Annapolis rentals with pool

We found 268 rentals with pool — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday rentals with a pool in Annapolis?
Consider one of our 268 holiday rentals with a pool and start organising your Annapolis trip. Whether you'd like to be in Historic District, Naval Academy, Murray Hill or another well-known neighbourhood, you'll discover the perfect poolside retreat on Bookabach.
How much does it cost to stay in a holiday rental with a pool in Annapolis?
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 holiday 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 holiday rentals that offer savings on longer stays.
When is the best time to book a holiday rental with a pool in Annapolis?
With temperatures ranging from around 21ºC to 29ºC, August is popular with the majority of Bookabach guests. Be sure to check out our holiday 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.
What holiday rentals with a pool in Annapolis have nice views?
After a big day out, return to your holiday 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.
Are there holiday rentals with a private pool in Annapolis?
Pick a holiday 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 holiday home.
What are the top things to do in Annapolis?
William Paca House, Chesapeake Bay Bridge and Sandy Point State Park are places to include on your must-visit list while staying at a holiday 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.
Why should I book my holiday rental with a pool with Bookabach?
Bookabach provides attentive customer support from the minute you book until your trip is over, so every aspect of your holiday is enjoyable and stress-free. It's all part of our Book with Confidence Guarantee, which also includes deposit and payment protection and flexible cancellation policies. Another great thing about us? You can use our filters to fine-tune your search by price, location, amenities and more. Whether you want a pet-friendly property or a countryside getaway for the family, we've got holiday rentals with a pool that fit your exact style and needs.
Rentals with Pool in Annapolis
Rentals with Pool in Eastport