Compare Cabins, Resorts, & Rentals in Jackson Square, Key West, Florida, USA
About Jackson Square Vacation Rentals
There are more than 3518 incredible getaway rentals that are available in Jackson Square. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Jackson Square.
Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.com in Jackson Square, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Jackson Square. Places to stay near Jackson Square are 781.6 ft² on average, with prices averaging US $714 a night.
Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Jackson Square. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.
Frequently Asked Questions About Jackson Square?
What are the top cabins, lake houses & summer homes in Jackson Square?
- ~ 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
- Everything Key West has to offer @ Mango Cottage
- ~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
- BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
- SEA CONCH~ Amazing location with shared pool, deck, and parking!
- *MAYA’S SECRET TREASURE @ DUVAL* Private Pool & Balcony over Duval + LAST KEY
- Old Town Retreat near Upper Duval St
- ~HORSE CONCH~ Amazing location with shared pool and covered balcony!
How many hotels, resorts, or cabin rentals are available in Jackson Square?
Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2025 is over 3518 in the Jackson Square area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Jackson Square.
Nearby Neighborhood (12)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Rental Cabins and Private Getaways in Key West, Florida | 2504 |
| Old Town Rental Cabins and Private Getaways in Key West, Florida | 2435 |
| Downtown Rental Cabins and Private Getaways in Key West, Florida | 1072 |
| Uptown - Upper Duval Rental Cabins and Private Getaways in Key West, Florida | 764 |
| Historic Seaport Rental Cabins and Private Getaways in Key West, Florida | 411 |
| Truman Annex Rental Cabins and Private Getaways in Key West, Florida | 342 |
| New Town Rental Cabins and Private Getaways in Key West, Florida | 115 |
| Bahama Village Rental Cabins and Private Getaways in Key West, Florida | 94 |
| Meadows Rental Cabins and Private Getaways in Key West, Florida | 88 |
| Midtown Rental Cabins and Private Getaways in Key West, Florida | 51 |
| Sunset Key Rental Cabins and Private Getaways in Key West, Florida | 3214 |
| Geiger Key Rental Cabins and Private Getaways in Key West, Florida | 35 |
