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Vacation rentals with a pool in Dennis Port

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Dennis Port

  • Total vacation rentals

    Explore 140 vacation rentals in Dennis Port

  • Nightly prices starting at

    Dennis Port vacation rentals start at $127 CAD per night before taxes and fees

  • Verified guest reviews

    Over 890 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    130 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

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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Top guest favourite
Guest suite in Centerville

“The Hideaway”Private Guest Suite/Pool/Beach Pass

Enjoy a bit of Cape Cod in a friendly and walkable neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Less than 2 miles from Craigville Beach and its beachside walk up shanty’s for lunch. A small beach on Lake Wequaquet is only 2 miles down the road . Main street Hyannis, a walkable downtown with many shops and restaurants is a quick 10-minute drive. Ocean marinas, and ferries to the islands, are a 15 minute drive.

ValueLocationComfort

4.99 out of 5 average rating, 105 reviews
Top guest favourite
An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.
Condo in Brewster

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.

ValueLocationAir conditioning

5.0 out of 5 average rating, 105 reviews
Top 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

Sea Salt Studio - Steps to Glendon Rd Beach

Funky studio (Unit #1) only 175 yards from a white sand beach on Nantucket Sound. 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.

LocationFamilyIndoor spaces

4.93 out of 5 average rating, 134 reviews
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

Bright and Lovely Cottage With Community Pool

(Reservations avail as of my 5/14/27 season opening. Prices now INCLUDE the Airbnb Guest Fee! Only state/local taxes added.) Skylights & lots of windows make this contemporary cottage appealing. A loved location. Just over 1/2 mile to the ocean! Quiet community w/ pool. One bedroom - queen bed. Loft - twin bed. WIFI, outside shower, locking shed, private deck, fenced yard. Come. Relax! Some flexibility re dates and arrival times. Will try to help. Incredible bike path nearby!!

FamilyLocationBiking

4.9 out of 5 average rating, 93 reviews
Top guest favourite
Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

LocationValueComfort

4.99 out of 5 average rating, 103 reviews
Guest favourite
The living area is furnished with two striped sofas and a white coffee table, creating a casual setting. Natural light is provided by a large window with light drapes. A decorative round tray rests on the coffee table, and a lamp stands on an adjacent side table.
Home in Dennis Port

Poolside studio home! A walk to the beach!

Your family will be close to everything when you stay at this central located studio in the heart of Dennis Port. The shared pool is located right outside your door! You’ll find all kitchen essentials, full stove and propane grill. The floor plan offers a large living area with a queen size bed and 2 pull out queen sofas. Step outside via sliders to outdoor seating. Condo is less than 1/4 mile from and within walking distance to the beach. Beach chairs and tent included. Parking on premises.

LocationValueCleanliness

4.94 out of 5 average rating, 62 reviews
Guest favourite
Apartment in Dennis Port

Deluxe Double Room | Full Studio w/ Kitchenette

Dennis Port Surf Club Boutique Hotel – Your ideal Cape Cod getaway at 329 Main Street. Newly renovated and family-friendly, we’re just 5 minutes from the beach and located on Route 28 near top dining, shopping, and attractions. Enjoy our outdoor pool, Jacuzzi, and mini arcade. Rooms include free Wi-Fi, microwave, and mini fridge. Steps from mini golf, arcade, bumper cars, and ice cream. Free parking and a welcoming stay for couples, families, and beach lovers. $85 pet fee not included

ValueLocationCleanliness

4.91 out of 5 average rating, 11 reviews
Superhost
Home in Yarmouth

Heated Pool | 5 Min Walk to Beach | Dog-Friendly

Relax at this charming South Yarmouth retreat featuring an electric-heated saltwater swimming pool and a prime walkable location to the beach. Perfect for families or couples, this spacious home offers modern comforts, a fully equipped kitchen, seven beds, and a peaceful yard. Air Conditioners throughout the home. Dog-friendly, so your furry companion can join the fun! Enjoy the best of Cape Cod with dining, shops, and attractions just minutes away! 23W - Hosted by Tuxfin Hospitality

LocationFamilyAccuracy

5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cottage in Yarmouth

Cottage at the Escape Inn

Guests will have a special experience as this cottage provides a fireplace. Featuring a private entrance, this air-conditioned cottage is consisted of 1 living room, 2 separate bedrooms and 1 bathroom with a bath and a shower. The well-equipped kitchen features a stovetop, a refrigerator, a dishwasher and kitchenware. The spacious chalet offers a tea and coffee maker, a seating area, a wardrobe, a sofa, as well as a flat-screen TV with cable channels. The unit offers 3 beds.

