House holiday rentals in South Shore

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Popular amenities for house rentals in South Shore

House rentals with a pool

Superhost
Home in Mashpee
5 out of 5 average rating, 7 reviews

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

MadisonRating, 5 stars8 months ago
Prescott’s house is such a relaxing place to stay with a big group. The house has a very pretty view and is very clean and peaceful. We are very grateful for such a nice stay at this beautiful house. The BBQ outside didn’t work great but other than that we had a wonderful time! Thank you Prescott.
Guest favourite
Home in Falmouth
5 out of 5 average rating, 15 reviews

Home in Falmouth ~ 5 min drive to beach

AnnieRating, 5 stars10 months ago
This rental is exactly as described with accurate pictures. It was recently renovated with all new furnishings, new kitchen, appliances and baths. Our family enjoyed the brand new outdoor deck, picnic tables, gas grill, swing and s’mores by the fire pit. Unfortunately it was too chilly to use the pool. The kitchen had all supplies to make a large pasta meal. Our daughter ran the Falmouth Road race and so Sunday was a bit chaotic and the owner gave us flexibility to check out a bit later, which was a huge help!!. A wonderful family vacation!! Highly recommend.
Guest favourite
Home in Mashpee
5 out of 5 average rating, 13 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

CarolRating, 5 stars2 months ago
We loved are family stay at Paul & Katie’s home for Easter Week. It is a dream home . The neighborhood was beautiful and walkable, with a peaceful path to a private beach. We enjoyed the shops and restaurants in Mashpee Commons about an 8 minute drive away.
Superhost
Home in Falmouth
4.83 out of 5 average rating, 6 reviews

Charming Home-Pool, Game Room, walk to quiet beach

TedRating, 5 stars11 months ago
We had a wonderful time at this home. The pool was clean and warm; we used it every day. The house was well stocked- dishes, spices, utensils, pots and pans… and plenty of chairs out by the pool for outdoor meals. The neighborhood was quiet and safe to take nice morning walks down to the little beach 1/4 miles away. Great quality seafood at Falmouth Fish Market, and many grocery/household store options less than 2 miles from the house. We paid extra for the linens; good choice for us since we had a full house.
Guest favourite
Home in Mashpee
5 out of 5 average rating, 21 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

DonnaRating, 5 stars3 days ago
This place worked out wonderfully for the 6 adults and 3 grandchildren we had with us, my 4 year old granddaughter even got her own room and loved it, along with the pool!! It was very clean and family friendly and stocked with more than we expected. There is also food and shops within walking distance. We enjoyed it immensely!! Thank you Michael, you have a wonderful place!!
Guest favourite
Home in Falmouth
5 out of 5 average rating, 8 reviews

Sunny Loft - Seasonal Pool & Beach access

JoannaRating, 5 stars10 months ago
Kerry was an amazing host. Very kind, very helpful, and very communicative. The house itself was very cute and had the best stocked kitchen I've ever seen. The outdoor shower was also a huge hit. The house was super close to the community beach and the community pool, which were both a ton of fun. The house was also close to some other things we did on our week vacation, like sailing on the Liberte, taking a ferry to Martha's Vineyard, and checking out some other town beaches. The house was a little tight for the 5 of us (2 adults and 3 kids)...while there were plenty of places to sleep, there were only 4 chairs at the kitchen table and the outdoor table. The house was also right off the main road, which made it convenient, but I think we would have preferred to be a little more secluded. But all in all, positives definitely outweigh the negatives.
Top guest favourite
Home in Oak Bluffs
4.93 out of 5 average rating, 199 reviews

Spectacular beach & pool combo; beautiful sunsets!

RobynRating, 5 stars1 week ago
Resort vibes with a chef's kitchen and stunning views! ***** Our stay at Larry's house was fantastic! The kitchen was absolutely amazing - spacious, modern, and fully equipped with everything we needed. We enjoyed cooking and gathering there. The real highlight was the outdoor space. The view was breathtaking! The pool and hot tub made it feel like we were staying in a private resort. Michael was helpful and responsive, making everything easy from check in to check out. We would love to come back.
Guest favourite
Home in Falmouth
4.95 out of 5 average rating, 39 reviews

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court

SydneyRating, 5 stars1 week ago
Emily was so kind and responsive and the house was exactly as expected. The walk to the beach was lovely and doable with the toddlers thanks to the wagon provided. It was a quick drive into all things Falmouth and a great home base for us. The stand outs for everyone were how comfy the beds were and we were all obsessed with the outdoor shower. Loved all the thoughtful amenities, such as games and kids dinnerware. Overall very stylish and comfortable. Highly recommend.

