Vacation rentals with a pool in Dennis

5 out of 5 average rating, 71 reviews

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.

4.97 out of 5 average rating, 180 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries 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. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

A clear blue pool is surrounded by a spacious patio area. Several lounge chairs are positioned nearby under the sun. The pool is accessed via a white gated area, with a clean, inviting atmosphere represented by the well-maintained surroundings.

4.85 out of 5 average rating, 61 reviews

Stylish & Modern Studio Condo - Steps to the Beach

Stay in a renovated modern, cozy studio style condo with walking distance to Glendon Beach. This stylish airy & bright poolside retreat is perfect for couples and solo travelers. A slider door offers direct access to the shared pool area. The kitchenette features quartz counters, a sink, refrigerator, 2-burner cooktop, and a microwave. Enjoy a restful night's sleep with a memory foam mattress and black-out curtains. The home also has a 24" Roku Smart TV for you to enjoy your favorite shows.

4.93 out of 5 average rating, 198 reviews

Home in Oak Bluffs

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

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.

4.9 out of 5 average rating, 98 reviews

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio 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, Bluetooth speaker, and 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.

4.96 out of 5 average rating, 47 reviews

An inviting studio space features a large bed positioned beside a modern kitchen. A dining setup is visible, ready for two people. The outdoors showcases a spacious pool area with loungers, while the greenery and sign add a touch of character to the space.

Condo in West Dennis

6 Min to Beach - Pool - Private Balcony - Central

Back for the 2025 season! Welcome to Seas the Day! This beautifully decorated and cozy condo is located in West Dennis with easy access to all the best attractions. On a warm sunny day, take a 6-min drive to West Dennis beach, walk to the local restaurants, lounge on the balcony, or relax at the pool area. In the evening, prepare a home cooked meal in the full kitchen that is equipped with basic cooking tools and a dining table for two. End the night with a cozy movie on the SmartTV in bed.

Apartment in Hyannis Port

A spacious studio features a queen bed with grey bedding, two chairs, and a small table. A ceiling fan is positioned above. A kitchenette area is visible in the background, alongside a door leading to additional space. Natural light comes through the window, highlighting the wood flooring.

4.88 out of 5 average rating, 125 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, and kettle. This studio has air conditioning.

4.88 out of 5 average rating, 17 reviews

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 South Yarmouth

Carolyn's Bass River Condo

This 600 Sq. Ft. condo is located on Bass River. This vacation unit has two levels. The upper level with balcony overlooking Bass River is a combination living room/dining area with a kitchenette plus a full bathroom. The lower level with access to patio is a bedroom with a Queen pillow top bed and a full bed plus a second full bath. Both levels have through the wall AC/heating units. The 18 unit condo complex has a heated pool . Take it easy at this unique and tranquil getaway.

4.92 out of 5 average rating, 50 reviews

Stylish Ocean Edge Condo #TheCouplesNest

Experience Cape Cod from our stylish 2nd floor condo in Fletcher Village at Ocean Edge, Brewster. Centrally located, it offers easy access to beaches, the Rail Trail, and local dining. Enjoy amenities like pools, tennis, and golf. The modern condo features a fully equipped kitchen and a balcony, perfect for relaxation or adventure throughout the year. Whether you're biking on scenic trails or relaxing by the pool, our condo provides the ideal setting for a memorable Cape Cod experience.

4.9 out of 5 average rating, 120 reviews

Home in Plymouth

Seaview Summit | Ocean Views, Indoor Pool, Beach

Welcome to Seaview Summit House, where you can enjoy breathtaking panoramic ocean views, take a dip in our heated swimming pool, and take a short walk to the beach. Our spacious and beautifully decorated home features a large living area with comfortable seating, a fully equipped kitchen with all the essentials, and a dining area that seats everyone. You'll have plenty of room to spread out and enjoy your time together, whether you're lounging inside or soaking up the sun outside.

4.9 out of 5 average rating, 31 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.

