Planning your Key West vacation should be exciting, not overwhelming. Below are answers to the questions we hear most often about our Vacation Planning Service.

ℹ️ What does this service provide?

Our personal Vacation Planning Service pairs you with a local Key West concierge who will create a customized itinerary based on your travel style, budget, interests, and schedule.
Instead of spending hours researching restaurants, tours, transportation, and activities, you’ll work with someone who knows the island and can help you make the most of your time in Key West.

 💵 Why do I have to pay $100?

We have a team of real human experts, working directly for you to ensure you have the best vacation possible. We take our time to sort through our meticulously vetted activities providers and accommodations, to find the best fit for you and your travel companions. Your payment is an assurance that your time spent in Key West is everything it can be. 

🤝 What do I get for my $100?

A personal concierge and travel planner will be assigned to you as soon as your form is submitted. You will receive a sample itinerary based on the profile created from your questionairre. You choose the best time to connect about the itinerary. Your concierge works for you, so if you want any changes made, or need questions answered– they are there to help. Once approved, your concierge will make all the necessary reservations for your itinerary. They will also be on call for the entire time leading up to your vacation, as well as during. Basically, for $100, you get a vacation secret agent, working hard to make sure you have the best time in Key West! 

🔄 Is my $100 refundable?

The $100 Trip Planner Fee is non-refundable. This fee secures the dedicated time, expertise, and personalized planning provided by OurKeyWest Concierge, including destination recommendations, itinerary development, and travel research. Because these services begin immediately, the fee cannot be refunded. 

📋 What is the overall cancellation policy?

Because every itinerary is custom-designed, cancellation policies vary depending on the hotels, vacation rentals, tours, attractions, transportation providers, and other vendors included in your trip. Each reservation is subject to the cancellation and refund policy of the individual vendor providing that service.

A summary of the applicable cancellation policies for each booked reservation will be included with your final itinerary and travel documents. By confirming your reservation, you acknowledge and agree to the cancellation terms of each vendor.

Please note that any non-refundable concierge or travel planning fees are separate from vendor cancellation policies and are not refundable.

📝 Can I make changes to my itinerary?

Yes, you may make changes to your itinerary as long as vendor cancellation policies are kept in mind. There may be cancellation fees associated with any last minute changes.

👤 Will I work with a real person?

Yes.
Your itinerary is personally created by a member of our local concierge team—not artificial intelligence or an automated booking platform.
If you have questions before or during your vacation, you’ll have a real local expert available to help.

🙋‍♂️ Why do you ask so many questions?

No two vacations are the same.
Some guests want relaxing beach days and romantic dinners, while others are looking for fishing charters, snorkeling adventures, live music, or family-friendly activities.
The questionnaire helps us understand what’s important to you so we can create recommendations that truly fit your vacation—not a generic itinerary

🌴 Why should I use OurKeyWest instead of planning everything myself?

Anyone can search online for things to do in Key West.
What you won’t find is local insight.
Our concierge team knows which tours consistently receive great feedback, the best times to visit popular attractions, where locals love to eat, and how to build an itinerary that fits your interests, pace, and budget.
Our goal isn’t simply to recommend activities—it’s to help you experience the very best of Key West with confidence.

📅 How long does it take to receive my personalized vacation plan?

Most vacation plans are completed within a few business days.
If you’re traveling soon, let us know. We’ll do our best to prioritize your request whenever possible.

🍽️ Will you recommend restaurants?
Yes!
Dining is one of the highlights of any Key West vacation.
We’ll recommend restaurants based on your preferences—from waterfront seafood and local favorites to fine dining, brunch, happy hours, and hidden neighborhood gems. We can even go the extra mile and make your reservations for you.

📞 Still Have Questions?

We’re always happy to help. 305-290-2049
If you have questions before getting started, reach out to our local concierge team by phone, text, or email. We’ll be happy to answer your questions and help you decide if our Personal Vacation Planning Service is the right fit for your trip.

Higgs Beach Dog Park 

Higgs Beach Dog Park on Atlantic Blvd has 2 fully enclosed play areas with unlimited fresh water for pups. Across the street, you can take a wonderful leashed walk on Knight Pier (White St Pier) & Higgs Beach for a great oceanfront scenery.

