating, 264 reviews

Welcoming 7-room house <15 miles to Boston & Salem

NancyRating, 5 stars3 weeks ago
We enjoyed staying at Karen’s! It was a super clean space which we really, really appreciated. The neighborhood is peaceful and quiet. Super easy to check-in and check-out. Karen is also super responsive and proactive which was great! Only bump in the road was that we unfortunately had to deal with a water leak issue which was stressful but Karen did what she could to be as helpful as possible. It was fixed shortly after reporting. We appreciated that Karen coordinated maintenance so quickly in a way that was accommodating to our schedule. Overall we are very pleased and would definitely recommend!
Top guest favorite
A wooden cabin with a sloped roof is surrounded by a snow-covered landscape. The porch is visible, along with two friendly dogs playing in the snow. Tall trees, dusted with snow, create a serene, wintry atmosphere.
Cabin in Rockport
4.97 out of 5 average rating, 454 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

JasonRating, 5 stars3 weeks ago
Wonderful getaway in the woods, but close to restaurants and shop in Rockport. We loved being greeted by the dogs and the hiking trails right outside the front door are amazing.
Guest favorite
An outdoor space is presented, featuring a wooden picnic table surrounded by a sprawling lawn. A slide is integrated into the landscape, complemented by vibrant greenery and a nearby garden area. Outdoor seating is also visible in the background, enhancing the communal atmosphere.
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars3 months ago
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.
Guest favorite
A welcoming living room is equipped with two comfortable sofas, a wooden coffee table at the center, and a wall-mounted TV. Natural light enters through multiple windows, while a modern electric fireplace adds warmth to the space, enhanced by a vibrant area rug.
Townhouse in Allston
4.93 out of 5 average rating, 189 reviews

Sparkling Condo With Modern Amenities

MelissaRating, 5 stars1 week ago
Had a wonderful stay with my friends in Boston. The rooms and living spaces were very comfortable and clean. Michelle was very reachable and responded quickly. Would recommend this home to anyone.
Guest favorite
A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.
Home in Salem
4.95 out of 5 average rating, 153 reviews

Quaint Little New Hampshire Lake House Getaway!

KevinRating, 5 stars4 weeks ago
We really enjiyed our stay and would recommend to anybody else.
Top guest favorite
A private entrance to a charming home is framed by well-maintained landscaping and a gravel driveway. Decorative flower boxes adorn the windows of the light-colored exterior, while surrounding trees provide a natural backdrop, creating a serene environment.
Apartment in Concord
4.96 out of 5 average rating, 214 reviews

Mema's Place --Lovely apartment in private home

MiebethRating, 5 stars3 days ago
We loved Ellen's place from the minute we walked in. It was warm, welcoming and had everything that we needed for a week's stay. The house/apartment is set on a quiet street set in the woods but a very close drive to Concord where we spend most of our time sightseeing. Helen's is the best restaurant to try in town. Ellen and her husband Kevin were there to welcome us and answered any concerns we had about the place. Her place is very comfortable with a large living room to relax in, a kitchen to cook in and a very comfortable bed to sleep in. I give her place 10 stars and more and I recommend it to anyone who is staying in Concord. Thank you Ellen for the wonderful stay and we look forward to seeing you again
Guest favorite
A newly remodeled kitchen features modern stainless steel appliances and ample counter space. White cabinetry contrasts with warm wood paneling and flooring. A dining area with a wooden table and chairs is visible, along with soft lighting from pendant fixtures above.
Cabin in Cohasset
4.92 out of 5 average rating, 335 reviews

Lionsgate at Cohasset

PritiRating, 5 stars2 weeks ago
Our stay in Lionsgate cabin in Cohasset was heavenly abode for a week during our stay in the last week of May. The cabin is located in peaceful surroundings with beautiful bird watching areas. The bird feeder outside our cabin kept me and my toddler daughter occupied throughout our stay here. The lawn areas and seating outside are great areas to take a stroll and listen to nature’s music. The cabin is comfortable and cozy with enough provided even for a long stay. It is located within short travel distance from many good restaurants, grocery shops and metro. Very close to the beach, we visited Nantasket and Hull many times during our stay. We loved our stay here and will stay here again. Highly recommend this cabin.

