Top Kent Island rentals with pool or private pool - Maryland

Explore Kent Island rentals with pools

Premier Host

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Sleeps 12 · 3 bedrooms · 2+ bathrooms

House, pond, property. Private beach and Chesapeake Bay is behind far tree line.

Premier Host

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Sleeps 25 · 5 bedrooms · 3+ bathrooms

Premier Host

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Sleeps 8 · 3 bedrooms · 2 bathrooms

Premier Host

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

Sleeps 16 · 7 bedrooms · 5+ bathrooms

Top rated rentals with pools - Kent Island

Premier Host

SPECTACULAR!!!

CONGRATULATIONS! You have found the best house on Kent Island and all of VRBO.We just finished an incredible stay here and were blown away from the moment we pulled up the driveway. The house is spotless, beautifully decorated, and fully stocked with everything you could possibly need. The amenities truly went above and beyond. The outdoor spaces are immaculate and luxurious, with a wraparound porch on both levels and a breathtaking pool. Our family especially enjoyed the daily deer sightings on the property.As for the host, John was extremely hospitable. His attention to detail is unmatched. He was accessible, accommodating, and made sure everything was perfect for our stay.We will forever cherish the family memories we made here. If you're lucky enough to see this place available, book it!

Charlene U.

Stayed June 2025

Premier Host

Great place for a family reunion

Our family was gathered in the area for a wedding. Although we only had nine people sleeping here, we accommodated other relatives for meals and a crab feast. The house has several seating areas, including the beach area, where people could sit down and catch up. Had it been warmer weather, we would have also enjoyed the kayaks and paddle boards. Overall, it suited our needs perfectly.

Kathryn A.

Stayed Oct 2023

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Frequently asked questions

How much does it cost to stay in a holiday rental with a pool in Kent Island?

If you're hoping to save on your holiday rental with a pool, Stayz's filters are here to help. Once you've done your initial search, narrow down your results according to your preferences, including price, location and features and amenities. We've got properties in Kent Island for all types of budgets, so make the most of our filters to discover the perfect stay.

When is the best time to book a holiday rental with a pool in Kent Island?

Think about visiting in May, when the temperature ranges from around 14ºC to 22ºC. This is the most popular month to stay in a holiday rental with a pool in Kent Island.

What holiday rentals with a pool in Kent Island have nice views?

Relaxing is effortless at our holiday rentals with a pool in Kent Island. Go for a swim or simply delight in the views. Tailor your search by "Recommended" or "Guest rating" to discover the very best accommodation where you can immerse yourself in the picture-perfect scenery as your cares drift away.

Are there holiday rentals with a private pool in Kent Island?

Morning, midday or evening, go for a refreshing swim whenever you please when you book a holiday rental with a private pool in Kent Island. To search for Stayz properties that'll increase the fun factor during your trip, use our "Private pool" filter.

What are the top things to do in Kent Island?

With plenty to see and do in Kent Island, you're bound to have a fantastic holiday. Unsure of where to begin? Look up tourism websites or consider booking a local guide. After a day of exploring all the sights, enjoy a swim or just lounge poolside with your loved ones in one of our holiday home rentals.

Why should I book my holiday rental with a pool with Stayz?

No sharing your space, no awkward encounters with strangers. When you select a Stayz holiday rental with a pool, you'll get the entire place to yourself to splash around. Need to amend or cancel your itinerary? Our flexible cancellation policies let you book your rental house with complete peace of mind.