Top Dennis Port rentals with pool or private pool - Massachusetts

Explore Dennis Port rentals with pools

Edgewater Beach Resort, a VRI resort

Sleeps 4 · 1 bedroom

Outside Unit 18 - End unit closest to the beach

Charming Studio less than 200 steps to Glendon Beach - 200 Captain Chase Rd #18

Sleeps 2 · 1 bathroom

Top rated rentals with pools - Dennis Port

Premier Host

Easy Getaway

Clear instructions, clean, recently renovated. Cold AC, clean linens. Full bed.

Tyler J.

Stayed Jul 2025

Perfect stay

Wow, perfect location. The condo was set up perfectly. Every morning we would get up and look out at the ocean right outside our window for our beach day. We just walked downstairs and set up chairs. It was very clean and it had everything we needed. Definitely going back.

Bob G.

Stayed Jun 2025

Spotlessly Clean

This little condo is fresh, clean, and updated. Owner sent access info ahead of time giving peace of mind, dedicated wifi for just this unit, 7 minute walk to Inman beach! Location is wonderful - close to beach and great food options in Dennisport. Ideal stay for a single or couple with a small child - tons of beach toys and supplies included on the private deck.

Kurt K.

Stayed Apr 2025

Queen size bed in open living area - 200 Captain Chase Road Dennis Port

Premier Host

Long Weekend Getaway

We enjoyed our stay very much! What a great little place with all the comforts of home. Very short walk to the beach and The Sailing Cow for great food and beverages! We will see you again! Dennis

Dennis L.

Stayed Sep 2024

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Frequently asked questions

Are there any vacation rentals with a pool in Dennis Port?

Pick one of our 201 vacation rentals with a pool and begin organizing your trip to Dennis Port. Whether you're staying in Northwest Harwich, Harwich Center, Bass River or another in-demand area, you'll discover the ideal poolside property on Vrbo.

How much does it cost to stay in a vacation rental with a pool in Dennis Port?

Prices vary depending on length of stay, time of year and exact location, so enter your trip details to find a stay where splashing good times await. Whatever your budget or style, Vrbo has vacation rentals with a pool in Dennis Port suited to all types of guests.

When is the best time to book a vacation rental with a pool in Dennis Port?

If you'd love to visit Dennis Port at one of its busiest times, plan your trip for May. That's when average temperatures range from 51ºF (11ºC) to 55ºF (13ºC), and when many guests book a vacation rental with a pool in this destination. Of course, there are other good times to visit this corner of Cape Cod, so do some research into which month or season is the best fit for your plans.

What vacation rentals with a pool in Dennis Port have nice views?

Unwinding is effortless at our vacation rentals with a pool in Dennis Port. Enjoy a leisurely swim or just take in the vistas. Filter your search by "Recommended" or "Guest rating" to discover exceptional properties where you can immerse yourself in the picture-perfect scenery as your stresses float away.

Are there vacation rentals with a private pool in Dennis Port?

Select a vacation rental with a private pool in Dennis Port and go for a morning swim or late-night dip — or anytime you want! You can keep your little ones easily entertained, and you'll never have to worry about sharing with anyone else. Use our "Private pool" filter to discover your ideal stay.

What are the top things to do in Dennis Port?

It's easy to see why many families love Dennis Port, with top-rated attractions like Cape Cod Museum of Art, Cape Cod Museum of Natural History and Hyannis Harbor to explore. Uncover this destination's best sights together and then return to the comforts of your vacation home rental.

Why should I book my vacation rental with a pool with Vrbo?

Whether you're traveling as a couple or with your besties, staying at a vacation rental with a pool promises a new level of fun and relaxation to your escape. And with our flexible cancellation policies, if you have to change plans, you'll get a complete refund as long as you cancel within the time frame set by the property owner. On top of all that, our One Key™ rewards program lets you earn OneKeyCash™* on all eligible bookings on Vrbo, Expedia and Hotels.com. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.