Vacation rentals with a pool in Dennis

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Dennis

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Yarmouth Port

4.9 out of 5 average rating, 42 reviews

Winslow Acres [heated] Pool Escape; pool May 15

Pool Open 5/15 Escape to the Cape at this beautifully maintained home with lovely seasonal heated pool (heated spring/fall). Hot tub available all year. Make s'mores and memories year-round at the fire pit table. 4 bedrooms and 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!

Guest favorite

Home in Cotuit

4.95 out of 5 average rating, 113 reviews

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!

Superhost

Home in Dennis

4.63 out of 5 average rating, 30 reviews

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.

Guest favorite

Home in Plymouth

4.96 out of 5 average rating, 28 reviews

Getaway with pool

Look no further! This stunning beach house offers everything you need. Situated on a quiet street on Cape Cod Bay, it is very close to area beaches and ponds. The outdoor space is perfect for entertaining and includes lap pool, three decks, patio and fire pit. The downstairs includes living room, family room, bedroom, full bath, eat-in kitchen, and enclosed porch overlooking the backyard. The second floor features 4 more bedrooms, 2 baths, laundry room, and en suite primary bedroom with deck.

Guest favorite

Villa in New Seabury

5 out of 5 average rating, 41 reviews

Heated Indoor Pool & Spa - Golf Course View

CHERRY BLOSSOM RETREAT Cold days, raining days, power outage won't be an issue if you can steal away to this home, with an indoor heated salt water pool and hot tub fully equipped with a backup generator, with a view of the famous 13-Hole Championship Golf Course Cape Cod. Our ultimate luxury home is filled with arcades, air hockey, foosball and other indoor entertainments for guests to enjoy, comfortably sleeps 6-8 and just a few minute drive to all of the amenities New Seabury has to offer.

Guest favorite

Home in Oak Bluffs

4.94 out of 5 average rating, 189 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Superhost

Home in Plymouth

4.9 out of 5 average rating, 183 reviews

Thanksgiving House Dining Table seats 12-14

This beautiful 2.5 acre fully fenced in private property has gardens, an in-ground pool & pool house with an outdoor heated shower. Our home offers 2 kitchens, dining room seating 12, a great room, 3 bedrooms with private sitting areas & lower level with 2 bunk beds (bottoms are full beds) & exercise area. Outside are 2 grills & chiminea. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod. POOL can be HEATED for $500.00/Visit.

Guest favorite

Home in Popponesset

5 out of 5 average rating, 9 reviews

Popponesset-Pool, hot tub, fire pit; 3-Bds, 4 bath

This home was custom built in 2022, and is designed to provide comfort, luxury and loads of charm for the discerning vacationer. New construction with a nod to the Nantucket Sea Captain's houses of yesteryear. Professionally decorated and landscaped, offering every amenity you could possibly desire; from an in-ground, heated, saltwater pool (with electric cover), hot tub, outdoor shower, fire-pit, and even a cabana with a sink, refrigerator, and smart TV. Just a 3 min walk to private beach.

Superhost

Home in Teaticket

4.83 out of 5 average rating, 6 reviews

Charming Home-Pool, Game Room, walk to quiet beach

Escape to your own private paradise at this stunning saltwater peninsula home in Falmouth. Perfect for families and groups, the backyard oasis features a heated pool, fire pit, and swingset, while a nearby quiet beach offers a tranquil setting to watch boats pass by. Just a short drive away, discover Falmouth's top-rated beaches including Menauhant and Surf Drive Beach. The vibrant Downtown Falmouth is also only minutes away, where you can explore local shops, restaurants, and attractions.

Superhost

Guest suite in Barnstable

4.92 out of 5 average rating, 25 reviews

Cozy 1-bedroom cottage with pool and beach access

Cozy apartment within short walking distance of a gorgeous private beach on the bayside of Cape Cod. The gentle bay is perfect for families. Walk the flats during low tide or float in the gentle bay waters. Later relax by the outdoor pool. Or take a walk on the Mass Audubon Long Pasture Wildlife Sanctuary trails. Note: this private apartment is attached to owner's residence but has its own private entrance and parking spot. IN SEASON RENTAL: SATURDAY TO SATURDAY unless approved by host

Guest favorite

Home in Brewster

4.97 out of 5 average rating, 31 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

Welcome to your perfect Cape Cod vacation! Nestled in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, bike trail etc. Vast serene private 1.5 acres adjacent to conservation land. Lighted Private heated salt water pool, Bocce Court, Putting green, corn hole, hammock, outdoor shower etc. Expansive double deck with awning . Chef’s kitchen & all essential amenities provided. Spacious Beautiful indoor/outdoor dining/entertaining. Pool heat 05/15 to 10/01

Guest favorite

Townhouse in Brewster

4.86 out of 5 average rating, 103 reviews

Ocean Edge Cape House with Beach, Pool, and AC

Classic Cape Cod Cottage with air conditioning in the heart of The Cape with access to a private beach, swimming pool, and tennis courts. Walk to the store, restaurants and easy access to the Cape Cod Rail Trail. Walk, bike or drive to Nickerson State Park for hiking trails, fresh water swimming, paddle boarding, and fishing. This is a perfect setting for families with plenty of green space and a gated community. The house has a grill and 2 balconies to enjoy.