Key West Jackson Square Hotels
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Our top choices for Jackson Square hotels
1. 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, (1,011 reviews)
"Great stay! Great location and friendly, helpful staff. Loved our stay here! Would recommend."
Linda
The price is HK$1,601
HK$1,801 total
includes taxes & fees
28 Jul - 29 Jul
2. Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & CottagesHistoric Seaport, 0.4 km from Jackson Square
9.8 out of 10, Exceptional, (1,010 reviews)
"Strongly recommend this place when staying in Key West. Such a charming place - much better option than a hotel.
Best part was the warm hospitality by every single staff we have interacted."
Jeannie
The price is HK$1,404
HK$1,579 total
includes taxes & fees
28 Jul - 29 Jul
3. The Gardens Hotel
The Gardens HotelDowntown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,003 reviews)
"It was a great stay."
Salvatore
The price is HK$1,579
HK$1,777 total
includes taxes & fees
10 Aug - 11 Aug
4. Orchid Key Inn - Adults Only
Orchid Key Inn - Adults OnlyUptown - Upper Duval, 0.6 km from Jackson Square
9.8 out of 10, Exceptional, (1,007 reviews)
"Wonderful place and staff!"
William
The price is HK$1,570
HK$1,766 total
includes taxes & fees
2 Aug - 3 Aug
5. Key West Villas
Key West VillasDowntown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (271 reviews)
"Great Villa right off Duval, the most helpful staff and kind people. My friends and I stayed for a bachelorette trip couldn’t say more positive things."
Mackenzie
The price is HK$1,546
HK$1,739 total
includes taxes & fees
9 Aug - 10 Aug
6. The Mermaid & Alligator
The Mermaid & AlligatorOld Town Key West, 0.8 km from Jackson Square
9.8 out of 10, Exceptional, (308 reviews)
"Beautiful property, the staff were so friendly! Loved the complimentary breakfast and happy hour. We can’t wait to come back."
Kayla
The price is HK$1,665
HK$1,873 total
includes taxes & fees
3 Aug - 4 Aug
7. The Conch House Heritage Inn
The Conch House Heritage InnOld Town Key West, 0.7 km from Jackson Square
9.8 out of 10, Exceptional, (181 reviews)
"We visit Key West several times per year. This was our first stay at the Conch House. It definitely will not be our last. This is now one of favorite places to stay."
Michael
The price is HK$1,487
HK$1,673 total
includes taxes & fees
9 Aug - 10 Aug
8. Tranquility Guest House
Tranquility Guest HouseBahama Village, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (9 reviews)
"It was a great property, very clean room and excellent price. Staff was great."
Hector
The price is HK$916
HK$1,727 total
includes taxes & fees
18 Aug - 19 Aug
9. Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Alexanders Guesthouse - Adult Exclusive, LGBTQ FriendlyOld Town Key West, 1.1 km from Jackson Square
9.8 out of 10, Exceptional, (152 reviews)
"Wonderful staff🙏🙏🙏"
Abhinav Shanth
The price is HK$699
HK$1,080 total
includes taxes & fees
28 Jul - 29 Jul
10. The Marquesa Hotel
The Marquesa HotelOld Town Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,001 reviews)
"Great location and beautiful property. I appreciate the parking which comes at a premium in Key West and the two swimming pools. Just enough off the beaten path to feel comfortable."
Darrell
The price is HK$1,772
HK$2,435 total
includes taxes & fees
11 Aug - 12 Aug
11. H2O Suites - Adults Only
H2O Suites - Adults OnlyUptown - Upper Duval, 1 km from Jackson Square
9.8 out of 10, Exceptional, (627 reviews)
"Our favorite hotel there is! Amazing rooms and an even better staff. Best turn down service we have ever experienced with yummy muffins and dove bars, housekeeping is amazing! Roof top pool is first class and the bar tender Angie makes you feel at home!"
James
The price is HK$2,267
HK$3,079 total
includes taxes & fees
16 Aug - 17 Aug
12. Douglas House - Adults Only
Douglas House - Adults OnlyUptown - Upper Duval, 0.8 km from Jackson Square
9.6 out of 10, Exceptional, (465 reviews)
"Good location"
Christina
The price is HK$915
HK$1,132 total
includes taxes & fees
29 Jul - 30 Jul
13. Island City House Hotel
Island City House HotelHistoric Seaport, 0.6 km from Jackson Square
9.6 out of 10, Exceptional, (1,004 reviews)
"We loved our time here! This was a child friendly space in a beautiful setting. The staff was very kind, the space was clean and comfortable. We will definitely be back!"
Brittany
The price is HK$1,459
HK$1,641 total
includes taxes & fees
2 Aug - 3 Aug
14. Tropical Inn
Tropical InnDowntown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (425 reviews)
"This property exceeded our expectations!!! We are exploring bringing our whole family to this location in Key West. Pool, hot tub, location and staff was amazing!"
Joel
The price is HK$1,471
HK$1,851 total
includes taxes & fees
30 Jul - 31 Jul
15. The Grand Guesthouse
The Grand GuesthouseOld Town Key West, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,002 reviews)
"Very quaint. A lot of nice amenities! Would stay there again."
Dan
The price is HK$905
HK$1,214 total
includes taxes & fees
28 Jul - 29 Jul
16. Silver Palms Inn & Historic Homes
Silver Palms Inn & Historic HomesOld Town Key West, 0.9 km from Jackson Square
9.4 out of 10, Exceptional, (1,040 reviews)
"Nice staff and close to everything. I would stay there again"
Alex
The price is HK$653
HK$1,264 total
includes taxes & fees
10 Aug - 11 Aug
17. Southernmost House - Adult Exclusive
Southernmost House - Adult ExclusiveUptown - Upper Duval, 1.1 km from Jackson Square
9.4 out of 10, Exceptional, (1,005 reviews)
"Great place!"
Dan
The price is HK$1,092
HK$2,222 total
includes taxes & fees
10 Aug - 11 Aug
18. Santa Maria Suites
Santa Maria SuitesUptown - Upper Duval, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,013 reviews)
"Great location. Friendly staff and clean property"
Veronica
The price is HK$2,188
HK$2,991 total
includes taxes & fees
18 Aug - 19 Aug
19. Duval House
Duval HouseDowntown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,065 reviews)
"The staff was excellent and location was perfect"
Melissa
The price is HK$925
HK$1,210 total
includes taxes & fees
30 Jul - 31 Jul
20. Coco Plum Inn
Coco Plum InnDowntown Key West, 0.1 km from Jackson Square
9.4 out of 10, Exceptional, (551 reviews)
"Perfect stay, we will be back!"
Jake
The price is HK$1,380
HK$1,553 total
includes taxes & fees
28 Jul - 29 Jul
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 1,011 reviews | View | ||||||
 Simonton Court Historic Inn & Cottages | 9.8 Exceptional 1,010 reviews | View | ||||||
 The Gardens Hotel | 9.8 Exceptional 1,003 reviews | View | ||||||
 Orchid Key Inn - Adults Only | 9.8 Exceptional 1,007 reviews | View | ||||||
 Key West Villas | 9.8 Exceptional 271 reviews | View |
Top Jackson Square Hotel Reviews
The Cabana Inn Key West - Adults Only
10/10 Excellent