Apartment in Dennis

Chic Pool Condo Near Mayflower Beach

Stylish, renovated condo with pool access—just 4 mins to Mayflower Beach! Sleeps 4 with queen bed + sofa bed, this summer. Enjoy a fully equipped kitchen, walk-in shower, in-unit laundry, smart TV, Roku, AC (Memorial Day Weekend-to mid September, roughly) and fireplace. Dedicated workspace makes remote work a breeze. Nestled in Dennis Village, steps from top restaurants and a short drive to Cape Cod Inflatable Park. Perfect for couples, small families, or a peaceful getaway!

4.92 out of 5 average rating, 50 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 association pool open mid 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.

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Popular amenities for Dennis rentals with a pool

Kitchen

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Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 18 reviews

The outdoor pool area features a clear blue pool surrounded by a concrete patio. Sun loungers and white Adirondack chairs are positioned nearby. A shaded cabana provides relief from the sun, complemented by lush greenery in the background, enhancing the serene atmosphere.

Home in North Eastham

Heated Pool, Game Room, Projector Room, Private

AstridRating, 5 stars3 weeks ago

If i could give more than 5 starts I would! Stephanie and her place were exceptional! We had a bachelorette party and we stayed at Stephanie’s place. Stephanie went out of her way to help me decorate for the bachelorette party. She was very responsive and so helpful throughout my planning. The house is amazing! Looks exactly like the photos and it is clean and in a safe and quiet neighborhood. There 11 of us and we fit comfortably! Thank you so much for hosting us Stephanie and to anyone booking I would 100% recommend staying here!

4.8 out of 5 average rating, 20 reviews

A spacious in-ground pool is surrounded by a sunbathing area featuring a lounge chair and umbrella. Lush greenery and flowering bushes frame the backyard, while a pool house is visible in the background, equipped with comfortable seating. The pool area invites relaxation and enjoyment.

Home in Barnstable

Stunning Cape Home - Inground Pool, 5 Min To Beach

KristenRating, 5 stars1 month ago

This house and property were charming and beautiful. The location was extremely close to beaches, restaurants, and stores all while being nestled in a quiet neighborhood. Highly recommend!

4.99 out of 5 average rating, 81 reviews

Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

JanelleRating, 5 stars3 weeks ago

We have stayed in multiple houses / penthouses throughout the U.S. , however, this home surpassed them all. Jennifer was amazing from the beginning of the booking with answering my questions and went above and beyond to make this special occasion memorable. The house is well equipped! The sounds of birds chirping in the morning , the breeze, and the view of the pond when drinking coffee was so serene. The space in the house was more than I expected with everyone having lots of space to enjoy all the designated areas for playing board games, Video game room( so cool) , reading , watching tv - there was a room for everyone’s enjoyment from our 12 year old, 17, 25, to my 78 year old parents. The well thought out toiletries in every bathroom, spa slippers and robes in each bedroom, ear plugs located by the bedside, laundry room that has labeled racks of beach items and games , kitchen with all its wonderful amenities- I can do on and on. We WILL be back !

4.95 out of 5 average rating, 19 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

LaurelRating, 5 stars2 weeks ago

This was our second time staying at Paul’s home, and once again had a wonderful experience! Paul and Meredith are welcoming, kind, and friendly. The house is spacious, and has plenty of room for our family to enjoy a week together - relaxing, cooking and playing games. The views are beautiful, and we enjoyed lots of time bird watching and soaking it in. We enjoyed easy access to our favorite Cape restaurants and shopping. This home is perfect for a Cape getaway, and Paul is a fantastic host!

5 out of 5 average rating, 27 reviews

A spacious backyard features a large swimming pool surrounded by a well-maintained lawn. Comfortable lounge chairs are arranged along the pool's edge, while a charming shed is visible in the background. Lush greenery borders the area, enhancing the outdoor setting.

Home in Buzzards Bay

Cape House with Pool by Canal

SamanthaRating, 5 stars9 months ago

This home was great for our family. The pool and backyard are beautiful, and the house was clean and welcoming. There are a lot of activities in the area. I would stay here again!

