Kid-friendly vacation rentals in Milton

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Top-rated kid-friendly rentals in Milton

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Boston

4.96 out of 5 average rating, 203 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.

Mar 16 – 23

G$26,372 GYD per night

Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 106 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Jan 1 – 8

G$26,186 GYD per night

Guest favorite

Guest suite in Boston

4.91 out of 5 average rating, 196 reviews

Cozy Private Garden Studio near the Heart of JP

Best of both worlds: this airy and light, newly renovated private studio is set in a beautiful, secluded backyard/garden. Easy walk to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is a microwave, fridge, counter and and sink but no stove or cooking options.

Oct 22 – 29

G$22,509 GYD per night

Guest favorite

Guest suite in Dover

4.98 out of 5 average rating, 183 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

Mar 22 – 29

G$31,193 GYD per night

Superhost

Apartment in Weymouth

4.81 out of 5 average rating, 167 reviews

Lovely studio on the coast! Beach close by!

Wonderful location located in north Weymouth. Quiet, Spacious studio apartment. Outdoor deck with patio furniture. Plenty of space for 3 guests max. - Walking distance to George lane beach & Wessagusset beach. - Convenience store, Pizza & Sandwich shop on our block. - 2 miles to Hingham shipyard - 5 miles to Nantasket beach - In between several commuter rail stations and across the street from a bus stop. - 4 miles to Quincy center - 30 minute drive to Boston!

Sep 26 – Oct 3

G$28,652 GYD per night

Guest favorite

Home in Dedham

4.98 out of 5 average rating, 185 reviews

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home, just 1.5 miles from Boston's transit. 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. Pets and families are warmly welcomed.

Jan 5 – 12

G$74,158 GYD per night

Guest favorite

Apartment in Milton

4.85 out of 5 average rating, 106 reviews

Retreat Milton/Boston line (transit close) Pets

The house is tastefully decorated and can accommodate a larger group , sleeps 6-8. 5 min to Boston , 1.3 miles to Central Ave Transit, or bus at end of street. The house is 20 min to Downtown Boston , it is a duplex totally separated for your own privacy. Reasonable alternative to Hotels , perfect for groups going to Convention Center. I recently added mini splits for additional cooling and heating needs , central ac .

Nov 15 – 22

G$97,833 GYD per night

Guest favorite

Cottage in Milton

4.95 out of 5 average rating, 172 reviews

Walk to it all-shops, market, dinner, coffee shops

Nestled in a quiet neighborhood, this enchanting cottage embodies the essence of coziness and charm, adorned with a delightful mid-century flair. Offering an idyllic sanctuary of seclusion, it has been thoughtfully crafted to become your cherished haven away from the hustle and bustle of everyday life. The number of people allowed to stay is 3 unless you are a family with younger children and then 4 people with be fine.

Oct 27 – Nov 3

G$57,476 GYD per night

Guest favorite

Apartment in Randolph

4.88 out of 5 average rating, 287 reviews

1 Bedroom basement apartment

Apartment is in a basement of a one family house with a separate entrance and parking. Includes a private kitchen , bathroom and living room. located in Randolph Ma South of Boston,6 minutes to public transportation reachable only by car since you can only get there by taking the highway. We recommend our guests to rent a car or use uber. Closest train station is Quincy Adams Train Station, beaches , ski area

Feb 2 – 9

G$27,426 GYD per night

Guest favorite

Home in Quincy

4.96 out of 5 average rating, 124 reviews

Artist's Haven (2)

Before booking, please conduct thorough research on Quincy, MA, to ensure it aligns perfectly with your needs. As a dedicated Superhost, I'm committed to earning your 5-star review. My home offers easy check-in with a keypad entry. The cozy second-floor one-bedroom has a private entrance, spa-like bathroom, well-equipped kitchen, queen-sized bed, 55" TV, high-speed WiFi, and on-site parking for one car.

Jul 21 – 28

G$24,165 GYD per night

Guest favorite

Apartment in Milton

4.96 out of 5 average rating, 108 reviews

Milton - Immaculate & renovated 3 bed 2 .5 bath!

Welcome to our attached duplex family home. We recently renovated this home from top to bottom with brand new finishes and custom design. Our home has three large bedrooms with two full bathrooms with two living room areas that are a great fit for your family and friends. Some key features of the home are hardwood floors, quartz counter, bright recessed lights, and large yard for outdoor play.

Feb 17 – 24

G$66,132 GYD per night

Guest favorite

Apartment in Natick

4.98 out of 5 average rating, 333 reviews

Scandi-Modern Apartment

Charming walk-out ground level apartment in a quiet residential neighborhood. Conveniently located west of Boston with easy access to highways. Walkable to grocery store, pharmacy, banks and restaurants. Walk the nearby trail to Lake Cochituate and the Cochituate Rail Trail is less than 1 mile away. Natick Mall is 1.3 miles. EV charging available.

Oct 24 – 31

G$26,522 GYD per night