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Search 105,200+ Vacation Rentals

South Orleans Vacation Rentals & Homes - 1254 Rentals Available

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1,254 Vacation rentals

1 / 29

South Orleans House

  • 5
  • 10
  • 7 nights min
  • Child friendly

$258.00

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from $258.00 / night

1 / 19

South Orleans House

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$158.00

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from $158.00 / night

(2)

1 / 19

South Orleans House

  • 5
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning

$200.00

Very Good (2 reviews)

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from $200.00 / night

1 / 29

South Orleans House

  • 3
  • 10
  • min stay varies
  • Child friendly
  • Pet friendly

$192.00

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from $192.00 / night

1 / 31

South Orleans House

  • 5
  • 12
  • min stay varies
  • Child friendly

$321.00

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from $321.00 / night

1 / 29

South Orleans House

  • 4
  • 10
  • 1 night min
  • Ask about children
  • Pet friendly

$328.00

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from $328.00 / night

Your search has been expanded 19.6 miles to include more rentals

(1)

1 / 8

Dennis Port Apartment - 9.5 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$181.00

Excellent (1 reviews)

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from $181.00 / night

(6)

1 / 1

South Yarmouth House - 13.6 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning

Responds fast! Avg. 2 hours 34 minutes

“This house was spacious, clean and affordable. It is an easy walk to the beach and is close to many attractions on the Cape. We plan on renting next year...”
- Review left on 08/08/2016

$221.00

Excellent (6 reviews)

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from $221.00 / night

1 / 14

Brewster Condo - 3.5 miles away

  • 3
  • 8
  • 1 night min
  • Ask about children
  • Air conditioning

$401.00

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from $401.00 / night

(8)

1 / 16

Dennis Port Cottage - 9.8 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 19 minutes

“We rented this cottage without seeing it. It was really nice to be so pleasantly surprised, everything was perfect. Great location, close to beaches and all Dennis activities and restaurants. It was immaculate, the central air conditioning was...”
- Review left on 08/14/2016

$221.00

Excellent (8 reviews)

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from $221.00 / night

1 / 33

Wellfleet House - 13.2 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Pet friendly

Responds fast! Avg. 10 minutes

$426.00

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from $426.00 / night

(7)

1 / 84

Wellfleet House - 12.6 miles away

  • 5
  • 11
  • min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 17 minutes

“Had a great week with extended family in the main house. Beach very tiny walk away and kids loved wandering the bay with the tide out...”
- Review left on 09/07/2010

$401.00

Excellent (7 reviews)

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from $401.00 / night

(1)

1 / 18

Dennis Cottage - 10.4 miles away

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Air conditioning

$169.00

Excellent (1 reviews)

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from $169.00 / night

(6)

1 / 12

Chatham Cottage - 5.2 miles away

  • 2
  • 5
  • 7 nights min
  • Nearest beach 0.85 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 28 minutes

“The cottage was located only about 1/2 mile from Cockle Cove Beach. It sits in a small private, loop road, surrounded by trees and beyond the trees is the beginnings of a salt marsh. The kitchen is very functional and there's a nice sized dining...”
- Review left on 09/30/2016

$123.00

Very Good (6 reviews)

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from $123.00 / night

(3)

1 / 14

Brewster House - 3.9 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
“Enjoyed our stay very much. Beautiful yard with room to play. Easy half mile walk to the beach. Nice association bayside beach. Safe to leave chairs/umbrella there the whole time, no need to carry back each day. A little noisy because of...”
- Review left on 07/14/2016

$573.00

Excellent (3 reviews)

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from $573.00 / night

(2)

1 / 44

Truro House - 16.8 miles away

  • 8
  • 20
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,832.00

Excellent (2 reviews)

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from $1,832.00 / night

(1)

1 / 16

West Yarmouth House - 14.9 miles away

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$1,031.00

Excellent (1 reviews)

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from $1,031.00 / night

(18)

1 / 18

North Truro House - 19.6 miles away

  • 2
  • 4
  • 7 nights min
  • Ask about children
  • Pet friendly

Responds fast! Avg. 34 minutes

“Just tidying my computer and came across this trip advisor bookmark. I've already left a positive review from our stay in 2014. We visited again last July with additional family/friends and had another wonderful vacation. We chose the same house...”
- Review left on 01/02/2017

$319.00

Excellent (18 reviews)

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from $319.00 / night

(10)

