Osterville Rentals

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56 Houses

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Contemporary Gem with Private Pool!

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$402

Great rentals within 20 miles that match your search

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.

Match: Private pool

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Price per night from

$456

Waterfront Resort in Falmouth - 5/31/24 - 6/7/24

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Private pool

All filters match

Price per night from

$172

Magical home built around Windmill with views of ocean

Centerville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private pool

All filters match

Price per night from

$1,712

Captain Gosnold Village - Studio Unit 7B

Hyannis hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Private pool

All filters match

Price per night from

$221

Water Views Private Pool Access to Cove!

West Dennis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$398

Spacious Home with Private In-Ground Pool!

Brewster house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$407

Private Pool, Large Deck, and Game Room!

South Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$285

Crew's Quarters at Captain Alexander’s

West Harwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

All filters match

Price per night from

$164

Heated Pool AC 1/2 Mile to Beach!

Harwich house

  • 8 bedrooms
  • 3 bathrooms
  • sleeps 20

Match: Private pool

All filters match

Price per night from

$600

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

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

Match: Private pool

All filters match

Price per night from

$6,870

Wow! Private Pool, Game Room, and Fire Pit!

Brewster house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Private pool

All filters match

Price per night from

$365

NEW LISTING! Captain Gosnold Village - Studio Cottage (Unit M1) - Walk to Beach

Hyannis hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Private pool

All filters match

Price per night from

$103

Summer vacation paradise, with private heated pool, sleeping 8

West Dennis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private pool

All filters match

Price per night from

$500

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

Dennis house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private pool

All filters match

Price per night from

$1,000

Luxury Waterfront Home w/ Heated Pool and Hot Tub

South Dennis house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

Match: Private pool

All filters match

Price per night from

$825

Sleeps 14 Home w/ Pool Great for Families!

West Harwich house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Private pool

All filters match

Price per night from

$417

Luxurious Estate, Private Heated pool!

West Harwich house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private pool

All filters match

Price per night from

$959

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: Private pool

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Price per night from

$572

Match: Private pool

All filters match

Price per night from

$687

In-Ground Plunge Pool Dog Friendly!

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Private pool

All filters match

Price per night from

$411

86 Spring Hill

East Sandwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

All filters match

Price per night from

$286

Beautiful Colonial Home in Edgartown with Pool

Edgartown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private pool

All filters match

Price per night from

$1,715

Modern Private & Expansive Oasis - Pool & Hot Tub

Oak Bluffs house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$2,143

Beautiful Tri-Level Katama Home with Heated Pool

Edgartown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$1,072

LUXURY WATERFRONT WITH POOL & HIGH END AMENITIES

Edgartown house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$5,000

Beautiful Mink Meadows Five Bedroom Home with Pool

Vineyard Haven house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Private pool

All filters match

Price per night from

$929

Katama Home with Heated Pool and Hot Tub near South Beach

Edgartown house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$786

CHARMING CAPE IN ISLAND GROVE THAT IS TRUE VINEYARD!

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Very good experience” House was just right for us--clean, bright, nice deck/table/outside shower; living room was cozy but big enough for 4-6. Missing a few basics in the kitchen that we had to buy, but other than that, no complaints.

Match: Private pool

All filters match

Price per night from

$679

Spacious Katama Home with Heated Pool

Edgartown house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Private pool

All filters match

Price per night from

$572

Beautiful Katama Home with Pool

Edgartown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$3,286

Beautiful Edgartown home with Pool

Edgartown house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$1,429

Great Four Bedroom Home Walking Distance to Town

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private pool

All filters match

Price per night from

$2,858

Beautiful Six Bedroom Edgartown Home with Pool

Edgartown house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private pool

All filters match

Price per night from

$786

CLASSIC COLONIAL LUXURY HOME IN EDGARTOWN WITH A HEATED POOL

Edgartown house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private pool

All filters match

Price per night from

$1,429

Katama Luxury with Pool

Edgartown house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private pool

All filters match

Price per night from

$4,372

Edgartown House and Guest House Walking Distance to Edgartown

Edgartown house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 9

Match: Private pool

All filters match

Price per night from

$2,000

In-town Luxury Retreat with Pool

Edgartown house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Private pool

All filters match

Price per night from

$2,143

Viewing 38 of 56
rentals in Osterville

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