South Dennis Vacation Rentals

Compare 7 vacation rentals.
USA > Massachusetts > South Dennis

Make South Dennis your next getaway

Discover the charm of South Dennis vacation rentals, where New England's coastal beauty meets a quaint village atmosphere. If you’re looking to experience the magic of Cape Cod, you’ve found the perfect home base for exploring. Between fresh seafood, stunning beaches, and family-friendly activities, you’ll find something new to love on your next trip to Massachusetts.

Explore South Dennis house rentals, and more

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House rentals

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Popular amenities for South Dennis vacation rentals

Popular
Dog-friendly Hot tub Internet
Miles Away
3 Bedroom | 2 Bath | Sleeps 6

Miles Away - South Dennis, MA

$365 avg / night
(excludes fees and taxes)
Villa Fairview
2 Bedroom | 1 Bath | Sleeps 6

Villa Fairview - South Dennis, MA

$230 avg / night
(excludes fees and taxes)
4.25 (12)
The White Pillars
7 Bedroom | 5.5 Bath | Sleeps 12

The White Pillars - South Dennis, MA

$810 avg / night
(excludes fees and taxes)
5.0 (1)
Skylight Tonight
3 Bedroom | 2 Bath | Sleeps 8

Skylight Tonight - South Dennis, MA

$254 avg / night
(excludes fees and taxes)
3.86 (35)
Cape Estate 6
4 Bedroom | 2 Bath | Sleeps 9

Cape Estate 6 - South Dennis, MA

$358 avg / night
(excludes fees and taxes)
4.75 (12)

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Browse more vacation rental amenities in South Dennis

Pool | Electric vehicle charger | Lake view | Lakefront | Ocean view | Riverfront | Sound view | Soundfront | Water view | Waterfront

Recent South Dennis guest reviews

Charming and Relaxing Stay at The White Pillars! We recently stayed at the beautiful and historic White Pillars house and couldn’t have been more pleased with the experience. From the moment we arrived, we were struck by the charm and history of the home. Inside, the house was spacious, with tasteful cape style décor and plenty of natural light. There were two living room spaces that had comfortable seating, a pool table, and a beautiful 3 seasoned porch where we enjoyed our breakfast each morning. The kitchen had a spacious pantry to store all our food and snacks. We enjoyed evenings outside by the fire pit, while kids played whiffle ball and other lawn games. The bedrooms were clean, airy, and comfortable, and additional towels were provided. Most bedrooms include their own private bathroom which was perfect if traveling with a large group. The location was ideal — there is a pond at the end of the street where we enjoyed kayaking each day. The house is close to local shops, seafood shacks, beaches, and scenic bike trails. We spent our days exploring nearby towns like Harwich and Dennis port, and our evenings enjoying seafood feasts and watching the sunset over the water. Overall, this Cape Cod house was the perfect retreat. Whether you're looking for a peaceful escape or a base to explore the Cape, this place has it all. We can’t wait to return!
Danielle N. | Jul 2025
It was very clean, great location. Everyone was comfortable. Supplied beach chairs and umbrellas ( very important). Will likely comeback next year. This was our second year. Had a great week.
cynthia m. | Jul 2025
Our family had such a fantastic week at Ace’s Cape Escape!! The home is beautiful. We loved how it was decorated. It felt cheerful and sunny ☀️ The location is great. We enjoyed the backyard and pool. The host was very friendly and responsive to our questions. Highly recommended !!!!
jennifer m. | Jun 2025
South Dennis vacation rental FAQ

Yes. 241 of our South Dennis vacation rentals have internet access, so you can stay connected throughout your trip.

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Some of the most popular amenities in our South Dennis vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local South Dennis team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for South Dennis, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Explore our South Dennis, MA, vacation rentals

Embrace the salty sea breeze with a South Dennis beach rental. Immerse yourself in historic treasures at the Cape Cod Museum of Art, savor fresh seafood at family-owned restaurants, or browse antique shops that line the streets. Feel the sand between your toes at West Dennis Beach, a haven for sunbathers and water sports enthusiasts. 

For nature lovers, Swan Pond River Trail offers serene walks amidst lush landscapes. With its inviting atmosphere and proximity to Cape Cod's attractions, South Dennis is an idyllic destination for a relaxing getaway filled with culture, cuisine, and coastal delights. Find a quiet hideaway close to it all in South Dennis.

Nearby destinations

New England   |   Cape Cod   |   East Dennis   |   Dennis Port   |   West Dennis   |   West Harwich   |   South Yarmouth   |   Dennis   |   Yarmouth Port   |   Harwich   |   Yarmouth   |   West Yarmouth   |   Harwich Port   |   Brewster   |   South Chatham   |   Hyannis   |   Barnstable   |   East Orleans   |   North Chatham   |   West Hyannisport   |   Chatham   |   Orleans   |   Centerville   |   West Barnstable   |   Eastham   |   Osterville   |   North Eastham   |   Marstons Mills   |   South Wellfleet   |   Cotuit   |   East Sandwich   |   Wellfleet   |   Mashpee   |   Sandwich   |   Forestdale   |   Sagamore   |   Sagamore Beach   |   Truro   |   East Falmouth   |   Bourne   |   North Truro   |   Pocasset   |   Cataumet   |   Buzzards Bay   |   Provincetown   |   North Falmouth   |   Falmouth   |   West Falmouth   |   Onset   |   Oak Bluffs   |   Edgartown   |   Vineyard Haven   |   Nantucket   |   Tisbury   |   Woods Hole   |   Wareham   |   Massachusetts
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