Vacation rentals with a pool in Dennis

A sandy beach extends along the shoreline, gently lapped by calm waves under a clear blue sky. Small groups of people can be seen enjoying the beach, with the distant landscape of grassy dunes and beach vegetation providing a natural backdrop.

4.86 out of 5 average rating, 58 reviews

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 from Father's Day weekend through Labor Day weekend.

4.92 out of 5 average rating, 49 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

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 - sorry, no parties - (plus pets - fee applies)! Only 3 miles to beaches. The ferry to Nantucket and Martha's Vineyard is not far, and a great addition to any Cape trip!

5 out of 5 average rating, 7 reviews

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

Steps to the Beach & Heated Pool!

World Cup visitors - Only 1.5 hours to Boston Stadium! Great Cape Cod /Boston Location! Sleeps 4. Super cute, remodeled 1 bedroom/ 1 bath, 1st floor condo! Partial Ocean Views! Steps away from Glendon Beach & Heated Pool. Master bedroom with queen-sized bed & large closet; queen sleeper sofa & smart tv in living area; fully equipped kitchen w/Keurig & dining space; cable tv, Strong Wi-Fi!; ac/heat; outdoor barbeque and seating area. Heated pool is open from Memorial weekend to mid September.

4.95 out of 5 average rating, 128 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!

4.72 out of 5 average rating, 39 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.

4.98 out of 5 average rating, 105 reviews

A cozy living area is furnished with a comfortable sofa adorned with decorative pillows. A dining table with seating for four is visible, alongside a well-equipped kitchen in the background. Natural light enters through the windows, highlighting the warm wood floors.

Apartment in Wellfleet

Rock on Wellfleet!

A wonderful Wellfleet location! This second floor rental has a spacious bedroom with a queen bed, bathroom with a tub and living area with a well stocked kitchen. You would have the whole upstairs to yourself with a private door to come and go. You are also invited to use our pool at anytime! We're located very close to the Cape Cod Rail Trail for miles of bike riding, PB Boulangerie Bistro, Marconi Beach, the iconic Wellfleet drive-in and so much more. Bedding, towels and essentials provided.

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.

4.91 out of 5 average rating, 115 reviews

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.

4.94 out of 5 average rating, 71 reviews

A bright studio unit features a queen-sized bed with a comfortable pull-out sofa nearby. Natural light floods the space through large windows. A small dining table with two chairs is positioned next to the seating area, providing a functional living space.

Home in Dennis Port

Walk to the beach or sit poolside! Updated studio!

Adorable condo in the heart of vacationland in Dennis Port! This studio unit is full of natural light and comfortable for two people! The floor plan offers a living area with a queen sized bed and a pull out full sofa. Step out the sliders onto a deck with outdoor seating. There is a shared pool open late June- Aug. All this and right in the middle of the summer fun of Dennis Port and all its activities. The beach is under 1/4 mile away in walking distance. Beach chairs and wagon included!

A cozy sleeping area features a metal bed frame with a blue comforter, accentuated by neatly arranged pillows. Two bedside lamps offer soft lighting beside the bed. Artwork is displayed on the wall behind the bed, with a rug on the floor enhancing the space's warmth.

4.58 out of 5 average rating, 12 reviews

Renovated Beach Condo - Pool - Hot Tub - Fire Pit!

Your family will be close to everything when you stay at this centrally-located beach condo! Swim in the outdoor pool and hot tub. Enjoy the BBQ or sunsets from your large private deck. Later in the evening, why not stop by the fire pit while your worries drift away. Nothing says summer on Cape Cod like a cozy beach condo in Dennis Port. Head straight to the pool or the beach! With a fully equipped Kitchen with all the necessities, this renovated condo is a beach lover’s paradise.

A bright studio space features a full-size bed with a white quilt and decorative pillows. Soft natural light streams through sliding glass doors, which lead to a private outdoor area. A small dining table and two chairs are visible, along with a wall-mounted television.

4.67 out of 5 average rating, 12 reviews

Charming Dennis Port Getaway – Close to Beach!

Escape to this cozy Dennis Port studio condo, just a 10-minute walk (0.4 miles) to Inman Ocean Beach and near Sea View Park Recreation Area. Featuring a full-size memory foam bed, A/C, a Smart TV, and a small kitchenette. Relax in the private fenced-in backyard or take a dip in the seasonal swimming pool after a day at the beach, then explore the many nearby restaurants and shops in downtown Dennis Port and Harwich Port. The perfect spot for a couple’s getaway or solo retreat!