 

 

 

 

 

Dog Beach 🐶

Dog Beach is next to Louie’s Backyard on Vernon Street. It’s the only dog-friendly public beach where dogs can swim & play. The area is small, but for “water dogs” it’s paradise. BYO fresh water for your pup.

🧭 Frequently Asked Questions: What to Know Before You Go

Everything you need to plan, book, and enjoy your Key West vacation package

✈️ Do you book my flights, or do I?

You’ll handle your flights or drive in—we’ll handle everything once you arrive in Key West. From the moment you land, we’ll guide you with local tips, insider access, and personalized vacation planning.

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🍴 Are food and drinks included in the package?

Meals and drinks aren’t included, but we’ll make it easy to dine like a local. We’ll recommend top-rated restaurants, local favorites, and even handle reservations for you.

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💵 Are taxes and fees included in the package price?

Yes! All taxes and standard fees are included in your package. Optional add-ons and upgrades may have additional costs, and we’ll always make that clear upfront.

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👨‍👩‍👧 Are vacation packages priced per person?

Some of our Vacation Specials feature pre-set pricing based on the number of guests—typically 1, 2, 3, or 4 people—so you can easily see the total cost at a glance. For larger groups or custom vacations, we’ll tailor your accommodations, transportation, and activities to fit your needs. Many properties allow additional guests at no extra cost, so just tell us what you’re looking for—we’ll build the perfect package around it.

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🏖️ Can I stay longer than the standard 3-night vacation?

Absolutely. We offer 4- and 5-night specials, and we’re happy to extend or customize any package to match your ideal stay. Just ask—we’re flexible!

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🌊 Can I upgrade to an ocean view room?

Absolutely! Our Vacation Specials include an easy upgrade option at checkout. If you’re booking a custom package, we’ll tailor everything to your preferences—including that dreamy ocean view. Just let us know, and we’ll make it happen with adjusted pricing.

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🏡 Do you offer vacation rentals instead of hotels?

Yes—we have a wide selection of vacation rentals available. Just give us your budget and preferences, and we’ll find the perfect home base for your Key West adventure.

ℹ️ Vacation Package Cancellation Policy

Our vacation packages are subject to varying cancellation terms depending on your selected lodging provider. However, the following is our standard cancellation policy, which applies unless otherwise specified in writing at the time of booking:

• 24-Hour Grace Period: You may cancel your vacation package for a full refund within 24 hours of purchase.

• Cancellations 45+ Days Before Arrival: Cancellations made more than 45 days prior to your scheduled arrival are eligible for a refund, minus a 10% cancellation fee based on the total package price.

• Cancellations Within 45 Days of Arrival: No refunds will be issued for cancellations made within 45 days of your scheduled arrival date.

We strongly recommend purchasing travel insurance to protect your investment in the event of illness, weather disruptions, or other unforeseen circumstances.

Please Note: All add-on services—including but not limited to grocery provisioning, alcohol, flowers, and other personalized items—are non-refundable once purchased.

Do I need transportation while I’m in Key West?

Yes! Having transportation in Key West can make your stay more fun, flexible, and enjoyable. With so many sights spread across the island, getting around easily lets you see more and do more. While our tropical climate offers beautiful scenery, walking everywhere can be hot and tiring—having wheels gives you the freedom to explore comfortably and at your own pace.

Is it better to have a bike, scooter, or golf cart while vacationing in Key West?
The best option depends on where you’re staying.

If you’re staying along Roosevelt Boulevard or Atlantic Boulevard, a golf cart is often the best choice due to the distance from most of Key West’s main attractions. Old Town, Duval Street, Mallory Square, and popular dining spots are several miles away, making a golf cart a comfortable and convenient way to get around. Golf carts park in standard vehicle spaces, and there are plenty of public parking lots available throughout Old Town.

If you’re staying within Old Town, a bike, scooter, or golf cart can all work well. The area offers plenty of bike racks and designated scooter parking, making it easy to explore at a relaxed pace.

