205+ Annapolis Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Annapolis

Discover more than 205 holiday rentals in Annapolis. Casai holiday homes have everything you need to find a place to stay near Annapolis, CA.

Whether you are looking for luxury villas in Annapolis, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartments for family holidays, or stylish accommodations for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Annapolis with a whole family or group, Casai holiday accommodations will make your trip memorable. We have plenty of places to stay in Annapolis for families, large parties, or private owner accommodations for long or short trips. Annapolis Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Annapolis with Casai. Casai makes it easy to compare and book holiday rentals today.

Show more
Show less

Frequently Asked Questions About Annapolis Holiday 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 Holiday Home Rentals in Annapolis:

There are many holiday rentals available in Annapolis; however, here are a few of the most popular holiday homes listed in Annapolis on our website:
At Casai.co.za most of our places to stay are perfect for families. Check out the complete list of holiday homes in Annapolis to find one that works for you.
Yes, there are 205 self-catering family homes and holiday rentals in Annapolis.
There are more than 205 luxury holiday homes in or near Annapolis, according to 2025 data from Casai.co.za. Consider these homes for your next holiday:
Yes, there are 205 pet friendly rentals that are available in Annapolis.