Entire home
Downtown 6 Bedroom/11 Beds Home with HotTub, Pool, Speakeasy, and Fireplaces
Family-friendly holiday home in Cadillac
Photo gallery for Downtown 6 Bedroom/11 Beds Home with HotTub, Pool, Speakeasy, and Fireplaces
6 bedrooms3 bathroomsSleeps 164000 sq ft
Popular amenities
Explore the area
Cadillac, MI
- Place, Wexford County Historical Museum3 min walk
- Place, Lake Cadillac5 min walk
- Place, Cadillac Lake Park and Boat Dock6 min walk
Rooms & beds
6 bedrooms (sleeps 16)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 Queen Bed
Bedroom 4
2 Queen Beds
Bedroom 5
2 Single Beds
Bedroom 6
2 Single Bunk Beds
3 bathrooms
Bathroom 1
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 3
Soap · Towels provided · Shower only · Shampoo · Hair dryer
Spaces
Deck or patio
Porch or lanai
Balcony
Separate dining area
Garden
Dining area
About this property
Downtown 6 Bedroom/11 Beds Home with HotTub, Pool, Speakeasy, and Fireplaces
Hot Tub~~~~~~~~~~Downtown
Pool~~~~~~~~~~~~~2 Blocks to Lake
Speakeasy~~~~~~~~6 Bedrooms
Fireplace~~~~~~~~~19 miles to Caberfae Peaks
Cornhole~~~~~~~~~Propane Grill
Theater Room~~~~~Wood Fire Pizza Oven
Pool Table~~~~~~~~Coffee & Cereal Bar
Board Games~~~~~Alexa Speakers
Fire-pit~~~~~~~~~~~Chef’s Kitchen
WELCOME TO THE ROOSEVELT: Cadillac's Most Luxurious & Historic Downtown Retreat
Step into a one-of-a-kind Northern Michigan escape combining restored historic charm with modern luxury. Located just one block off Main Street, The Roosevelt puts you steps from Cadillac’s best restaurants, breweries, boutiques, and lakefront attractions — all while offering your own private pool, year-round hot tub, brick oven pizza maker, and a hidden speakeasy unlike anything else in town.
Whether you’re planning a family vacation, a friends’ weekend, a golf or ski trip, or a relaxing retreat, this home delivers unforgettable comfort and entertainment in every season.
PROPERTY HIGHLIGHTS
RESORT-LEVEL OUTDOOR LIVING
* Private Pool (open 5/8–Labor Day)
* Year-Round Hot Tub for stargazing and snowy-night soaks
* Wood-Fired Brick Pizza Oven — create your own gourmet pies
* Fully Fenced Backyard - high privacy walls
* Outdoor Dining & Lounging with string lights and gas tiki torches
* 3-Stall Heated Garage for cars, gear, and winter convenience
Two blocks from Lake Cadillac — perfect for boating, beach days, and waterfront sunsets.
HIDDEN SPEAKEASY AND GAME LOUNGE
Welcome to your private underground hangout:
* 85” Theater TV for movies & game days
* Pool Table for late-night competitions
* Cozy bar-style seating and moody speakeasy lighting
* Your own “secret” entrance vibe — a true guest-favorite experience
* Arcade Machines coming soon
Perfect for gatherings, movie nights, or just unwinding after exploring Cadillac.
CHEF'S KITCHEN AND ENTERTAINING SPACES
Create, cook, and connect in a kitchen built for hosting:
* Professional Cooktop & Premium Appliances
* Coffee & Wine Bar (complimentary coffee included!)
* Large island perfect for groups
* Beautiful dining area for shared meals
Ideal for holidays, celebrations, or weekend feasts with friends and family.
6 BEDROOMS — SLEEPS LARGE GROUPS COMFORTABLY
Room for everyone, thoughtfully designed for comfort:
* Primary Suite — King bed, patio access
* Bedroom 2 — Two Queen beds
* Bedroom 3 — Queen bed
* Bedroom 4 — Two Bunk Beds (kid-approved!)
* Bedroom 5 — Two Twin beds
* Bedroom 6 — King bed with lake view
Perfect for multi-family trips, retreats, or larger gatherings.
