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Our top choices for Jackson Square hotels

Almond Tree Inn Hotel - Adults Only
Almond Tree Inn Hotel - Adults OnlyDowntown Key West, 0.6 km from Jackson Square
10.0 out of 10, Exceptional, (1,000 reviews)
The price is ฿13,524
฿15,214 total
includes taxes & fees
29 Mar - 30 Mar

Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & CottagesHistoric Seaport, 0.4 km from Jackson Square
9.8 out of 10, Exceptional, (922 reviews)
The price is ฿13,065
฿14,699 total
includes taxes & fees
19 Apr - 20 Apr

The Gardens Hotel
The Gardens HotelDowntown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,002 reviews)
The price is ฿14,057
฿15,814 total
includes taxes & fees
22 Apr - 23 Apr

Orchid Key Inn - Adults Only
Orchid Key Inn - Adults OnlyUptown - Upper Duval, 0.6 km from Jackson Square
9.8 out of 10, Exceptional, (1,000 reviews)
The price is ฿13,409
฿15,085 total
includes taxes & fees
29 Mar - 30 Mar

H2O Suites - Adults Only
H2O Suites - Adults OnlyUptown - Upper Duval, 1 km from Jackson Square
9.8 out of 10, Exceptional, (592 reviews)
The price is ฿19,614
฿24,276 total
includes taxes & fees
19 Apr - 20 Apr

Tropical Inn
Tropical InnDowntown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (384 reviews)
The price is ฿6,920
฿8,604 total
includes taxes & fees
1 Apr - 2 Apr

Weatherstation Inn
Weatherstation InnTruman Annex, 0.3 km from Jackson Square
9.4 out of 10, Exceptional, (1,002 reviews)
The price is ฿12,495
฿14,057 total
includes taxes & fees
30 Mar - 31 Mar

The Grand Guesthouse
The Grand GuesthouseOld Town Key West, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,001 reviews)
The price is ฿9,680
฿11,709 total
includes taxes & fees
29 Mar - 30 Mar

Ambrosia Key West
Ambrosia Key WestOld Town Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,002 reviews)
The price is ฿11,171
฿12,567 total
includes taxes & fees
29 Mar - 30 Mar

Silver Palms Inn
Silver Palms InnOld Town Key West, 0.9 km from Jackson Square
9.4 out of 10, Exceptional, (1,029 reviews)
The price is ฿9,106
฿12,455 total
includes taxes & fees
1 Apr - 2 Apr

Ella's Cottages - Key West Historic Inns
Ella's Cottages - Key West Historic InnsOld Town Key West, 0.5 km from Jackson Square
9.4 out of 10, Exceptional, (452 reviews)
The price is ฿13,143
฿16,455 total
includes taxes & fees
5 Apr - 6 Apr

Caribbean House
Caribbean HouseBahama Village, 0.4 km from Jackson Square
9.2 out of 10, Wonderful, (338 reviews)
The price is ฿7,049
฿8,749 total
includes taxes & fees
29 Mar - 30 Mar

Southernmost House
Southernmost HouseUptown - Upper Duval, 1.1 km from Jackson Square
9.4 out of 10, Exceptional, (1,000 reviews)
The price is ฿10,452
฿15,903 total
includes taxes & fees
19 Apr - 20 Apr

Ridley House - Key West Historic Inns
Ridley House - Key West Historic InnsHistoric Seaport, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (893 reviews)
The price is ฿12,417
฿15,627 total
includes taxes & fees
16 Apr - 17 Apr

The Garden House
The Garden HouseHistoric Seaport, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (688 reviews)
The price is ฿12,547
฿14,825 total
includes taxes & fees
27 Apr - 28 Apr

Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic InnsOld Town Key West, 0.8 km from Jackson Square
9.2 out of 10, Wonderful, (1,221 reviews)
The price is ฿13,143
฿16,455 total
includes taxes & fees
5 Apr - 6 Apr

Opal Key Resort & Marina, Key West
Opal Key Resort & Marina, Key WestOld Town Key West, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (1,072 reviews)
The price is ฿12,495
฿15,356 total
includes taxes & fees
19 Apr - 20 Apr

The Marker Key West Harbor Resort
The Marker Key West Harbor ResortHistoric Seaport, 0.7 km from Jackson Square
9.2 out of 10, Wonderful, (1,005 reviews)
The price is ฿14,657
฿18,566 total
includes taxes & fees
27 Apr - 28 Apr

The Saint Hotel Key West, Autograph Collection, Adult Only
The Saint Hotel Key West, Autograph Collection, Adult OnlyHistoric Seaport, 0.2 km from Jackson Square
9.0 out of 10, Wonderful, (356 reviews)
The price is ฿13,393
฿15,067 total
includes taxes & fees
30 Mar - 31 Mar

Heron House - Adult Only
Heron House - Adult OnlyDowntown Key West, 0.3 km from Jackson Square
9.0 out of 10, Wonderful, (1,126 reviews)
The price is ฿5,999
฿7,900 total
includes taxes & fees
1 Apr - 2 Apr
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Compare popular hotels close to Jackson Square
Property | Property class | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included | |
|---|---|---|---|---|---|---|---|---|
![]() Almond Tree Inn Hotel - Adults Only | 10.0 Exceptional 1,000 reviews | View | ||||||
![]() Simonton Court Historic Inn & Cottages | 9.8 Exceptional 922 reviews | View | ||||||
![]() The Gardens Hotel | 9.8 Exceptional 1,002 reviews | View | ||||||
![]() Orchid Key Inn - Adults Only | 9.8 Exceptional 1,000 reviews | View | ||||||
![]() H2O Suites - Adults Only | 9.8 Exceptional 592 reviews | View |
Top Jackson Square Hotel Reviews

Duval House
10/10 Excellent











































































