Compare Vacation Rentals & Rent By Owner Homes in Jackson Square, Key West, Florida, USA
About Jackson Square Vacation Rentals
With more than 3617 Jackson Square 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 Jackson Square.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Jackson Square, 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 Jackson Square. Places to stay near Jackson Square are 781.51 ft² on average, with prices averaging AU $1,226 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Jackson Square 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 Jackson Square?
What are the top vacation rentals in Jackson Square?
- Almond Tree Inn Hotel - Adults Only
- Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
- Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
- Perfect Location, nPrivate Heated Pool,nPristine Luxury Home!
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
How many Rentbyowner vacation rentals are available in Jackson Square?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 3617 in the Jackson Square 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 Jackson Square.
Nearby Neighborhood (12)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2387 |
| Old Town Vacation Rentals in Key West, Florida | 2335 |
| Downtown Vacation Rentals in Key West, Florida | 1007 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 724 |
| Historic Seaport Vacation Rentals in Key West, Florida | 385 |
| Truman Annex Vacation Rentals in Key West, Florida | 333 |
| New Town Vacation Rentals in Key West, Florida | 106 |
| Meadows Vacation Rentals in Key West, Florida | 98 |
| Bahama Village Vacation Rentals in Key West, Florida | 93 |
| Midtown Vacation Rentals in Key West, Florida | 55 |
| Sunset Key Vacation Rentals in Key West, Florida | 3595 |
| Geiger Key Vacation Rentals in Key West, Florida | 51 |
