Holiday rentals with a pool in Harwich

5 out of 5 average rating, 9 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

Heated Pool. Hot Tub. Game Room. Beach Nearby!

Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home features high-end furniture, a pool, hot tub & games including ping pong & air hockey. With kid-friendly amenities, everyone will feel at home. Relax, play & create unforgettable memories in this upscale oasis designed for fun & relaxation! Walk to small neighborhood beach 3 min drive to Jacknife Beach 6 min drive to downtown Chatham Experience Chatham with us & Learn More Below!

5 out of 5 average rating, 100 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.

Apartment in Brewster

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

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

Come to our beautiful, spacious, and comfortable home away from home. Near to many ponds, nature trails, and the Rail Trail bike path. 4 BDs (1 king, 2 queens, 2 twins), 2 1/2 baths, with AC, patio, and in ground pool. Four separate living spaces- cozy living room with large TV, sun filled family room, furnished basement (with entertainment center, perfect for kids & teens), and patio with a pool & BBQ grill- make our place perfect for family gatherings. There's plenty of room to spread out!

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 6/20-9/15/24. The reviews tell all!

4.89 out of 5 average rating, 19 reviews

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

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.

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.

Flat 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.

4.91 out of 5 average rating, 115 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.

Apartment in Dennis Port

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.

5 out of 5 average rating, 10 reviews

Home in Chatham

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.

5 out of 5 average rating, 33 reviews

An aerial view showcases a tranquil swimming pool surrounded by a spacious lawn. Adjacent seating areas, including sun loungers and a fire pit with chairs, are positioned within the private fenced yard. Lush greenery and garden beds enhance the outdoor space.

Home in Harwich Center

Harwich Haven: Pool & Fire Pit

Welcome to The Harwich Haven! This 4-bed, 3.5-bath retreat in Harwich, MA offers a spacious family room, modern kitchen, swimming pool, fire pit, two decks with outdoor dining, an outdoor grill, private fenced in yard, two newly renovated ensuite bathrooms with spa amenities and more. With easy access to beaches, restaurants, and shops, it's your perfect vacation getaway! Saturday to Saturday weekly rentals only July & August. 4 night Thursday to Sunday minimum in June.

4.9 out of 5 average rating, 144 reviews

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.

Flat in Hyannis Port

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.

5 out of 5 average rating, 23 reviews

Home in Brewster

Cape Cod Oasis: pool, hot tub, firepit & grill!

Over 4500 sqft of living space in the heart of Cape Cod, with an inviting pool, a hot tub, magnificent garden and expansive outdoor living space big enough to fit your entire party. Welcome to your own private resort! This beautiful custom-built center entrance colonial has room to roam, both inside and out. 5 beds, 5 baths, eco pool, The building is surrounded by lush landscape and tastefully decorated. Fully equipped chef's kitchen. Short drive to the beach!

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.

4.9 out of 5 average rating, 147 reviews

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.

Popular amenities for Harwich rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 22 reviews

A private backyard features a large swimming pool surrounded by a patio with stone paving. Lush greenery and low shrubs border the area, while a wooden table and chairs are positioned nearby. The house is visible in the background, framed by trees.

Home in Mashpee

Beautiful Mashpee Home with Pool

4.88 out of 5 average rating, 40 reviews

Home in Barnstable

Beachside Retreat pool&spa bball court

4.97 out of 5 average rating, 29 reviews

An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.

Home in New Seabury

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

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.

4.88 out of 5 average rating, 25 reviews

Mansion with Heated Pool Near Ocean

4.74 out of 5 average rating, 69 reviews

Summer pool, game room arcade and room for 10!

4.85 out of 5 average rating, 66 reviews

A charming Cape-style house is surrounded by lush green grass, featuring a well-maintained front yard adorned with flower beds and small American flags. The entrance is highlighted by a decorative door with a wreath, framed by neatly arranged bushes. A single-car garage is visible on the right.

Home in Mashpee

Sunny Cape w/Private Pool, Steps to Private Lake

The exterior of the beach house is presented, featuring multiple stories and a light grey facade. A lap pool is nestled beside a spacious patio, equipped with lounge chairs and an umbrella. Lush greenery surrounds the property, enhancing the serene environment.

4.94 out of 5 average rating, 48 reviews

Getaway with pool

Apartment rentals with a pool

4.82 out of 5 average rating, 74 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.

Apartment in Dennis Port

Cozy Studio Just Steps Away From the Beach!

4.93 out of 5 average rating, 44 reviews

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.

Apartment in West Dennis

1BR 2nd Floor Condo with pool

4.84 out of 5 average rating, 87 reviews

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.

Apartment in Dennis Port

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

4.85 out of 5 average rating, 55 reviews

The living room features two comfortable sofas adorned with colorful cushions, situated around a wooden coffee table on a vibrant area rug. Natural light fills the space, highlighting the dining area and fully equipped kitchen visible in the background.

Apartment in Brewster

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

4.85 out of 5 average rating, 61 reviews

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.

Apartment in West Dennis

Hidden Hideaway

Apartment in Hyannis Port

A serene waterfront view features a wooden dock extending into calm waters, reflecting a colorful sunset with shades of orange and blue. Silhouettes of boats and poles can be seen against the horizon, enhancing the tranquil atmosphere.

4.82 out of 5 average rating, 17 reviews

Beachfront Complex in Hyannis

5 out of 5 average rating, 87 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.

Apartment in Brewster

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

4.97 out of 5 average rating, 68 reviews

A bright and airy studio features a queen bed with a soft blanket, paired with a small dining table and chairs. The kitchenette is equipped with modern appliances, while a flat-screen TV hangs above. A large window opens to a private balcony with outdoor seating.

Apartment in West Dennis

Oct + Nov Discount | Central | Private Balcony

Other holiday rentals with a pool

4.78 out of 5 average rating, 32 reviews

A bright kitchenette area features light wood cabinetry and a blue countertop. Three wooden bar stools are positioned at the counter. A ceiling fan hangs above, and a flat-screen TV is mounted to the wall. Sliding glass doors open to an outdoor view.

Flat in Dennis Port

Beachside Condo with Balcony - Oceanside Condos

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

5 out of 5 average rating, 14 reviews

Home in South Yarmouth

Fenced Pool, Fire pit, Outside dining, Coffee bar

4.89 out of 5 average rating, 57 reviews

A modern kitchen area features sleek cabinetry and elegant lighting that highlights a minimalist dining table set for four. Stainless steel appliances, including a refrigerator and oven, complement the design. Morning light streams through a nearby door, enhancing the inviting atmosphere.

Flat in Dennis

Chic Pool Condo Near Mayflower Beach

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!

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.

Flat in Dennis Port

Steps to the Beach & Heated Pool!

4.94 out of 5 average rating, 31 reviews

The exterior of the cottage is showcased with a textured shingle facade and a white door framed by two green shutters. Surrounding the entrance, vibrant blue hydrangeas bloom, complemented by a neatly trimmed evergreen shrub. A gravel pathway leads to the door, enhancing the inviting appearance.

Cottage in East Sandwich

Charming E. Sandwich Cottage Near Beaches, Dogs OK