Mad Men Vacation Rentals

Your Kissimmee Bucket List

Whether you are looking to escape the cold for a sunny holiday, are a Walt Disney World annual pass holder or taking the kids to meet Mickey for the first time Kissimmee, Florida is not only right next to Walt Disney World but also close to other fun amusements the area has to offer! Our bucket list guides will help you plan the perfect trip!

It doesn’t matter where you come from or how old you are, Walt Disney World has something for everyone! Check out this guide to see what not to miss when you visit!

Get your thrills on the cutting-edge rides, shows and attractions that bring your favorite movies, television and more to life at Universal Studios! This guide will give you a taste of all the fun to come!

Sea World is a wonderland of ocean animals, rides and dazzling shows! There is so much to do and this guide will give you all the details to help you plan your best trip there!

Your Deep Creek Bucket List

This four season resort town is only a few short hours drive from Washington DC, Baltimore, Philadelphia, Pittsburgh and New York and our bucket list guides will help you plan the perfect trip!

The lake! Need I say more? Deep Creek Lake covers approximately 3,900 acres and has 69 miles of shoreline for endless hours of fun and adventure in the spring, summer and fall! This guide gives you all details you need to know!

Every season in Deep Creek offers a different lens to the see the beauty of nature. Whether you want a short easy hike or a more advanced hiking adventure this guide will help you plan what is right for you!

Maryland’s only downhill ski resort is the perfect activity for you best winter getaway. This guide gives you all you need to know to plan your ski  or snowboard trip vacation!

Your Ocean City Bucket List

If you are in search of the best vacation town with pristine beaches, endless fun exploring the bay and an iconic, award-winning boardwalk with endless amusements, our bucket list guides will help you plan the perfect trip!

Whether you are looking to catch a wave, catch a fish, or catch an unforgettable sunrise on the beach our Ocean City Beach guide is for you!


You can’t get the full Ocean City experience unless you take in the bay life. This guide will show you all the bay adventures waiting for you!

The famous Ocean City boardwalk is on everyone’s bucket list! This guide will tell you everything you need to know about where to shop, eat and more!

Welcome To Ocean City, Maryland

Welcome To Kissimmee, Florida

Visit Our Ocean City Guide

See our hand picked recommendations

The definitive guide to what’s on, what to see, what to do and where to eat and drink.

Visit Our Kissimmee Guide

See our hand picked recommendations

The definitive guide to what’s on, what to see, what to do and where to eat and drink.

Our Properties

All our Mad Men Vacations properties have a mid century modern feel with a few signature features like a swing chair/chairs, a record player with blue tooth capability, outdoor string lights and a custom painted geometric wall design. 

This is a 3 bedroom and two full bath (one en suite) bay front home (sleeps 8) that is only a 5-8 minute walk to the beach! It was a lovely covered deck that is wonderful all year round. We offer two Kayaks and our community has two pools, two tennis courts, shuffle board and mini golf!

This is a 8 bedroom, 4.5 bath home (sleeps 16) has a screened in porch with a heated pool and in ground jacuzzi hot tub. It is only 6 miles from Walt Disney World and 17 miles from Universal Studios! The main living space has a “Disney Glam” theme and every bedroom has a theme based on the Magic Kingdom theme park!

Coming in 2020!

 Follow our Facebook and Instagram page for updates and to get promotions and deals when we go live with the property! Look up: @madmenvacationrentals

What Makes Us Different

We are a small, military family run vacation rental company with a passion to give our guests the best experience on their vacation! The locations of our vacation homes are places our family has treasured all our lives and we love giving others the chance to make life long memories in these unique and special places. We renovated all the properties ourself and designed every small detail.  We also donated $10 for every reservation to an orphanage in Haiti called “Kay Marie”. Check out their amazing non profit: www.Haiti180.com.  We believe doing a little makes a big difference and when you book with us you are also part of making the world a little bit better.  We truly hope we can be part of your family’s best memories while making the world a better place at the same time! We hope to host you soon!

Why Book With Us?

Deal directly with the rental owner

Deal Direct With Owner

Best Price Guarantee

Best Price

Family Run Business

Family Run

No Booking Fees Ever

No Booking Fees

Shared Local Knowledge

Shared Local

Secure Payment

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If you have any questions regarding the area, the property or availability please drop us a line

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