1 / 15

West Yarmouth House - 14.5 miles away

  • 3
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
“Enjoyed our vacation at Leap of Faith. House was clean and very roomy. Great yard to sit in and play games. Very quiet neighborhood. Had a couple of minor issues but the owner took my call immediately and had them fixed. The only thing to be aware of...”
- Review left on 08/14/2015

$262.00

Excellent (10 reviews)

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from $262.00 / night

(6)

1 / 17

Eastham House - 6.7 miles away

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
“This is a great location! A short walk to the bay where you must go with your camera, blanket/chair to watch the sunsets. This year we took a short ride to the ocean to view the seals - neat. The Cape Cod Bike trail is a 20+ mile journey for the...”
- Review left on 03/26/2015

$573.00

Very Good (6 reviews)

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from $573.00 / night

(9)

1 / 21

Harwich Port House - 7.1 miles away

  • 3
  • 6
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Private garden
“This was the perfect place for our family. It was close to the village and beaches, but on a quiet street with a lovely garden. We loved the outdoor shower and sunny deck. This is a classic Cape house...”
- Review left on 07/21/2016

$226.00

Very Good (9 reviews)

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from $226.00 / night

1 / 24

Barnstable House - 15.8 miles away

  • 5
  • 8
  • 14 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

Responds fast! Avg. 2 hours 48 minutes

$409.00

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from $409.00 / night

1 / 23

Chatham House - 5.7 miles away

  • 4
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

$429.00

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from $429.00 / night

(1)

1 / 17

Chatham House - 5.3 miles away

  • 2
  • 5
  • 7 nights min
  • Ask about children
  • Pet friendly

$129.00

Excellent (1 reviews)

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from $129.00 / night

1 / 26

Truro House - 17.3 miles away

  • 5
  • 12
  • min stay varies
  • Nearest beach 0.75 mi
  • Child friendly
  • Air conditioning

$916.00

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from $916.00 / night

1 / 48

Eastham House - 7.7 miles away

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$916.00

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from $916.00 / night

(4)

1 / 28

Eastham House - 7.5 miles away

  • 7
  • 18
  • min stay varies
  • Nearest beach 0.8 mi
  • Swimming pool
  • Child friendly
“The property worked well for our family reunion. Though we ran into a few issues, the owner was quick to address them. Location was great as we were able to walk to the beach and shopping was a short car ride away. We made full use of the kitchens in...”
- Review left on 07/23/2015

$1,145.00

Very Good (4 reviews)

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from $1,145.00 / night

(1)

1 / 24

Eastham House - 7.5 miles away

  • 3
  • 8
  • min stay varies
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 31 minutes

$102.00

Very Good (1 reviews)

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from $102.00 / night

(12)

1 / 37

Truro House - 16.6 miles away

  • 2
  • 6
  • min stay varies
  • Nearest beach 2 mi
  • Child friendly

Responds fast! Avg. 3 hours 13 minutes

“We had an incredible week. As always. The weather was perfect, we had the beaches to ourselves, esp. Longnook, mornings, for a swim. It doesn't get any better! We did all our favorite things, a couple days at Herring Cove, to swim, paddle, biked to...”
- Review left on 07/05/2016

$229.00

Excellent (12 reviews)

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from $229.00 / night

1 / 21

Eastham House - 6.3 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$208.00

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from $208.00 / night

1 / 17

Eastham Cottage - 7 miles away

  • 2
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning

$128.00

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from $128.00 / night

1 / 22

Eastham Cottage - 6.2 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$129.00

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from $129.00 / night

1 / 25

North Eastham House - 8 miles away

  • 3
  • 8
  • 7 nights min
  • Child friendly

$286.00

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from $286.00 / night

1 / 14

Barnstable House - 17.1 miles away

  • 5
  • 11
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$295.00

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from $295.00 / night

1 / 33

Brewster House - 3.7 miles away

  • 5
  • 12
  • min stay varies
  • Child friendly
  • Pet friendly

$468.00

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from $468.00 / night

1 / 39

East Orleans House - 3.6 miles away

  • 5
  • 14
  • min stay varies
  • Child friendly

$462.00

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from $462.00 / night

1 / 15

Brewster House - 3.8 miles away

  • 5
  • 12
  • 7 nights min
  • Child friendly
  • Air conditioning

$285.00

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from $285.00 / night

(1)

1 / 15

East Orleans House - 3.8 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$222.00

Excellent (1 reviews)

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from $222.00 / night

(1)

1 / 10

Brewster House - 1.7 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$200.00

Average (1 reviews)

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from $200.00 / night

1 / 25

Chatham House - 4.9 miles away

  • 2
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$465.00

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from $465.00 / night