Weekly house rentals

Guest favourite
Home in Nantucket
4.98 out of 5 average rating, 51 reviews

Duck Duck Goose - Renovated Historic 6BR Near Town

ElizabethRating, 5 stars2 weeks ago
We had an amazing stay at Duck Duck Goose for a bachelorette! The house was well decorated and looked exactly like the pictures; we were pleasantly surprised at how open the living/dining area was. We had one small issue and Cail arrived almost immediately to help. The location of the house was nice because you could walk to town, but it was pretty busy on the streets in front and behind, making it difficult to come and go and tough to pick up Ubers. Otherwise, everything about the house was perfect and would definitely stay again!
Guest favourite
Home in Nantucket
4.95 out of 5 average rating, 59 reviews

Charming Sconset cottage in Codfish Park

AlyssaRating, 5 stars4 weeks ago
Unfortunately I cant fairly judge Nantucket in general as the weather was absolutely awful the whole week (a May nor’easter!). But Janet did her best to make it better and we did enjoy her place. She was very responsive and attentive and even gave us a free night at the end to make up for the weather. Recommend! Thank you.
Top guest favourite
Home in Nantucket
4.98 out of 5 average rating, 52 reviews

Charter House Luxury Home 2 Blocks from Town

LindsayRating, 5 stars3 weeks ago
Our family of five absolutely fell in love with this gorgeous home. We all slept so well in the deluxe beds and made lots of memories playing games in the living rooms. The kitchen was well stocked and very fun to cook in. We loved using the grill, and the back patio is so picturesque. My kids loved using the house’s sound system. The house is EVEN BETTER in person than in the photos. We didn’t want to leave. The decor is very chic. The home should be featured in magazines!! The location is so convenient. The home is surrounded by homes from the 18th and 19th centuries- so cool!! We hope to return soon. Thank you!!
Guest favourite
Home in Nantucket
4.85 out of 5 average rating, 13 reviews

Romantic and Walkable to Town and Water, Queen Bed

AndrewRating, 5 stars12 months ago
Wonderful stay! While cozy, the unit is larger and even more beautiful than it appears in the pictures. There was a lovely spot beneath the stairs for a pack and play for our baby (that isn’t shown in pictures). The unit was spotless and felt extremely clean. Having access to a washer and dryer was extremely helpful given the beach trips and having a baby. The best part was how walkable the apartment was from town. If you are new to the area it is absolutely worth spending extra (although Kate’s prices are quite reasonable!) to be a walkable distance from town. She had comfortable beach chairs, a cooler, and umbrella available as well as beach towels. Kate was a fantastic host, responsive, and wonderful with our young daughter. We would 100% stay again!
Top guest favourite
Home in Nantucket
5 out of 5 average rating, 37 reviews

In-Town, Historic District, Nantucket Home + Yard

JocelynRating, 5 stars2 weeks ago
Jill’s house was the perfect home base for our family vacation. The house was spotless, toddler-friendly, and ideally located. Jill was incredibly responsive to all my questions and provided clear, easy-to-follow check-in and check-out instructions. We’d definitely stay here again!
Guest favourite
Home in Edgartown
5 out of 5 average rating, 24 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

LaurenRating, 5 stars2 weeks ago
We had a wonderful two week stay with our dog! The hosts were kind and responsive. Would definitely recommend this home, but we did have an issue with the front door during our trip. We had to exit through the sliding back door when leaving the house and could not lock the front door at night. Fortunately, it’s a safe and quiet neighborhood. I suspect this will be resolved for future guests!
Top guest favourite
Home in Falmouth
5 out of 5 average rating, 62 reviews

