Compare Villas, Resorts, & Rentals in Jackson Square, Key West, Florida, USA
About Jackson Square Vacation Rentals
There are more than 3624 incredible getaway rentals that are available in Jackson Square. These choices include villas, 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. Relax with BedroomVillas and uncover great stays in Jackson Square.
BedroomVillas features numerous last-minute deals on villas, hotels, and 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 BedroomVillas 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 BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Jackson Square. Places to stay near Jackson Square are 786.16 ft² on average, with prices averaging US $809 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime 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 place to stay today.
Frequently Asked Questions About Jackson Square?
What are the top hotels or resorts 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
- ~ 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 hotels, resorts, or rentals are available in Jackson Square?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 3624 in the Jackson Square area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas 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 Villas and Private Getaways in Key West, Florida | 2409 |
| Old Town Rental Villas and Private Getaways in Key West, Florida | 2371 |
| Downtown Rental Villas and Private Getaways in Key West, Florida | 992 |
| Uptown - Upper Duval Rental Villas and Private Getaways in Key West, Florida | 761 |
| Historic Seaport Rental Villas and Private Getaways in Key West, Florida | 387 |
| Truman Annex Rental Villas and Private Getaways in Key West, Florida | 349 |
| New Town Rental Villas and Private Getaways in Key West, Florida | 107 |
| Meadows Rental Villas and Private Getaways in Key West, Florida | 100 |
| Bahama Village Rental Villas and Private Getaways in Key West, Florida | 92 |
| Midtown Rental Villas and Private Getaways in Key West, Florida | 49 |
| Geiger Key Rental Villas and Private Getaways in Key West, Florida | 51 |
| Sunset Key Rental Villas and Private Getaways in Key West, Florida | 3595 |
