Monthly Stays in Jackson Square by Sonder
Find monthly stays across Jackson Square’s neighborhoods.
Where to stay in Jackson Square
Design-led rooms, walkable streets, and neighborhoods worth staying in rather than passing through.
Featured Monthly Stays Stays
Monthly Stays preferred by Jackson Square travelers
A curated selection of Jackson Square monthly stays chosen for their location, design, and overall stay experience across the city.
US $953/Night
30 Nights - US $28,598
US $295/Night
30 Nights - US $8,839
US $1,339/Night
30 Nights - US $40,170
US $1,461/Night
30 Nights - US $43,826
US $252/Night
30 Nights - US $7,575
US $1,094/Night
30 Nights - US $32,820
House
10.0(2 Reviews)
2 Bedrooms
8 Guests
EV Charge Station
Parking
Pool
Balcony/Terrace
US $1,658/Night
30 Nights - US $49,740
US $168/Night
30 Nights - US $5,029
US $891/Night
30 Nights - US $26,727
Hotel
9.0(372 Reviews)
Breakfast- Parking
- Pool
Ocean View
US $239/Night
30 Nights - US $7,155
Apartment
10.0(2 Reviews)
1 Bedroom
4 Guests
- Pool
- Balcony/Terrace
View
Air Conditioner
US $609/Night
30 Nights - US $18,270
US $704/Night
30 Nights - US $21,109
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
Pet Friendly
Child Friendly
Security/Safety
US $540/Night
30 Nights - US $16,193
Hotel
9.0(989 Reviews)
- Breakfast
- Pool
- Balcony/Terrace
- Air Conditioner
US $292/Night
30 Nights - US $8,756
Apartment
10.0(2 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $405/Night
30 Nights - US $12,150
Apartment
1 Bedroom
Internet- Child Friendly
Guest Services
US $781/Night
30 Nights - US $23,435
House
10.0(2 Reviews)
1 Bedroom
4 Guests
- Pet Friendly
- Child Friendly
- Security/Safety
US $274/Night
30 Nights - US $8,225
Apartment
1 Bedroom
- Parking
- Internet
- Child Friendly
US $1,533/Night
30 Nights - US $45,998
House
10.0(2 Reviews)
1 Bedroom
2 Guests
- Breakfast
- Parking
- Pool
- View
US $333/Night
30 Nights - US $9,976
Hotel
9.2(954 Reviews)
- Breakfast
- Pool
- Balcony/Terrace
Kitchen
US $269/Night
30 Nights - US $8,081
House
10.0(1 Review)
4 Bedrooms
12 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $2,823/Night
30 Nights - US $84,693
US $279/Night
30 Nights - US $8,374
House
10.0(1 Review)
4 Bedrooms
8 Guests
Oceanfront
Hot Tub- Breakfast
- Parking
US $2,211/Night
30 Nights - US $66,330
US $206/Night
30 Nights - US $6,165
Where to Stay in Jackson Square
Places made for checking in and heading out.
Each part of Jackson Square offers its own way to spend the stay, from the streets you walk in the morning to the tables you end up at after dark.
Jackson Square, Florida
Duval Street
Jackson Square, Florida
Smathers Beach
Jackson Square, Florida
Southernmost Point
Jackson Square, Florida
Mallory Square
Jackson Square, Florida
South Beach
Jackson Square, Florida
Higgs Beach
Jackson Square, Florida
Key West Harbour
Jackson Square, Florida
Key West Aquarium
Booking Your Stay
How stays in Jackson Square are booked.
Discover a stay
Browse a curated selection of Jackson Square hotels, shaped by location, design, and experience.
Review the details
Explore layout, amenities, and the neighborhood to see how each stay fits your trip.
Reserve through a partner
Complete your booking securely through a trusted partner, with confirmation handled there.
Hotel FAQs
Everything to know before you check in to
Everything to know before you check in to
Jackson Square.
01 / 06
What are the top rated Monthly Stays in Jackson Square?
There are a lot of options in Jackson Square. If you plan on staying in the Jackson Square area, consider making a reservation for a few nights at one of these properties as these have been rated the top Monthly Stays in Jackson Square:
- Parrot Perch by Avantstay Old Town Key West w/Shared Pool Month-long Stays Only
- Duke of Catherine by Last Key Realty
- Casa Serendipity by Last Key Realty
- Pescado Penthouse
- Casita Angelita by Last Key Realty
- Natures Edge by Last Key Realty
- Two Duval Street Condos w parking and pool
- Sunnyside Up by Brightwild Pool Parking
- Walking on Sunshine by Last Key Realty
- Duval Dream Loft by Brightwild Right on Duval
02 / 06
How do I book a month's stay in Jackson Square on Sonder?
To book any amount of stay in Jackson Square visit Sonder rental listings, click length of stay, choose the number of days, weeks, or months you want to spend, then enter the date and destination. Some properties may need you to inquire with the property prior to booking to learn more about extended or monthly stays.
03 / 06
What are the best pet-friendly monthly rentals in Jackson Square?
We have many pet-friendly long-term rentals in or near Jackson Square. The top pet-friendly rentals in Jackson Square are:
04 / 06
Do any monthly or weekly vacation rentals in Jackson Square have a pool?
Yes, there are more than 706 vacation rentals in Jackson Square that have indoor and private swimming pools. Check out our filter option and find your best extended stay near Jackson Square.
05 / 06
What are some great rentals in Jackson Square that have internet access?
Internet access is a requirement for most extended-stay travelers. Most of the holiday rentals we list have internet availability on premises.
06 / 06
How many monthly rentals with hot tubs are available for rent in Jackson Square?
There are 706 monthly stays available for rent in Jackson Square.
There are a lot of options in Jackson Square. If you plan on staying in the Jackson Square area, consider making a reservation for a few nights at one of these properties as these have been rated the top Monthly Stays in Jackson Square:
- Parrot Perch by Avantstay Old Town Key West w/Shared Pool Month-long Stays Only
- Duke of Catherine by Last Key Realty
- Casa Serendipity by Last Key Realty
- Pescado Penthouse
- Casita Angelita by Last Key Realty
- Natures Edge by Last Key Realty
- Two Duval Street Condos w parking and pool
- Sunnyside Up by Brightwild Pool Parking
- Walking on Sunshine by Last Key Realty
- Duval Dream Loft by Brightwild Right on Duval
To book any amount of stay in Jackson Square visit Sonder rental listings, click length of stay, choose the number of days, weeks, or months you want to spend, then enter the date and destination. Some properties may need you to inquire with the property prior to booking to learn more about extended or monthly stays.
We have many pet-friendly long-term rentals in or near Jackson Square. The top pet-friendly rentals in Jackson Square are:
Yes, there are more than 706 vacation rentals in Jackson Square that have indoor and private swimming pools. Check out our filter option and find your best extended stay near Jackson Square.
Internet access is a requirement for most extended-stay travelers. Most of the holiday rentals we list have internet availability on premises.
There are 706 monthly stays available for rent in Jackson Square.
