Vacation rentals with a pool in Dennis

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Top-rated rentals with a pool in Dennis

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

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Guest favourite

Home in Dennis Port

4.97 out of 5 average rating, 33 reviews

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 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. Parking on premises. All this in the middle of peak summer fun!

Guest favourite

Condo in Brewster

5 out of 5 average rating, 72 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.

Guest favourite

Condo 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

Condo 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

Condo 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.

Top guest favourite

Home in Oak Bluffs

4.93 out of 5 average rating, 199 reviews

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!

Guest favourite

Condo in Dennis Port

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.

Guest favourite

Condo in West Dennis

4.96 out of 5 average rating, 47 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.

Guest favourite

Apartment 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, and kettle. This studio has air conditioning.

Guest favourite

Condo in Brewster

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.

Superhost

Home in Plymouth

4.9 out of 5 average rating, 120 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

Apartment 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!