
Holiday rentals with outdoor seating in South Boston Waterfront
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Top-rated Holiday Houses with Outdoor Seating in South Boston Waterfront
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Holiday House Rentals with Outdoor Seating

Cozy Stylish 4br3ba 3mins to Somerville Subway
We really enjoyed this place. It gave us plenty of room to spread out. The absolute best part was also the location to the green line. So easy to get to and therefore we could easily get everywhere in the city. Would stay here again and recommend to others.

The Gatehouse, Cheerful 3 bedroom 3 bathroom house
We loved the house; very clean and modern. Great communication from the hosts and short distance to great local restaurants and family fun!

Family Friendly City Oasis! Free Parking, King Bed
Great property! Everything looks just as advertised and was extremely clean and welcoming. The location was also great - 5 min walk to the train station and very easy to get around. Fully exceeded all of our expectations!

Stone Cottage with meadow view
Lauren was an excellent host! Cottage is absolutely beautiful! Felt right at home , she was very responsive and very helpful. This place has all the amenities, perfectly located for everything we had planned .

The Nest | A peaceful retreat in the city
Pema and Jonathan are wonderful hosts. This was our second stay at The Nest and we were able to really take advantage of the deck overlooking their beautiful garden and the city beyond, for morning coffee and afternoon snacks. Their place is very spacious and charming. It's walking distance to stores, restaurants and the Gilman Square T-stop. For trips further afield, it's great to have a designated, off-street parking spot right by the entrance to the unit, with motion sensor lights for nighttime arrivals. The kitchen is fully equipped and the bed is very comfortable, with reading lights on both sides of the bed. Highly recommend.

City Oasis |Yard |Walk To Harvard MIT Train
I had an amazing stay at Juan Carlos’s place. He responded immediately and was very helpful whenever I needed anything. The kitchen is brand new and fully equipped with all the utilities you could possibly need. The apartment is located in a quiet, nice neighborhood and everything was spotlessly clean. It’s within walking distance to Harvard Business School and probably also to MIT. There’s also a Whole Foods just a 5-minute walk away. The place was easy to access, very comfortable, and felt safe at all times. Juan Carlos is a super friendly host. I had a late flight and he kindly let me check out an hour later without any problem. I’d definitely recommend this place and would be happy to stay here again!

Tribeca chic | 2 BR w/private patio
Beautiful home. Perfect for a couple days in Boston. The home had everything we needed. Hosts always responded quickly to questions. Easy walk to local transportation.

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free
Great place to stay! very welcoming. The place was clean and had everything I needed. It reminded me of my own home! Nathan was very responsive. The only problem was the banging noises with kids jumping around a lot on the second floor. It becomes unbearable more so during my work from home (remote) days. Even during some late nights, you can still hear them. I completely understand as I also have a 6 y/o.. But, Nathan was very responsive when I reached out to him. Otherwise, I would definitely go there anytime!
Apartment rentals with outdoor seating

Couples Retreat - Apt in Charming Colonial Home
This was without a doubt the best Airbnb I've ever stayed in (and I've stayed in a lot). The host Lisa was very communicative. The Airbnb was the most well stocked Airbnb I've ever seen: Full pantry of snacks, a well-stocked kitchen cabinet with every appliance you can think of, and even a full basket of toiletries just in case you forgot something. The apartment was tastefully decorated and the furniture high quality. The bathroom was simply stunning, with a bathtub complete with bath salts, and an electronic shower with jets on the walls too! The bed was comfortable and I had no issues sleeping. The neighborhood around the house is very peaceful and walkable. However, be warned that it is not well connected to Boston via public transit compared to other locations. I would recommend this place to someone with access to a car. Nevertheless, this was the best Airbnb I've ever stayed in. Highly recommended for a nice getaway!

Winter Island Retreat
Look no more! Winter Island Retreat is a seaside oasis that creates an atmosphere of tranquility and peace. From the moment I arrived I was struck by it's beauty captivated by the stunning sunrises to start each day The retreat is charming and a place of solace. The beautifully manicured lawn and gardens filled with lush floral designs adds to its magic. while the front porch with its rocking chairs, invite you to slow down and savor your morning coffee or lose yourself in a good book. Evenings are equally special walking the path to the beach and settling into the adriondack chair with a glass of wine It's a peaceful ritual that grounds you in gratitude. The home itself is cozy, comfortable and thoughtfully decorated with calming beachy touches that make you feel at ease. It's perfectly located just minutes from downtown Salem. I'm grateful to be one of the lucky guests to stay in David's home. He was a kind and gracious host. A truly memorable retreat I will be back

-Traditional 3 BR/2 Bath/Prkng By Arprt/Bos
Great place to stay. Very clean. Lots of restaurants within walking distance. The coffee shop/bakery directly across the street is enough to come back for.