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed

JudithRating, 5 stars1 month ago
Beautifully remodeled home, lovely setting on a large pond. Everything was clean, the kitchen was well stocked. I am an avid cook/home chef and appreciate the decent cookware. So many places have understocked kitchens and wounded cookware. Comfortable King bed. Thoughtfully decorated. Nice quiet neighborhood. We travel with our 13 year old boxer who has traveled the country and we appreciated the one level living. We did not mind being farther from town, we love the wildlife and the beautiful swan swimming on the pond! The host, Benjamin, was easy to get ahold of, though we had no issues with anything at all. The booklet on Salt Crystal that was sent ahead to us was extremely helpful to us! We would definitely stay here again!
Guest favourite
Home in Nantucket
4.92 out of 5 average rating, 12 reviews

The Boucher Beachcoma

KristenRating, 5 stars9 months ago
We loved our stay at the Boucher Beachcoma!! The house was beautiful, everything looked brand new, very nicely decorated, clean and spacious. It was very well stocked and great amenities. Good location close to everything. Elise was extremely friendly, helpful, communicative and accommodating to work with through our time renting with her. Would absolutely stay here again!!

Private house rentals

Guest favourite
Home in Oak Bluffs
5 out of 5 average rating, 26 reviews

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course

JayneRating, 5 stars2 months ago
The home was clean and cozy. Updated decor and well supplied with everything we would need. I would stay again.
Guest favourite
Home in Edgartown
4.98 out of 5 average rating, 60 reviews

Walk to Town/Golf Club - Renovated Edgartown Home

EricRating, 5 stars3 days ago
The house was perfect for our week on the island. The location was nice and quiet, but conveniently located within a short walking distance of everything in downtown Edgartown. Our host Claire was kind enough to suggest recommendations on some favorite locations and activities around the island. The house had everything we needed for a family of 4 and a baby. And the outdoor shower was so relaxing.
Superhost
Home in Nantucket
4.72 out of 5 average rating, 46 reviews

Cozy house for 4, 5 min walk from beach

MeredithRating, 5 stars9 months ago
Loved staying in this house! It's a very charming older house with incredible vibes, just an easy jaunt to Jetties. We will absolutely be trying to stay here in the future.
Top guest favourite
Home in Woods Hole
5 out of 5 average rating, 63 reviews

Modern Marvel in Woods Hole - Walk to town & ferry

DoreenRating, 5 stars2 weeks ago
We traveled with 4 couples who have know each other since HS, 40 years ago. It was a great home to relax and catch up. The house is lovely and we loved that we each had our full bath! I highly recommend this home and this location.
Top guest favourite
Home in Nantucket
5 out of 5 average rating, 30 reviews

‘Sconset Charmer, steps to beach

DavidRating, 5 stars8 months ago
If you’re visiting Nantucket staying at Connor’s is a must do. Very charming and super close to the beach. Quite neighborhood which is a great escape from how busy downtown can be. Nothing beats listening to the waves as you fall asleep instead of a sound machine.
Superhost
Home in Nantucket
4.78 out of 5 average rating, 23 reviews

Nantucket Cottage Getaway

JeffreyRating, 5 stars11 months ago
Our stay at 260 Madaket Road was perfect. The house was walking distance to the shuttle to town. Short distance from the beach and the beautiful Nantucket sunsets. Michael was very responsive with our questions and was a great host. Would look to stay again next summer.
Top guest favourite
Home in Edgartown
5 out of 5 average rating, 53 reviews

Walk to town - Beautiful, quiet Edgartown home

JessicaRating, 5 stars3 days ago
We loved our stay! The house was beautiful, immaculate, spacious, and well-stocked. The location was perfect, we walked into Edgartown every day, and rented bikes to get to the beach. Amy was super responsive and the house manual she provided in advance had all of the info we needed. The only downside was construction on a neighboring house— the work was noisy and a little disruptive, and large construction vehicles sometimes blocked the road getting into and out of the house. No fault of Amy’s, though, and hopefully the work will be done soon!
Guest favourite
Home in Oak Bluffs
5 out of 5 average rating, 22 reviews

#CozyBluffs #OakBluffs Walk to Beach/Town/Ferries

CaraRating, 5 stars8 months ago
Fran and Susan's house is even more beautiful in person than in the photos. The spotlessly clean interior is thoughtfully decorated with impeccable style, and every amenity has been carefully considered to ensure a comfortable stay. It is within easy walking distance of downtown Oak Bluffs and the waterfront. Thanks to Fran for the exceptional communication and responsiveness. Cozy Bluffs made for a truly cozy escape!

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