Annapolis Rentals By Owner

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 Vacation Rentals in Annapolis:

• Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
• 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
• Upscale home with parking for 4 cars in driveway. Walk to downtown.
• Your Annapolis Adventure Starts Here!
• Historic Downtown Charmer, Water Views and Parking!

There are many large, family-friendly vacation homes available in Annapolis; however, here are the most popular family rentals listed on our site:

• Great Entertaining Spot for any Occassion!
• PERFECT LOCATION in the heart of history
• Neptune By The Water
• USNA Luxury Home, parking, pet friendly
• Charming Historic Annapolis Home With Two Off-street Parking Places!

Yes, there are 1 self-catering vacation homes in Annapolis that have hot tubs, swimming pools, & other amenities.

There are many luxury villas and vacation homes in or near Annapolis. Filter by price to compare find the most expensive places to stay on Lakekeoweecabins.

Yes, there are many pet friendly vacation homes and places to stays that are available in or near Annapolis that you may consider.