Vacation rentals in Deer Island

Grand 2BR Sleeps 6 • Boston • Airport & Beaches

Whether you’re traveling for work or vacation, solo, as a couple, with friends or family, this spacious, sun-filled 7-room apartment is the perfect home base. Comfortably sleeps up to 6 guests with 2 bedrooms, a full kitchen, living room, dining room, sunroom, 2 private porches, free off-street parking, oak hardwood floors, original gumwood trim, and on-site coin laundry. Minutes from Logan Airport, public transportation, beautiful Winthrop and North Shore beaches, and Boston’s top attractions.

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

Truly Oceanfront! Spacious Family Petfriendly Home

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. An historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two condos and renovated).

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

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 8 guests, making it perfect for families or groups of friends. Located on the 2nd floor of a historic building, this home offers a 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, kitchen and private deck with ocean views.

Modern & Cozy Apt close to Boston and Salem

New & Modern, Close to the beach , 15 minutes to the airport & BOSTON. Close to the beach, Salem, & Boston. minutes away from the commuter rail 5 People can comfortably stay here. minutes away from the commuter rail 10 minutes away from Salem 15 minutes to the Airport Several basic amenities included like snacks, water, mouthwash, toothbrushes, toothpastes, etc. Washing and Drying machine are included in the stay. Free Parking (Private Driveway) Smart TV with Netflix access included

4br SouthBoston free parkg nrBeach, 6 min>BCEC

Bring the whole family or team -- you'll love our quiet, safe, beachside neighborhood. Our location on the South Boston peninsula means more peace and less traffic, yet a short scenic walk up K Street brings you to great restaurants. <5min walk to a great grocery store, the legendary L St Tavern and L St Bathhouse. <1.5 mi to Convention Center & Seaport. 3 BRs w queen beds and 1 sm BR w bunks, large kitchen, liv & dining rooms, & bonus sunroom w/desk. Call us today -- we'd

Waterfront Escape - Close to Airport & Downtown

Experience the best of Boston from the Harborview House. This stunning waterfront home is only 5 minutes from the airport and 15 minutes from downtown Boston - yet feels like a world away. Enjoy panoramic views of the water from every floor, a terraced backyard patio with fire pit, gas grill and Constitution Beach only 1 block away. If you’re looking for a unique, luxury home for your group or family while you’re in Boston, the Harborview House should be your destination!

Winthrop Hideaway | Near Airport, Beaches & Boston

Escape to Get to the Point Boston, a cozy private studio in charming Winthrop just minutes from Logan Airport and downtown Boston. Enjoy free off-street parking, high-speed WiFi, premium linens, a Nespresso coffee station, complimentary snacks, and no cleaning fee. Walk to beaches, parks, restaurants, and stunning Boston skyline sunsets. Perfect for couples, business travelers, airline crews, and weekend explorers seeking comfort, convenience, and value.

Family Home + Near Downtown + Cool Backyard!

Welcome to our family home. It's convenient, comfortable, safe, and close to downtown Boston! We have a backyard and open space with a beautiful deck. It's a great place to spend time and enjoy a peaceful outdoor setting in the city. Located in the waterfront neighborhood of Jeffries Point, East Boston. A 5-minute walk to lovely parks and the HarborWalk. And just ONE SUBWAY STOP to downtown Boston. We love Boston - and hope we can share it with you!