Family-friendly home rentals with a pool

An open-concept kitchen and dining area features modern furnishings, including a long dining table surrounded by black chairs. Large windows offer views of greenery, allowing natural light to fill the space. A sleek kitchen island with bar stools complements the contemporary design.
Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars42 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
Guest favorite
The backyard features a tranquil swimming pool with sunlit reflections, surrounded by elegant outdoor seating arranged on a stone patio. Large windows in the main house offer views of the inviting outdoor space, enhancing the serene atmosphere.
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars3 weeks ago
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.
Guest favorite
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars5 days ago
Brad was very friendly and helpful. Beautiful home!
Top guest favorite
A light yellow cottage is positioned adjacent to a spacious swimming pool, surrounded by lush greenery. The pool features a diving board and a decorative tile border. Two lounge chairs sit nearby, while steps lead up to the entrance of the cottage.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 196 reviews

Country Cottage in the City

JulieRating, 5 stars2 weeks ago
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.
Guest favorite
A spacious backyard is shown, featuring a wooden playset with a slide and swings. Lush greenery surrounds the yard, with tall trees providing shade and privacy. The grass is well-maintained, creating a suitable area for outdoor activities.
Guest suite in Canton
4.71 out of 5 average rating, 107 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars8 months ago
The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.
Guest favorite
A spacious outdoor area features a crystal-clear pool surrounded by a paved deck. Several lounge chairs are positioned nearby for relaxation. The house in the background displays a welcoming design with a cozy porch. Lush greenery provides a serene backdrop to this inviting space.
Apartment in Winthrop
4.96 out of 5 average rating, 313 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

BethRating, 5 stars2 weeks ago
We had a wonderful stay! It's very close to Boston, and other area attractions like Salem and beaches, but still peaceful. We enjoyed sitting at the pool. Kathy was very responsive and checked in with us to make sure we had everything we needed. They provided clear instructions for getting into the space and I had no issues navigating in and out of the neighborhood or to the basement apartment. I would definitely stay again if I'm needing a place in the area!
Superhost
A spacious outdoor pool area is surrounded by lounge chairs and tables, offering a relaxing atmosphere. The pool is clear and inviting, with steps leading into the water. A rustic building with large windows is positioned nearby, set against a backdrop of lush greenery.
Cottage in Westford
4.92 out of 5 average rating, 39 reviews

Beach & pond cottage ! Westford MA and Boston!

KatherineRating, 5 stars1 month ago
We needed a nice little place to stay while we visited family and friends. This was perfect. Cute and convenient, plus lots of fun amenities like a clubhouse, ball courts, kayaks and the lake. We went off season, so the pool was closed and it was too cold to boat, but it was still fun. We enjoyed walking the community, playing ping-pong and driving the golf cart.
Top guest favorite
The exterior of a historic yellow house is highlighted, featuring various architectural details and large windows. A welcoming front porch leads to well-maintained gardens, with paths leading to lush greenery and shrubs, creating a tranquil entrance.
Townhouse in Groton
5 out of 5 average rating, 80 reviews

Potager Farm Private Townhouse

WesleyRating, 5 stars2 weeks ago
We had a wonderful stay in Christine’s place in Groton. The apartment is very comfortable, lots of light and beautiful. The kitchen is stocked and the bathroom is great. Cozy little TV den. Upstairs large bedroom was great; and upstairs bedroom for our son was comfy, too. The gardens/lawn were beautiful and the house is walkable to Main St in Groton. Great communication and Christine was very accommodating with checkin and departure time. We would definitely return to her lovely home.

Quick stats about vacation rentals that are family-friendly in Medford

  • Total rentals

    220 properties

  • Nightly prices starting at

    G$8,359 GYD before taxes and fees

  • Total number of reviews

    11K reviews

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wifi availability

    210 properties include access to wifi

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