Short-Term Rentals in Jackson Square, FL: Compare 10+ Sites & Save

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2250 Best Short-Term Rentals in Jackson Square (Starting from $162)

New KAMP - Rooftop Penthouse
New KAMP - Rooftop Penthouse
Apartment
Key West, FL, USA
0.1k from Jackson Square center

Apartments, Accommodations, Lodgings, Places to stay, Family

1 Bedroom6 Guests
New to Booking
$889
Average price / night
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Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
Apartment
Key West, FL, 33040, United States
0.0k from Jackson Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.6

Exceptional

52 reviews

$1128
Average price / night
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Breezy Bungalow by AvantStay Close 2 Zachary Taylor State Park Beach w Shared Pool Week Long Stays
Breezy Bungalow by AvantStay Close 2 Zachary Taylor State Park Beach w Shared Pool Week Long Stays
House
Key West, FL, USA
0.2k from Jackson Square center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$475
Average price / night
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Lavender Jungle | Great Location w/ Patio & Shared Pool | Month-Long Stays
Lavender Jungle | Great Location w/ Patio & Shared Pool | Month-Long Stays
House
Key West, FL, 33040, United States
0.0k from Jackson Square center

AC, Dryer, Internet, Kitchen, Laundry, No Smoking, Patio, Pool, TV

2 Bedrooms4 Guests
8.8

Fabulous

15 reviews

$329
Average price / night
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Beautiful Downtown Truman Annex Condo
Beautiful Downtown Truman Annex Condo
House
Key West, FL, USA
0.2k from Jackson Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Condos

2 Bedrooms4 Guests
New to Booking
$472
Average price / night
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Luxe Designer Oasis + Guest House steps off Duval
Luxe Designer Oasis + Guest House steps off Duval
House
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, Living Area

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1050
Average price / night
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Rooftop Penthouse
Rooftop Penthouse
House
Key West, FL, USA
0.2k from Jackson Square center

Internet, Laundry, Security/Safety, Child Friendly

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$661
Average price / night
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**VOGUE VILLA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...
**VOGUE VILLA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms7 Guests
New to Booking
$643
Average price / night
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The Perch on Duval
The Perch on Duval
Apartment
Key West, FL, USA
0.2k from Jackson Square center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$575
Average price / night
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Sunset Overlook - Waterfront Condo at Harbour Place with Sunset View
Sunset Overlook - Waterfront Condo at Harbour Place with Sunset View
Condo
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Dryer, Elevator, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$325
Average price / night
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Peak Of Duval
Peak Of Duval
House
Key West, FL, USA
0.2k from Jackson Square center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$421
Average price / night
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Coco Plum Inn
Coco Plum Inn
House
611 Whitehead Street, Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Breakfast Included, Housekeeping, Internet, Microwave, Outdoor Space, Pool, TV

9.4

Superb

507 reviews

$381
Average price / night
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Bahamian Bamboo by Last Key Realty
Bahamian Bamboo by Last Key Realty
House
Key West, FL, USA
0.2k from Jackson Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$3038
Average price / night
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The Cabana Inn Key West - Adults Only
The Cabana Inn Key West - Adults Only
House
413 Applerouth Lane, Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Breakfast Included, Hot Tub, Housekeeping, Laundry, Microwave, Outdoor Space, Parking Available, Pool

8.8

Fabulous

1003 reviews

$366
Average price / night
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Villa Angelita by Last Key Realty
Villa Angelita by Last Key Realty
House
Key West, FL, USA
0.2k from Jackson Square center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$1547
Average price / night
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Southard Getaway | Covered Patio, Great Location, Shared Pool | Month Long Stays
Southard Getaway | Covered Patio, Great Location, Shared Pool | Month Long Stays
House
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Dryer, Extra Bed, Internet, Kitchen, Laundry, No Smoking, Patio, Pool

2 Bedrooms5 Guests
9.4

Superb

13 reviews

$396
Average price / night
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Trumans Trove by Last Key realty
Trumans Trove by Last Key realty
House
Key West, FL, USA
0.2k from Jackson Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$946
Average price / night
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A Siesta Bay | Walk to Key West, Gated Community, Shared Pool | Month-Long Stays
A Siesta Bay | Walk to Key West, Gated Community, Shared Pool | Month-Long Stays
House
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, No Smoking, Patio

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$410
Average price / night
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Casita Angelita by Last Key Realty
Casita Angelita by Last Key Realty
House
Key West, FL, USA
0.2k from Jackson Square center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$329
Average price / night
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KAMP - Rooftop Penthouse Overlooking Duval
KAMP - Rooftop Penthouse Overlooking Duval
Apartment
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Arcade, Balcony, Dryer, Elevator, Extra Bed, Heater, Internet, Kitchen

2 Bedrooms6 Guests
8.4

Very Good

21 reviews

$1190
Average price / night
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The Perch on Duval- Hip & Modern Duval Suite
The Perch on Duval- Hip & Modern Duval Suite
Apartment
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms5 Guests
9.8

Exceptional

15 reviews

$772
Average price / night
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The Collins on Duval by Brightwild
The Collins on Duval by Brightwild
Apartment
505 Duval St Key West FL 33040 USA, Key West, FL, 33040, United States
0.2k from Jackson Square center

Internet, Living Area

New to Booking
$1018
Average price / night
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Duval s Duet on Duval by Brightwild
Duval s Duet on Duval by Brightwild
Apartment
505 Duval St Key West FL 33040 USA, Key West, FL, 33040, United States
0.2k from Jackson Square center

Internet, Living Area

New to Booking
$2399
Average price / night
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Casa Mamisa - 2 bedroom home in Old Town
Casa Mamisa - 2 bedroom home in Old Town
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.4

Superb

3 reviews

$162
Average price / night
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OCEAN BREEZE BUNGALOW-Stunning 2 Bedroom / 2.5 Bathroom in Truman Annex
OCEAN BREEZE BUNGALOW-Stunning 2 Bedroom / 2.5 Bathroom in Truman Annex
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
New to Booking
$385
Average price / night
Check Availability
1 PARTICULAR HARBOR. Beautiful corner 2 bedroom townhome in Truman Annex
1 PARTICULAR HARBOR. Beautiful corner 2 bedroom townhome in Truman Annex
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$574
Average price / night
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Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms7 Guests
New to Booking
$837
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Jackson Square.

Where to stay in Jackson Square? Best neighborhoods & areas

Jackson Square Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 2250 verified short-term rentals in Jackson Square, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Jackson Square vary depending on location, property size, and travel dates. Rates typically start from around $162 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Jackson Square include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Jackson Square, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Jackson Square often include amenities such as Internet, Wellness Facilities, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Jackson Square are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.