Compare Vacation Rentals & Rent By Owner Homes in Midtown, Key West, Florida, USA
About Midtown Vacation Rentals
With more than 89 Midtown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Midtown.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Midtown, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Midtown. Places to stay near Midtown are 981.17 ft² on average, with prices averaging AU $831 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Midtown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Frequently Asked Questions About Midtown?
What are the top vacation rentals in Midtown?
- Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
- *BELLE OF THE BEACH @ CASA EAST* Beach House + LAST KEY SERVICES…
- *LARGE PRIVATE HEATED POOL and PATIO*1/3 Mile from Beach
- BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
- Perfect 2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!
- Gorgeous beach bungalow just steps from the beach!
- SOUTHERNMOST SWIM AND SOCIAL CLUB
- *MIDTOWN MOSAIC @ MIDTOWN* Modern Private Home & Pool + LAST KEY SERVICES…
- Atlantis House Suites
- Orchid Oasis - Only Minutes from Smather's and Rest Beaches!
How many Rentbyowner vacation rentals are available in Midtown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 89 in the Midtown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Midtown.
Nearby Neighborhood (5)
| Neighborhood | Property Count |
|---|---|
| Old Town Vacation Rentals in Key West, Florida | 2210 |
| The Meadows Vacation Rentals in Key West, Florida | 103 |
| New Town Vacation Rentals in Key West, Florida | 89 |
| White St. Gallery Vacation Rentals in Key West, Florida | 4531 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4527 |