Spacious, private apartment in perfect location
As mentioned in other reviews, this place was truly amazing! While other accommodations in Boston were quite expensive, this one was much more affordable without compromising on quality. There were many places within walking distance, which made it easy to enjoy shopping and great food. The neighborhood was quiet and peaceful, making it a perfect environment for studying. If I ever come back to Boston, I’d definitely stay here again. Highly recommend it!

Harvard/MIT/BU Riverside Studio w/parking
Great spot in an awesome location! Very clean and easy check in/out. Close to restaurants and a quick drive to museums/galleries. Would definitely book again.

Charming South-End condo with large outdoor patio
This is a really nice AirBnB close to museums and within walking distance of fun shopping and eating areas. It was spotlessly clean, and Mike communicated clearly and was very responsive. There was a plethora of reading material, including some books in German and vintage children's books such as The Chocolate Touch. The Farmer's Horse is a great nearby place to nab a breakfast burrito or bagel. We would definitely stay here again!

Charming 1 BR private entrance apt commuters dream
Domingo was a fantastic host. I had a couple of requests and Domingo was extremely responsive and was always accessible. He also provided some excellent restaurant suggestions. As far as the location itself, it's in a nice quiet neighborhood but there's not really much around within walking distance. A car or an Uber is a must to get to some of the great restaurants that Domingo suggested. Other than that, it's a great place with a fantastic host. Since this was a work trip for me, I would definitely consider staying here again. Thank you Domingo!

Short Train 2 Boston, Luxury prvt unit w parking
Chris made us feel right at home. The place looks brand new. I’m pretty sure I was the first to use the coffee maker. All the amenities were great and made it easy to cook and clean. Parking place was great and bed was great. Pull out sofa was comfortable for sleeping too. There are so many restaurants (especially Asian) within a 10 minute walk and the Wollaston T stop is 5 minutes away making a 25 minute ride into Boston painless. Our stay was a pleasure! Thanks Chris.
Condo rentals with outdoor seating

Condo in downtown Boston
This was such a charming place in a wonderful location. Griffin and Carolyn were responsive and took really good care of us. They are great hosts who we highly recommend and would book with again!

Family Home + Near Downtown + Cool Backyard!
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA
Reda was so wonderful with us!! Extremely communicative and friendly, the apartment is exactly like the pictures and so much better in person. My family & I had a great time in Boston but the apartment was definitely a big highlight. I recommend this place 10/10🩵

Spacious Dorchester Retreat | 2-bdrm condo
We very much liked staying there. It is a nice neighborhood and very close to South Bay shopping mall with many restaurants and easy and convenient shopping. It is also very close to all major attractions in Boston but much quieter environment. Our host, Marian was extremely helpful, proactive and super responsive, the best we have had so far in our trips. I strongly recommend this place to families.

Spacious, cozy home near Boston!
What a gem!! Ana's appartement is amazing. The bedrooms are large with good mattresses and furniture. Kitchen is great too. There is a nice patio to sit on at the back. Ana's house is extrememy clean, cosy and very well maintained, we will definitely stay here again when we visit Boston!

Samuel Tucker House - Downtown Luxury 2 Bed Condo
Lovely trip back to Marblehead for my granddaughter’s graduation. This home was comfortable and great care taken to provide more than the basics making it welcoming and like home!

Luxury Condo in Boston w/ backyard & parking
Had a nice weekend visiting our son in Boston with his sisters. We spent less time in the Airbnb than we had expected (never got to check out the local beach but also it was a colder weekend than we'd hoped for anyway) but the kitchen was pristine, beds were comfy, shower and bathroom was well stocked and it was nice to know that there were extra chairs and towels if we had needed them. Thanks for hosting!

3BR Salem Home: Parking, Terrace, Walk to Downtown
Very comfortable place with deck where our dogs could be outside with us while we enjoyed the weather and a glass of wine. Kitchen well-equipped with everything we needed to cook and enjoy ourselves. The nespresso machine was wonderful. Also, Starbucks was just a short walk. The in-unit laundry was very convenient. The college was also a short walk where our pups could enjoy some green space. There is a park by the beach which is also a short walk, it was a little harder to get there because one must cross a busy street but, well worth it, once you got there. Downtown was a bit of a hike but, again well worth it once you were there and you did not have to worry about parking. We really enjoyed our stay and highly recommended this condo.
Quick stats about holiday rentals with outdoor seating in South Boston Waterfront
Total rentals
30 properties
Nightly prices starting at
$93 AUD before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
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- Hampton Beach
- Boston Common
- Fenway Park
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- TD Garden
- Harvard University
- Lynn Beach
- Brown University
- Duxbury Beach
- North Hampton Beach
- New England Aquarium
- Sagamore Beach
- Faneuil Hall Marketplace
- Freedom Trail
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- Sandwich Glass Museum
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- Prudential Center
- Roger Williams Park Zoo
- MIT Museum
- Rye North Beach
- Museum of Fine Arts, Boston
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