Vacation rentals with a pool in Dennis

4.96 out of 5 average rating, 140 reviews

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

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 6/20-9/15/26. The reviews tell all!

4.92 out of 5 average rating, 127 reviews

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.

4.73 out of 5 average rating, 40 reviews

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

This single family house is located at the end of a cul de sac in a quite neighborhood in walking distance to Mayflower and Bayview beaches. You enter through the bright and open kitchen, looking out over the patio and the pool. The open living and dining room open up to a sun room where you can relax after a fun day at the beach. The two smaller bedrooms share a big bathroom with tub and double sink, whereas the master bedroom has its own bathroom. A big dining table can host up to 8 people.

4.96 out of 5 average rating, 27 reviews

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!

Welcome to your Italian Villa in the center of Cape Cod! My father, Sal, created this property to make memories that will last a lifetime. What could be better than a secluded yard that feels like a hidden oasis, but is also walking distance or a short drive to tourism? Walk 0.2mi to ice cream and mini golf. Or, drive 10 mins to local beaches, Hyannis Main Street, island ferries, fishing excursions, whale watching, The Cape Cod Melody Tent, the mall, rt 6, Cape Cod Gateway Airport, and more!

5.0 out of 5 average rating, 8 reviews

Home in South Dennis

Modern Oasis, Heated Saltwater Pool, Beach, Golf

Welcome to an exceptional modern Cape Oasis on a private & quiet cul-de-sac Mins. to Golf, beaches, lakes, bike path Bright airy, spacious, central AC, modern/new furnishing，enjoyable year-round Expansive deck, pool lounge & yard Fenced in w/full privacy Thoughtfully curated for multi families/groups Resort style retreat w/tranquility & fun games Location is virtually close to everything Pool heat: Memorial day weekend -last Sun. of Sept. All essentials provided 6+ free parking

4.83 out of 5 average rating, 12 reviews

Dennis Deluxe King Room | Full Studio w/ Kitchenet

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

4.81 out of 5 average rating, 42 reviews

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!

Stunning in-ground pool HEATED in May, June, Sept only. Pool is opened in May! 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. 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!

4.88 out of 5 average rating, 40 reviews

A compact studio layout features a spacious bed adorned with neutral tones and decorative pillows. A modern kitchen area showcases stainless steel appliances and cabinetry, with a light tile floor enhancing the space. Natural light filters through sheer curtains, creating a bright and airy environment.

Home in Dennis Port

Beachwalk cozy studio with pool!

Your family will be close to everything at this central located studio in the heart of Dennis Port. Walkable 1/2 mile to Haigis Beach or relax by the shared pool! This furnished apt is perfect for 2 people/ baby with a queen bed, a newly renovated full kitchen with stove, fridge, Keurig, microwave and all essentials. Studio has air conditioning, smart TV with cable, Wifi, and access to back patio area with grill and furniture. Parking on premises. Beach chairs and beach wagon included!

4.89 out of 5 average rating, 107 reviews

The exterior of the cottage features a well-maintained lawn with lush green trees in the background. A wooden deck extends from the house, along with patio chairs overlooking a tranquil pond surrounded by vibrant flowers and plants.

Cottage in Centerville

The Holly Cottage

Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

Apartment in Hyannis Port

A private deck is showcased with outdoor furniture, including a round table and chairs. A colorful striped umbrella provides shade, while surrounding greenery and flowers add a natural touch. The deck is well-lit by sunlight, creating a warm and inviting space.

4.9 out of 5 average rating, 155 reviews

Great Location. Near Beach & Main Street. Unit M1

Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker. Keurig, and kettle.

4.96 out of 5 average rating, 28 reviews

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

September: FIVE (5) night minimum stay. August: SEVEN night minimum stay Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. It's all about the views. Our home overlooks the pool, beach and bay. We include: 2-Bikes, 2-Kayaks, and a Barnstable beach pass with beach chairs. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six adult guests plus children. Pool closes: Columbus Day

Home in Barnstable County

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.

