Annapolis Summer Rentals, Cottages & Cabins

Book a Place to Stay in Annapolis for Your Summer Getaway

About Annapolis Summer Rental on Casai.co.za

With 197 summer rental in or near Annapolis? Look no further than Casai for your upcoming summer getaway. Whether you're traveling with family, friends, or a group, we offer a wide selection of holiday homes and villas designed for the perfect summer retreat.

Our holiday homes and villas in Annapolis come with a range of top amenities, including private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.

Searching for a relaxing retreat in Annapolis to make unforgettable summer memories? Casai has you covered with a variety of options, including unique condos, luxury resorts, bungalows, cozy cabins, RVs, and cottages in Annapolis.

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Frequently Asked Questions About Annapolis Luxury Rentals

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 Summer Rentals in Annapolis:

In 2025, Casai offers 197 summer rentals in or around Annapolis. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Annapolis is $492. Check the full list of summer accommodations in Annapolis.
There are 197 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Casai.co.za.

Yes, here are some popular summer holiday rentals in Annapolis that have a private or indoor pool:

Check all holiday rentals with a pool in Annapolis on Casai.co.za.

Yes, We have 197 summer rental homes in Annapolis and types of place to stay in Annapolis include:

  • Vacation Homes: 197 available for rent
  • Villas: 197 Rentals available for rent
  • Holiday Apartments: 197 Rentals available for rent
  • Hotels with Suites: 197 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Annapolis. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Annapolis.