Owner Direct Vacation
Rentals in Madison
The Best Owner Direct Vacation Rentals in Madison. Explore thousands of vacation home rentals, large cabins, and villas near Madison
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Explore the Best Madison Vacation Homes
Looking for the perfect place to stay in Madison? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Madison character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Madison Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Madison
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Popular Neighborhoods for Madison Vacation Rentals
What are the best areas to stay in Madison
Discover the top neighborhoods in Madison and choose a place that suits your stay.
Saturday Feb 7
Madison, Wisconsin
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Madison vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Madison
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How to Reserve Your Madison Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Madison Vacation Rental FAQs
1. What are the top vacation rentals in Madison?
There are a lot of options in Madison. If you plan on staying in the Madison area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Madison:
- A Home Away from Home in the Quaint Village of New Glarus
- A Pleasant Retreat- No Cleaning Fee & New Discounts
- Clarance Gonstead Guest Cottage, Prairie Style, Stone & Tide Water Cypress
- Madison & ~UW~-Madison Area Lakefront Home
- Amazing townhouse, amazing attractions, amazing city!
- A TOUCH OF COUNTRY LIVING Minutes from Madison
- Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
- ONE OF A KIND vacation rental with a view
- Conveniently Located just off University Avenue on Madison's West Side
- Original cozy farmhouse homestead 2 blocks from the bike path and
2. How many vacation rentals have private pools in Madison?
There are 69 vacation rentals with private pools near Madison. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Madison are best for families?
If you are looking for a family-friendly vacation home in Madison, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Madison:
4. How many vacation rentals are available in Madison?
Currently, the total number of properties listed in 2026 is over 728 in the Madison area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Madison.