Owner Direct Vacation
Rentals in Annapolis
The Best Owner Direct Vacation Rentals in Annapolis. Explore thousands of vacation home rentals, large cabins, and villas near Annapolis
GUESTS
Explore the Best Annapolis Vacation Homes
Looking for the perfect place to stay in Annapolis? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Annapolis character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
- Parking
- Accessibility
- Security/Safety
- Parking
- Pool
- View
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- Pool
- Parking
- Pool
- TV
- Parking
- Pool
- TV
- Pet Friendly
- TV
- Balcony/Terrace
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- View
- Parking
- Pool
- View
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- View
- Parking
- Pet Friendly
- Pool
Why Travelers Love Using
Owner Direct to
Find Annapolis Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Annapolis
- Parking
- Accessibility
- Security/Safety
- Parking
- Pool
- View
- Parking
- Pet Friendly
- Pool
Popular Neighborhoods for Annapolis Vacation Rentals
What are the best areas to stay in Annapolis
Discover the top neighborhoods in Annapolis and choose a place that suits your stay.
Sunday Feb 1
Annapolis, Cazadero
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Annapolis vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Annapolis
- Parking
- Pet Friendly
- Pool
- Parking
- Pool
- TV
- Parking
- Pool
- TV
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- Pool
How to Reserve Your Annapolis Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Annapolis Vacation Rental FAQs
1. What are the top vacation rentals in Annapolis?
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:
- Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
- RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do.
- Come take in the ocean, gaze at the starry skies, commune with nature.
- Windsong.Oceanfront Views from ALL rooms, Single Story, & Private Hot Tub
- Spacious Sea Ranch Home With Great Ocean Views
- Stunning Oceanfront Home w/Incredible Ocean Views
- Wake to Whales, Golf the Coast, Unwind in Style
- Amazing ocean views, relaxing home surrounded by nature.
- Kid-friendly, ocean views, private and quiet
- Friends and family will love staying at Tranquility Base in the Sea Ranch
2. Which vacation homes in Annapolis are best for families?
If you are looking for a family-friendly vacation home in Annapolis, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Annapolis:
3. How many vacation rentals are available in Annapolis?
Currently, the total number of properties listed in 2026 is over 213 in the Annapolis area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Annapolis.