Annapolis rentals with pool

Consider one of our 95 vacation rentals with a pool and start organizing your Annapolis trip. Whether you’d like to be in Historic District, Naval Academy, Murray Hill or another well-known neighborhood, you’ll discover the perfect poolside retreat on Vrbo.

Indoor or outdoor pool, one bedroom or many, peak season or low season — what you’ll pay for your Annapolis stay is influenced by all sorts of factors. But the one enduring aspect? Our vacation rentals with a pool are something special. To find a place that suits your budget, narrow your search results by the maximum nightly or total price. You can also use our “Discounts” filter to find vacation rentals that offer savings on longer stays.

With temperatures ranging from around 69ºF (21ºC) to 84ºF (29ºC), August is popular with the majority of Vrbo guests. Be sure to check out our vacation rentals with a pool in this part of Central Maryland during other months too. There may be more options outside of Annapolis’s peak months.

After a big day out, return to your vacation rental with a pool to kick back poolside. The cherry on top? Some of these properties in Annapolis also boast superb views of historic areas.

Pick a vacation rental with a private pool in Annapolis and enjoy a refreshing morning swim or late-night dip under the stars — or whenever you please! You can keep your kids easily entertained, and you won’t have to worry about sharing with other guests. Use our “Private pool” filter to discover your ideal vacation home.

William Paca House, Chesapeake Bay Bridge and Sandy Point State Park are places to include on your must-visit list while staying at a vacation home rental with a pool in Annapolis. The only thing that beats discovering this city’s top attractions? Chilling out poolside with the fam after an action-packed day of tours and activities.

When you select a Vrbo vacation rental with a pool, the only people you have to share your living space with are the people you bring with you. It’s only you and your closest companions with the whole place to yourselves having a splashing good time. Also, with our free rewards program, One Key™, you can earn and spend OneKeyCash™* on eligible bookings made through Vrbo, Expedia and Hotels.com. Plus, our flexible cancellation policies also mean you can book your rental house with peace of mind if your plans change. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.