Vacation rentals in Deer Island

My Three Suns

Enjoy quiet, seaside peninsula living in this waterfront home w/ ocean views from every bedroom. Endless possibilities to explore. Curl up in the sunporch watching the sunrise w/ your favorite book. Or have your coffee on the seawall. Biking/walks/runs/paddleboard. Pack a lunch & head down to historic Nantasket Beach. Plan an evening out & walk to catch the ferry into Boston’s North End for dinner. A 22 minute boat ride between you & the city. Rest & recharge in this coveted neighborhood. ☀️ ☀️☀️

Family · Location · Hospitality

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Guest favorite

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.

Location · Family · Nearby

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Guest favorite

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).

Value · Location · Comfort

Kasa at Boston Common | Three Bedroom

Stellar location meets generous space at Kasa at Boston Common. Choose from 1, 2, 3, or 4-bedroom furnished apartments with full kitchens and in-unit laundry, giving you more reason to stay longer, and with more room for people you want to travel with. The feeling of home, with all of downtown Boston’s best dining, shopping and attractions right at your doorstep. Our tech-enabled rooms offer self check-in at 4pm, 24/7 guest support by text and Virtual Front Desk accessed via mobile device.

Location · Cleanliness · Hospitality

Top guest favorite

Guest favorite

Sky harbor wine lounge experience Plane Watching

Treat yourself to a getaway at my newly renovated nautical themed home nestled in Winthrop’s charming friendly seaside neighborhood close to Logan Airport and downtown Boston. We are delighted to offer you a spacious private bedroom with full bed, refrigerator & AC. You’ll share my home with me (Shirley) my two cats, Caleb & Otto and one other airbnb guest room. For an additional $40 you have access to the Sky Lounge overlooking Boston harbor. You would share the rest of my home with us.

Location · Family · Beach

(S104) Beach Studio, Sleeps 3, 15 min to Airport!

🌊 Welcome to Winthrop! Discover the charm of this quaint seaside town just minutes from downtown Boston. From your doorstep, you can stroll to 🏖️ serene beaches, 🌳 scenic parks, and cozy local eateries that capture the spirit of New England’s coast. Whether you’re seeking a peaceful retreat by the ocean or planning to explore Boston’s historic landmarks, vibrant neighborhoods, and world-class dining, ✨ Enjoy the calm of the shoreline with the convenience of quick access to the city.

Value · Family · Kitchen

Ocean view 2 bedroom spacious apartment w/parking

Welcome to our cozy spacious top-floor apartment. This bright and comfortable home features two bedrooms, one full bathroom, and a fully equipped space perfect for families, couples, or business travelers. The sofa in the living room expands to queen sleeper. Enjoy the convenience of a dedicated driveway parking spot and a peaceful location close to local attractions, restaurants, shopping, and the waterfront. Relax, unwind, and enjoy a comfortable stay that feels like home.

Parking · Indoor spaces · Cleanliness

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Guest favorite

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!

Value · Family · Beach

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Guest favorite

Beachfront escape

Experience true coastal luxury in this breathtaking second-floor apartment where panoramic ocean views form the perfect backdrop for your stay. This beachfront haven blends modern elegance with relaxed coastal charm. Inside you’ll find a thoughtfully designed space with everything needed for comfort: high-speed WiFi, a smart TV, and air conditioning. Whether you’re here for romance, family time, or quiet relaxation, every detail has been curated for an effortless stay.

Location · Family · Checkout

In The Heart of Boston’s Seaport + Rooftop Bar

The Envoy Hotel connects Boston with food, drink, and skyline views that define the city. At Para Maria, Chopped champion Tatiana Rosana serves eclectic dishes inspired by French training, Cuban roots, her wife’s Korean heritage, and New England grit. Rooftop at The Envoy offers craft cocktails and fire pits with stunning harbor views. With art‑filled spaces, vibrant design, and Seaport originality, The Envoy delivers hospitality that rises above the ordinary.

Value · Location · Check-in

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Guest favorite

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.

Value · Family · Decor

The Strand on the Beach

Welcome to the 129 The Strand! This accommodation will transport you to a tropical paradise where you can relax and enjoy the sun, sand and sea. Located a few steps from the beach, our Airbnb is the perfect place for your dream vacation. The interior is decorated in a modern and cozy style, and is equipped with everything you need for a comfortable and relaxed stay, it has 1 bed, 1 bath, living room, private entrance, parking, & refrigerator.

Value · Family · Heating