For safety, we recommend scooters for guests with some prior riding experience, as they travel at higher speeds and navigate more dynamic street traffic.

How far is the airport to Duval Street? The airport to mid-Duval Street is approximately 3.9 miles. This is about a 13-minute car ride.

Does Key West have Uber & Lyft? Yes, Key West has both Uber & Lyft.

How much does an Uber cost to go from the airport to Old Town, Key West? It cost approximately $22 depending on the exact location.

Does Key West have a free shuttle bus? No, not any longer. It was called the Duval Loop.

Golf Cart, Bikes & Scooter Rentals

Golf Carts

Hands down, golf carts are the most fun & safest way to get around the island. They offer the best scope to explore the entire island. This is the perfect choice for families, seniors, or those not wanting to walk a lot. You can get to all the beaches, attractions, and events by golf cart. For those who have a hard time walking, or not great on a bike, this is your option.

How do I rent a golf cart? Follow the link here to reserve your 4, 6, or 8 seater golf cart. The free shuttle will pick you up anywhere on the island and take you to get your golf cart. The free shuttle will also give you a ride back after your rental time is over. Fast & Easy Golf Cart Rental Reservation Link

Bikes

If you ride bikes often at home or on vacation, you will find bikes a great, affordable choice to get around Old Town. I wouldn’t recommend them if you’re staying in New Town, due to the distance and traffic you will encounter. Bikes offer a lot of freedom from parking, and offer easy access to most attractions. You will want to ride defensively, as Old Town is a regular town with delivery trucks, and traffic.

How do I rent a bike? Follow this link to set up your bike reservation. Bikes will be delivered and picked up anywhere on the island free of charge. Fast & Easy Bike Rental Reservation Link

Scooters

Scooters are an affordable way to get around the island. They provide flexibility and easy parking. They’re great for single or double riders. You can get to all the beaches, attractions, and events on a scooter. You will want to drive defensively, as Old Town has a lot going on with pedestrians and traffic.

How do I rent a scooter? Follow the link here to reserve your 1 or 2 person scooter. The free shuttle will pick you up anywhere on the island and take you to get your scooter. The free shuttle will also give you a ride back after your rental time is over. Fast & Easy Scooter Rental Reservation Link

Frequently Asked Questions

Why are golf cart rentals the best choice for transportation in Key West? Since Key West has a lot more to see than just Duval Street. Having a fun and safe way to get around to all the best spots will provide additional opportunities for fun. There are beaches & parks for swimming & snorkeling, restaurants & bars, museums and historic houses, and the popular Southernmost Point. Because some point of interest are close, but others are spread out on the island, walking around the island to see everything can be very challenging when it’s hot outside. So, if you want to see as much as you can without wearing yourself out, rent a golf cart.

Can golf carts really be fun and safe? Absolutely! When cruisin’ around with your family and friends to check out ALL the best spots, you’ll really enjoy having the shade from the canopy and feeling the salty breeze. Additionally, riding in a golf cart makes sightseeing much easier because you have more visual area than riding in a car. The best part is that golf carts are easy to drive, and are street legal with all the required safety additions. They’re safer for families who want to travel together than bikes, and the best way to get around for those who have mobility issues.

Where should I go on a golf cart? Some of my favorite spots to take a golf cart ride to are Ft Zachary Taylor State Park to enjoy the view of the historic Key West Harbor, Higgs Beach Park for snorkeling off the beach, and Salute on the Beach! for lunch and a glass of wine. I have a lot more special spots that I can share with you, depending on your interests.  😎

Can I get a Golf Cart rental at the Key West Airport? No, there are no golf cart rentals available at the airport. However, if you give us a call 305-290-2049 we have a service that will pick you up at the airport and bring you to the golf cart rental area.

Where can I rent a golf cart? Directly from me, a local in Key West. Let me set up the perfect rental for you and your group. My free concierge service is available to anyone and there are no hidden fees. Golf cart rentals are available in gas & electric versions, and can come with 4, 6 or 8 seats. Additionally, you can rent golf carts for 3, 5, 8 hours or daily and it will also include Free Delivery!

