Vacation rentals with a pool in Osterville

“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.

Relaxing Cape Home <3mi-beach

Escape to this recently updated vacation home, perfectly situated near Hyannis Main Street’s charming shops and delightful restaurants. Immerse yourself in history with a visit to the Kennedy Museum, explore the Legacy Trail, or discover the serene natural conservation areas. Spend sun-soaked days at the nearby beach, return home to unwind by the climate-controlled pool or fire pit as dinner sizzles on the grill. Book your stay today and experience the perfect blend of relaxation and adventure!

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!

Beautiful Cotuit Home w/Amazing Pool, near Beaches

Welcome to your Cape Cod escape at "Poppy", where comfort meets coastal elegant charm. This spacious 4-bedroom home offers inviting indoor and outdoor spaces ideal for family vacations, friend gatherings, or peaceful retreats. With a heated seasonal pool (open May 6), entertainment room, and easy access to local beaches and shops, it’s a destination designed for relaxation and fun! Loop Beach - 3 min Oregon Beach - 5 min Popponesset Marketplace - 14 min Explore the Cape Cod magic & Learn More

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!

Family Sandwich Coastal RetreatPool/firepit

Welcome to your perfect Cape Cod getaway in beautiful East Sandwich! This spacious 4-bedroom, 2.5-bath home was designed for relaxing vacations, family gatherings, and unforgettable summer memories. Enjoy the best of indoor and outdoor living with a private outdoor pool, cozy fire pit area, and comfortable spaces throughout the home for everyone to unwind after a day at the beach. Inside, the home offers bright and welcoming living areas, a fully equipped kitchen, and a spacious dining area.

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

Stunning in-ground pool HEATED in May, June, Sept, Oct 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!

ShoestringBayHouse, waterfront & pool in Cotuit

September: FIVE (5) night minimum stay. NOTE: airbnb has given the hosts notice that they are raising the fees that we pay to airbnb, this will be passed onto the guest. Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. It's all about the views. Our home overlooks the pool, beach and bay. We include: 2-Bikes, 2-Kayaks, and a Barnstable beach pass with beach chairs. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six adult guests plus children.

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.

Great Location. Near Beach & Main Street. Unit M1

Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker. Keurig, and kettle.

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.

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.