
Holiday rentals with outdoor seating in South Boston Waterfront
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in South Boston Waterfront
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Popular amenities for South Boston Waterfront outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Beverly Beach House- Upper Deck
We stayed here for a week, and fell in love with it! The house has so much charm and character. We thoroughly enjoyed our stay, and want to stay there again. It was within walking distance to many places, including a beach. A definite charm in Beverly! The host was amazing! She was very responsive to our questions, and checked in a few times to see if we needed anything, which I appreciated. You are missing out if you don’t stay here!

the house of id; vintage shop, accessible space
UNBRIDLED JOY. Dara and Paige's house is welcoming right away, with a comfortable open living, dining, and kitchen area filled with fun, bright decor. The house radiates joy and fun and comfort. My friend and I took a last-minute getaway here, and it was exactly what we needed. The colors are both cheerful and calm, and the place is furnished for relaxing cozily. We had a blast shopping the items in the house, which is a wonderful unique twist. Everything was exactly as described and better. Communication was SUPERB. You couldn't ask for two kinder or more caring hosts. We especially appreciated the attention to accessibility since I have some mobility issues. We can't wait to go back again. Everything about this house raises our spirits and makes us laugh out loud with delight. We loved every moment and are already looking forward to our next stay. THANK YOU!!!!!

Charming Home in Reading with a Large Yard
We thoroughly enjoyed our stay. The location was wonderful and the hosts were extremely easy to work with

Stone Cottage with meadow view
Loved the spotless antique home lovingly restored. It is a unique stone cottage in the neighborhood. The back of the house overlooks wetlands, so great views from the back of the house. The main bedroom has a very soft mattress, which we know our adult children would have loved, and since we prefer a firmer bed, we were able to move to the second bedroom after a few nights. We were visiting our 2 year old grandson and we spent most of our time at his parent's home but cooked at the stone cottage, which had all that we needed, and brought it to their house. The outdoor space of steep grades to the wetlands and inside space of steep stairs would be challenging for toddlers. but it was fine for us. We were so appreciative of Lauren's flexibility with both our arrival and departure; it made a big difference to us. Thank you, Lauren.

Residential home ▪ Billerica ▪ quiet, clean & cozy
We will definitely be visiting our family again and now are thrilled to know we have a wonderful Airbnb to stay at while visiting. It has all the amenities you might need and more, as well as entertainment, such as games, TV, and children’s outdoor and indoor activities. We will be back to visit before long. This will be our home away from home. Thank you Barry!

City Oasis |Yard |Walk To Harvard MIT Train
Sweet and clean place with a luxurious bed and everything you need.

LargeDuplex10Beds w/prkg near Downton
Fatima's place was welcoming, clean, and well-equipped. She was extremely accommodating and helpful. I enjoyed the amount of space we had for a large group. The transit nearby was down but they still had busses to accommodate. Definitely an amazing value for what we paid. I'd definitely recommend it for a bachelor party or any large group outing. We couldn't have had a better time!

2BR—Charming 1900s Home—1st Floor—25min to Boston
Amazing price and amazing place to spend Halloween! Great places to eat and adventure around! The house was peaceful but had very friendly atmosphere with the neighbors. If I could have Andrea be the host for every air bnb I would be greatful knowing I have someone that's reliable and great with communication. She will treat you right and has great recommendations!
Apartment rentals with outdoor seating

Stunning Union Square 2 bed/2 bath w/ shared patio
Absolutely beautiful place!! It has one of the best equipped kitchens, including nice plates, mugs and even wine glasses. It was perfect for my colleague and I’ve for the business trip. Two beautiful bedrooms either individual bathrooms, and the living room was great for having a few casual meetings. The unit next to us has small kids, so it can get pretty noisy early in the morning. For us it didn’t matter since we have to head out early anyway, but if you want to sleep in, it can be a challenge. Highly recommend! Will book again in the future.

Two bedroom Apt with a deck
Rhona’s place was in a great location with places nearby and not too far from all of the places we wanted to go. Her home was as described in the pictures and description. For two people it was fairly comfortable, but we weren’t able to get very comfortable in the living room as furniture was too small for us to hang out. There was also no outlet in one of the bedroom, but we were able to find an extension cord that reached the other bedroom. Besides that, the place was great for us to come and go. The owner made our reservation special by providing a gift for my friend’a birthday and breakfast which was very thoughtful!

Newly Renovated Ocean View 2 Bdrm Apt
Our first trip to the Boston area couldn’t have been better! This Airbnb was absolutely perfect for our family of four. The bedroom I stayed in had its own balcony with a beautiful ocean view—ideal for peaceful summer mornings or warm, relaxing nights. The open-concept living room and kitchen gave us plenty of space to unwind after a day of exploring. But what really sets this place apart are two unbeatable features: first, you won’t find easier access to public transportation—there’s a bus stop just a 30-second walk away that takes you right into Boston. Second, the hosts, Milan and Anna, were some of the kindest and most helpful we’ve ever met. Their local tips made our stay even better. Great amenities, smartTV, updated shower, dishwasher, laundry, grill available to use, etc. Right next to the house is a beautiful walkway that stretches down the beachfront of Winthrop. We’re already talking about coming back as the Boston area is second to none!

