Vacation rentals with a pool in Dennis Port

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Dennis Port

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

0 of 0 items showing

1 of 3 pages

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

An inviting studio space features a large bed positioned beside a modern kitchen. A dining setup is visible, ready for two people. The outdoors showcases a spacious pool area with loungers, while the greenery and sign add a touch of character to the space.

Condo in West Dennis

4.97 out of 5 average rating, 63 reviews

6 Min to Beach - Pool - Private Balcony - Central

*Pool will be closed on 9/15. Welcome to Seas the Day! This beautifully decorated and cozy condo is located in West Dennis with easy access to all the best attractions. On a warm sunny day, take a 6-min drive to West Dennis beach, walk to the local restaurants, lounge on the balcony, or relax at the pool area. In the evening, prepare a home cooked meal in the full kitchen that is equipped with basic cooking tools and a dining table for two. End the night with a cozy movie on the SmartTV in bed.

Guest favorite

Condo in Brewster

4.97 out of 5 average rating, 189 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 bright studio unit features a queen-sized bed with a comfortable pull-out sofa nearby. Natural light floods the space through large windows. A small dining table with two chairs is positioned next to the seating area, providing a functional living space.

Home in Dennis Port

4.94 out of 5 average rating, 69 reviews

Walk to the beach or sit poolside! Updated studio!

Adorable condo in the heart of vacationland in Dennis Port! This studio unit is full of natural light and comfortable for two people! The floor plan offers a living area with a queen sized bed and a pull out full sofa. Step out the sliders onto a deck with outdoor seating. There is a shared pool open late June- Aug. All this and right in the middle of the summer fun of Dennis Port and all its activities. The beach is under 1/4 mile away in walking distance. Beach chairs and wagon included!

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

5 out of 5 average rating, 5 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

Guest favorite

Condo in Brewster

4.94 out of 5 average rating, 63 reviews

Stylish Ocean Edge Condo #TheCouplesNest

Experience Cape Cod from our stylish 2nd floor condo in Fletcher Village at Ocean Edge, Brewster. Centrally located, it offers easy access to beaches, the Rail Trail, and local dining. Enjoy amenities like pools, tennis, and golf. The modern condo features a fully equipped kitchen and a balcony, perfect for relaxation or adventure throughout the year. Whether you're biking on scenic trails or relaxing by the pool, our condo provides the ideal setting for a memorable Cape Cod experience.

Top guest favorite

Home in Harwich Center

5 out of 5 average rating, 28 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.

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.

Superhost

Home in Plymouth

4.89 out of 5 average rating, 133 reviews

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.

Guest favorite

A welcoming living area features a comfortable sectional sofa and two wooden armchairs arranged around a circular coffee table. Natural light fills the space, highlighting a large area rug on the hardwood floor. A well-equipped kitchen is visible in the background.

Condo in New Seabury

4.97 out of 5 average rating, 154 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).