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1,566 houses

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Match: Rental types Private outdoor pool (heated)

All filters match

Price per night from

$689

Luxury Waterfront Home With Heated Pool

Orleans house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (heated)

All filters match

Price per night from

$1,312

Magical home built around Windmill with views of ocean

Centerville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Rental types Private outdoor pool (heated)

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Price per night from

$1,716

BEAUTIFUL AND PEACEFUL RESORT-LIKE SPLIT LEVEL HOUSE FOR NON-SMOKERS ONLY

Worcester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Rental types Private outdoor pool (heated)

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Price per night from

$172

Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

Match: Rental types Private outdoor pool (heated)

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Price per night from

$6,890

Responds fast! avg. 37 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$2,869

Beautiful five bedroom home with private swimming pool

Dennis Port house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Excellent accommodations” The rental agent as well as the owner are easily accessible and ensure the house is ready upon arrival. The owner is gracious and gives a thorough explanation of how to use the pool, jacuzzi and fire pit. Walks to the beach are quite easy from this home.

Match: Rental types Private outdoor pool (heated)

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Price per night from

$574

Hedgebound of Cape Cod

Truro house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

Match: Rental types Private outdoor pool (heated)

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Price per night from

$3,442

Crew's Quarters at Captain Alexander’s

West Harwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$164

7 bedroom home sleeping 14! Located on the Bayside with private pool!

Dennis house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Rental types Private outdoor pool (heated)

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Price per night from

$1,002

2/10 Mile to Nauset Beach

Orleans house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 39 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$2,601

Summer vacation paradise, with private heated pool, sleeping 8

West Dennis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (heated)

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Price per night from

$501

78 Main Street 152267

Falmouth house

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 18

Match: Rental types Private outdoor pool (heated)

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Price per night from

$2,148

Fabolous with Pool and Walk to Town

Nantucket house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (heated)

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Price per night from

$3,442

Heated Pool and Hot Tub 5 Minutes to Nauset Beach

Orleans house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 39 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$1,222

457 Prince Hinkley Road 151768

Centerville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$688

On to of Wigwam

Nantucket house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (heated)

All filters match

Price per night from

$3,557

These homes match some but not all of your filters. Clear all filters

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Rental types, Private outdoor pool (heated)

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Price per night from

$137

4 acre private retreat setting

Middleborough house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$144

Popponesset Beach-Mashpee, MA. 4 minute walk to pristine beach.

New Seabury house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$373

BEACHFRONT - Directly on Long Beach Rockport MA

Rockport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 44 minutes

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$689

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$327

3bd 2 bath steps to private association beach

Dennis Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$623

Classic Cottage, walk to Private Beach/ Wiley Park

Eastham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$320

Close to Main Street and harbor beaches

Nantucket house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 38 minutes

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$1,721

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$631

Connors Cottage

West Hyannisport house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$201

Classic Bayfront House on Cape Cod Bay, North Truro near Provincetown

North Truro house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$1,393

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$494

Luxurious & Spacious Waterfront Home on Swimmable Private Beach. Pet OK.

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$1,312

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$783

Barnstable Village Private Pool

Barnstable house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Great place to stay” The home was clean and well maintained. The pool was a huge hit with my niece and the rest of the family. We were in a great location, close to a beach, some shops and restaurants.

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$457

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$525

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$1,640

Perfect for two families!

Orleans house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$738

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$603

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$631

Executive modern oceanview hilltop home

Martha's Vineyard house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$1,033

Viewing 38 of 1,566
rentals in Massachusetts

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