Vacation rentals with a pool in Dennis Port

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Top-rated rentals with a pool in Dennis Port

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

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Guest favorite

A crystal-clear pool is framed by a deck lined with blue lounge chairs. The setting includes landscaped greenery and trees, with two-story buildings in the background providing serene surroundings. The clear blue sky enhances the tranquil atmosphere of this communal outdoor space.

Condo in West Dennis

4.86 out of 5 average rating, 56 reviews

Mid Cape Cod, 3 Season Haven by Bass River

This hidden gem has everything an outdoor enthusiast could want. Bring your own canoe or kayak, or rent one across the street, to enjoy the Bass River. Across from Bass River Marina complex, Sundancer's restaurant and nightclub, town landing, and conservation parks. Short drive or bike to West Dennis Beach and rail trail. Double unit offers sliders in both living area and bedroom to large furnished patio with electric grill. Pool available from Father's Day weekend through Labor Day weekend.

Top guest favorite

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

4.95 out of 5 average rating, 127 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!

Top guest favorite

A cozy seating area is presented with woven furniture beneath soft lighting. The pool glistens quietly in the background, surrounded by natural scenery. The space allows for relaxed outdoor gatherings, with easy access to the water views beyond.

Apartment in Barnstable

4.95 out of 5 average rating, 55 reviews

Studio Apartment

Private Studio apartment on lower level of Main House with deck overlooking Pond. Queen bed, single sleeper sofa and small sleeping loft. Very comfortable for 2 people but could sleep up to 4. Kitchenette with dinnerware and cookware. Coffee maker, full size fridge, microwave, toaster oven, outside gas grill. Private bath with shower. TV, WiFi, A/C. Pond access, SUP, kayaks available. Pool and hot tub at Main House. Sunrise views. Golf courses, shopping, restaurants, and beaches nearby.

Guest favorite

Condo in Brewster

4.97 out of 5 average rating, 191 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Guest favorite

A communal pool area features a clear blue pool surrounded by concrete decking. Lounge chairs are arranged neatly on the sides, with greenery visible in the background. A wooden fence encloses the area, providing a private atmosphere.

Condo in Dennis Port

4.91 out of 5 average rating, 111 reviews

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio 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, Bluetooth speaker, and 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.

Guest favorite

A cozy sleeping area features a metal bed frame with a blue comforter, accentuated by neatly arranged pillows. Two bedside lamps offer soft lighting beside the bed. Artwork is displayed on the wall behind the bed, with a rug on the floor enhancing the space's warmth.

Condo in Dennis Port

4.86 out of 5 average rating, 7 reviews

Renovated Beach Condo - Pool - Hot Tub - Fire Pit!

Your family will be close to everything when you stay at this centrally-located beach condo! Swim in the heated outdoor pool and hot tub. Enjoy the BBQ or sunsets from your large private deck. Later in the evening, why not stop by the fire pit while your worries drift away. Nothing says summer on Cape Cod like a cozy beach condo in Dennis Port. Head straight to the pool or the beach! With a fully equipped Kitchen with all the necessities, this renovated condo is a beach lover’s paradise.

Guest favorite

An outdoor area features a spacious table with four chairs under a large yellow umbrella, providing shade. Nearby, a private hot tub is tucked away among trees, while a small white side table and a blue adirondack chair complete the relaxing ambiance.

