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Annapolis Beach House Rentals & Places to Stay

Find the best beach rentals in Annapolis - We found 110 exact matches

About Annapolis Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Annapolis? PickleTrip™ features more than 110 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Annapolis. Several of these vacation rentals in Annapolis are kid-friendly & family-friendly, and are near top local attraction spots, to give guests an unforgettable travel experience. PickleTrip™’s rental listings come in all shapes and sizes for large groups, friends, or couples, or wedding retreats in Annapolis.

PickleTrip™ Offers 110 holiday homes and places to stay in Annapolis. The site provides unique Airbnb, VRBO, PickleTrip-style accommodations to fit your trip or get away with your friends and family.

PickleTrip™ beachfront rentals give you the best travel experience that makes it easy to find and book the best place to stay at the best destinations.

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Frequently Asked Questions About Annapolis Beach Rentals

There are a lot of options in Annapolis. If you plan on staying in the Annapolis area, consider making a reservation for a few nights at one of these properties as these have been rated the top Beach Home Rentals in Annapolis:

The average cost for a beach rental in Annapolis is $487 per night. PickleTrip has a wide assortment of great beachfront homes near Annapolis that would suit your needs.
Yes, we have 110 beach rentals with pools available in Annapolis. Check our search bar to find a selection of vacation rentals available near Annapolis.
Yes, here are the top beach rentals in Annapolis that allow you to bring your pet:

See all pet-friendly beach rentals in Annapolis on PickleTrip

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Annapolis to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 110 properties with private swimming pools or private homes with indoor pools in the Annapolis area.
About 110 properties in Annapolis boast of having access to hot tubs.