Vacation rentals in Deer Island

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Top-rated vacation rentals in Deer Island

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Guest favorite

A comfortable living area features a cozy sectional sofa and a patterned accent chair. A round glass coffee table sits in the center, complementing the serene atmosphere. Large windows illuminate the space, while a mounted TV and a decorative fireplace add functional elegance.

Home in Hull

4.95 out of 5 average rating, 22 reviews

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. ☀️ ☀️☀️

Guest favorite

A well-furnished living area features a light-colored sofa adorned with patterned cushions, complemented by a blue ottoman. A large area rug in soft tones enhances the warmth of the hardwood floor. Natural light enters through multiple windows, while a decorative chandelier hangs from the ceiling.

Home in Winthrop

4.88 out of 5 average rating, 72 reviews

Cozy & Modern Entire Residential Home ❤️

Discover your dream stay in this cozy 2bed, 1bath property located in picturesque Winthrop, Ma. It's perfectly situated 5-min from Yirrell Beach offering access to relaxation & city excitement. A convenient 20min drive from the bustling heart of Boston & 15min from Logan Airport & Encore Casino. Walking distance to public transportation & easy access to city adventures. clean & beautifully furnished and has a fully stocked eat-in kitchen, and a spacious deck. Short & long term stays are welcome

Guest favorite

A cozy living area showcases a light-colored sofa adjacent to a white coffee table with a puzzle setup. A small dining table with two wooden chairs is positioned nearby. A bright entrance door provides natural light, and shelves display maritime-themed decor.

Guest suite in Winthrop

4.92 out of 5 average rating, 1,311 reviews

Licensed Boston airport studio 5 stars, subway

We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.

Top guest favorite

The living room features a spacious layout with leather seating and a colorful area rug. A large TV is mounted on the wall, and windows offer an ocean view. A furry dog rests comfortably on the floor, adding to the welcoming ambiance.

Condo in Winthrop

4.99 out of 5 average rating, 192 reviews

Truly Ocean-Front!: Spacious Family Home + Pets

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.

Top guest favorite

The exterior of the private studio is shown, featuring a light blue siding with a gray shingled roof. A welcoming front door is flanked by a light fixture and a decorative sign. Flowering plants are arranged in front, enhancing the outdoor space.

Cottage in Winthrop

4.98 out of 5 average rating, 471 reviews

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.

Guest favorite

A spacious outdoor pool area is showcased, flanked by lounge chairs and surrounded by modern architecture. The pool features a clear blue water and a surrounding deck with light-colored tiles, inviting relaxation under the sun.

Apartment in Boston

5 out of 5 average rating, 7 reviews

Monthly Skyline Apartment

Welcome to your next retreat, a waterfront haven of fully furnished corporate housing that blends luxury with urban ease. Highlights: • Exceptional location 5-min to the center of downtown • Direct Harborwalk access near Lo Presti Park • Rooftop lounge with skyline vistas, and cozy seating • Pool terrace with grills and herb garden • Chef’s kitchen, billiards, and stylish social spaces • 24/7 fitness center with Peloton and harbor views • Private work rooms and a creative music studio

Guest favorite

An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.

Guest suite in Winthrop

4.95 out of 5 average rating, 947 reviews

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Top guest favorite

The exterior of a three-story building is showcased, featuring a welcoming entrance with steps leading up to a covered porch. Surrounding gardens are visible, displaying a variety of plants and flowers. The building's facade is painted in light colors, complementing its modern architectural style.

Apartment in Winthrop

5 out of 5 average rating, 36 reviews

Pleasant Place 1

This stylish place to stay is perfect for a single person or couple. It is a very beautiful space in a lovely 2 family, owner occupied home. Winthrop is a beautiful oceanside residential community situated at the entrance of the most beautiful harbors in New England. Winthrop offers small town suburban living, within minutes to Boston. We have public transportation to downtown Boston in about 20 minutes, Logan Airport in 15 minutes. We also have a Ferry Service to Boston.

Top guest favorite

A cozy living area features a comfortable gray sofa with striped cushions, positioned near a large window that allows natural light to fill the space. A small desk on wheels complements the seating area, and a decorative plant sits on a side table, enhancing the inviting atmosphere.

Apartment in Winthrop

5 out of 5 average rating, 22 reviews

Boston in 15 Mins!

Stylish 1BR Near Logan & Ocean This stylish 1-bedroom apartment in Winthrop offers the best of both worlds—peaceful coastal charm and quick city access. Key Features: • 15 mins to Logan Airport, 15 mins to Boston • Steps from the beach & scenic harbor views • Modern & cozy space. • Easy access to public transit & ride-shares • Walk to local cafés & restaurants. Whether you’re here for business or a relaxing retreat by the water, this is the perfect spot.

Superhost

A spacious bedroom features a large bed adorned with decorative pillows and a cozy throw. Two bedside tables hold lamps. Art depicting serene seascapes is displayed on the wall. Natural light enters through a window covered by a white curtain.

Guest suite in Winthrop

4.85 out of 5 average rating, 123 reviews

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.

A spacious bedroom is featured with a comfortable Queen-sized bed, adorned with teal pillows. Natural light fills the room, reflecting off the polished wooden floors. A bedside table holds a small plant, while a piece of abstract artwork decorates the wall above the bed.

Apartment in Winthrop

4.63 out of 5 average rating, 32 reviews

(S209) Cute Studio near Airport, hospitals & beach

Welcome to Winthrop! Our Airbnb offers the charm of a quaint coastal town with the convenience of city life. Just minutes from downtown Boston, you can easily explore historic landmarks, vibrant neighborhoods, and renowned dining. Enjoy Winthrop's serene beaches, scenic parks, and local eateries right at your doorstep. Ideal for a peaceful retreat or a city adventure, our location offers the best of both worlds.

Top guest favorite

A pathway lined with brick leads to a cozy cottage with maroon siding, framed by lush greenery. A seating area with chairs is positioned on a well-maintained lawn, inviting relaxation on a sunny day. Tall trees provide shade, enhancing the tranquil ambiance.

Barn in Nahant

5 out of 5 average rating, 145 reviews

Entire Beach-Town Cottage, Barn Charm, near Boston

A nicely renovated, old barn, fully furnished, where contemporary style meets barn-charm. Located in a quiet neighborhood with private yard and only minutes to the beach. Parking on premises. The ideal location for a short getaway with family or friends or to unwind after a long day at work. Only 25' from downtown Boston and other North Shore towns with restaurants and bars.