Vacation Rentals

Question

Hi there. We are considering renting a vacation property (condom cottage, home ---dont really care as long as pool access) for a couple of weeks or a month in Key West--preferably in Old Town. Have you used a rental company and been happy with it? Currently looking at Historic Key West Vacation Rentals but wondering if there are others we should be looking at as well. We prefer a rental company/management company over an airbnb or VRBO.

Thanks for any experience you may be able to share.

Answer

For a vacation rental in Key West, especially if you prefer being in Old Town and want a pool, using a professional management company can provide added reliability, local knowledge, and responsive support during your stay. Many companies specialize in Key West properties and offer a range of options including condos, cottages, and single-family homes.

Some well-regarded rental companies in Key West include:

Historic Key West Vacation Rentals: You are already looking here; they are reputable, offer properties with pools, and focus on Old Town locations. They provide full-service management including check-in, housekeeping, and local advice.
Island City Rentals: Offers a wide selection of Old Town properties with pools, often includes concierge services, and has a good reputation for customer service and responsiveness.
Key West Vacation Rentals: Professional company with a variety of property types in Old Town, many with private or shared pools. They also handle longer-term stays, which is ideal if you plan to stay for a few weeks or a month.
Key West Vacation Homes: Focused on full-service management with multiple properties in Old Town, including luxury homes and cottages with pools.
KRE (Key West Real Estate) Vacation Rentals: Offers both short-term and monthly rentals, with options for pool access and central locations. They often provide local insights and extra services like bike rentals and guided suggestions.

When booking through a rental company versus Airbnb/VRBO directly, advantages include:

Guaranteed support and responsiveness if any maintenance issues arise.
More predictable check-in and check-out procedures.
Professional cleaning standards and property management oversight.
Access to vetted properties with accurate descriptions and verified photos.

Tips for choosing the right property:

Confirm the exact pool access and size—some properties have shared pools, others private.
Check proximity to the attractions you want to be near in Old Town. Walking distance to Duval Street, restaurants, and shops is highly desirable.
Ask about utilities and fees, especially for longer stays (internet, water, cleaning, etc.).
Read reviews from past guests to get insight on responsiveness and property condition.

Overall, if you want a worry-free vacation rental experience with pool access in Old Town, using a management company like Historic Key West Vacation Rentals, Island City Rentals, or Key West Vacation Homes is recommended over booking directly via Airbnb or VRBO.

Vacation Rentals

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