LocationValueNearby

4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in East Dennis

Charming Cape Escape with Pool, Hot Tub & Fire Pit

Welcome to Searside Retreat, your ultimate Cape Cod escape in South Dennis! This charming home offers a private pool, open layout, and modern comforts just minutes from top beaches, restaurants, and shops. Relax in a quiet neighborhood in the heart of the Cape. Mayflower Beach - 10min Chapin Beach - 6 min Cape Cod Rail Trail – 10min The Marshside Restaurant – 2min Sesuit Harbor Cafe - 5 min Scargo Cafe - 5 min Smugglers Ice Cream - 5 min Learn more below!

LocationFamilyHospitality

5.0 out of 5 average rating, 11 reviews
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

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!

FamilyLocationIndoor spaces

4.97 out of 5 average rating, 34 reviews
Guest favourite
The lighthouse features a round white structure topped with a lantern room. A spacious deck wraps around the building, accompanied by a well-maintained lawn and a decorative pumpkin. American flags are displayed, and the surrounding area includes additional nearby structures and views of the water.
Home in West Dennis

Jolly Captain Lighthouse

Ever wanted to stay in a lighthouse?! Well this your opportunity. The Jolly captain lighthouse was originally built in 1960 and recently renovated in 2024-2025. Including breathtaking views of Bass River. Access to community pool is available. In addition, dock slip is available for additional cost. Please contact host privately for additional information.

FamilyLocationHospitality

4.85 out of 5 average rating, 26 reviews

Popular amenities for Dennis Port rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

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

Private Pool, near beaches, 3 BR/3 BA, Central Air

FamilyLocationComfort

4.96 out of 5 average rating, 146 reviews
Guest favourite
Home in West Yarmouth

Coastal Luxury Oasis - Ag2 Luxury Home

FamilyLocationKitchen

4.83 out of 5 average rating, 6 reviews
Guest favourite
A spacious outdoor area is highlighted by a seasonal heated pool surrounded by a wooden deck. Multiple blue lounge chairs are arranged around the pool, and a fire pit table is situated at the center. A large checkers board and garden beds add to the inviting atmosphere.
Home in Yarmouth Port

Winslow Acres [heated] Pool Escape; pool May-Oct

LocationFamilyOutdoor spaces

4.93 out of 5 average rating, 54 reviews
Guest favourite
A bright dining area is illuminated by natural light from large windows, offering views of the waterfront. A small table is surrounded by four blue stools, while a vase of flowers adds a touch of color. A comfortable gray sofa is positioned nearby.
Home in Barnstable County

Waterfront Bass River Jolly Captain

LocationFamilyQuiet

4.87 out of 5 average rating, 39 reviews
Top guest favourite
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

Resort Home, Heated Pool, Putting Green, Game Room

LocationFamilyHospitality

4.93 out of 5 average rating, 29 reviews
Top guest favourite
A refreshing swimming pool is surrounded by a concrete deck, featuring several lounge chairs positioned along one side. Umbrellas provide shade near the pool's edge, and a fenced yard is adorned with greenery, creating a serene outdoor setting.
Home in Barnstable

Beach Pass Included! Brand New Spa! Central AC!

LocationFamilyGrill

4.97 out of 5 average rating, 32 reviews
Top guest favourite
Home in Brewster

Modern Cape, Private Heated Pool, Beach, Golf

ValueFamilySleep quality

4.98 out of 5 average rating, 54 reviews
Top guest favourite
An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.
Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

FamilyLocationBeach

4.97 out of 5 average rating, 32 reviews

Condo rentals with a pool

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

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

ValueLocationAir conditioning

5.0 out of 5 average rating, 113 reviews
Guest favourite
A wooden sign is displayed on a light-colored wall, featuring the phrase 'Heaven is a little closer by the Beach' in white lettering on a teal background. The sign is framed in a rustic white border, enhancing its coastal charm.
Condo in West Dennis

Hidden Hideaway

ValueLocationLayout

4.88 out of 5 average rating, 72 reviews
Superhost
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

