House vacation rentals in South Shore

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Popular amenities for South Shore house rentals

House rentals with a pool

Superhost
A spacious bedroom features large glass sliding doors that provide access to a private deck. The room includes a comfortable bed with light bedding, two bedside lamps, and a desk positioned beside a window, allowing natural light to illuminate the space.
Home in Mashpee
5 out of 5 average rating, 7 reviews

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

MadisonRating, 5 stars6 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 favorite
The charming exterior of the newly renovated home is highlighted by a sloping roof and a welcoming front door. Framing the entrance are neatly trimmed bushes and a small pathway leading to the door. A garage is located on the side, complemented by grassy green surroundings.
Home in Falmouth
5 out of 5 average rating, 15 reviews

Home in Falmouth ~ 5 min drive to beach

AnnieRating, 5 stars8 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 favorite
An outdoor deck is visible, featuring a wooden table surrounded by blue cushioned chairs. The light-colored house exterior is complemented by a finished roofline and large glass doors, allowing natural light to brighten the space. Trees provide a natural backdrop.
Home in Mashpee
5 out of 5 average rating, 12 reviews

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

CarolRating, 5 stars1 week 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.
Guest favorite
An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.
Home in Mashpee
5 out of 5 average rating, 18 reviews

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

BryanRating, 5 stars7 months ago
Michael is a great host with a phenomenal property. The house was clean, the amenities are great, the pool was warm (we were there at the end of September when highs were in the mid-60s), kitchen is well equipped, and the location is great. We were a group of 3 families - 6 adults and 5 kids - and the layout of the house is perfect for multiple families. Each floor has its own main bedroom, it's own bathroom, plus ample extra space for a crib, pack n play, mattress, etc. We couldn't have asked for a better setup. Unfortunately for our stay the weather didn't cooperate with nearly non-stop rain, but we still had fun in the house (great spaces for movie watching, games, and ping pong), at the nearby children's museum, the beach, and Mashpee commons. We'll be back for sure!!
Top guest favorite
Home in Oak Bluffs
4.94 out of 5 average rating, 194 reviews

Spectacular beach & pool combo; beautiful sunsets!

JillRating, 5 stars3 weeks ago
The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!
Superhost
Home in Falmouth
5 out of 5 average rating, 3 reviews

Spacious home with Pool! Close to Beaches & Town!

michaelRating, 5 stars8 months ago
it is a nice comfy house esp for a family. Swimming pool and game room down in the basement would be alot of fun for kids to keep them busy at day time and night time. Beach, restaurants, grocery stores, liquor stores, etc are all right there esp. only like less than 5 to 15 minutes drive and also less than 25 minutes drive to go to north Falmouth or Wood Hole. They have a nice downtown with many stores, restaurants, bowling ally, etc which that is only less than 15 minutes drive from the house Also taking a walk from the house to the beach is so beautiful esp morning time. i walked every morning, and love every bit of the walk. It rained once during our vacation week and rest were sunny days for the rest of the week. We were lucky to have the good weather. Anyway, the house is approximately about less than a mile and half from the beach. Driving to Chetham is about little a hour drive from the house. To Provincetown, about 1 hour and 45 minutes drive.
Top guest favorite
A spacious backyard is highlighted by a private, unheated in-ground pool surrounded by paved areas. Colorful lounge chairs and an inflatable float add to the inviting atmosphere. A patio table with patterned cushions is positioned nearby, offering a space for relaxation and outdoor dining.
Home in Barnstable
4.95 out of 5 average rating, 113 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

CamilleRating, 5 stars7 months ago
There should be more than 5 stars for this lovely property and its hosts!!! We were three couples vacationing for the first time on the Cape and this charming home was perfect for us. Conveniently located to serve as home base for many excursions we felt immediately at home. We each had our own themed bedroom with en suite bathroom and TV. All common areas including the sun porch and outdoor deck were fantastic places to gather and enjoy our time together. Our hosts were so pleasant and helpful throughout our stay. As only one example, on a rainy day the host proactively contacted us wth suggestions on things to do in the event of rain on the Cape. We so appreciated this thoughtful gesture and there were many more. When I think about it, this really sums up why we had such a wonderful time. Everything about this property speaks to how much these hosts care about their guests! Hope to return one day. Thank you!
Guest favorite
The image shows a spacious pool area surrounded by sun loungers. The inviting inground pool is complemented by a paved patio, featuring a vibrant array of floats. Lush greenery enriches the setting, while adjacent outbuildings provide additional outdoor space.
Home in Falmouth
5 out of 5 average rating, 16 reviews

Secluded Cape Cod home in Falmouth with pool

DanielleRating, 5 stars7 months ago
This house was perfect for our large group getaway. Lots of bedrooms and bathrooms and the detached pool house apartment was a nice option for those who wanted to be a bit more separate from the big group. The yard/pool was beautiful and Renaldo was extremely responsive to any questions we had. Would definitely stay here again!

