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South Dennis Vacation Rentals

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41 rentals in South Dennis.
Swan Pond Cottage, Waterfront Central A/C,  Open Floor Plan, vacation rental in South Dennis
Swan Pond Cottage, Waterfront Central A/C,  Open Floor Plan, vacation rental in South Dennis
Swan Pond Cottage, Waterfront Central A/C,  Open Floor Plan, vacation rental in South Dennis

Swan Pond Cottage, Waterfront Central A/C, Open Floor Plan

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Big House in Heart of Cape.  Close to Everything!, vacation rental in South Dennis
Big House in Heart of Cape.  Close to Everything!, vacation rental in South Dennis
Big House in Heart of Cape.  Close to Everything!, vacation rental in South Dennis

Big House in Heart of Cape. Close to Everything!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dog friendly home w/ deck and private gas grill - on the bay side of the Cape, vacation rental in South Dennis
Dog friendly home w/ deck and private gas grill - on the bay side of the Cape, vacation rental in South Dennis
Dog friendly home w/ deck and private gas grill - on the bay side of the Cape, vacation rental in South Dennis

Dog friendly home w/ deck and private gas grill - on the bay side of the Cape

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious home with patio, beach gear, & W/D - central location, vacation rental in South Dennis
Spacious home with patio, beach gear, & W/D - central location, vacation rental in South Dennis
Spacious home with patio, beach gear, & W/D - central location, vacation rental in South Dennis

Spacious home with patio, beach gear, & W/D - central location

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Thayer Thicket | Newly renovated house in South Dennis with great location, vacation rental in South Dennis
Thayer Thicket | Newly renovated house in South Dennis with great location, vacation rental in South Dennis
Thayer Thicket | Newly renovated house in South Dennis with great location, vacation rental in South Dennis

Thayer Thicket | Newly renovated house in South Dennis with great location

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Petite beach home overlooking Follins Pond w/ central A/C and private gas, vacation rental in South Dennis
Petite beach home overlooking Follins Pond w/ central A/C and private gas, vacation rental in South Dennis
Petite beach home overlooking Follins Pond w/ central A/C and private gas, vacation rental in South Dennis

Petite beach home overlooking Follins Pond w/ central A/C and private gas

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lovely Cottage With Private Yard Close to Dennis Shopping and Dining (2244), vacation rental in South Dennis
Lovely Cottage With Private Yard Close to Dennis Shopping and Dining (2244), vacation rental in South Dennis
Lovely Cottage With Private Yard Close to Dennis Shopping and Dining (2244), vacation rental in South Dennis

Lovely Cottage With Private Yard Close to Dennis Shopping and Dining (2244)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Great location to everything 5 mins to some of the best beaches fenced in yard, vacation rental in South Dennis
Great location to everything 5 mins to some of the best beaches fenced in yard, vacation rental in South Dennis
Great location to everything 5 mins to some of the best beaches fenced in yard, vacation rental in South Dennis

Great location to everything 5 mins to some of the best beaches fenced in yard

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay, vacation rental in South Dennis
Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay, vacation rental in South Dennis
Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay, vacation rental in South Dennis

Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Idyllic 3BR classic Cape Cottage in a beautiful waterfront setting, with sunsets, vacation rental in South Dennis
Idyllic 3BR classic Cape Cottage in a beautiful waterfront setting, with sunsets, vacation rental in South Dennis
Idyllic 3BR classic Cape Cottage in a beautiful waterfront setting, with sunsets, vacation rental in South Dennis

Idyllic 3BR classic Cape Cottage in a beautiful waterfront setting, with sunsets

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Cape Cod House, vacation rental in South Dennis
Cape Cod House, vacation rental in South Dennis
Cape Cod House, vacation rental in South Dennis

Cape Cod House

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Located in the heart of Dennis, vacation rental in South Dennis
Located in the heart of Dennis, vacation rental in South Dennis
Located in the heart of Dennis, vacation rental in South Dennis

Located in the heart of Dennis

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 bedroom home with ac, vacation rental in South Dennis
3 bedroom home with ac, vacation rental in South Dennis
3 bedroom home with ac, vacation rental in South Dennis

3 bedroom home with ac

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Newly Updated Home Stone Patio & Fire Pit!, vacation rental in South Dennis
Newly Updated Home Stone Patio & Fire Pit!, vacation rental in South Dennis
Newly Updated Home Stone Patio & Fire Pit!, vacation rental in South Dennis

Newly Updated Home Stone Patio & Fire Pit!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Walk to the Beach - Four Bedroom, vacation rental in South Dennis
Walk to the Beach - Four Bedroom, vacation rental in South Dennis
Walk to the Beach - Four Bedroom, vacation rental in South Dennis

