1227+ Private Villas and Holiday Rentals in Annapolis |
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Annapolis Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Annapolis

Discover more than 1227 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 937.58 ft², with nightly prices averaging US $599.

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.

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Top Accommodation Types in Annapolis

Type Count
Vacation Homes 914
Holiday Apartments 114
Cottages 29
Villas 9

Use these Quick Filters to Find a Holiday Rental in Annapolis

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Annapolis.

Weather in Annapolis, MD

View the weather forecast for Annapolis before booking your Annapolis Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Annapolis, MD

Casai offers a large selection of top attractions around Annapolis . Research things to do on your vacation before you visit Annapolis.


U.S. Naval Academy
Six Flags America
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Bowie State University
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
Annapolis Maritime Museum
Allen Pond Park
Maryland Quiet Waters Park
St John's College
Bay Hills Golf Club
Maryland World War II Memorial
William Paca House
The Kunta Kinte Alex Haley Memorial

Other Places to Stay in Annapolis, MD


Northern Chesapeake Bay 10,355 Properties
West Annapolis 710 Properties
Historic District 423 Properties
Parole 78 Properties
Kent Island 67 Properties
Bowie 65 Properties
Eastport 65 Properties
Stevensville 57 Properties
Edgewater 44 Properties
Selby-on-the-Bay 35 Properties
Arnold 30 Properties
Lake Arbor 24 Properties

Frequently Asked Questions About Annapolis?

What are the top holiday rentals in Annapolis?

With numerous options available in Annapolis, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Annapolis:

How many holiday rentals have private pools in Annapolis?

Discover a selection of holiday rentals with private pools near Annapolis with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Annapolis are best for families?

If you're searching for a family-friendly holiday home in Annapolis, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Annapolis:

How many Casai.com holiday rentals are available in Annapolis?

As of 2025, Casai boasts over 1227 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 423
Eastport Vacation Rentals in Annapolis, Maryland 65
West Annapolis Vacation Rentals in Annapolis, Maryland 710
Murray Hill Vacation Rentals in Annapolis, Maryland 427
Hillsmere Vacation Rentals in Annapolis, Maryland 718
Arundel on the Bay Vacation Rentals in Annapolis, Maryland 155
Homewood Vacation Rentals in Annapolis, Maryland 722
Epping Forest Vacation Rentals in Annapolis, Maryland 329
Oyster Harbor Vacation Rentals in Annapolis, Maryland 220
Atlantis Vacation Rentals in Annapolis, Maryland 89
Anchorage Vacation Rentals in Annapolis, Maryland 631
Cape St. John Vacation Rentals in Annapolis, Maryland 176
Hunt Meadows Vacation Rentals in Annapolis, Maryland 776
Kingsport Vacation Rentals in Annapolis, Maryland 737
Winchester-on-the-Severn Vacation Rentals in Annapolis, Maryland 505
Downs on the Severn Vacation Rentals in Annapolis, Maryland 149

People Also Ask

There are 1227 Annapolis, MD Holiday Rentals

Recently Booked Holiday Rentals in Annapolis