Weekly house rentals

Top guest favorite
The exterior of a newly constructed home is presented, featuring a sloped roof and two skylights. A welcoming porch extends across the front, lined with decorative lighting. Green shrubs and a gravel driveway lead up to the entrance, surrounded by trees that enhance the private setting.
Home in Edgartown
4.96 out of 5 average rating, 68 reviews

Newly constructed home with AC , new furniture.

BillRating, 5 stars6 months ago
Again, we had a wonderful stay. The home was clean and has everything you need. Would definitely book again.
Superhost
A spacious living area is highlighted by a large blue sectional sofa, complemented by several accent pillows. Large glass doors provide a view of the deck, while pendant lights hang from a vaulted wooden ceiling, enriching the open atmosphere.
Home in Tisbury
4.69 out of 5 average rating, 159 reviews

Carolyn's Vineyard Haven

ZackRating, 5 stars4 days ago
Highlights: Outdoor shower, fancy living room TV for movies, stocked kitchen, and more! :)
Guest favorite
A serene bedroom space features a blue quilted bedspread and vibrant accent pillows. Above, decorative sailboat models are displayed against a light wall. Natural light streams in through a window, illuminating wooden furniture, including a dresser and built-in closet doors.
Home in Nantucket
4.86 out of 5 average rating, 22 reviews

Beautiful Custom Nantucket Home

RobertRating, 5 stars1 month ago
Perfect Madaket location in a great neighborhood of year around residents. The beach is a 10-minute walk through amazingly beautiful conservation land. Our dogs loved every minute. The house is clean, well-appointed and equipped with all of the amenities you need for a Nantucket holiday. Adam is a top notch communicative host who goes out of his way to ensure your stay is special. We will be returning to the Pineapple House.
Guest favorite
A two-story cape cod home is showcased, featuring a light-colored exterior with blue shutters. A well-maintained driveway leads to a covered entryway, and a lush green lawn surrounds the property. Mature trees provide shade, enhancing the welcoming outdoor space.
Home in Falmouth
4.84 out of 5 average rating, 74 reviews

Expansive & Renovated Teaticket Cape

AnnieRating, 5 stars3 weeks ago
Great house for a larger group. It has all the amenities and lots of beds. Very close to the ocean and Brien was easy to communicate with. Thank you for having us at your home!
Guest favorite
A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.
Home in Oak Bluffs
4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

LaurenRating, 5 stars6 months ago
We stayed at Lisa’s place for three nights and it was a 10/10 experience. Lisa was a fantastic host and was very helpful with island recommendations prior to our trip. The property itself is stunning and although we wanted to explore the island, the property also provided a beautiful landscape to just relax. Even given its private, peaceful location, it was still so convenient to town. The house is an adorable converted barn that has incredible, rustic charm and the decor was so beautifully thought out. Before we even left we were talking about booking again in the future. We definitely recommend booking here!
Guest favorite
The exterior of a two-story house features natural shingle siding and a welcoming front porch. Lush hydrangeas line the walkway, providing a vibrant green and white contrast against the home. Multiple large windows invite natural light into the living spaces.
Home in Tisbury
4.86 out of 5 average rating, 69 reviews

Your home away from home

CristinaRating, 5 stars8 months ago
Patricia was very responsive before and during our stay. She was easy to communicate with and gave great suggestions for beaches to visit. The house is about a 10 minute drive from the closest beach. It’s near water but it’s more for fishing or boating. It’s less than 10 minutes from the center of town where there are great places to eat and shop around. The house is beautiful and spacious. Two bedrooms and a full bathroom on the main level and 2 bedrooms and a full bathroom the second level. Highly recommend.
Guest favorite
The open living space features comfortable leather seating, a coffee table, and decorative pillows. A ceiling fan provides airflow, while natural light enters through large windows. The kitchen and dining area are visible in the background, showcasing a well-equipped space with modern appliances.
Home in Falmouth
4.93 out of 5 average rating, 122 reviews

Cute Single Family Home in Nice Neighborhood

NicoleRating, 5 stars6 months ago
This little beach oasis is such a great value! We thoroughly enjoyed our stay here. As mentioned in the description, Patty & Bruce's spot is legitimately only a few minute walk from multiple beaches and is in such a cute little neighborhood! They have plenty of beach items should you not bring your own, which is great. The space itself is perfect for a quick little weekend getaway.
Superhost
A farmers porch is complemented by two wooden chairs adorned with cushions, positioned beside a small table. Colorful hydrangeas bloom in the foreground, enhancing the peaceful outdoor setting against a backdrop of a rustic wooden façade.
Home in West Tisbury
4.78 out of 5 average rating, 67 reviews

Beautiful Quiet Country Cottage

DevoraRating, 5 stars7 months ago
This is a lovely tiny cottage In the woods. it has everything you might need: a lovely front porch. A perfect kitchen, outside tables, and a clean comfortable. place to stay with a big tv. A great place I would highly recommend!

