Monroe County rentals with pool

We found 5,949 rentals with pool — enter your dates for availability

Find spaces that suit your style

Frequently asked questions

Are there any holiday homes with a pool in Monroe County?
Pick from 4,577 holiday homes with a pool in Monroe County. Take the family on an adventure to Key West or check out other vibrant cities like Marathon and Key Largo. Wherever your travels take you and whether you want to swim or just lounge poolside, we've got your ideal stay.
How much does it cost to stay in a holiday home with a pool in Monroe County?
In-ground or above-ground pool, sprawling or compact, low season or peak season — how much you'll pay for your stay in Monroe County is influenced by all sorts of variables. But the one thing that stays the same? Our holiday homes with a pool are something special. To find an escape that suits your budget, narrow your search results by price. You can also use our "Discounts" filter to find holiday homes that offer savings on longer stays.
When is the best time to book a holiday home with a pool in Monroe County?
If you're planning on visiting Monroe County during the busiest time, book your holiday home with a pool in January. You'll get to experience the hustle and bustle of this destination during one of the most popular times of the year. But be sure to book early to get the holiday house you want for some poolside fun.
What holiday homes with a pool in Monroe County have nice views?
From lounging poolside to practicing your cannonballs, a holiday home with a pool offers fun and excitement by the water. Toss in some outstanding views and you won't want your break to end. Use our filters to customise your search for a Monroe County property that has all the amenities you want and vistas that inspire wonder.