Vacation rentals with a pool in Dennis

“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.

Value · Location · Beach

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.

Family · Value · Bathroom

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!

Location · Family · Kitchen

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.

Location · Family · Nearby

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.

Location · Value · Access

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 (plus pets - fee applies) - sorry, no parties! Only 3 miles to beaches. The ferry to Nantucket and Martha's Vineyard is not far, and a great addition to any Cape trip!

Family · Location · Outdoor spaces

Modern Oasis, Heated Saltwater Pool, Beach, Golf

Welcome to an exceptional modern Cape Oasis on a private & quiet cul-de-sac Mins. to Golf, beaches, lakes, bike path Bright airy, spacious, central AC, modern/new furnishing，enjoyable year-round Expansive deck, pool lounge & yard Fenced in w/full privacy Thoughtfully curated for multi families/groups Resort style retreat w/tranquility & fun games Location is virtually close to everything Pool heat: Memorial day weekend -last Sun. of Sept. All essentials provided 6+ free parking

Value · Location · Backyard

Cottage at the Escape Inn

Guests will have a special experience as this cottage provides a fireplace. Featuring a private entrance, this air-conditioned cottage is consisted of 1 living room, 2 separate bedrooms and 1 bathroom with a bath and a shower. The well-equipped kitchen features a stovetop, a refrigerator, a dishwasher and kitchenware. The spacious chalet offers a tea and coffee maker, a seating area, a wardrobe, a sofa, as well as a flat-screen TV with cable channels. The unit offers 3 beds.

Family · Location · Sleep quality

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.

Family · Value · Checkout

Charming Cape Escape with Pool, Hot Tub & Fire Pit

Welcome to Searside Retreat, your ultimate Cape Cod escape in South Dennis! This charming home offers a private pool, open layout, and modern comforts just minutes from top beaches, restaurants, and shops. Relax in a quiet neighborhood in the heart of the Cape. Mayflower Beach - 10min Chapin Beach - 6 min Cape Cod Rail Trail – 10min The Marshside Restaurant – 2min Sesuit Harbor Cafe - 5 min Scargo Cafe - 5 min Smugglers Ice Cream - 5 min Learn more below!

Family · Location · Hospitality

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.

Value · Family · Walkability

Seaview Summit | Ocean Views, Indoor Pool, Beach

Perched above the coastline with panoramic Atlantic views, Seaview Summit House is Plymouth's premier oceanfront retreat. Designed for discerning travelers seeking serenity, space, and sophistication. With a heated indoor pool, expansive outdoor living areas, and direct beach access just moments away, this stunning property delivers a five-star experience in every season. Book your stay today. You'll be glad you did.

Location · Family · Pool