Holiday rentals with a pool in Dennis Port

4.82 out of 5 average rating, 38 reviews

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.

Flat in Dennis Port

Beachside Condo with Balcony - Oceanside Condos

Charming Cape Cod oceanside condominium unit, located just steps from the warm waters of Nantucket Sound. Queen bed, futon, heated pool, BBQ grill with outdoor table, high-speed wifi, cable, & 2 TVs. Do your own cooking with fully-furnished kitchenette (stove, fridge, microwave, coffeemaker, & utensils), or go out to local restaurants, ice cream sundaes, go-carts, mini-golf, kayaking, or jetskiing. World Cup fans welcome, combine football with a beach holiday. 90 min drive to stadium/matches!

4.92 out of 5 average rating, 119 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

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.

4.8 out of 5 average rating, 10 reviews

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.

Flat in Dennis Port

Skip to Beach, Cape Cod Condo!

Adorable condo with ocean views! We are across the street from Glendon Beach, less than 500 feet away! One private bedroom with a queen bed and a full size pull out couch in the living room that sleeps 2. Kitchen includes full size stovetop, sink, and large fridge. Bathroom is a full bath with shower and tub. Heated pool is right outside the door. Next door to Sailing Cow Cafe for breakfast, lunch and dinner and down the road from the famous Dog House. No pets please! LINENS ARE NOT PROVIDED.

5 out of 5 average rating, 5 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

5 out of 5 average rating, 11 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!

Super cute, remodeled 1 bedroom/ 1 bath, 1st floor condo! Steps away from Glendon Beach & Heated Pool. Saturday to Saturday rentals ONLY for the weeks of 8/15 & 8/22. 2/3 night minimum in Sept/Oct. Master BR has queen bed, closet & smart tv; queen sleeper & 60’ smart tv in living area, Full kitchenette w/Keurig & dining space; Wi-Fi; ac/heat; outdoor barbecue, Patio seeting area w/ sunrise/sunset views, Heated pool open to mid-September. You must bring your own towels & bed linens.

4.96 out of 5 average rating, 50 reviews

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.

4.93 out of 5 average rating, 102 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.

4.9 out of 5 average rating, 151 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.

4.9 out of 5 average rating, 88 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

Skylights and lots of windows make this contemporary cottage appealing. Just over 1/2 mile to the ocean! Quiet community with pool. One bedroom with queen bed. Loft with twin bed. WIFI, outside shower, locking shed, private deck, fenced yard. Come and relax. Please inquire for any possible flexibility in calendar dates and arrival or check-out times. We will try to help. Incredible bike path nearby!! Sorry - no smoking and no pets.

4.97 out of 5 average rating, 30 reviews

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 home 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!

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!

Come stay at the Cape and enjoy this comfortable, DOUBLE-UNIT condominium to do so! Bring your family, or even your friends, and sleep well on the three queen-sized beds in this space! Enjoy breakfast in the 5-chair nook after preparing it in the quaint yet amenable kitchen. Then, walk 5 minutes down to the beach and relax. Come back and cook-out on the large grill on the spacious, private patio.

4.87 out of 5 average rating, 118 reviews

The exterior of the Cape Cod cottage is shown, featuring a light-colored siding and a unique turret-like structure. Lush green landscaping surrounds the home, which is set back from a gently curved pathway. Tall trees provide natural shade in the area.

Townhouse in Brewster

Ocean Edge Cape House with Beach, Pool, and AC

Your dream Cape Cod getaway awaits! This classic Cape Cod cottage is nestled in the heart of Brewster, offering a perfect blend of comfort, relaxation, and outdoor adventure. With access to a private beach, resort-style amenities, and iconic local attractions, this is the ultimate retreat for families, couples, or groups looking to experience the best of the Cape.

Popular amenities for Dennis Port rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 37 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

Harwich Haven: Pool & Fire Pit

4.79 out of 5 average rating, 38 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!

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

4.9 out of 5 average rating, 29 reviews

Home in Brewster

Heated In-Ground Pool and New Central AC!

4.88 out of 5 average rating, 25 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

4 BD slice of Harwich Heaven

4.93 out of 5 average rating, 42 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

Coastal Charm New Seabury: 5BRs with Private Pool

4.92 out of 5 average rating, 51 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

4.95 out of 5 average rating, 133 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

Apartment rentals with a pool

4.85 out of 5 average rating, 60 reviews

Resort Pools & Golf Views · Walk to Bay Beaches

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.

4.96 out of 5 average rating, 99 reviews

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

4.85 out of 5 average rating, 62 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

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.

5 out of 5 average rating, 104 reviews

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

4.97 out of 5 average rating, 61 reviews

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.

Apartment in West Dennis

Mary's Cape Escape

4.86 out of 5 average rating, 59 reviews

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.

Apartment in West Dennis

Mid Cape Cod, 3 Season Haven by Bass River

Apartment in West Yarmouth

A spacious lawn alongside the river features several lounge chairs arranged for guest relaxation. The water reflects the clear blue sky, while boats are visible along the shore. The pathway leads to a low wooden railing that borders the scenic waterfront.

4.75 out of 5 average rating, 4 reviews

Cape Cod, South Yarmouth July 18-25. Sleeps 8

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.

5 out of 5 average rating, 88 reviews

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

Other holiday rentals with a pool

5 out of 5 average rating, 18 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!

5 out of 5 average rating, 3 reviews

A living area features a comfortable sofa and an ottoman positioned on a textured blue carpet. A dining table for four occupies a corner, with large windows showcasing ocean views. A flat-screen television and a fireplace are visible in the entertainment area, enhancing the space.

Flat in Yarmouth

Oceanfron-private beach/pool/balcony views

4.92 out of 5 average rating, 38 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 Orleans

5-bedroom Cape with a pool and yard games.

5 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

4.9 out of 5 average rating, 59 reviews

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.

Flat in Dennis

Breezy Pool Retreat Near Mayflower Beach

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.

Flat in West Dennis

Town House for Cape Cod fun, by Bass River.

4.96 out of 5 average rating, 24 reviews

Home in Sandwich

Coastal Retreat in East Sandwich - Dogs OK!