Walk to the Beach - Four Bedroom

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular three bedroom home with central air, vacation rental in South Dennis
Spectacular three bedroom home with central air, vacation rental in South Dennis
Spectacular three bedroom home with central air, vacation rental in South Dennis

Spectacular three bedroom home with central air

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Waterfront-Relaxin' on the River!, vacation rental in South Dennis
Beautiful Waterfront-Relaxin' on the River!, vacation rental in South Dennis
Beautiful Waterfront-Relaxin' on the River!, vacation rental in South Dennis

Beautiful Waterfront-Relaxin' on the River!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Pristine condition! Three bedroom sleeping 8 with contemporary beach decor!, vacation rental in South Dennis
Pristine condition! Three bedroom sleeping 8 with contemporary beach decor!, vacation rental in South Dennis
Pristine condition! Three bedroom sleeping 8 with contemporary beach decor!, vacation rental in South Dennis

Pristine condition! Three bedroom sleeping 8 with contemporary beach decor!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pinefield Ln 15: 3  BR, 2.5  BA House in South Dennis, Sleeps 6, vacation rental in South Dennis
Pinefield Ln 15: 3  BR, 2.5  BA House in South Dennis, Sleeps 6, vacation rental in South Dennis
Pinefield Ln 15: 3  BR, 2.5  BA House in South Dennis, Sleeps 6, vacation rental in South Dennis

Pinefield Ln 15: 3 BR, 2.5 BA House in South Dennis, Sleeps 6

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming 4 bedroom 2 1/2 bath Cape house, vacation rental in South Dennis
Charming 4 bedroom 2 1/2 bath Cape house, vacation rental in South Dennis
Charming 4 bedroom 2 1/2 bath Cape house, vacation rental in South Dennis

Charming 4 bedroom 2 1/2 bath Cape house

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Short walk to Sesuit Harbor, vacation rental in South Dennis
Short walk to Sesuit Harbor, vacation rental in South Dennis
Short walk to Sesuit Harbor, vacation rental in South Dennis

Short walk to Sesuit Harbor

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Pristine Vacation Home on Aunt Patty's Pond (2208), vacation rental in South Dennis
Pristine Vacation Home on Aunt Patty's Pond (2208), vacation rental in South Dennis
Pristine Vacation Home on Aunt Patty's Pond (2208), vacation rental in South Dennis

Pristine Vacation Home on Aunt Patty's Pond (2208)

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Getaway on the Cape Cod Bikepath **New!**, vacation rental in South Dennis
Gorgeous Getaway on the Cape Cod Bikepath **New!**, vacation rental in South Dennis
Gorgeous Getaway on the Cape Cod Bikepath **New!**, vacation rental in South Dennis

Gorgeous Getaway on the Cape Cod Bikepath **New!**

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bayside five bedroom sleeping 10 with air conditioning, vacation rental in South Dennis
Bayside five bedroom sleeping 10 with air conditioning, vacation rental in South Dennis
Bayside five bedroom sleeping 10 with air conditioning, vacation rental in South Dennis

Bayside five bedroom sleeping 10 with air conditioning

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Kelly's Bay House - Short walk to Kelly's Bay and Public Park - 16 Town Beaches, vacation rental in South Dennis
Kelly's Bay House - Short walk to Kelly's Bay and Public Park - 16 Town Beaches, vacation rental in South Dennis
Kelly's Bay House - Short walk to Kelly's Bay and Public Park - 16 Town Beaches, vacation rental in South Dennis

Kelly's Bay House - Short walk to Kelly's Bay and Public Park - 16 Town Beaches

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Dog-friendly 4 bedroom 4 bathroom sleeps 10 home near bay side beaches and, vacation rental in South Dennis
Dog-friendly 4 bedroom 4 bathroom sleeps 10 home near bay side beaches and, vacation rental in South Dennis
Dog-friendly 4 bedroom 4 bathroom sleeps 10 home near bay side beaches and, vacation rental in South Dennis

Dog-friendly 4 bedroom 4 bathroom sleeps 10 home near bay side beaches and

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Brewster – Lots of Lovable, Like-New Living Spaces, Inside and Out: 730-B, vacation rental in South Dennis
Brewster – Lots of Lovable, Like-New Living Spaces, Inside and Out: 730-B, vacation rental in South Dennis
Brewster – Lots of Lovable, Like-New Living Spaces, Inside and Out: 730-B, vacation rental in South Dennis

