Vacation rentals with a pool in Dennis Port

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Top-rated rentals with a pool in Dennis Port

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Mashpee

4.97 out of 5 average rating, 101 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to our beautiful Cape Condo located in The Mews at New Seabury Country Club in Mashpee, MA. Our unit provides access to a private condo association pool a 3 min walk from the unit. Also, we have: -5 min bike/car ride to beach -2 bicycles available for use -Central air, wifi, cable, gas grill -Located on Championship Golf Course -Beach chairs, beach towels/toys -New Seabury Village restaurants, mini-golf, bowling, museums -20 min drive to Hy-Line Ferry to Nantucket/Martha's Vineyard

Nov 7 – 14

G$42,556 GYD per night

Guest favorite

Condo in Brewster

4.97 out of 5 average rating, 158 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!

Jan 2 – 9

G$51,675 GYD per night

Guest favorite

Condo in Dennis

4.93 out of 5 average rating, 29 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.

Oct 25 – Nov 1

G$31,443 GYD per night

Guest favorite

Condo in Dennis

4.9 out of 5 average rating, 70 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.

Feb 9 – 16

G$34,523 GYD per night

Guest favorite

Cottage in Sandwich

4.92 out of 5 average rating, 133 reviews

Blue Anchor Cottage - private hot tub getaway!

This newly renovated cottage is an amenity-filled launching point to explore all of Cape Cod! Just 0.4miles to the beach and with our own salt water pool, you’ll be able to fully enjoy the Cape's most historic town. Some of our favorites nearby: 2min- your local coffee shop 2min- great fish tacos + bar 2min- nice conservation area hike 2min- local convenience store 7min- downtown Sandwich 7min- golf course 9min- Sandwich Boardwalk 10min- Heritage Museums & Gardens 22min- Cape Cod Rail Trail

Sep 5 – 12

G$96,359 GYD per night

Guest favorite

Apartment in Dennis

4.88 out of 5 average rating, 16 reviews

Pool condo in Dennis Village, 4 mins to Mayflower

Relax in this calm, stylish, new, fully equipped 1 BR condo. “Cape Storia d’ Amore” is 4 mins from Mayflower in the heart of Dennis Village. Located less than 5 minutes from The Merc, Scargo, Oliver's & Planck's Tavern & more. 12 minutes from Cape Cod Inflatable Park. Large, fully enclosed pool is just steps away. new: - kitchen with new range, DW, fridge, Keurig/drip coffee maker, cookware. New bathroom w/walk in shower, washer & dryer. Smart TV, Roku, internet, fireplace, AC in summer.

Nov 3 – 10

G$29,586 GYD per night

Guest favorite

Apartment in Hyannis

4.89 out of 5 average rating, 102 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.

Sep 29 – Oct 6

G$39,288 GYD per night

Superhost

Condo in Dennis

4.83 out of 5 average rating, 18 reviews

1BR 2nd Floor Condo with pool

This 1 bedroom condo has a king size bed, living room, and kitchenette. Close to everything including Bass River Marina across the street with 2 restaurants and boat rentals. Many more dining options close by. In the mood for the beach? Beautiful West Dennis beach is less than a 5 minute drive away. Popular Mayflower beach is less than 20 minutes north. Clean outdoor pool in case you want to stay close. 1 bathroom with shower to wash up after! Smart TV and internet for rainy days.

May 6 – 13

G$30,182 GYD per night

Guest favorite

Home in Dennis

4.89 out of 5 average rating, 28 reviews

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.

Apr 9 – 16

G$47,971 GYD per night

Guest favorite

Condo in Dennis

4.92 out of 5 average rating, 25 reviews

April promo-Location-5 mins to beach-Pvt balcony

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.

Apr 2 – 9

G$37,103 GYD per night

Guest favorite

Home in Barnstable

4.93 out of 5 average rating, 104 reviews

Magical pool home with windmill/new kitchen

This magical, luxurious property has 6 bedrooms, 5 bathrooms & sleeping arrangements for 14 – it’s an excellent choice for a family, an offsite business meeting or a group of close friends looking for the ultimate beachside, pool experience with a four story windmill tower. The welcoming home has everything you’ll need for a comfortable stay, including wireless internet, central A/C, & a new pool. Its 4 story magical windmill will amaze you and your guests.

Nov 4 – 11

G$239,544 GYD per night

Superhost

Condo in West Dennis, Dennis

4.8 out of 5 average rating, 30 reviews

Hidden Hideaway

Welcome to Mid Cape Cod. Location, Location, Location. Wake up in the morning and have coffee on your private patio. The view overlooks the well manicured back yard bordered by tress and bunnies running around. After coffee, walk down main street for breakfast and more coffee at 3 Fins. Now that you are hyped, walk across the street and rent a Kayak or SUP for the day. Paddle out the Bass river down to the Nantucket sound. Have lunch next door at Sundancers.

Apr 22 – 29

G$21,831 GYD per night