Call direct for best rates or more information, 305-290-2049.

Looking for more recommendations or help to plan your Key West vacation?
Use our FREE Key West Vacation Planner: https://zurl.co/Tcqv

To reserve your golf cart, click here: https://ourkeywest.com/things-to-do/key-west-golf-cart-rentals

 

Planning your island stay and wondering how our Key West Equipment Rentals work?
You’re in the right place! Below you’ll find helpful answers about delivery, cleaning, and how to reserve your gear while keeping your trip simple and stress-free.

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🏝️ How do I reserve my equipment in Key West?

Reserving your rental gear is easy! You can call 305-290-2049 or stop by our OurKeyWest Welcome Lounge at 613 Simonton Street.
You can also browse our Things to Do in Key West page for activity ideas while you’re here.

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🚚 Do you offer delivery and pickup for equipment rentals?

Yes! Our Key West equipment rentals can be delivered anywhere in Old Town and most vacation properties on the island for a small additional fee. Pickup is available at the end of your stay—just let us know your preference.

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🧺 Is the equipment clean and sanitized?

Absolutely. All of our baby gear, beach chairs, and snorkel sets are professionally cleaned and sanitized before every rental. We know how important safety is for families visiting Key West.

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💳 How does payment work?

Payment for all Key West equipment rentals is collected when you pick up or schedule delivery. We accept major credit cards and digital payments for your convenience.

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🔁 What if something breaks or goes missing?

We understand accidents happen! If an item is lost or damaged, please contact us right away so we can arrange a replacement.

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🕓 Can I extend my rental or add more items?

Yes! You can extend your rental or add new items anytime—just call 305-290-2049, and we’ll update your reservation.

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🌴 What other rentals or services are available in Key West?

In addition to baby and beach gear, we also offer Pickleball Kits, Rod & Reel Rentals, and Mask & Snorkel Sets for your island adventures.
For more local tips, visit our Key West Vacation Planner.

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💬 Need More Help?

If you still have questions about our Key West Equipment Rentals, call 305-290-2049 or visit 613 Simonton Street. Our friendly team is happy to help you make the most of your Key West vacation.

What’s the weather like in Key West? Beautiful! In Summer, the temperature is an average 89 degrees during the day to 80 at night. It can be humid with a slight breeze. The ocean temperature is an average of 85 degrees. These temperatures make for ideal water based activities where the water is crystal clear, warm and calm. In winter, the temperature is an average 75 degrees during the day to 68 at night. The ocean temperature is on average 74 degrees. These ideal temperatures attract many visitors in the winter months to enjoy a variety of activities on land and sea. 

Cayo Hueso is the original Spanish name for the island of Key West. Translated it means “bone cay”, cay referring to a small, low island or reef. It is said that the island was littered with the remains (bones) of prior native inhabitants, many Calusa Indians, who used the isle as a communal graveyard. When the English came to Cayo Hueso they mistook the name as Key West, and the island was henceforth known as Key West.

By texting OurKeyWest, you agree to receive messages related to your Key West visit — including concierge support, reservations, and local updates. Message frequency may vary depending on your trip and services.

Standard message and data rates may apply. You can reply STOP at any time to unsubscribe or HELP for assistance.

OurKeyWest is not responsible for delayed or undelivered messages. By providing your number, you confirm that you own it or have permission to use it.

For any questions, reach us by calling 305-290-2049.

Effective Date: 01/01/2025

At OurKeyWest, your privacy is part of our island hospitality. When you share your phone number or message us, we only collect the information needed to help plan your trip, confirm bookings, and keep you updated on Key West experiences.

We may store your name, contact info, and message details — but only to serve you better. We’ll never sell, rent, or share your information with anyone for marketing purposes.

You can stop receiving texts anytime by replying STOP.
For questions about how we use your information, contact us by calling 305-290-2049.

We have been providing Free Concierge Services in Key West since 2007

Absolutely! Our Premium Concierge Call Center Service is complimentary and free of charge. We do charge for provisioning, deliveries, special events and Luxe Concierge Services.

No 🙂 We are a homegrown local, family owned business.