Hotels in Jackson Square, FL: Compare 10+ Sites & Save

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  4.  Florida

  5.  Key West
  6.  Jackson Square

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254 Best Hotels in Jackson Square (Starting from $232)

The Cabana Inn Key West - Adult Exclusive
The Cabana Inn Key West - Adult Exclusive
Hotel
Key West, FL, USA
0.1k from Jackson Square center

B&bs, Accommodations, Pools, Parking, Inns, Romantic, 3-star, Lodgings, Hot tubs

8.2

Very Good

843 reviews

$232
Average price / night
Check Availability
La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
Hotel
430 Duval St, Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Bar, Breakfast Available, Business Services, Crib, Elevator, Fitness Equipment, Frontdesk 24 Hour, Housekeeping

8.8

Fabulous

371 reviews

$414
Average price / night
Check Availability
The Saint Hotel Key West, Autograph Collection, Adult Only
The Saint Hotel Key West, Autograph Collection, Adult Only
Hotel
Key West, FL, USA
0.2k from Jackson Square center

Accommodations, Pools, Parking, 4-star, Lodgings, Places to stay, Family, Accessible hotels

8.8

Fabulous

44 reviews

$268
Average price / night
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Pegasus International Hotel
Pegasus International Hotel
Hotel
Jackson Square, Key West, Florida, USA
0.2k from Jackson Square center

Accommodations, Pools, Parking, 3-star, Lodgings, Jacuzzis, Places to stay

7.5

Good

1269 reviews

$460
Average price / night
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The Key West Hotel
The Key West Hotel
Hotel
Key West, FL, USA
0.3k from Jackson Square center

Cheap, Accommodations, Pools, Pet-friendly, 3-star, Lodgings, Places to stay, Family

10.0

Exceptional

1 reviews

$420
Average price / night
Check Availability
Key West Villas
Key West Villas
Hotel
512 Angela St, Key West, FL, 33040, United States
0.3k from Jackson Square center

AC, Bar, Breakfast Included, Housekeeping, Internet, Laundry, Microwave, Outdoor Space, Parking Available

9.8

Exceptional

257 reviews

$392
Average price / night
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Duval Inn - Key West
Duval Inn - Key West
Hotel
Jackson Square, Key West, Florida, USA
0.3k from Jackson Square center

Accommodations, Pools, Motels, Parking, Romantic, Lodgings, Places to stay

8.1

Very Good

902 reviews

$460
Average price / night
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The Marquesa Hotel
The Marquesa Hotel
Hotel
600 Fleming Street, Key West, FL, 33040, United States
0.3k from Jackson Square center

AC, Bar, Business Services, Frontdesk 24 Hour, Housekeeping, Laundry, Outdoor Space, Parking Available, Pool

9.8

Exceptional

1002 reviews

$504
Average price / night
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The Gardens Hotel
The Gardens Hotel
Hotel
Jackson Square, Key West, Florida, USA
0.3k from Jackson Square center

Accommodations, Pools, Parking, Romantic, 4-star, Lodgings, Places to stay, Accessible hotels

9.7

Exceptional

141 reviews

$1074
Average price / night
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Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & Cottages
Hotel
320 Simonton St, Key West, FL, 33040, United States
0.4k from Jackson Square center

AC, Breakfast Included, Frontdesk 24 Hour, Housekeeping, Internet, Laundry, No Smoking, Outdoor Space, Parking Available

9.8

Exceptional

927 reviews

$365
Average price / night
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Classic King Balcony at the James House
Classic King Balcony at the James House
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

8.7

Fabulous

9 reviews

$469
Average price / night
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Hyatt Vacation Club at Sunset Harbor, Key West
Hyatt Vacation Club at Sunset Harbor, Key West
Hotel
200 Sunset Lane, Key West, FL, 33040, United States
0.4k from Jackson Square center

AC, Internet, Microwave, No Smoking, Parking Available, Pool, TV

8.6

Fabulous

349 reviews

$536
Average price / night
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Grand Maloney Hotel
Grand Maloney Hotel
Hotel
529 Caroline St, Key West, FL, 33040, United States
0.4k from Jackson Square center