Brewster – Lots of Lovable, Like-New Living Spaces, Inside and Out: 730-B

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Spacious house located on Swan River, vacation rental in South Dennis
Spacious house located on Swan River, vacation rental in South Dennis
Spacious house located on Swan River, vacation rental in South Dennis

Spacious house located on Swan River

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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'Bayside' 2 story Colonial with Guest Quarters & Central Air, vacation rental in South Dennis
'Bayside' 2 story Colonial with Guest Quarters & Central Air, vacation rental in South Dennis
'Bayside' 2 story Colonial with Guest Quarters & Central Air, vacation rental in South Dennis

'Bayside' 2 story Colonial with Guest Quarters & Central Air

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Charming Cape Cod Escape!  ️�⛱️, vacation rental in South Dennis
Charming Cape Cod Escape!  ️�⛱️, vacation rental in South Dennis
Charming Cape Cod Escape!  ️�⛱️, vacation rental in South Dennis

Charming Cape Cod Escape! ️�⛱️

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming 3 bedroom sleeping 7 with central air!, vacation rental in South Dennis
Charming 3 bedroom sleeping 7 with central air!, vacation rental in South Dennis
Charming 3 bedroom sleeping 7 with central air!, vacation rental in South Dennis

Charming 3 bedroom sleeping 7 with central air!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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South Dennis Vacation Rental ~ 5 Mi to Beach!, vacation rental in South Dennis
South Dennis Vacation Rental ~ 5 Mi to Beach!, vacation rental in South Dennis
South Dennis Vacation Rental ~ 5 Mi to Beach!, vacation rental in South Dennis

South Dennis Vacation Rental ~ 5 Mi to Beach!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Renovated Cape Cod Retreat, vacation rental in South Dennis
Renovated Cape Cod Retreat, vacation rental in South Dennis
Renovated Cape Cod Retreat, vacation rental in South Dennis

Renovated Cape Cod Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming pet friendly cottage steps from Follins Pond., vacation rental in South Dennis
Charming pet friendly cottage steps from Follins Pond., vacation rental in South Dennis
Charming pet friendly cottage steps from Follins Pond., vacation rental in South Dennis

Charming pet friendly cottage steps from Follins Pond.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming home with private pool, deeded bay access, firepit, & W/D, vacation rental in South Dennis
Charming home with private pool, deeded bay access, firepit, & W/D, vacation rental in South Dennis
Charming home with private pool, deeded bay access, firepit, & W/D, vacation rental in South Dennis

Charming home with private pool, deeded bay access, firepit, & W/D

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Newly renovated, three bedroom, 1 1/2 bath Bass River water front home, vacation rental in South Dennis
Newly renovated, three bedroom, 1 1/2 bath Bass River water front home, vacation rental in South Dennis
Newly renovated, three bedroom, 1 1/2 bath Bass River water front home, vacation rental in South Dennis

Newly renovated, three bedroom, 1 1/2 bath Bass River water front home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Recently Remodeled "Pet Friendly" Property In Dennis, vacation rental in South Dennis
Recently Remodeled "Pet Friendly" Property In Dennis, vacation rental in South Dennis
Recently Remodeled "Pet Friendly" Property In Dennis, vacation rental in South Dennis

Recently Remodeled "Pet Friendly" Property In Dennis

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lovely Dennis Cottage - Walk to Beach!, vacation rental in South Dennis
Lovely Dennis Cottage - Walk to Beach!, vacation rental in South Dennis
Lovely Dennis Cottage - Walk to Beach!, vacation rental in South Dennis

Lovely Dennis Cottage - Walk to Beach!

Holiday Rental House
6 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Near Follins Pond in South Dennis. Roomy and adorable!, vacation rental in South Dennis
Near Follins Pond in South Dennis. Roomy and adorable!, vacation rental in South Dennis
Near Follins Pond in South Dennis. Roomy and adorable!, vacation rental in South Dennis

Near Follins Pond in South Dennis. Roomy and adorable!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Near Mayflower Beach 7 Bedrooms 3 baths Sleeps 14 CENTRAL A/C, vacation rental in South Dennis
Near Mayflower Beach 7 Bedrooms 3 baths Sleeps 14 CENTRAL A/C, vacation rental in South Dennis
Near Mayflower Beach 7 Bedrooms 3 baths Sleeps 14 CENTRAL A/C, vacation rental in South Dennis

Near Mayflower Beach 7 Bedrooms 3 baths Sleeps 14 CENTRAL A/C

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Panoramic views and pond access, vacation rental in South Dennis
Panoramic views and pond access, vacation rental in South Dennis
Panoramic views and pond access, vacation rental in South Dennis

Panoramic views and pond access

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-41 of 41
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