Holiday rentals with a pool in Osterville

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Guest favourite

“The Hideaway”Private Guest Suite/Pool/Beach Pass

Enjoy a bit of Cape Cod in a friendly and walkable neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Less than 2 miles from Craigville Beach and its beachside walk up shanty’s for lunch. A small beach on Lake Wequaquet is only 2 miles down the road . Main street Hyannis, a walkable downtown with many shops and restaurants is a quick 10-minute drive. Ocean marinas, and ferries to the islands, are a 15 minute drive.

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Guest favourite

Private Pool, near beaches, 3 BR/3 BA, Central Air

Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/26. The reviews tell all!

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Large Home Heated Swimming Pool Private Beach

Perfect for extended-family fun in this stunningly built home (3300 sqft) with 5 bedrooms and 4 bathrooms. First-floor shower. Walk 1000 feet to a private beach with full access rights. Along the beach, you can stroll further east to Sandy Neck Beach. Open kitchen, dining and great rooms are perfect for entertaining! Swim in the ocean or jump right into a beautiful 16x40 heated fiberglass pool with pool lights! Hosted by an extremely experienced host who's committed to making your stay perfect.

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Beach Pass Included! Brand New Spa! Central AC!

Welcome to your Italian Villa in the center of Cape Cod! My father, Sal, created this property to make memories that will last a lifetime. What could be better than a secluded yard that feels like a hidden oasis, but is also walking distance or a short drive to tourism? Walk 0.2mi to ice cream and mini golf. Or, drive 10 mins to local beaches, Hyannis Main Street, island ferries, fishing excursions, whale watching, The Cape Cod Melody Tent, the mall, rt 6, Cape Cod Gateway Airport, and more!

Beach house in Hyannis with pool

Bright and sunny, 3 bedrooms and 2 1/2 baths townhouse in oceanfront Yachtsman resort! Open kitchen/dining area, a living room with 85'' TV. Outdoor patio and top level deck with ocean views. Private beach, heated pool, meticulously landscaped grounds. Walk to downtown, Hyannis marina, Hy-Line Cruises and Kalmus Beach. Accommodates up to 8 people in 6 beds (3 queens, 2 twins, 1 sleeper sofa in the den) Pool is open Memorial Day to Labor Day as weather permits and only on weekends in June.

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!

Stunning in-ground pool HEATED in May, June, Sept only. Pool is opened in May! 5 minutes from Craigville, Dowses and Covell's Beach! Perfect for mid-size groups or families, this home sleeps 8 and boasts a dreamy, private, fenced-in backyard w/ a, pool house w/ TV & bar, outdoor shower, and cozy patios. Complete w/ all your beach essentials. We're 13 minutes from Mashpee Commons and 10 minutes from local grocery stores, local bakeries& restaurants. Central to all the Cape has to offer!

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Hyannis Port Coastal Escape – Pool & Walk to Beach

Nightly price includes all Airbnb fees. Welcome to "The Sand Box” in Hyannis Port, our Cape Cod Rental. We can’t wait to answer all your questions about our property! Our home is 4 bedroom, 2 full bath that was fully renovated in October of 2021. It’s walking distance to two beaches and central to many more across Barnstable. Lush outdoor entertainment area with an in-ground pool and patio with an outdoor gas grill. 5 minute drive from downtown Hyannis. Cert# C0457270200

Upscale Secluded Home w/Central AC, Pool & Firepit

Experience the charm of Centerville, a quaint village on Cape Cod! This property is 1.7 acres with beautiful coastal scenery. Centerville offers a peaceful vibe loved by visitors and locals. Enjoy the serene Centerville Lakes or our stunning Saltwater Private Pool! 5 mins to Craigville Beach 5 mins to Wequaquet Lake Boat Ramp- one of Centerville’s largest and most scenic lakes. 8 mins to downtown Osterville 10 mins to Ferry to Nantucket and MV 10 mins from Hyannis Airport

The Holly Cottage

Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

New Seabury Cape Condo | Pool & Beach Escape

Top 5% of Air Bnbs! Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

Cape Cod multi-structure family compound with Pool

Amazing family compound! Three structures to spread out, connected by an amazing outdoor space for creating memories. This gorgeous multi-building home is located on New Seabury's Ocean Golf Course. Main home and two, 2-bedroom guest homes connected by private court yard with beautiful pool and outdoor bar. Plenty of room for family/friends. Short distance to beaches, within walking distance to restaurants, marketplace and so much more.

Summer Serenity on Cape Cod (heated pool)

Beautiful and spacious 4 bedroom, 3 bathroom Cape Cod home on Bumps River (salt water). Relax and catch-up on summer reading by our new 17 X 40 pool. Or jump in one of our kayaks to explore and paddle your way directly to Nantucket Sound and Long Beach. Just a short paddle, walk or drive to our local beaches (Craigville Beach, Covell's Beach). A great home for intimate family gatherings, cookouts with friends, and entertaining.