AC, Heater, Internet, Laundry, No Smoking, Outdoor Space, Pool

7.8

Good

13 reviews

$502
Average price / night
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Blue Room at the Grand Maloney
Blue Room at the Grand Maloney
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

9.3

Superb

3 reviews

$403
Average price / night
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Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
Hotel
Key West, FL, 33040, United States
0.5k from Jackson Square center

AC, Balcony, Breakfast Included, Free Parking, Heater, Internet, No Smoking, Patio, TV

New to Booking
$680
Average price / night
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Yellow Room at Grand Maloney
Yellow Room at Grand Maloney
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Accommodations, Pools, Inns, Lodgings, Places to stay

5.0

Review score

1 reviews

$551
Average price / night
Check Availability
Bohemian Retreat with Pool in Old Town Key West | Free Breakfast Onsite!
Bohemian Retreat with Pool in Old Town Key West | Free Breakfast Onsite!
Hotel
Key West, FL, 33040, United States
0.5k from Jackson Square center

AC, Breakfast Included, Free Parking, Heater, Internet, No Smoking, TV

10.0

Exceptional

2 reviews

$462
Average price / night
Check Availability
Green Room at the Grand Maloney
Green Room at the Grand Maloney
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Cheap, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

8.5

Very Good

4 reviews

$429
Average price / night
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Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Hotel
Key West, FL, 33040, United States
0.5k from Jackson Square center

AC, Balcony, Breakfast Included, Free Parking, Heater, Internet, No Smoking, TV

New to Booking
$560
Average price / night
Check Availability
Carriage House at Grand Maloney
Carriage House at Grand Maloney
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Accommodations, Pools, Parking, Inns, Lodgings, Places to stay

New to Booking
$403
Average price / night
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Bunk Room at the Grand Maloney
Bunk Room at the Grand Maloney
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Cheap, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

9.7

Exceptional

3 reviews

$402
Average price / night
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Red Room at the Grand Maloney
Red Room at the Grand Maloney
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Cheap, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

8.5

Very Good

2 reviews

$285
Average price / night
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King Suite at Curry Mansion with Heated Pool!
King Suite at Curry Mansion with Heated Pool!
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

8.2

Very Good

35 reviews

$273
Average price / night
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Deluxe King with Balcony - at James House with Parking!
Deluxe King with Balcony - at James House with Parking!
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

6.4

Good

17 reviews

$276
Average price / night
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Classic Queen - Curry Mansion with Heated Pool
Classic Queen - Curry Mansion with Heated Pool
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

5.0

Review score

2 reviews

$256
Average price / night
Check Availability
Deluxe King - Curry Mansion with Pool!
Deluxe King - Curry Mansion with Pool!
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

4.7

Review score

4 reviews

$269
Average price / night
Check Availability
Deluxe Queen at the Curry Mansion - Parking & Heated Pool!
Deluxe Queen at the Curry Mansion - Parking & Heated Pool!
Hotel
Key West, FL, USA
0.4k from Jackson Square center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

7.2

Good

8 reviews

$288
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 Hotels in Jackson Square.

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Frequently Asked Questions

You can explore 254 verified hotels in Jackson Square. These include a range of options from luxury resorts and boutique hotels to budget-friendly accommodations suitable for different travel styles.

Hotel prices in Jackson Square vary depending on the season, location, and property type. Rates typically start from around $232 per night, with higher prices for premium hotels, central locations, or peak travel dates.

Most hotels in Jackson Square include amenities such as Pool, Internet, and View. Additional features like breakfast, parking, or resort facilities may vary by property, so it’s helpful to review the details before booking.

You can identify top-rated hotels in Jackson Square by sorting listings based on guest ratings and reviews. Looking at recent feedback, overall scores, and review volume can help you find properties that consistently deliver a high-quality experience.

For popular travel periods or busy locations, booking 30 to 60 days in advance is generally recommended to secure preferred options. During quieter periods, you may find more flexibility and availability closer to your travel dates.

Yes, some hotels in Jackson Square welcome pets. Currently, 22 listings allow pets, although policies may vary. It’s a good idea to review any pet-related rules before booking.

Many hotels in Jackson Square offer flexible or refundable booking options. Checking the cancellation policy before confirming your reservation can help you choose a rate that suits your travel plans.