Holiday rentals with a pool in Barnstable County

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!

Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home features high-end furniture, a pool, hot tub & games including ping pong & air hockey. With kid-friendly amenities, everyone will feel at home. Relax, play & create unforgettable memories in this upscale oasis designed for fun & relaxation! Walk to small neighborhood beach 3 min drive to Jacknife Beach 6 min drive to downtown Chatham Experience Chatham with us & Learn More Below!

Winslow Acres [heated] Pool Escape; pool May-Oct

Pool Closes 10/14/25; reopens mid-may for 2026 season. Hot tub open year-round Escape to the Cape at this beautifully maintained home with lovely seasonal heated pool (heated spring/fall). Hot tub available all year. 4 bedrooms, 2.5 baths (2 showers) plus an outside shower May through October. Plenty of room for up to 8 people - sorry, no parties - (plus pets - fee applies)! Only 3 miles to beaches. The ferry to Nantucket and Martha's Vineyard is not far, and a great addition to any Cape trip!

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!

House on Cape Cod with pool close to beach

This single family house is located at the end of a cul de sac in a quite neighborhood in walking distance to Mayflower and Bayview beaches. You enter through the bright and open kitchen, looking out over the patio and the pool. The open living and dining room open up to a sun room where you can relax after a fun day at the beach. The two smaller bedrooms share a big bathroom with tub and double sink, whereas the master bedroom has its own bathroom. A big dining table can host up to 8 people.

Sea Salt Studio - Steps to Glendon Rd Beach

Funky studio (Unit #1) only 175 yards from a white sand beach on Nantucket Sound. 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.

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!

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!

Fenced Pool, Fire pit, Outside dining, Coffee bar

Our family friendly home which has three bedrooms and 2 1/2 bathrooms with an open floor plan. A electric fireplace in the living room. Seating enough for 10 in the living and dinning room. Renovated kitchen with coffee/tea bar Our backyard is equipped with a fenced in in-ground solar cover heated pool, lounge chairs with free standing umbrellas, patio seating, fire pit with Adirondack chairs. Outside grill. Outside dinning table for 10 with canopy for shade and bug screen.

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.

Heated Pool | Waterfront | A/C | Kayaks | 3 Acres

Relax at this serene waterfront home on Mill Pond in Yarmouth Port. This spacious 4 bedroom (6 bed), 3 bath retreat offers beautiful water views, a private in-ground heated saltwater pool, sunroom, and expansive outdoor living space with 3 acres of land. Paddle our kayaks from the backyard, enjoy nearby bike paths and walking trails, or unwind just minutes from Cape Cod beaches. Perfect for families or peaceful group getaways. 18C - Hosted by Tuxfin Hospitality

Wellfleet~Beautiful One Day Perfect The Next

Are you looking for the perfect getaway in charming Wellfleet? This two-bedroom cottage is located in a private, detached cottage village. Enjoy the beautiful SEASONAL in-ground pool (OPENS July 4th & CLOSES LABOR DAY) and a welcoming family-friendly atmosphere. The cottage is centrally located with a five-minute drive to both bay and ocean side beaches, freshwater kettle ponds, Wellfleet center, and the rail trail!