LOCATION PERKS — WALK TO EVERYTHING
* 1 block – Downtown Cadillac (restaurants, shops, breweries, coffee, nightlife)
* 2 blocks – Lake Cadillac (beach, marina, park, lakefront path, White Pine trail)
* 5 min – Kenwood Beach & Boat Launch
* 8 min – Adventure Island Theme Park
* 9 min – Mitchell State Park
* 10 min – Mountain Biking at Cadillac Pathway
* 25 min – Caberfae Peaks Ski Resort
* 50 min – Crystal Mountain Ski Resort
* 1 hour – Traverse City (wineries, dining, festivals, airport)
A perfect base for skiing, boating, hiking, biking, fishing, snowmobiling, golfing, or relaxing by the pool.
FOUR-SEASON ADVENTURE HUB
Summer: boating & jet skiing (rentals available nearby), swimming, hiking, beaches
Fall: color tours, local breweries, golf, scenic drives, biking the 92 mile White Pine Trail
Winter: Caberfae Peaks skiing, x-country skiing, snowmobiling (rentals available nearby), ice fishing Spring: trails, fishing, brewery hopping, quiet getaways, biking the 92 mile White Pine Trail
Your garage offers easy storage for boats, bikes, trailers, snowmobiles, and adventure gear.
PARKING MADE EASY
* Heated 3-stall garage
* Spacious driveway Total room for 6+ vehicles, trailers, or adventure gear.
*Additional parking available on the public lot across the street
GOOD TO KNOW
* No smoking ($750+ extra cleaning fee if violated)
* No parties (immediate eviction)
* No pets
* Pool cleaned weekly (Fridays)
* Rental Agreement and liability waiver required upon booking
* Late checkout without approval = $150+
Safety first: children must be supervised at all times
YOUR LUXURY DOWNTOWN CADILLAC RETREAT AWAITS
Relax by the pool, walk to dinner, unwind in the speakeasy, or soak under the stars — The Roosevelt offers a truly unique blend of history, luxury, and unbeatable location.
Book your stay now and experience Cadillac’s most iconic, amenity-packed retreat!
Pool~~~~~~~~~~~~~2 Blocks to Lake
Speakeasy~~~~~~~~6 Bedrooms
Fireplace~~~~~~~~~19 miles to Caberfae Peaks
Cornhole~~~~~~~~~Propane Grill
Theater Room~~~~~Wood Fire Pizza Oven
Pool Table~~~~~~~~Coffee & Cereal Bar
Board Games~~~~~Alexa Speakers
Fire-pit~~~~~~~~~~~Chef’s Kitchen
WELCOME TO THE ROOSEVELT: Cadillac's Most Luxurious & Historic Downtown Retreat
Step into a one-of-a-kind Northern Michigan escape combining restored historic charm with modern luxury. Located just one block off Main Street, The Roosevelt puts you steps from Cadillac’s best restaurants, breweries, boutiques, and lakefront attractions — all while offering your own private pool, year-round hot tub, brick oven pizza maker, and a hidden speakeasy unlike anything else in town.
Whether you’re planning a family vacation, a friends’ weekend, a golf or ski trip, or a relaxing retreat, this home delivers unforgettable comfort and entertainment in every season.
PROPERTY HIGHLIGHTS
RESORT-LEVEL OUTDOOR LIVING
* Private Pool (open 5/8–Labor Day)
* Year-Round Hot Tub for stargazing and snowy-night soaks
* Wood-Fired Brick Pizza Oven — create your own gourmet pies
* Fully Fenced Backyard - high privacy walls
* Outdoor Dining & Lounging with string lights and gas tiki torches
* 3-Stall Heated Garage for cars, gear, and winter convenience
Two blocks from Lake Cadillac — perfect for boating, beach days, and waterfront sunsets.
HIDDEN SPEAKEASY AND GAME LOUNGE
Welcome to your private underground hangout:
* 85” Theater TV for movies & game days
* Pool Table for late-night competitions
* Cozy bar-style seating and moody speakeasy lighting
* Your own “secret” entrance vibe — a true guest-favorite experience
* Arcade Machines coming soon
Perfect for gatherings, movie nights, or just unwinding after exploring Cadillac.
