Curated short-term rentals for every destination
At UP-DOWN TRAVEL, we curate a collection of luxury vacation rentals and executive stays designed for travelers who expect more than the ordinary. From vibrant city penthouses to peaceful coastal retreats, every property in our portfolio blends high-end comfort, distinctive design, and five-star service—so you can feel at home wherever you go.
Our guests range from multi-generational families gathering for quality time, to bachelor and bachelorette groups celebrating in style, to business travelers seeking refined, fully equipped accommodations. Whether you’re staying for a weekend or a month, we deliver the same seamless experience: elevated, personalized, and unforgettable.
Explore our hand-picked short-term rentals across top destinations—each offering the perfect mix of sophistication and ease. Wherever your travels take you, UP-DOWN TRAVEL ensures you always stay exceptional.
Where Every Stay Feels Effortlessly Exceptional
Discover our collection of luxury vacation rentals across Wisconsin and Florida, designed to deliver comfort, style, and a sense of place. Each property in the UP-DOWN TRAVEL portfolio offers a distinctive experience—whether you’re unwinding by the lake in Door County, soaking up the city vibe in Milwaukee, or basking in Florida’s coastal sunshine.
Curated Stays. Thoughtful Experiences. Every Detail Matters.
Stylish, fully equipped homes with premium finishes, modern kitchens, and private outdoor spaces.
Spacious layouts perfect for multi-generational vacations or group getaways.
Enjoy curated outdoor spaces and activities, from sunny Florida beaches to Wisconsin’s lakes and trails.
Properties with high-speed Wi-Fi, workspaces, and convenient locations for seamless corporate travel.
Enhance your stay with local experiences, from private chefs to outdoor adventures.
Personalized services like private chefs, local tours, and curated experiences for an effortless stay.
Meet your hosts
Michael and Kayla are passionate hosts dedicated to delivering luxury, personalized experiences. As proud Airbnb Superhosts, they have earned top reviews for their attention to detail, seamless communication, and exceptional guest care.
Their hosting style combines professionalism with warmth, ensuring every property feels like a home while offering five-star comfort and thoughtful amenities. From arranging local recommendations to providing concierge-style support, Michael and Kayla go the extra mile to make every stay effortless and memorable.
Trusted by travelers for unforgettable stays in Wisconsin and Florida.
We do not offer pet-friendly rentals. All properties maintain a no-pets policy to ensure comfort and quality for every guest.
Yes! Most of our luxury vacation rentals provide private or designated parking, making arrivals and departures seamless.
Standard check-in is 4:00 PM and check-out is 10:00 AM. Early or late arrangements may be available upon request at select properties.
You can easily book your Wisconsin or Florida vacation rental directly through our website or trusted platforms like Airbnb and VRBO. Our team is available to answer questions and ensure a smooth reservation process.
Absolutely! Many of our homes are designed for multi-generational families, group getaways, and bachelor/bachelorette retreats, offering spacious living areas and modern amenities.
Yes! Our hosts, Michael and Kayla, provide personalized recommendations and concierge services, including local tours, dining suggestions, and activity bookings, to make your stay unforgettable.
