Hotel - Pool

Question

Anyone know of a good hotel with pool side service. Coming first week in Nov and under $500 if possible or close to it.

Answer

Great question. Key West has a few really solid hotels with pools and good service, and staying in early November can give you more options and slightly better rates than peak season. Below are some good picks near or around your $500/night target (or close), plus a few details on their pool-service vibes and what to expect.

Casa Marina Key West, Curio Collection by Hilton — This is probably your best bet for the full “resort” pool experience. The hotel has two gorgeous pools, and the newer fact sheet mentions a “pampering pool concierge” with things like chilled towels and popsicles. Rates vary, but in early November you may find rooms not too far from your $500 target (depending on how historic/standard the room is).
The Reach Key West, Curio Collection by Hilton — A more relaxed resort feel, very classy, with a pool and beach access. According to Expedia, it’s listed around $232/night for some dates, which gives you room in your budget for splurging on food or other extras. While not “poolside service” like beach cabana dining, the resort bar and staff are attentive, and you should be able to order drinks or snacks to your lounger or nearby.
DoubleTree Resort by Hilton Grand Key – Key West — Has a large outdoor pool and a solid pool-bar setup. Expedia shows rates around $153/night for some off-peak dates. This place is less luxe than Casa Marina, but it's very good value and still upscale enough to enjoy poolside food and drink service.
Hilton Garden Inn Key West / The Keys Collection — More budget-friendly for Key West standards, with an outdoor pool, cabanas, and a poolside bar. Expedia shows some very low rates for November. Great pick if you want pool access with service but don’t need a luxury resort feel.

Local insights & community feedback:

People on Reddit mention Casa Marina positively for its “chair service.”
Redditors also recommend The Reach as a more relaxed option with good pool vibes.
For a more budgeted pool stay, some mention smaller inns and guesthouses, but these often have shared or limited pool service.

Things to watch out for:

Even “under $500” in Key West can stretch a lot, depending on room type, view, and how far in advance you book.
Poolside service (drinks + food) isn’t always guaranteed to include full waiter-style service — some resorts have pool bars, others have “concierge”-type service with towel/refreshment delivery, so double check when booking or call ahead.
Some hotels enforce “no outside food/drinks” at their pools, particularly the nicer ones — be prepared to order from the hotel.

Bottom line: For early November and a budget around $500 or slightly below, Casa Marina is your top pick if you want a true resort-pool experience with service. If you prefer slightly lower cost or a more laid-back feel, The Reach or Hilton Garden Inn Key West are strong alternatives. Book early — Key West hotels with pools are very popular.