Frequently Asked Questions

Browse Our Most Common Questions About Our Boutique Accommodations

Below are answers to commonly asked questions we receive from guests about our Key West boutique hotels. Please read our Terms & Conditions fully to understand all information and disclosures BEFORE booking. 


Does Dwell Key West own and control the vacation rental properties?

No, we are the liaison/property manager between the private owners and the guests. We must always yield to the owner’s decisions but work diligently with both parties to ensure satisfaction. We ask that guests are conscientious of the fact that the owner is entrusting them with their private property to enjoy and create incredible memories. Please realize the difference in this situation from a hotel and treat the property with the utmost respect and care. 


What is the best way to start a vacation rental search and/or the booking process?

Please email our reservation team at,, to discuss your search and receive a formal quote with all tax and fees included. Our knowledgeable team are experts on our inventory and the amenities each property offers so, be sure to be specific with your requests so we are able to offer the best fit.


How do guests pay for the Key West rental?

Once you have received your formal quote and have decided to book our reservation team will email you the agreement to complete. You will choose whether you wish to pay with credit, a wire transfer or if you will be mailing a check.


50% of your balance total is due upon booking with the balance due 60 days prior to your arrival. If you are booking within the 60-day window the entire balance is due upfront to reserve the property.


Is parking included?

Unless specifically noted, no parking is included in the reservation. Guests who have specific parking needs must make arrangements prior to arrival. In the event there is no off-street parking at the selected residence there are limited on street options. If the rental you booked does not offer parking then you can use street parking that is unmarked and not in a 'Pay to Park' zone. Some spots will say 'RESIDENTIAL' meaning you cannot park there as those spaces are designated for locals (residents who live on the island for at least 4 months) who have been issued a residential parking pass. If you park in these spaces you can either be towed or issued a ticket. 


Special parking requirements may include but are not limited to camper/RV, boats/ boat trailers, oversized trucks and SUV’s. If guest vehicle exceeds a standard size that guest should verify the capacity of published off street parking space. 


Can guests pay with a credit card?

Yes, we accept Visa, Master Card, Discover and AmEx.


What happens if a guest needs to cancel a reservation?

We have a strict cancelation policy and suggest guests purchase trip insurance to protect against an unfortunate loss. If you do not purchase insurance or it does not apply to your situation please notify our team. We will try our best to rebook the stay for you but cannot offer a refund unless it is replaced by a booking with similar rates and dates.


Do guests need to bring sheets and towels?

No, all of our properties offer linens and towels including beach towels.


Do guests need to bring plates and kitchen utensils?

No, our kitchens are equipped with most cooking essentials you need to make regular meals. This does not include pantry items, spices or groceries. If you have specific requests please inquire with our team to learn whether the property offers the item in question.


How do guests gain access to the property?

The Arrival Plans Request or Self Check-In email will be sent to you 10 days prior to your arrival. If you do not receive this email around that time please contact our office to schedule your arrival and receive the necessary information to gain access.


When is check-in and check-out?

The rental period begins at 3:00 PM on the day of arrival and terminates at 11:00 AM on the day of departure. It is important that guests fully read the guest manual provided in each property. If you cannot find the manual please contact your property manager or our office.