Pet-friendly holiday rentals in Milton

Beach Home next to Boston & T, King Bed, Park Free

Enjoy a comfortable stay in this beautiful, newly renovated 3 bed 2 bath apartment only 150 yards to the beach and convenient access to Boston by car (15-25min) or public transport (30-45min). It's a spacious 1300 sqft, was just fully remodeled, retains plenty of character and boasts loads of windows and light. Recharge from your trip in style with a fully equipped kitchen, three new comfortable beds, 55" TV, sofa, work & dining area, new bathrooms, walk-in closet, and free off-street parking.

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and abundance on-street parking. Pet friendly!

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

Relax in the Bostonian, a stylish, pet-friendly apartment on the semi-basement level of a charming multi-family house. The apartment is air conditioned & overlooks a beautiful patio and backyard. Located in quiet Hyde Park neighborhood, a 30 minute drive into downtown Boston. Plenty of free streetside parking. Private in unit laundry. Professionally cleaned. Room 1: Queen size bed Room 2: Queen size bed Room 3: Living room couch, TV, electric fireplace Dining room: includes two wall arcades

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

FREE Parking, Cozy Kid-Friendly Near Adams Park

🔥 SPECIAL OFFER: SAVE UP TO 30% ON SELECTED STAYS! Step into a bright, modern townhouse designed for comfort, space, and effortless living. Ideal for family getaways, business trips, or group stays, this home combines upscale finishes with thoughtful amenities to make every stay smooth and enjoyable. ★ Convenient Parking ★ Baby crib provided – kid-friendly ★ Central A/C & heating ★ High-speed Wi-Fi ★ Fully equipped modern kitchen ★ Fresh linens, towels & essential toiletries ★ Washer & dryer

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

Cozy Guesthouse Near T-Station - Family Friendly

Welcome to your getaway home! You are sure to enjoy a wonderful experience in this newly renovated Guesthouse Studio, situated in Weymouth Landing. • Just a 5-minute walk to the Commuter Rail station for easy access to Boston and beyond. • Explore local stores, restaurants, and bars, all within walking distance. • Only 10 minutes away from South Shore Hospital. • A short 12-mile drive to Downtown Boston. Perfect for couples, small families, groups, business stays, and long-term rentals.

Conveniently Located Private Garden Apartment

Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

Upscale Boston 2 BR w/ Off Street Parking

Spacious 2 bedroom is perfect for your Boston getaway. This unit features one king and one queen bed, one pullout twin bed in the office, WIFI, TVs in each room, and in-unit laundry. Located in the safest neighborhood of Boston, West Roxbury is minutes from from Brookline, the Longwood Medical Area, and downtown Boston. MBTA bus stop located directly in front of the house and readily available Uber and Lyft options, this is a perfect location to stay when exploring the city.

Apartment 1BR mins from JFK/UMASS free parking

Airbnb Superhost offering meticulous and spacious 1 bedroom 1 bath, queen bed plus sleep sofa and airbed (please request it when booking). Free street parking or in the driveway, free laundry, full kitchen, hardwood and tile floors. Wireless internet, smart TV. 10 min walk to Red Line JFK/UMass station and Savin Hill station. Free parking on the street or in our driveway. Well kept front yard and back yard with porch, chairs and table.

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.