Top Highland Beach rentals with pool or private pool - Annapolis

Explore Highland Beach rentals with pools

Premier Host

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

Sleeps 12 · 3 bedrooms · 2+ bathrooms

Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast

Sleeps 4 · 1 bedroom · 1 bathroom

Premier Host

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Sleeps 5 · 2 bedrooms · 2 bathrooms

Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger

Sleeps 14 · 7 bedrooms · 4+ bathrooms

Top rated rentals with pools - Highland Beach

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

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Frequently asked questions

How much does it cost to stay in a holiday home with a pool in Highland Beach?

Infinity pool or plunge pool, sprawling or compact, peak season or low season — what you'll pay for your stay in Highland Beach depends on various factors. But one thing that remains consistent? Our holiday homes with a pool are where precious family memories are made. To find a place that fits your budget, narrow your search results by price. You can also use our "Discounts" filter to find properties with discounts for longer stays.

When is the best time to book a holiday home with a pool in Highland Beach?

Consider booking your poolside getaway to Highland Beach in August, when the average temperature ranges between 21ºC (21ºC) and 29ºC (29ºC). This is the most popular month for Stayz guests to get a holiday home with a pool in this well-known destination, which is located in Annapolis.

What holiday homes with a pool in Highland Beach have nice views?

Use our convenient "Location" filter to find a holiday home with a pool and the views you'd love to wake up to. Begin by entering the dates you plan to travel to Highland Beach, then narrow your search based on the type of area you'd prefer to stay in. All that's left is to pack your swim gear and you're ready for a splashing good time.