Light-Filled Luxury Apartment with View
This was the best Airbnb experience I’ve ever had. Place was adorable and homey. Loved the decor and the little touches like area rugs and flowers. Even Kleenex in every room which believe me is rare. So many hosts don’t think of those little things but those things matter. If and when I visit Boston again, I hope his place is available!!

Oceanfront Pool. Close to Boston. Free Parking.
This was a perfect location for a long weekend getaway! Proximity to public transportation makes this place an awesome option for Boston travels, the ocean is absolutely gorgeous! I ran the Boston marathon on my visit and the hot tub was incredible for recovery! The bed is so comfortable and even though we didn’t cook anything, we easily could have! Having a washer and dryer in the unit available meant that I don’t have piles of laundry to do when I get home!

2 BDR/2b- walk to Seaport & BCEC
We stayed here while we were attending a conference at the convention center and it was a great location! The neighborhood felt safe and it was an easy walk to the conference and also to good local restaurants and coffee shops. The apartment was clean and comfortable with everything we needed. Thanks for a great stay!

Cambridge Retreat - Sunny 2BR - Close to Harvard
We had a wonderful stay at Shelley’s Cambridge Retreat! We were in town to visit our daughter, who is in college, and it was super special to have her over for a couple of home-cooked dinners and catch up in a relaxing, comfortable home setting. We didn’t have a car, but the location was perfect—we walked to Harvard Yard at least once a day and enjoyed exploring the neighborhood. La Saison Bakery became our go-to spot for morning coffee, and Whole Foods was conveniently nearby for quick shopping trips. We slept incredibly well, and the space was an ideal base for both working and spending quality time with our daughter. We loved the place so much that we’ve already booked it again for our next visit to Cambridge in October!

Executive Hotel Penthouse 1 Bedroom Residence
Beautiful home that looked as it's pictured. its close to major roads, dining etc and the owner was friendly and proactive with information. I would recommend this property if coming to the area.
Condo rentals with outdoor seating

Luxury 2 Bed, 2 Bath, Plus Loft, Modern Condo
Our family really enjoyed our long weekend at Donald’s place. The location is great, right in the middle of Marblehead, walkable to old town and the various shops and restaurants that dot the area— a great base for visiting friends and family on the north shore. We’ll definitely look to stay here again if available the next time we’re in the area.

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee
Dan’s apartment blew us away! Beautiful neighborhood and historic building with the wonderful smells of fresh flowers as we walked in. My 20 something daughter was ready to move in permanently ! We go to Boston often and plan to come back if it’s available. This place is popular with reason!

My Place - 2 Bedroom Condo with Parking
We loved everything about our stay!! The place was immaculate and just as pictured! Kelly was super responsive to all of my questions and went above and beyond!! The neighborhood was quiet and the neighbors extremely friendly! Easy to find! Driveway parking! Kitchen functionality was great to cook instead of eating out. Plenty is towels and linens! Beds were comfy and CLEAN! Could walk to downtown however we chose to drive and park! Already planning to stay here again next year! Thanks Kelly!!

Harbor Hideaway
Our stay was very comfortable in this warmth, clean, beautiful home with a comfy bed with all the amenities given. Kristen’s hospitality is amazing from her gestures and extra special touches of food, drinks and yummy snacks. Inviting home away from home with a raining season we enjoy staying in too. Thank You. Kenneth & April Phillips Ranch , California

Stunning South End 1BR - private roof deck
Great neighborhood, plenty of restaurants, walking distance to everything needed. Walked to Fenway for the Red Sox game. The apartment was nice and clean, easy to get in. Instructions were clear and concise. The rooftop is an added bonus!! Would stay again if I go to Boston.

Spacious 5BR Condo w/parking near METRO
We had a great stay again. I knew this house from then and didn't look at another place because they knew this was fine. In terms of house, host, communication and starting point for Boston.

New Super Modern 2 bed in Waltham
I stayed at Sue’s place with my two small children for 3 weeks. While I did bring my own crib because a pack n play isn’t an option for our toddler, the condo was very well supplied. In fact, I purchased and had an Instacart delivery upon arrival because I did not anticipate clothes detergent, shower toiletries, paper towels, etc. There is so much natural light, great parking, a nice porch, so close to the Charles River walk and Moody Street. We frequented Common Grounds cafe- highly recommend! The garbage disposal and sink backed up the day after we arrived and Sue had it fixed within 24 hours. Coming from a pretty rural area, I found the street noise and lights a bit problematic for sleep.

Large 1+bed in historic Charlestown, Boston!
We really enjoyed our stay and would certainly come back. The place was comfortable and had everything you need. The location was quiet and situated well to travel in and out of downtown. Jennifer was also a great host.
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
- Revere Beach
- TD Garden
- Fenway Park
- Lynn Beach
- Duxbury Beach
- Harvard University
- North Hampton Beach
- Brown University
- New England Aquarium
- Sandwich Glass Museum
- Faneuil Hall Marketplace
- Sagamore Beach
- Prudential Center
- Freedom Trail
- Onset Beach
- Roger Williams Park Zoo
- Oakland Beach
- Good Harbor Beach
- Crane Beach
- Symphony Hall
- Pinehills Golf Club
- Boston Public Library