Home in Dennis Port

4.93 out of 5 average rating, 15 reviews

Sauna, Hot Tub, Walk to Beach -Seaglass Cottage

Come enjoy our cozy year-round beach house! Located a short walk to Haigis Beach in Dennis Port, and less than .5 miles to multiple restaurants, cafes, ice cream and shops. Our home features an infrared sauna, private outdoor hot tub, wood burning fireplace, outdoor shower and a large sun lit deck. The sauna and hot tub are brand new this Spring!! Multiple outdoor games as well as relaxation areas make this a wonderful home for a Cape escape. Please read about our space for more details

Top guest favorite

Home in Harwich Center

5 out of 5 average rating, 30 reviews

Harwich Haven: Pool & Fire Pit

Welcome to The Harwich Haven! This 4-bed, 3.5-bath retreat in Harwich, MA offers a spacious family room, modern kitchen, swimming pool, fire pit, two decks with outdoor dining, an outdoor grill, private fenced in yard, two newly renovated ensuite bathrooms with spa amenities and more. With easy access to beaches, restaurants, and shops, it's your perfect vacation getaway! Saturday to Saturday weekly rentals only July & August. 4 night Thursday to Sunday minimum in June.

Guest favorite

A modern kitchen area features sleek cabinetry and elegant lighting that highlights a minimalist dining table set for four. Stainless steel appliances, including a refrigerator and oven, complement the design. Morning light streams through a nearby door, enhancing the inviting atmosphere.

Apartment in Dennis

4.9 out of 5 average rating, 50 reviews

Chic Condo Near Mayflower Beach

Stylish, renovated condo with pool access—just 4 mins to Mayflower Beach! *Pool is being repaired and not usable until mid- July. We are very sorry.* Sleeps 4 with queen bed + sofa bed. Enjoy a fully equipped kitchen, walk-in shower, in-unit laundry, smart TV, Roku, AC (Memorial Day Weekend-to mid September, roughly) and fireplace. Dedicated workspace. Nestled in Dennis Village, steps from top restaurants. Perfect for couples, small families, or a peaceful getaway!

Superhost

An elevated deck overlooks a serene river view, featuring several white Adirondack chairs and a red picnic table. The warm wooden floor enhances the inviting outdoor space, complemented by lush greenery in the background under a clear blue sky.

Apartment in South Yarmouth

4.75 out of 5 average rating, 4 reviews

Studio w/ Kitchenette & Patio in Cape Cod

Discover comfort and charm in this cozy studio at Riverview Resort in South Yarmouth. Ideal for couples or small families, the unit features a queen bed and sleeper sofa, perfect for up to 4 guests. Enjoy a private balcony, a convenient kitchenette, and a relaxing living area with a flat-screen TV. With free WiFi, air conditioning, and a welcoming atmosphere, it's a perfect Cape Cod escape close to beaches and local attractions.

Guest favorite

A cozy living area features light wood paneling and large windows allowing natural light. A gray sofa is paired with a wicker rocking chair, and a white TV console sits opposite. A decorative sign displaying 'COTTAGE' adds a charming touch.

Tiny home in Dennis Port

4.96 out of 5 average rating, 26 reviews

Cozy cottage steps to the beach!

PLEASE NOTE BED LINENS (QUEEN) AND TOWELS NOT PROVIDED. You’ll treasure your time at this memorable place that is steps from a heated outdoor pool, gas grills, and the beach! Close to shopping and restaurants and everything mid Cape Cod has to offer. The complex is located directly across the street from Glendon Road Beach and next to the Sailing Cow restaurant. Relax onsite or explore, it is up to you!

Guest favorite

An inviting living space is highlighted with a grey sofa, modern dining table with four chairs, and bright windows allowing natural light. The kitchen has sleek cabinets and appliances. Below, the scenic Keyes Memorial Beach is shown with soft sand and a sunset. A community pool featuring turquoise water and lounge chairs is also visible.

Apartment in Hyannis Port

4.87 out of 5 average rating, 101 reviews

Cute Cottage Near Beach & Main Street 3BR/3BA (15)

Stay at a charming 3-Bedroom cottage in a beautiful setting within walking distance to Cape Cod's warm sandy beaches and Main Street Hyannis. Captain Gosnold Village is ideally located within a short walk from three of the Cape's best beaches and nestled between picturesque Hyannis Port and the vibrant atmosphere of Hyannis Harbor with its island ferries, sightseeing and fishing charters.