Key West Rentals with a Pool

A pool can make a rental the center of the trip, especially for families who want a break from the main attractions.

We found 10 of the 196 Key West rental listings with real details in our directory whose own title mentions pool. Most are in Key West (8), Big Pine Key (1), Islamorada (1).

Beach destinations are busiest in summer and around school breaks, so feature-specific homes can book up early.

3 of these also mention waterfront in the title, so see the Key West waterfront page too.

Quick facts

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10 Key West listings that mention pool

Order: listings with a photo and a direct booking site first, then A–Z. This is not a ranking, and no one pays to appear in this list.

Before you book

FAQ

How many pool rentals are listed in Key West?

As of October 19, 2026, BnB Search lists 10 Key West rentals whose listing title mentions pool, out of 196 Key West rental listings with details in our directory.

How did you choose these listings?

We include a listing only when its own public title mentions pool. We do not inspect homes, so confirm the feature and house rules with the owner or manager before you book.

Which Key West areas have the most pool rentals?

In our data: Key West (8), Big Pine Key (1), Islamorada (1).

Can I book through BnB Search?

No. BnB Search is a free directory. Use the Visit site link to book directly with the owner or manager, or open the details page for the map and contact options.

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