Vacation rentals in Deer Island

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Top-rated vacation rentals in Deer Island

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Guest favorite

Private room in Boston

4.9 out of 5 average rating, 780 reviews

★ Chic, Clean & Large ★ Professionally Cleaned! ★

Need a safe, clean, and comfortable place to stay? You’ve found it. Yes, we are currently hosting guests. You can book for a short or extended stay. PROFESSIONALLY CLEANED AND SANITIZED regularly. Our housekeepers are taking extra care to disinfect frequently touched surfaces between reservations. • MODERN, ULTRA-CLEAN WITH A TON OF SUNLIGHT • JUST 2 SUBWAY STOPS AWAY FROM DOWNTOWN • ULTRA COMFY, LUXURY BED • PRIVATE ROOM WITH LOCK & KEY • AVAILABLE STREET PARKING • 5 MINS TO AIRPORT BY UBER

Guest favorite

Apartment in Quincy

4.88 out of 5 average rating, 8 reviews

Cozy KING BED Suite in Greater Boston Area

ROOF TOP LEVEL Entire Private Apt Suite in Beach City ❀ One Bedroom, One bath ❀ with: ♡ Only about 25min to Harvard Square, MIT, Freedom Trails, Boston Garden, Boston Harbor. A truly convenient location ♡ FREE 01 reserved PARKING space on our parking lot and additional free overnight street parking. ♡ Private Kitchenette ♡ MINUTES DRIVE TO ALL THE NEARBY BEACHES ♡ Countless of dining, hiking, shopping options, everyday eateries are within walking distant ♡ Minutes drive to Quincy Center Station

Top guest favorite

A private roof deck is showcased with a round table and four high-backed chairs beneath a vibrant red umbrella. Wooden decking and a slatted privacy screen provide an inviting outdoor space, complemented by a small potted plant in the corner.

Condo in Winthrop

4.99 out of 5 average rating, 68 reviews

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. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

Top guest favorite

Condo in Winthrop

4.99 out of 5 average rating, 186 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

A sandy beach stretches along the shoreline, gently illuminated by a vibrant sunset. A staircase leads down to the beach, hinting at accessibility. In the distance, the silhouette of a water tower marks the community, while the sun sets over the calm ocean waves.

Cottage in Winthrop

4.98 out of 5 average rating, 466 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.

Top guest favorite

A three-story yellow Victorian house is shown, featuring elegant architectural details such as a central entryway with a rounded arch and large balcony. Windows adorned with black shutters frame the façade, while colorful flowers and shrubs decorate the front yard.

Apartment in Dorchester

4.89 out of 5 average rating, 676 reviews

2 bedroom 1st Floor Apartment in Savin Hill

This is a private apartment: living room, one bedroom with a queen size bed and 2 single bed 'Castro Convertibles' and one bedroom with a single bed, bathroom, fully equipped eat in kitchen, back porch and yard. Excellent access to public transportation, downtown area, and tourist attractions. Also suitable for longer stays. One of your hosts is a nurse and we would be happy to host travel nurses. Very convenient to MGH and Longwood Medical area. Please let us know if you are interested.

Guest favorite

A wooden pier extends into calm waters, flanked by metal railings. Lanterns stand at intervals along the walkway, which leads toward the horizon. Soft clouds are visible above, with a mellow sun illuminating the scene.

Guest suite in Winthrop

4.95 out of 5 average rating, 933 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

Apartment in Winthrop

4.97 out of 5 average rating, 62 reviews

Pleasant Place 2

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 panoramic view of a scenic harbor features numerous boats anchored in the calm waters. The coastline is lined with charming homes and small buildings, while the blue sky above complements the vibrant ocean, creating a peaceful seaside atmosphere.

Apartment in Winthrop

5 out of 5 average rating, 12 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 decorative lamp features a cylindrical base filled with an assortment of seashells, showcasing a variety of shapes and sizes. The lamp is topped with a white shade, creating a cohesive coastal-inspired design. A decorative flower vase in light blue adds a complementary touch.

Guest suite in Winthrop

4.86 out of 5 average rating, 118 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.

Guest favorite

A spacious communal area features large windows allowing ample natural light. Curved green seating arrangements are complemented by small wooden tables. A modern billiards table occupies the center, while vibrant greenery is visible through the glass doors leading to the outdoor space.

Apartment in Everett

5 out of 5 average rating, 17 reviews

Elegant Oasis with Pool and Gym

Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa

Top guest favorite

Private room in Winthrop

4.95 out of 5 average rating, 354 reviews

Shirley's Sea Breeze airport getaway 2 single beds

Our home is nestled in this charming seaside neighborhood close to Boston Logan Airport and close to down town Boston. We are delighted to be able to offer you a spacious private bedroom and access to our home. You’ll share my home with me (Shirley) and my two cats, Caleb and Otto. Come enjoy the front porch or back deck and take in the Salty air and harbor breeze we would be delighted to host you

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Popular amenities for Deer Island vacation rentals

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Pool

Free parking on premises

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Other great vacation rentals in Deer Island

Guest favorite

A modern kitchen is showcased with sleek white cabinetry and a spacious layout. Stainless steel appliances include an oven and refrigerator, complemented by a built-in microwave. A clean white backsplash adds brightness to the area, while warm wood flooring completes the inviting atmosphere.

Private room in Boston

4.93 out of 5 average rating, 15 reviews

Modern Home - w/ Comfort Amenities

AlexandriaRating, 5 stars2 weeks ago

this is a wonderful place to stay and Alix is such a great host! can't wait to stay here again :)

Top guest favorite

A clean, modern bathroom features a shower-tub combination with a minimalist design. Wall-mounted shelves hold toiletries for easy access. Natural light filters through a small window, illuminating the white subway tile walls and enhancing the space's brightness.

Private room in Lynn

5 out of 5 average rating, 15 reviews

Cozy Private Room

ErinRating, 5 stars1 day ago

I loved staying here. Phuong is kind and welcoming, and her dog is a great co-host. Bed is very comfortable and room darkening shades were available. Would definitely stay here again.

A multi-story house with a red trim stands under a clear blue sky. The symmetrical façade features large front windows and a prominent entrance with steps leading to the door. Vehicles are parked nearby, and trees provide some shade in the foreground.

Private room in Boston

4.67 out of 5 average rating, 311 reviews

The Jazzy Airbnb

JinyoungRating, 5 stars3 weeks ago

I really enjoyed the stay. I stayed here to catch the transportation from the south station the next day. The room was clean and well maintained, although a bit old, although it was a bit difficult to move the suitcases as the room was located on the second floor. The neighborhood felt quiet and safe while walking 10 minutes from the metro station. The hosts are very friendly, responsive and do their best to help.