Lodging Recommendations with older teens

Question

I am hoping for some recommendations on places to say in Key West. We are a family of 4 with an 18 year old and almost 20 year old going in May. I have reservations at the Doubletree and the Hilton Garden Inn as back ups but I keep reading we should stay in Old Town and I'm struggling to figure out the right fit for us. We would like something as reasonably priced as possible......which I know is difficult. Not looking to spend $700+ per night. Our only must is that we must have queen size beds instead of doubles. We cannot share doubles. Would love a pool or view of the ocean. Is this possible in the Old Town area? Will we really regret staying elsewhere?

Thank you very much for any info!

Answer

Key West is a compact island, and staying in Old Town is ideal if your goal is to experience the heart of the city, walk to restaurants, shops, and attractions, and soak in the historic charm. Old Town can be pricier, but there are some options that might fit your requirements if you book early and are flexible on amenities.

Since your main requirements are queen-size beds for all, a pool or ocean view, and a reasonable price under $700 per night, here are some considerations:

Historic Inns and Small Hotels: Many smaller boutique inns in Old Town offer rooms with queen beds and sometimes pools. Some may not have ocean views but are within walking distance to beaches and Duval Street.
Oceanfront Hotels Near Old Town: Places like The Southernmost Inn, Banana Bay, or other boutique oceanfront properties sometimes have queen bed rooms and pools. Rates can vary, so booking well in advance is important for May travel.
Vacation Rentals: Airbnb or VRBO can offer condos or small homes with multiple queen beds and pools or private decks overlooking the water. Sometimes this can be more economical than hotels, especially with a family of four. Look for properties in the Old Town vicinity (especially Truman Annex, near Duval, or Bahama Village) to stay central.

Regarding your backup options:

The Doubletree and Hilton Garden Inn are typically located slightly outside Old Town, so you may need to drive or bike to central attractions. They are reliable brands and may offer more standard amenities, like pools, but the “walkable charm” of Old Town will be reduced.
If convenience and atmosphere are important to you, staying in Old Town is preferred. If cost or brand loyalty matters more, the backup hotels are fine and you can always explore Old Town by bike or rideshare.

Additional tips:

Book early: May is a popular month, and reasonable rates disappear quickly.
Check for suites or adjoining rooms in Old Town properties if you want more space.
Even if you stay slightly outside Old Town, Key West is small, and a short bike ride or scooter can get you into the center quickly.

In summary, it is possible to find queen beds, a pool, or ocean view in Old Town, but flexibility and early planning are key. Staying elsewhere won’t ruin your trip, but the convenience and charm of Old Town make it a preferred choice for first-time visitors with older teens.

Lodging Recommendations with older teens

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