Private house rentals

Guest favorite
A light-filled living area features a beige couch with a decorative pillow, facing a wooden coffee table set with a chessboard. A soft rug lies underneath, while a kitchen with gray cabinetry and bar stools is visible in the background. A staircase leads to the upper level.
Home in Oak Bluffs
5 out of 5 average rating, 25 reviews

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

JayneRating, 5 stars1 week ago
The home was clean and cozy. Updated decor and well supplied with everything we would need. I would stay again.
Top guest favorite
A charming entryway is framed by a white picket fence and an inviting porch. A stone pathway leads to the house, with a wooden bench positioned on one side. Small American flags are placed near the pathway, surrounded by lush greenery and colorful flowers.
Home in Tisbury
4.97 out of 5 average rating, 33 reviews

Classic MV House with Rare Private Beach Access

JuliaRating, 5 stars6 months ago
Absolutely loved Elisa’s house in Vineyard Haven. We went for my 30th birthday weekend with some friends and we legitimately could not have had a better time. The house is phenomenal and couldn’t be in a better location. The kitchen is modern, the rooms are spacious, the backyard is perfect for hanging out. The three season room was an awesome place to hang out. I have so so many nice things to say about this house and Elisa’s hospitality. I can’t wait to come back & could not recommend more!
Top guest favorite
A spacious outdoor deck is surrounded by greenery and blooming flowers. A table with matching chairs occupies the center, complemented by an outdoor grill nearby. The soft colors of the area rug add warmth to the inviting space, perfect for gatherings.
Home in Falmouth
4.92 out of 5 average rating, 78 reviews

Private home with walkable freshwater beach access

MatthewRating, 5 stars7 months ago
The house was as advertised. In a nice quiet area. The house was well set up and as advertised. We felt right at home for the weekend.
Guest favorite
The two-story house is framed by bare trees and a spacious lawn. A wraparound porch with white railings provides a welcoming entry. The adjacent garage features separate entrances, adding to the property's convenience and privacy.
Home in Edgartown
4.85 out of 5 average rating, 26 reviews

Classic Edgartown Stunner close to Town and Beach

MeganRating, 5 stars8 months ago
This house was amazing! Beautiful and very clean! Megan had timely responses to messages and was clear in her instructions regarding the check in process. The beds were comfortable. The outdoor shower was maybe our favorite part of the trip, all the ladies enjoyed being outside and also the coolness of the inside of the house. There was tons of room. The overall aesthetic of the house was a calm, beachy vibe and made you feel like you were right beside the water. I wish we had played horseshoes in the back yard! If we need a place to stay in the future for a group trip with the ladies I would try to book here if it was available!
Superhost
An open concept living area features high cathedral ceilings with natural wood finishes. A modern gray sofa with red and black accent pillows is positioned near a vibrant wall art piece. Doorways lead to a dining area and kitchen, enhancing the spacious layout.
Home in Mashpee
4.91 out of 5 average rating, 34 reviews

New Seabury home, private yard, great location

MikeRating, 5 stars6 months ago
Comfortable yet spacious home nestled in the woods of New Seabury. Great location to visit beaches and restaurants. Just minutes from Mashpee Commons and Falmouth for shopping and dining. Beautiful place, Thanks Alex!
Guest favorite
A serene garden setting features a stone pathway winding through lush greenery. A figure in traditional attire stands amidst the foliage, bordered by various plants and a bird feeder. The area is accented with gravel and stone elements, creating a tranquil atmosphere.
Home in Mashpee
4.83 out of 5 average rating, 109 reviews

New Seabury Retreat. Butchart Gardens' Inspired

ErinRating, 5 stars7 months ago
Vlad’s home was a wonderful place to stay with many people! Really appreciated all the decor and attention to detail. My friends and I stayed for a wedding, and we were so glad all communication was smooth. Would definitely stay again!
Top guest favorite
An open living area features a light-colored sofa adorned with blue and white cushions. A flat-screen TV is mounted above a white brick fireplace. Large windows provide natural light, and a dining area with a table and chairs is visible in the background.
Home in Oak Bluffs
4.96 out of 5 average rating, 93 reviews

**Vineyard Vacation Retreat** -3 BR

DianeRating, 5 stars7 months ago
We loved staying at Whitney’s house! It was the first time an Airbnb exceeded our expectations! The home was stocked with everything we needed and more. The home is so pretty and cozy and tucked into the neighborhood which was very private. It was about a mile from the Town center so we could easily ride a bike or drive to the beach and there’s so much to do in town. The beds were comfortable and there were plenty of extra pillows and blankets and towels. I have absolutely no complaints. We would definitely stay here again. :)
Top guest favorite
An inviting living room features a light-colored sofa and a natural wood coffee table. Artwork and plants add warmth, while natural light fills the space through ample windows. A large television is mounted on the wall, providing entertainment options for guests.
Home in Edgartown
5 out of 5 average rating, 18 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

DaniellaRating, 5 stars1 week ago
Genainna’s place was great! It was very big so my group was comfortable with the beds available, there were many amenities and detailes like extra toothbrushes or other things that I thought were great! It is a beautiful home

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