4.88 out of 5 average rating, 17 reviews

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

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

4.93 out of 5 average rating, 100 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.

Popular amenities for Dennis rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.78 out of 5 average rating, 36 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!

5 out of 5 average rating, 15 reviews

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!

4.91 out of 5 average rating, 33 reviews

The backyard features an inground pool illuminated at night, surrounded by wooden decking. Nearby, a shed with white shutters enhances the outdoor space, while lush greenery provides a serene backdrop.

Home in South Orleans

5-bedroom Cape with a pool and yard games.

4.97 out of 5 average rating, 65 reviews

A saltwater pool is set within a stone patio area, surrounded by lush greenery. Lounge chairs and a shaded table with a red umbrella offer comfortable seating options. The serene view of Morey Pond is visible beyond the pool, framed by trees under a clear blue sky.

Home in Plymouth

Our families slice of heaven

4.88 out of 5 average rating, 25 reviews

An aerial view of a spacious backyard features a heated pool surrounded by a grey stone patio. Lounge chairs and umbrellas are positioned around the pool. The house showcases multiple large windows and a deck, with green grass and trees creating a private setting.

Home in Plymouth

Mansion with Heated Pool Near Ocean

4.82 out of 5 average rating, 17 reviews

A heated saltwater pool glistens under the sun, surrounded by a spacious paver patio. The fenced backyard provides privacy, while a light-colored house with a deck offers a welcoming ambiance. Lush trees stand in the background, enhancing the serene outdoor space.

Home in Barnstable

Centerville Oasis, Heated Saltwater Pool!

4.88 out of 5 average rating, 24 reviews

The exterior of the home is presented with natural wood siding, complemented by green shutters. Solar panels are mounted on the roof. A welcoming front porch leads to the main entrance, while a garage is visible to the left amidst well-maintained landscaping.

Home in Harwich Center

4 BD slice of Harwich Heaven

4.9 out of 5 average rating, 155 reviews

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

Condo rentals with a pool

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.

4.82 out of 5 average rating, 74 reviews

Cozy Studio Just Steps Away From the Beach!

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.

4.93 out of 5 average rating, 44 reviews

1BR 2nd Floor Condo with pool

The spacious living area features a queen-sized bed and a comfortable sofa. A dining table with two chairs sits near the window, allowing natural light to brighten the room. Simple decor includes star-shaped wall accents, enhancing the relaxed coastal ambiance.

4.84 out of 5 average rating, 87 reviews

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

4.96 out of 5 average rating, 95 reviews

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

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.

4.85 out of 5 average rating, 61 reviews

Hidden Hideaway

5 out of 5 average rating, 101 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.

4.97 out of 5 average rating, 60 reviews

Mary's Cape Escape

5 out of 5 average rating, 88 reviews

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

Other vacation rentals with a pool

5 out of 5 average rating, 19 reviews

A modern home with light grey siding is featured in the background, surrounded by landscaped gardens. A heated saltwater pool, with clear blue water, is framed by grey stone paving. Lounge chairs and shaded seating are situated beside the pool, enhancing the outdoor space.

Home in Popponesset

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

4.95 out of 5 average rating, 22 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.

4.95 out of 5 average rating, 58 reviews

A view from the deck reveals a well-maintained pool area surrounded by lounge chairs and umbrellas. Adjacent to the pool is a tennis court, framed by greenery, providing a serene backdrop. The water sparkles under a clear blue sky, inviting relaxation.

Home in East Falmouth

Family + Dog Retreat | Fenced Yard + Pool + Beach

4.91 out of 5 average rating, 35 reviews

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

Home w/ golf view, salted heat pool, mins to beach

5 out of 5 average rating, 23 reviews

A sandy beach extends toward calm waters bordered by a tree-lined shore, creating a serene natural setting. The gentle curve of the waterway leads to a distant point, where lush greenery enhances the picturesque landscape. The bright blue sky adds to the tranquil atmosphere.

Home in East Falmouth

Renovated ranch with pool access

Guest suite in Centerville

4.99 out of 5 average rating, 93 reviews

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

4.56 out of 5 average rating, 9 reviews

A well-maintained lawn area features manicured greenery, leading towards the ocean in the background. Beachside umbrellas stand near the building, while picnic tables are positioned for outdoor enjoyment. The expansive grounds are illuminated by sunlight, creating a welcoming environment for guests.

Apartment in Dennis Port

Edgewater Beach Resort - Interval Weeks 30, 31