Vacation rentals with a pool in Dennis Port

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Top-rated rentals with a pool in Dennis Port

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The exterior of the cottage-style condo displays a welcoming entrance under a clear blue sky. Lush green shrubs and flowering plants add a vibrant touch, while a grill is positioned on the porch, inviting outdoor gatherings.
Condo in Harwich Port
4.71 out of 5 average rating, 28 reviews

Cape Cod Condo,Walk to Beach, near Nantucket Ferry

Enjoy your next beach vacation at this charming cottagecore-style condo located in the quintessential seaside town of Harwich Port, just a short walk to nearby Wyndemere Bluffs beach.This delightful beach cottage includes 1 bedroom, 1 bathroom, with an additional queen pull out to accommodate 2-4 guests. Grill out on the porch, take a stroll down Main St for ice cream or lobster rolls, or take a dip in the private community pool (steps from your front door)!Nantucket ferry 1 mile down the road!

Guest favourite
A spacious backyard is featured, highlighting a refreshing oval pool surrounded by a textured patio. Lounge chairs are positioned for relaxation under the sun. Lush greenery and trees provide a natural border, while a well-kept lawn enhances the inviting outdoor space.
Home in Chatham
5 out of 5 average rating, 8 reviews

Heated Pool. Hot Tub. Game Room. Beach Nearby!

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!

Top guest favourite
The balcony offers a view of the lush golf course, framed by trees and natural landscape. A round table with two high stools sits center stage, accompanied by a candle, creating a peaceful outdoor setting for relaxation.
Condo in Brewster
5 out of 5 average rating, 100 reviews

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth

Modern 2nd floor 2 bed/2 full bath Ocean Edge condo located in the heart of Brewster with balcony overlooking the resort golf course. Access to OE resort amenities (additional fees apply). Easy access to Cape Cod Rail Trail. Scenic route 6A offers arts & crafts galleries, coffee places 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. 15 minute walk to Ellis Landing Beach, great sunsets! Central A/C and heat

Guest favourite
A paved outdoor seating area is visible with several round tables and chairs arranged to provide views of the water at sunset. The sky features warm hues of orange and purple as the sun dips below the horizon, with the ocean beyond and neighboring houses in the background.
Apartment in Dennis Port
5 out of 5 average rating, 7 reviews

Steps to the Beach & Heated Pool!

Super cute, remodeled 1 bedroom/ 1 bath, 1st floor condo! Partial Ocean Views! Steps away from Glendon Beach, Heated Pool & The Sailing Cow Restaurant! Master bedroom with queen-sized bed & large closet; queen sleeper sofa & smart tv in living area; fully equipped kitchen & dining space; cable tv, Strong Wi-Fi!; ac/heat; outdoor barbeque and seating area. Heated pool is open from Memorial weekend to mid September. Sorry, BED LINENS AND TOWELS ARE NOT PROVIDED**BRING YOUR OWN** No pets :(

Top guest favourite
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, 128 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 favourite
A bright and airy studio features a queen bed with a soft blanket, paired with a small dining table and chairs. The kitchenette is equipped with modern appliances, while a flat-screen TV hangs above. A large window opens to a private balcony with outdoor seating.
Condo in West Dennis
4.97 out of 5 average rating, 67 reviews

Oct + Nov Discount | Central | Private Balcony

Enjoy Fall on the Cape! 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 favourite
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, 115 reviews

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio (Unit #1) 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 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.

Top guest favourite
An aerial view showcases a tranquil swimming pool surrounded by a spacious lawn. Adjacent seating areas, including sun loungers and a fire pit with chairs, are positioned within the private fenced yard. Lush greenery and garden beds enhance the outdoor space.
Home in Harwich Center
5 out of 5 average rating, 32 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.

Top guest favourite
The exterior of a contemporary cottage is seen, featuring a light-colored wooden facade and a circular window. An American flag is displayed proudly from the front. A fenced yard surrounds the property, complemented by greenery and a gravel pathway.
Cottage in Dennis Port
4.9 out of 5 average rating, 87 reviews

Bright and Lovely Cottage With Community Pool

Skylights and lots of windows make this contemporary cottage appealing. Just over 1/2 mile to the ocean! Quiet community with pool. One bedroom with queen bed. Loft with twin bed. WIFI, outside shower, locking shed, private deck, fenced yard. Come and relax. Please inquire for any possible flexibility in calendar dates and arrival or check-out times. We will try to help. Incredible bike path nearby!! Sorry - no smoking and no pets.

Top guest favourite
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, 164 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).

Top guest favourite
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 homes in Dennis Port
4.97 out of 5 average rating, 29 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 favourite
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
4.86 out of 5 average rating, 107 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.

Popular amenities for Dennis Port rentals with a pool

When is the best time to visit Dennis Port?

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Avg. price$652 CAD$652 CAD$652 CAD$683 CAD$452 CAD$539 CAD$661 CAD$676 CAD$504 CAD$442 CAD$633 CAD$633 CAD
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Quick stats about vacation rentals with a pool in Dennis Port

  • Total vacation rentals

    Explore 120 vacation rentals in Dennis Port

  • Nightly prices starting at

    Dennis Port vacation rentals start at $126 CAD per night before taxes and fees

  • Verified guest reviews

    Over 830 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    120 of Dennis Port vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Dennis Port rentals

  • 4.7 Average rating

    Dennis Port stays receive an average rating of 4.7 out of 5 from guests