CHEF'S KITCHEN AND ENTERTAINING SPACES
Create, cook, and connect in a kitchen built for hosting:
* Professional Cooktop & Premium Appliances
* Coffee & Wine Bar (complimentary coffee included!)
* Large island perfect for groups
* Beautiful dining area for shared meals
Ideal for holidays, celebrations, or weekend feasts with friends and family.
6 BEDROOMS — SLEEPS LARGE GROUPS COMFORTABLY
Room for everyone, thoughtfully designed for comfort:
* Primary Suite — King bed, patio access
* Bedroom 2 — Two Queen beds
* Bedroom 3 — Queen bed
* Bedroom 4 — Two Bunk Beds (kid-approved!)
* Bedroom 5 — Two Twin beds
* Bedroom 6 — King bed with lake view
Perfect for multi-family trips, retreats, or larger gatherings.
LOCATION PERKS — WALK TO EVERYTHING
* 1 block – Downtown Cadillac (restaurants, shops, breweries, coffee, nightlife)
* 2 blocks – Lake Cadillac (beach, marina, park, lakefront path, White Pine trail)
* 5 min – Kenwood Beach & Boat Launch
* 8 min – Adventure Island Theme Park
* 9 min – Mitchell State Park
* 10 min – Mountain Biking at Cadillac Pathway
* 25 min – Caberfae Peaks Ski Resort
* 50 min – Crystal Mountain Ski Resort
* 1 hour – Traverse City (wineries, dining, festivals, airport)
A perfect base for skiing, boating, hiking, biking, fishing, snowmobiling, golfing, or relaxing by the pool.
FOUR-SEASON ADVENTURE HUB
Summer: boating & jet skiing (rentals available nearby), swimming, hiking, beaches
Fall: color tours, local breweries, golf, scenic drives, biking the 92 mile White Pine Trail
Winter: Caberfae Peaks skiing, x-country skiing, snowmobiling (rentals available nearby), ice fishing Spring: trails, fishing, brewery hopping, quiet getaways, biking the 92 mile White Pine Trail
Your garage offers easy storage for boats, bikes, trailers, snowmobiles, and adventure gear.
PARKING MADE EASY
* Heated 3-stall garage
* Spacious driveway Total room for 6+ vehicles, trailers, or adventure gear.
*Additional parking available on the public lot across the street
GOOD TO KNOW
* No smoking ($750+ extra cleaning fee if violated)
* No parties (immediate eviction)
* No pets
* Pool cleaned weekly (Fridays)
* Rental Agreement and liability waiver required upon booking
* Late checkout without approval = $150+
Safety first: children must be supervised at all times
YOUR LUXURY DOWNTOWN CADILLAC RETREAT AWAITS
Relax by the pool, walk to dinner, unwind in the speakeasy, or soak under the stars — The Roosevelt offers a truly unique blend of history, luxury, and unbeatable location.
Book your stay now and experience Cadillac’s most iconic, amenity-packed retreat!
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Laundry
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House Rules
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Load and start the dishwasher
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Ensure hot tub cover is on
Failure to complete these may result in a negative review from the host.
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
We should mention
This property does not have any lifts
About the area
Cadillac
Located in Cadillac, this holiday home is in the city centre and on a lake. McGuire's Resort and Adventure Island Family Fun Park are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Jennings Community Playground and Little Creek Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Cadillac, MI
What's nearby
- Wexford County Historical Museum - 3 min walk - 0.3 km
- Lake Cadillac - 5 min walk - 0.5 km
- Cadillac Lake Park and Boat Dock - 6 min walk - 0.6 km
- Diggins Park - 6 min walk - 0.6 km
- Cadillac Sound Garden - 11 min walk - 1.0 km
Restaurants
- McDonald's - 5 min drive
- Culver's - 5 min drive
- The Truck Stop - 4 min drive
- Taco Bell - 4 min drive
- G & D Pizza & Party Store - 6 min walk
Frequently asked questions
About the host
Your host
Premier Host
They consistently provide great experiences for their guests
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