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Holiday rentals with a pool in Dennis

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Dennis

  • Total holiday rentals

    Explore 270 holiday rentals in Dennis

  • Nightly prices starting at

    Dennis holiday rentals start at $157 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    270 of Dennis holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Dennis rentals

  • 4.7 Average rating

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

Top-rated rentals with a pool in Dennis

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.

4.99 out of 5 average rating, 105 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

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 through 9/15 this year. Beaches free after Labor Day

4.86 out of 5 average rating, 65 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.

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.

4.93 out of 5 average rating, 134 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

Pool Closes 10/14/25; reopens mid-may for 2026 season. Hot tub open year-round Escape to the Cape at this beautifully maintained home with lovely seasonal heated pool (heated spring/fall). Hot tub available all year. 4 bedrooms, 2.5 baths (2 showers) plus an outside shower May through October. Plenty of room for up to 8 people (plus pets - fee applies) - sorry, no parties! Only 3 miles to beaches. The ferry to Nantucket and Martha's Vineyard is not far, and a great addition to any Cape trip!

4.93 out of 5 average rating, 54 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

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

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.

4.97 out of 5 average rating, 37 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!

5.0 out of 5 average rating, 11 reviews
Top Guest favourite
Condo in New Seabury

New Seabury Cape Condo | Pool & Beach Escape

Top 5% of Air Bnbs! Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

4.97 out of 5 average rating, 183 reviews
Guest favourite
A heated indoor pool is framed by sleek gray walls and illuminated with recessed lighting. Large sliding glass doors offer a view of the outdoor patio. Colorful pool floats and equipment are neatly arranged nearby, providing options for leisure activities.
Home in Plymouth

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.

4.89 out of 5 average rating, 179 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

Not only will you enjoy your stay surrounded by waterfront views from two floors of living space, you’ll be centrally-located to dining, shopping, nightlife, outdoor activities, on-site heated pool, but you’ll be staying next to a Cape Cod landmark! The iconic Lighthouse with the Jolly Captain perched above, has been welcoming visitors over the Bass River Bridge since 1960!

4.87 out of 5 average rating, 39 reviews

Popular amenities for Dennis rentals with a pool

KitchenWi-FiPoolFree 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

4.96 out of 5 average rating, 145 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

4.66 out of 5 average rating, 44 reviews
Superhost
Home in Hyannis

Unique Hyannis house w pool, playground basketball

5.0 out of 5 average rating, 3 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

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!

4.97 out of 5 average rating, 32 reviews
Superhost
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

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!

4.8 out of 5 average rating, 49 reviews
Top Guest favourite
An outdoor oasis showcases a large in-ground pool with sparkling blue water, surrounded by a wooden deck and lounge chairs. A luxurious hot tub sits nearby, with cozy lighting strung overhead, offering a serene atmosphere for relaxation and enjoyment.
Home in Barnstable

Luxury retreat, in-ground pool, 10-person hot tub

5.0 out of 5 average rating, 42 reviews
Superhost
Home in Chatham

7-BR Retreat: Pool, Hot Tub, Sauna, Barn

4.95 out of 5 average rating, 80 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

5.0 out of 5 average rating, 113 reviews
Top Guest favourite
A light-filled living area features a cozy sofa layered with a soft throw, accompanied by a stylish coffee table. The calming wall art depicts ocean waves, while lamps provide additional lighting. A door leads outside, and a chair adds a pop of color.
Condo in West Dennis

1BR 2nd Floor Condo with pool

4.92 out of 5 average rating, 51 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

4.9 out of 5 average rating, 30 reviews
Guest favourite
Condo in West Dennis

Steps from Bass River Marina · Private Balcony

4.96 out of 5 average rating, 83 reviews
Guest favourite
Condo in Brewster

Bright Cape Condo in Ocean Edge

4.92 out of 5 average rating, 25 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

4.88 out of 5 average rating, 72 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

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

Resort Pools & Golf Views · Walk to Bay Beaches

4.87 out of 5 average rating, 77 reviews

Other holiday rentals with a pool

Guest favourite
A private pool area features a rectangular swimming pool surrounded by a concrete deck. Several blue lounge chairs are positioned along the perimeter. Lush greenery and trees provide secluded shade, while a gravel pathway leads to the pool area, enhancing the outdoor experience.
Apartment in West Dennis

Town House for Cape Cod fun, by Bass River.

4.97 out of 5 average rating, 30 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

4.9 out of 5 average rating, 93 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

5.0 out of 5 average rating, 37 reviews
Superhost
Apartment in Dennis Port

King Bed Suite (Pet Friendly) in a Great Location

4.82 out of 5 average rating, 39 reviews
Guest favourite
A charming cottage exterior is showcased, featuring natural wood shingles and red shutters. A bright orange door provides a welcoming entrance. Lush green leaves frame the image, highlighting the serene surroundings of the property against a clear sky.
Cottage in Wellfleet

Wellfleet~Beautiful One Day Perfect The Next

4.87 out of 5 average rating, 67 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!

4.94 out of 5 average rating, 33 reviews
Guest favourite
Home in Sandwich

Family Cape Cod Oasis-Pool-Hot Tub-Game&Kids Room

5.0 out of 5 average rating, 30 reviews
Guest favourite
An inviting outdoor space showcases a rectangular pool surrounded by a spacious patio. Lounge chairs are placed for relaxation, and an umbrella provides shade near the water. Lush greenery frames the area, enhancing the natural setting of the home.
Home in Chatham

Amazing Chatham Pool/patio/deck, 5 BR 4 1/2 Bath

4.95 out of 5 average rating, 62 reviews

When is the best time to visit Dennis?

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Avg. price$393 NZD$376 NZD$577 NZD$412 NZD$393 NZD$468 NZD$802 NZD$798 NZD$611 NZD$367 NZD$384 NZD$524 NZD
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