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Vacation rentals with a pool in Dennis Port

Find and book unique homes with a pool on Airbnb

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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Home in Harwich

4.79 out of 5 average rating, 14 reviews

4 BD slice of Harwich Heaven

Come to our beautiful, spacious, and comfortable home away from home. Near to many ponds, nature trails, and the Rail Trail bike path. 4 BDs (1 king, 2 queens, 2 twins), 2 1/2 baths, with AC, patio, and in ground pool. Four separate living spaces- cozy living room with large TV, sun filled family room, furnished basement (with entertainment center, perfect for kids & teens), and patio with a pool & BBQ grill- make our place perfect for family gatherings. There's plenty of room to spread out!

Home in Cotuit

4.95 out of 5 average rating, 113 reviews

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

Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/24. The reviews tell all!

Condo in Brewster

4.97 out of 5 average rating, 177 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!

Condo in West Dennis

4.89 out of 5 average rating, 28 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.

Condo in Dennis Port

4.84 out of 5 average rating, 58 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.

Condo in Dennis Port

5 out of 5 average rating, 4 reviews

Cape Cod 1BR Condo on lovely Ocean Front Resort

Take full advantage of the central location and breathtaking beauty of Nantucket Sound when you stay at The Soundings Seaside Resort. The nicely-appointed room on 365 feet of private beach is a great place to base yourself from to experience all that Cape Cod has to offer you and your family. This 1-bedroom suite has a full bath. This unit features a fireplace, while the property offers sweeping views of Nantucket Sound. The suite features balcony/porches and a kitchenette w/full refrigerator

Rental unit in Dennis

4.9 out of 5 average rating, 30 reviews

New condo in Dennis Village, 4 mins to beaches

Cozy up & relax in this calm, stylish, new, fully equipped 1 BR condo (sofa bed in 2025). Cape Storia d’ Amore is 4 mins from Mayflower in the heart of Dennis Village. Less than 5 minutes from all the great dining options in Dennis Village. 12 mins from Cape Cod Inflatable Park. Large, fenced in pool is just steps away. new: - kitchen w/ new range, DW, fridge, Keurig/drip coffee maker, cookware. New bath w/walk in shower, washer & dryer. Smart TV, Roku, internet, fireplace, AC in summer.

Condo in Dennis Port

4.91 out of 5 average rating, 95 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.

Rental unit in West Dennis

5 out of 5 average rating, 11 reviews

New Listing-Bass River Townhouse

Directly across the street from Bass River Marina, this is the perfect spot for your Cape getaway. Spend the day boating, beachcombing, relaxing by the backyard pool or on your own private patio and private balcony. Golf at two of the Cape's best courses and enjoy the best beaches on Nantucket Sound and Cape Cod Bay. Enjoy dinner and live music at one of two restaurants across the street or one of many other wonderful restaurants close by. Come check out all that Cape Cod has to offer!

Home in Yarmouth Port

5 out of 5 average rating, 6 reviews

Luxury heated Pool hot tub near mayflower beach

My newest rental home. I am a Super host. Come book with me with confidence!!! Bring the whole family to this great property with lots of room for fun and relaxing. We have our own Movie theater room in the finished basement including so many games to play. Our backyard is immaculate with a plunge pool that is heated salt water and a hot tub that is open year round. This is the perfect summer vacation spot for your family and friends. So close to all of the Beaches, Restaurants shops etc.

Home in Dennis Port

4.92 out of 5 average rating, 49 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.

Guest suite in Harwich Port

5 out of 5 average rating, 40 reviews

The Port - #5

Come and stay at this classic cape cod oasis directly across the street from Allan Harbor. Tucked in a quiet, family friendly neighborhood. This space has a private entrance with a table for 2, where you can sit, relax and enjoy the fresh air off the comfort of your room. Enjoy easy access to popular shops, restaurants, beaches and a ferry to Nantucket from this cozy getaway. Easy self check in with free parking for 1 car. *Pack n' Play upon request

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Popular amenities for Dennis Port rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in New Seabury

5 out of 5 average rating, 7 reviews

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

Home in Barnstable

4.67 out of 5 average rating, 12 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

Home in Sandwich

4.99 out of 5 average rating, 80 reviews

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

Home in Centerville

4.87 out of 5 average rating, 23 reviews

beautiful cape cod home with pool and hot spa

Home in New Seabury

5 out of 5 average rating, 18 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

Home in East Falmouth

5 out of 5 average rating, 8 reviews

Sunny Loft - Seasonal Pool & Beach access

Home in Plymouth

4.72 out of 5 average rating, 57 reviews

The Poppy: Tranquil Family Home With Arcade

Home in Sandwich

5 out of 5 average rating, 8 reviews

Cape Oasis with pool + privacy. New Summer 2024

Condo rentals with a pool

Condo in Dennis Port

4.84 out of 5 average rating, 76 reviews

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

Condo in Brewster

4.9 out of 5 average rating, 39 reviews

Ocean Edge: 2 bed/2 bath - Indoor Pools/Gym!

Condo in Brewster

4.98 out of 5 average rating, 56 reviews

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

Condo in West Dennis

4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

Condo in West Yarmouth

4.75 out of 5 average rating, 4 reviews

Cape Cod, South Yarmouth July 19-26. Sleeps 8

Condo in Hyannis Port

4.82 out of 5 average rating, 17 reviews

Beachfront Complex in Hyannis

Condo in Brewster

5 out of 5 average rating, 71 reviews

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

Condo in Dennis Port

4.75 out of 5 average rating, 8 reviews

A Beautiful Es-Cape

Quick stats about vacation rentals with a pool in Dennis Port

Total rentals
120 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
630 reviews
Family-friendly rentals
40 properties are a good fit for families
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
110 properties include access to wifi

Destinations to explore