Compare Villas, Resorts, & Rentals in Jackson Square, Key West, Florida, USA
About Casai's Private Villas and Holiday Rentals in Jackson Square
Discover more than 3727 vacation rentals available in Jackson Square. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Jackson Square.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Jackson Square, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Jackson Square. On average, places to stay near Jackson Square offer 777.39 ft², with nightly prices averaging CA $1,067.
With Casai, finding and comparing holiday rentals in Jackson Square is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Frequently Asked Questions About Jackson Square?
What are the top holiday rentals in Jackson Square?
- Almond Tree Inn Hotel - Adults Only
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Walkable Cottage w/Pool Access in Key West!
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Everything Key West has to offer @ Mango Cottage
- ~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
How many Casai.ca holiday rentals are available in Jackson Square?
As of 2026, Casai boasts over 3727 properties listed in the Jackson Square area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Jackson Square.
Nearby Neighborhood (12)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2066 |
| Old Town Vacation Rentals in Key West, Florida | 1988 |
| Downtown Vacation Rentals in Key West, Florida | 845 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 651 |
| Historic Seaport Vacation Rentals in Key West, Florida | 350 |
| Truman Annex Vacation Rentals in Key West, Florida | 272 |
| Meadows Vacation Rentals in Key West, Florida | 102 |
| New Town Vacation Rentals in Key West, Florida | 96 |
| Bahama Village Vacation Rentals in Key West, Florida | 68 |
| Midtown Vacation Rentals in Key West, Florida | 41 |
| Sunset Key Vacation Rentals in Key West, Florida | 3800 |
| Geiger Key Vacation Rentals in Key West, Florida | 54 |
