Vacation rentals in Deer Island

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Top-rated vacation rentals in Deer Island

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Superhost

Private room in Boston

4.83 out of 5 average rating, 160 reviews

Comfortable Boston Bedroom 03

This beautiful Boston private bedroom is outfitted with a queen sized Casper mattress, Casper pillows, hypoallergenic bedding, free wifi and digital door lock. This space also has a shared kitchen, shared living room and shared bathroom with all the amenities needed to feel at home. NO PARTIES, NO EVENTS, NO DRUGS On the morning of your arrival the full check-in instructions will be sent, including all codes to make your self check-in process seamless. Our space is perfect if you want to be close to the heart of the City: Walk Score: 88 Logan Airport: driving: 15 mins | transit: 43 mins Downtown Boston: driving: 15 mins | transit: 30 mins South Bay Center (Movie theater, Nike Town, Target, plenty of shopping): driving: 5 mins | transit: 11 mins Dorchester Brewery: driving: 5 mins | transit: 11 mins Boston Children’s Hospital: driving: 15 mins | transit: 30 mins Brigham and Women’s Hospital: driving: 15 mins | transit: 30 mins Boston Medical Center: driving: 10 mins | transit: 25 mins Northeastern University: driving: 10 mins | transit: 22 mins Boston University: driving: 16 mins | transit: 43 mins Public Transportation (from apartment): SAVIN HILL STATION (red line): Driving: 0.8 miles | 1.3 km | 4 mins Walking: 0.7 miles | 1.13 km | 15 mins 125 Savin Hill Ave, Dorchester, MA 02124 UPHAMS CORNER STATION (Franklin Line/Foxboro): Driving: 0.6 miles | 0.97 km | 3 mins Walking: 0.6 miles | 0.97 km | 13 mins 691 Dudley St, Dorchester, MA 02125 BUS STOP: BUS #15: stops right down the street and northbound takes you to Ruggles Stations (orange line) or southbound takes you to Fields Corner Station (red line). BUS #17: stops right down the street and northbound takes you to Andrew Station (red line) or southbound takes you to Fields Corner Station (red line). Public Transportation (from apartment): SAVIN HILL STATION (red line): Driving: 0.8 miles | 1.3 km | 4 mins Walking: 0.7 miles | 1.13 km | 15 mins 125 Savin Hill Ave, Dorchester, MA 02124 UPHAMS CORNER STATION (Franklin Line/Foxboro): Driving: 0.6 miles | 0.97 km | 3 mins Walking: 0.6 miles | 0.97 km | 13 mins 691 Dudley St, Dorchester, MA 02125 BUS STOP: BUS #15: stops right down the street and northbound takes you to Ruggles Stations (orange line) or southbound takes you to Fields Corner Station (red line). BUS #17: stops right down the street and northbound takes you to Andrew Station (red line) or southbound takes you to Fields Corner Station (red line).

Superhost

The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.

Condo in Winthrop

4.99 out of 5 average rating, 78 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).

Superhost

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, 1,327 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.

A spacious living area is designed with large windows providing expansive views of the ocean. A comfortable white sofa faces a wooden coffee table, complemented by a cozy throw. Natural light fills the room, accentuating the warm wooden floors and tasteful decor.

Home in Nahant

5 out of 5 average rating, 7 reviews

Sea Forever - Oceanfront Home in Nahant!

Experience oceanfront luxury in this stunning 3 bed, 3 bath Nahant home with breathtaking water views on every level. Spanning three beautifully designed floors, this upscale retreat features high-end finishes, open-concept living, and plenty of space to relax. Overlooking the bay and Short Beach, you're just a short stroll from both Short and Long Beach and near top-rated local restaurants, A rare coastal gem offering comfort, elegance, and unbeatable location—your dream seaside escape awaits.

Superhost

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, 198 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.

Superhost

A modern living area features a gray sofa with colorful throw pillows, positioned on a geometric patterned rug. A round blue ottoman complements the seating. Natural light floods through large windows, illuminating a kitchen area with white cabinetry and stainless steel appliances.

Apartment in Winthrop

4.9 out of 5 average rating, 84 reviews

Vibrant Winthrop Apartment - Close to Ocean!

Whether you're traveling for work or leisure, this modern Winthrop apartment is a gem! The 1-bed, 1-bath vacation rental has everything needed for a stress-free stay, like a fully equipped kitchen, WiFi, and a workspace for those clocking in remotely. Downtown Boston is easily accessible with multiple transportation options nearby, so spend time at the New England Aquarium or catch a ball game at Fenway Park. Plus, breathe in the ocean breeze and take advantage of the proximity to the beach.

Superhost

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, 475 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.

Superhost

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, 960 reviews

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with 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.

Superhost

The kitchen features a vibrant blue base cabinet beneath a polished countertop, equipped with modern appliances including a washing machine, stove, and refrigerator. Minimalist decor is present, with utensils displayed above and ample natural light illuminating the space.

Home in Hull

5 out of 5 average rating, 18 reviews

Cozy by the coast! Long Term deals!

The Hideaway is a private, family-owned beach bungalow in Hull, MA, between Nantasket and Gunrock beaches. Ideal for solo retreats, couples, small families, remote workers, commuters or best-friend adventures. The Hideaway experience is a unique blend of natural beauty, creative spirit and relaxation. Enjoy nearby beaches, paddle boarding, trails, fresh seafood, and local gems. Convenient access to ferries and trains makes commuting and city adventures just beyond nature simple.

Superhost

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, 41 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.

Superhost

A serene view of the ocean horizon is captured during twilight, showcasing soft gradients of color from orange to blue in the sky. The coastline is visible with a curve of land meeting the calm waters, surrounded by lush greenery and a few architectural structures.

Apartment in Hull

5 out of 5 average rating, 68 reviews

Cozy Coastal Apt w/ Ocean View Patio & Fireplace

Escape to the charming and historic town of Hull! This ocean-facing studio is the epitome of relaxation: a plush king bed, private patio, fireplace, huge TV, and a spacious bath. Enjoy complete privacy and convenience featuring free parking, walking distance to Nantasket Beach, local restaurants, and shops within a short drive (or ferry!) to Boston. Don't miss your chance to soak up the gorgeous weather in one of the most unique and picturesque properties on the MA coast!

Superhost

Private room in Boston

4.87 out of 5 average rating, 835 reviews

Spacious, Modern & Comfy East Boston Hidden Gem

Welcome to Boston! This bright, modern private room is perfect for solo travelers or couples. Located in East Boston, you’re just 5 minutes from Logan Airport and 2 subway stops to Downtown, the North End, Seaport, and more. Enjoy a comfy bed, fast Wi-Fi, and a secure room with key access. Thoughtfully designed shared spaces include a fully equipped kitchen. Walk to parks and cafes, a. We look forward to hosting you!