4.91 out of 5 average rating, 33 reviews

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!

Popular amenities for Dennis rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5.0 out of 5 average rating, 15 reviews

An expansive in-ground heated saltwater pool is surrounded by a spacious patio. A gazebo is situated nearby, framed by lush trees. Lounge chairs with umbrellas provide shaded seating, while a hammock offers a relaxing spot. The pool reflects the clear blue sky, creating a serene outdoor setting.

Home in North Eastham

Lovely villa w pool/hottub, central AC, near beach

4.92 out of 5 average rating, 52 reviews

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

4.83 out of 5 average rating, 6 reviews

Home in Hyannis Port

Beach house in Hyannis with pool

5.0 out of 5 average rating, 7 reviews

Home in East Dennis

Charming Cape Escape with Pool, Hot Tub & Fire Pit

5.0 out of 5 average rating, 15 reviews

An outdoor seating area features gray cushioned sofas arranged around a dark table. Surrounding trees provide a natural backdrop, while colorful potted flowers add a vibrant touch. The area extends towards a pool visible in the background, enhancing the inviting outdoor atmosphere.

Home in Yarmouth

Fenced Pool, Fire pit, Outside dining, Coffee bar

5.0 out of 5 average rating, 36 reviews

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, 13 reviews

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

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!

5.0 out of 5 average rating, 3 reviews

Home in Falmouth

Pool Escape in East Falmouth

Condo rentals with a pool

4.97 out of 5 average rating, 178 reviews

Condo in New Seabury

New Seabury Cape Condo | Pool & Beach Escape

5.0 out of 5 average rating, 108 reviews

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

A serene pool area is visible, featuring clear blue water under a sunny sky. Poolside loungers are arranged for relaxation, while the two-story condo building with balconies lines the background. Lush greenery and trees enhance the outdoor space.

4.95 out of 5 average rating, 65 reviews

Mary's Cape Escape

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.

4.94 out of 5 average rating, 48 reviews

1BR 2nd Floor Condo with pool

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.

4.86 out of 5 average rating, 63 reviews

Mid Cape Cod, 3 Season Haven by Bass River

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.

4.9 out of 5 average rating, 30 reviews

Carolyn's Bass River Condo

4.83 out of 5 average rating, 82 reviews

A spacious sleeping area features a large bed with neutral bedding and colorful accent pillows. A TV is mounted on the wall. Natural light filters through a sliding glass door, which opens to an outdoor area with a small table and chairs.

Condo in Dennis Port

Cozy Studio Just Steps Away From the Beach!

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.

4.86 out of 5 average rating, 66 reviews

Hidden Hideaway

Other vacation rentals with a pool

The image showcases a heated fresh-water pool surrounded by white lounge chairs, with a fenced area providing a sense of privacy. In the background, the calm waters of Nantucket Sound are visible, alongside a portion of the condominium's exterior, creating a serene poolside environment.

4.83 out of 5 average rating, 40 reviews

Beachside Condo with Balcony - Oceanside Condos

4.96 out of 5 average rating, 28 reviews

Cottage in Yarmouth

Cottage at the Escape Inn

A bright bedroom features blue walls and a floral accent wall. A spacious bed with a textured quilt is positioned prominently. Natural light enters through a skylight, and a flat-screen TV is mounted on the wall. Storage units in warm wood tones complement the space.

4.78 out of 5 average rating, 37 reviews

King Bed Suite (Pet Friendly) in a great location

A covered walkway leads to a grassy area with well-maintained landscaping. Lounge chairs are arranged around a heated pool, with ocean views visible beyond a fenced area. The building's exterior features a wooden overhang, providing shade along the path.

4.82 out of 5 average rating, 11 reviews

Skip to Beach, Cape Cod Condo!

4.9 out of 5 average rating, 92 reviews

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

4.87 out of 5 average rating, 67 reviews

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

4.96 out of 5 average rating, 26 reviews

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.