4.92 out of 5 average rating, 50 reviews

A spacious, inviting pool is surrounded by a stone patio and lush greenery. Several lounge chairs are positioned around the pool, offering relaxation spots. The clear blue water reflects the sunlight, while a gentle slope leads to a grassy area beyond.

Home in Dennis

Cape Cod Lakefront Home

JustinRating, 5 stars9 months ago

Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.

5 out of 5 average rating, 13 reviews

An in-ground pool is surrounded by a spacious patio, featuring several blue lounge chairs. Lush greenery frames the area, with a clear blue sky overhead. The pool’s water reflects the sunlight, creating a refreshing ambiance for relaxation and entertainment.

Home in Hyannis Port

Home in Hyannis Port

Ryan & LindsayRating, 5 stars3 days ago

Our family of five had a wonderful stay! We picked the location because it was in the middle of the Cape and easy for us to explore the coast. The house is newly renovated and in pristine condition. The beds were comfortable and the bathrooms were fresh and new. We had plenty of space and felt right at home. The host was very responsive. We highly recommend!

4.95 out of 5 average rating, 114 reviews

A private, gated pool is surrounded by a concrete deck and bordered by lush greenery. The sparkling blue water is enhanced by a bright yellow floating ring. In the background, a spacious sunroom and outdoor seating areas are visible, offering convenience and leisure options.

Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

ZackRating, 5 stars7 months ago

Awesome stay! Great house/location and Sandy is an awesome host. Highly recommend

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Condo rentals with a pool

5 out of 5 average rating, 21 reviews

A clear, inviting pool is seen with a smooth surface reflecting the sky above. Lounge chairs are arranged neatly around the pool area, with several placed alongside a white picket fence. The tranquil setting is enhanced by distant views of the horizon.

Condo in Vineyard Haven

Relax....You're on Island Time......

JocelynRating, 5 stars9 months ago

Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

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.

4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

NupurRating, 5 stars9 months ago

Perfect little studio for two people! Great location - close to beaches and restaurants and there’s even a pool! Michael was super responsive and the place was exactly like the pictures!

4.9 out of 5 average rating, 29 reviews

A clean outdoor pool is framed by a spacious concrete deck with lounge chairs positioned nearby. Lush greenery and landscaped areas are visible around the pool, contributing to a serene environment. The sky above is clear, enhancing the bright atmosphere of the setting.

Condo in West Dennis

1BR 2nd Floor Condo with pool

MorganRating, 5 stars1 week ago

Amazing stay!! Me and my best friends had a great weekend away!!!! Keith was great!!! Would 100% recommend!

A charming, single-story building is visible from the road, featuring a gray exterior and a white picket fence that encloses a well-kept yard. Leafy trees provide shade, and clear blue skies are overhead, creating a welcoming ambiance for guests.

4.84 out of 5 average rating, 76 reviews

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

ChrisRating, 5 stars9 months ago

Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.

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.

4.88 out of 5 average rating, 40 reviews

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

JasonRating, 5 stars8 months ago

Had a great weekend at Josh’s place! Smooth booking process, great communication, easy checkin. The space was clean and exactly as advertised. I’d definitely recommend both Josh as a host and this location as a Cape getaway!

5 out of 5 average rating, 3 reviews

An outdoor swimming pool is surrounded by chairs and loungers, providing ample space for relaxation. Several guests enjoy the refreshing water, while the building features multiple balconies overlooking the pool area. Lush greenery is visible, adding a touch of nature to the setting.

Condo in West Yarmouth

Family-Friendly 1BR Condo w/ Pools & Kitchenette

JoshuaRating, 5 stars7 months ago

Great hosts! Would definitely stay again.

4.9 out of 5 average rating, 72 reviews

An unheated communal pool is framed by a tan patio and white fencing. Surrounding the pool, blue lounge chairs and umbrellas provide seating options. The two-story building in the background features a deck with stairs leading to the second floor, bordered by green trees.

Condo in Vineyard Haven

Sunny 2bedroom condo w pool, walk to town

ShayRating, 5 stars7 months ago

We had a great time at Leah’s place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.