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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An inviting outdoor space is depicted, featuring a spacious in-ground pool surrounded by lounge chairs. String lights are strung across the pool area, illuminating the backyard. A pool house and umbrellas provide additional amenities, while the home's facade is visible in the background.
Home in Barnstable
4.76 out of 5 average rating, 33 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

Stunning in-ground pool HEATED in May, June, Sept, Oct only. Just 5 minutes from Craigville, Dowses and Covell's Beach! Perfect for mid-size groups or families, this home sleeps 8 and boasts a dreamy, private, fenced-in backyard w/ a, pool house w/ TV & bar, outdoor shower, and cozy patios. Complete w/ all your beach essentials. Conveniently located, we're 13 minutes from Mashpee Commons and 10 minutes from local grocery stores, local bakeries& restaurants. Central to all the Cape has to offer!

Top guest favorite
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 favorite
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 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, 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!

Guest favorite
A sunny outdoor area is showcased, featuring a private heated pool surrounded by lounge chairs. Large blue umbrellas provide shade next to the pool, while decorative landscaping and a wooden playset are visible in the background. The space invites relaxation and comfort.
Home in Harwich
4.89 out of 5 average rating, 19 reviews

Cape Cod Heated Pool Putt-Putt Golf Speak Easy Gam

Nestled in a serene neighborhood, our spacious and beautifully appointed pool house offers the perfect balance of comfort, style, and convenience. The centerpiece is the private heated pool, perfect for taking refreshing dips or lounging. Enjoy alfresco dining with the gas grill and outdoor seating area, ideal for family barbecues or sunset cocktails. As night falls, gather around the firepit to share stories and enjoy the starry sky—your own private escape just steps away from the front door.

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, 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 favorite
Home in Chatham
5 out of 5 average rating, 9 reviews

Luxury Home w/ Salt Water Pool Overlooking Ocean

Welcome to your dream Cape Cod getaway! Our brand-new, fully renovated 4-bedroom, 5-bath luxury home offers breathtaking views of Buck’s Creek and Nantucket Sound, creating the perfect backdrop for your vacation. Inside, you'll find a stunning cathedral-ceiling living room designed for relaxation and gathering. The chef’s kitchen features a massive 15-foot eat-in island, perfect for family breakfasts or evening cocktails. Each of the spacious bedrooms offers comfort and privacy.

Guest favorite
A dining area features a large wooden table surrounded by eight chairs, positioned on a soft area rug. Natural light filters through the sliding glass doors, enhancing the space that opens to the kitchen, which is equipped with modern appliances and ample cabinetry.
Home in East Dennis
4.85 out of 5 average rating, 13 reviews

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10

Welcome to Sesuit Harbor Hideaway – your perfect Cape Cod getaway! This spacious 4-bedroom, 3-bathroom home offers a relaxing escape, complete with all the amenities you need for an unforgettable vacation. Nestled in a quiet, charming neighborhood, it’s ideal for families, friends, or groups looking to enjoy the best of the Cape. 6min to Cold Storage beach 5min to Sesuit Harbor Café 3min to Dennis Pines Golf Course 3min to Scargo Tower 10 minutes to Mayflower Beach

Top guest favorite
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.

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
4.97 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 favorite
Home in East Dennis
5 out of 5 average rating, 18 reviews

Hot Tub, Game Room, near mayflower beach

Your family will be close to everything when you stay at this centrally-located place. 3 miles to Mayflower beach and Coorporation beach. 10 minutes to Harwich port and Chatham. Great location. Private new hot tub. 4 bedrooms. Sleeps up to 12. Game room fire pit bbq and so much more. Create your cape memories year after year at this perfect cape cod gem. No parties.

Top guest favorite
The exterior of the Cape Cod cottage is shown, featuring a light-colored siding and a unique turret-like structure. Lush green landscaping surrounds the home, which is set back from a gently curved pathway. Tall trees provide natural shade in the area.
Townhouse in Brewster
4.87 out of 5 average rating, 113 reviews

Ocean Edge Cape House with Beach, Pool, and AC

Your dream Cape Cod getaway awaits! This classic Cape Cod cottage is nestled in the heart of Brewster, offering a perfect blend of comfort, relaxation, and outdoor adventure. With access to a private beach, resort-style amenities, and iconic local attractions, this is the ultimate retreat for families, couples, or groups looking to experience the best of the Cape.

Popular amenities for Dennis Port rentals with a pool

When is the best time to visit Dennis Port?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$97,287 GYDG$97,287 GYDG$97,287 GYDG$101,889 GYDG$67,368 GYDG$80,340 GYDG$98,542 GYDG$100,843 GYDG$75,109 GYDG$65,904 GYDG$94,358 GYDG$94,358 GYD
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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 G$18,830 GYD 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 & kid-friendly amenities

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Dennis Port vacation rentals include wi-fi 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