Vacation rentals with a pool in Osterville

Heated Pool Oasis | 5 Min to Cape Cod Beaches!

Stunning in-ground pool HEATED in May, June, Sept, Oct only. Just 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. Conveniently located, 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!

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

~~ You Have Arrived! Welcome to "The Fore Seasons" in desirable New Seabury on Cape Cod. ⛳️🏖🌸☀️ You will be sure to fall in love with old Cape Cod in this 4,500 sqft private home located on the 10th hole fairway of the championship golf course. With its 4 bedrooms, 4 bathrooms, Heated Inground Pool, Outdoor Shower, Putting Green, Ping Pong table and Ctrl Air there is enough room for the largest families. Pool open from Mid-May until through Columbus Day! Available year round for all gathering

Hyannis Port Coastal Escape – Pool & Walk to Beach

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. It’s a fantastic getaway for 4 couples or for a whole family. Cert# C0457270200

CapeSearenity-Large Pool-Beach Passes-Family Fun!

Visit Cape SeaRenity–a stunning home w/solar heated pool and outdoor lounge, perfect for a memorable family vacation and a fabulous Cape Cod experience. Escape to Cape SeaRenity—a beautifully updated home near Barnstable Village with a pool, outdoor lounge, & stylish interiors. Minutes from beaches, shops, dining, & whale-watching. Enjoy a modern kitchen, game-filled garage, bikes & kayaks. With thoughtful design & ProHost® support, it’s the perfect base for exploring Cape Cod with your family.

“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.

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 6/20-9/15/24. The reviews tell all!

Renovated ranch with pool access

Renovated home in E. Falmouth offers endless relaxation and recreation: swim, bike, fish, kayak, walk, lounge. Short walk to Assoc beach or to the Seashores Clubhouse pool (seasonal). Bring your kayak: explore Washburn Island & Waquoit Bay. Sleeps 6 with 1-floor living, AC, laundry, large back deck, and outdoor shower. Nearby, you'll find dining/shopping areas, wineries/breweries, & more. A short drive to Woods Hole offers fast boats to Martha's Vineyard. Book now and enjoy Sandy Feet Retreat.

Heated Indoor Pool & Spa - Golf Course View

CHERRY BLOSSOM RETREAT Cold days, raining days and power outage won't hinder your stay at this luxurious home, boasting an indoor heated salt water pool and hot tub fully equipped with a backup generator, overlooking the renowned 3-Hole Championship Golf Course. Our ultimate luxury home features an array of indoor entertainment options including arcades, air hockey, foosball PS5, Switch, etc. comfortably accommodating 6 to 8 guests, and merely a short drive to all all New Seabury's amenities.

Home in Sandwich with 5 star Resort Amenities

Looking for a luxurious getaway w/ amenities you can only dream of, located near trails on conservation behind the house, beaches (10min drive)& ponds(2min drive) on Cape Cod? Look no more! Lavish in opulence w/ top amenities of a 5-star resort made entirely available to you all in one place. Relax & unwind w/ saltwater pool, enjoy a game of volleyball, or cook outdoors while the kids play in the playground. S'mores anyone? Unite all around the fire pit! U can truly live the way you dream.

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio (Unit #1) only 175 yards from white sand Glendon Road beach. Soak up the sun at the beach, relax by the pool or enjoy a relaxing cocktail on your own private patio. This studio is equipped with a fridge, microwave and gas stove as well as a fully stocked kitchenette and cable/Roku TV. A futon couch offers extra sleeping space, if needed. Outside, enjoy a natural gas grill. Walk or bike to multiple restaurants, ice cream shops and all the amenities Dennis Port has to offer.

Carolyn's Bass River Condo

This 600 Sq. Ft. condo is located on Bass River. This vacation unit has two levels. The upper level with balcony overlooking Bass River is a combination living room/dining area with a kitchenette plus a full bathroom. The lower level with access to patio is a bedroom with a Queen pillow top bed and a full bed plus a second full bath. Both levels have through the wall AC/heating units. The 18 unit condo complex has an outside heated pool which is open during summer season.

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.