Compare Vacation Rentals & Rent By Owner Homes in Annapolis, Maryland, USA
About Annapolis Vacation Rentals
With more than 1285 Annapolis vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Annapolis.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Annapolis, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Annapolis. Places to stay near Annapolis are 999.38 ft² on average, with prices averaging US $569 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Annapolis with prices often at a 30-40% discount versus the price of a hotel. Just 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 vacation 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 Rentbyowner vacation rentals are available in Annapolis?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1285 in the Annapolis area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO 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 |
