Compare Villas, Resorts, & Rentals in Annapolis, Maryland, USA
About Casai's Private Villas and Holiday Rentals in Annapolis
Discover more than 1287 vacation rentals available in Annapolis. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Annapolis.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Annapolis, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Annapolis. On average, places to stay near Annapolis offer 998.72 ft², with nightly prices averaging US $569.
With Casai, finding and comparing holiday rentals in Annapolis is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Annapolis, MD
Frequently Asked Questions About Annapolis?
What are the top holiday rentals in Annapolis?
- Annapolis waterfront "tiny house" in garden setting
- Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
- Stunning Waterfront Cottage in the Sailing Capital of the World!
- PERFECT LOCATION in the heart of history
- Ultraclean Family Waterfront Home Annapolis Area - 200+ Top Reviews!
- Charming Historic Annapolis Home With Two Off-street Parking Places!
- Island Life! Kent Island Waterfront with Pool-Bring your boat!
- 240' Private Beachfront @Kent Island Love Point - Great for Families
- Renovated Apt In Historic Dist w/2 Parking Spots
How many Casai.com holiday rentals are available in Annapolis?
As of 2026, Casai boasts over 1287 properties listed in the Annapolis area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Annapolis.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Historic District Vacation Rentals in Annapolis, Maryland | 370 |
| Eastport Vacation Rentals in Annapolis, Maryland | 60 |
| Murray Hill Vacation Rentals in Annapolis, Maryland | 796 |
| West Annapolis Vacation Rentals in Annapolis, Maryland | 771 |
| Hillsmere Vacation Rentals in Annapolis, Maryland | 797 |
| Homewood Vacation Rentals in Annapolis, Maryland | 777 |
| Arundel on the Bay Vacation Rentals in Annapolis, Maryland | 157 |
| Epping Forest Vacation Rentals in Annapolis, Maryland | 346 |
| Oyster Harbor Vacation Rentals in Annapolis, Maryland | 229 |
| Atlantis Vacation Rentals in Annapolis, Maryland | 113 |
| Cape St. John Vacation Rentals in Annapolis, Maryland | 161 |
| Hunt Meadows Vacation Rentals in Annapolis, Maryland | 825 |
| Kingsport Vacation Rentals in Annapolis, Maryland | 801 |
| Anchorage Vacation Rentals in Annapolis, Maryland | 689 |
| Winchester-on-the-Severn Vacation Rentals in Annapolis, Maryland | 562 |
| Downs on the Severn Vacation Rentals in Annapolis, Maryland | 144 |
