Holiday 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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Superhost

Flat in Dennis Port

4.76 out of 5 average rating, 17 reviews

Beachside Condo with Balcony - Oceanside Condos

This charming Cape Cod oceanside condominium unit is located only a few steps from the warm waters of Nantucket Sound. Offers a heated fresh-water pool, BBQ grill with outdoor table, high-speed wifi, cable, and 2 TVs. Do your own cooking with the fully furnished kitchenette (stove, refrigerator, microwave, coffeemaker, and utensils), or go out to the local restaurants, ice cream sundaes, go-carts, mini-golf, batting cages, kayaking, & jetskiing. This comfy unit has a Queen bed & pull-out futon.

Guest favourite

Apartment in Brewster

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!

Guest favourite

Apartment in West Dennis

4.9 out of 5 average rating, 30 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 (seasonal). 1 bathroom with shower to wash up after! TV and internet for rainy days.

Guest favourite

Apartment in Dennis Port

4.85 out of 5 average rating, 62 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.

Guest favourite

Apartment in Dennis Port

4.9 out of 5 average rating, 99 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.

Guest favourite

Apartment in West Dennis

4.96 out of 5 average rating, 48 reviews

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.

Superhost

Home in Plymouth

4.89 out of 5 average rating, 121 reviews

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.

Guest favourite

Flat in Dennis

4.91 out of 5 average rating, 33 reviews

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!

Guest favourite

Home in Dennis Port

4.92 out of 5 average rating, 51 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 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.

Guest favourite

Flat in Hyannis Port

4.88 out of 5 average rating, 126 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. Keurig, and kettle.

Superhost

Apartment in West Dennis

4.84 out of 5 average rating, 51 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.

Top guest favourite

Apartment in Dennis Port

5 out of 5 average rating, 22 reviews

Oceanview Condo w/ Fireplace & Patio

Experience the charm of Cape Cod at this spacious 2-bedroom suite at Edgewater Beach Resort in Dennis Port. Overlooking the Nantucket Sound, this beautifully furnished condo offers stunning ocean and courtyard views, private outdoor space, and cozy fireplaces. Families or couples will enjoy the full kitchen, ample living space, and beach access steps away. Perfect for relaxing getaways or year-round escapes by the sea.