Mid Cape Cod, 3 Season Haven by Bass River

LocationFamilyWalkability

4.86 out of 5 average rating, 65 reviews
Superhost
The exterior of a multi-story building showcases a charming design with cedar shingles and large windows. A covered porch with seating is visible at the entrance, while light clouds drift across a blue sky above.
Condo in Dennis Port

Cape Cod 1BR Condo on lovely Ocean Front Resort

LocationFamilyView

5.0 out of 5 average rating, 4 reviews
Guest favourite
Condo in Brewster

Bright Cape Condo in Ocean Edge

LocationValueAir conditioning

4.92 out of 5 average rating, 25 reviews
Guest favourite
A view of Bass River is presented, featuring a calm waterway with several boats docked at a marina. Well-maintained lawns and planted shrubs frame the scene, while a flagpole with an American flag stands in the foreground under a clear blue sky.
Condo in West Dennis

Carolyn's Bass River Condo

LocationBathroomBeach

4.9 out of 5 average rating, 30 reviews
Guest favourite
The living area features a light-colored sofa paired with matching armchairs. A small table holds fresh flowers. Soft lighting from lamps creates a comfortable environment. Large sliding doors provide natural light and open to an outdoor patio with a dining set.
Condo in Brewster

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

LocationFamilyBiking

4.96 out of 5 average rating, 99 reviews
Guest favourite
Condo in Brewster

Resort Pools & Golf Views · Walk to Bay Beaches

FamilyValueHot tub

4.87 out of 5 average rating, 77 reviews

Other vacation rentals with a pool

Superhost
Townhouse in Dennis Port

X Marks the spot

LocationFamilyKitchen

4.86 out of 5 average rating, 7 reviews
Guest favourite
A modern kitchen is displayed, featuring stainless steel appliances, sleek cabinetry, and contemporary lighting along the countertops. A dining table with high-backed stools is positioned near the kitchen, with a decorative vase of yellow flowers adding a touch of color.
Apartment in Dennis

Fall Into Cape Cod | Cape Storia d'Amore

FamilyLocationSleep quality

4.9 out of 5 average rating, 70 reviews
Guest favourite
A spacious bed is adorned with a decorative pillow that reads 'BEACH' in soft hues. A bedside lamp emits a warm glow, and window treatments allow for natural light. A touch of greenery is provided by a potted plant in the corner.
Guest suite in Harwich Port

The Beachcomber - #9

FamilyLocationParking

4.88 out of 5 average rating, 98 reviews
Top guest favourite
Bright and airy living space is highlighted by a spiral staircase leading to an open loft. A plush light grey sofa faces a coffee table on a woven area rug, while a dining table and chairs are visible in the background. Modern kitchen cabinetry offers a sleek contrast.
Apartment in Brewster

Townhouse at Ocean Edge 2B/2B + Loft

FamilyLocationCheckout

5.0 out of 5 average rating, 37 reviews
Guest favourite
A light-filled living area features a beige sofa and a matching loveseat, accented by navy and white decorative pillows. A round wooden coffee table sits in the center, surrounded by a patterned area rug. Sliding glass doors provide access to the outdoor space.
Townhouse in Brewster

Ocean Edge Townhouse/Pool Access

LocationFamilyBathroom

4.87 out of 5 average rating, 46 reviews
Top guest favourite
Home in Popponesset

Popponesset, Exclusive, 3-Bdrm, 4-Bths, Sleeps 6,

LocationFamilyBeach

5.0 out of 5 average rating, 23 reviews
Superhost
A serene backyard setting features a private pool surrounded by a spacious patio. A sunbathing chair and a BBQ grill are positioned nearby, with a house showcasing large windows that invite natural light. Lush greenery frames the area, providing a sense of tranquility.
Home in Dennis

House on Cape Cod with pool close to beach

LocationFamilyGetting around

4.66 out of 5 average rating, 44 reviews
Top guest favourite
A charming single-story home is presented with a neatly manicured lawn, adorned with blooming blue hydrangeas. A flag is displayed on the front porch, and large windows provide a view of the inviting interior. The clear blue sky complements the home's fresh appearance.
Home in Hyannis Port

Renovated Cape Oasis W/ New Pool and Game Room!

FamilyLocationQuiet

4.94 out of 5 average rating, 33 reviews

When is the best time to visit Dennis Port?

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Avg. price$236 CAD$296 CAD$465 CAD$275 CAD$240 CAD$362 CAD$664 CAD$680 CAD$506 CAD$285 CAD$220 CAD$254 CAD
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