4 Stars Hotels in Old Town Key West, Key West from CA $571

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Check availability on Old Town Key West 4 Star Hotels

Top Old Town Key West 4 Star Hotels

Southernmost Beach Resort
3 outdoor pools, pool umbrellas, sun loungers

Southernmost Beach Resort

4.0 star property
8.6 out of 10, Excellent, (2233)
"We stayed here during some torrential tropical storm weather but we had one of the incredible rooms at La Mer, which allowed us to sit outside of our room and enjoy the storm. Highly recommend La Mer! Absolutely adorable beautiful room. We noticed that they started bringing the beach loungers in and tying them up WELL before the storm so that was quite an inconvenience for some folks. We were lucky enough to get our chairs before they started doing that so at least they didn’t make us leave our...
The price is CA $672
CA $854 total
includes taxes & fees
Jan 22 - Jan 23
Southernmost Beach Resort
Winslow's Bungalows - Key West Historic Inns
3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers

Winslow's Bungalows - Key West Historic Inns

4.0 star property
9.0 out of 10, Wonderful, (1000)
"This is a very interesting property. We stayed in one of the bungalows though there are other types of rooms available. It is an old property, but recently refurbished/renovated. The room was small but well appointed and had a nice bathroom with a tiled walk-in shower. There is a nice full service outdoor bar adjacent to the kitchen area. A very nice breakfast is included with the reservation. There is free WiFi which is pretty good. The biggest downside to Winslow’s is the satellite tv. There...
The price is CA $571
CA $702 total
includes taxes & fees
Jan 28 - Jan 29
Winslow's Bungalows - Key West Historic Inns
Opal Key Resort & Marina, Key West
Front of property - evening/night

Opal Key Resort & Marina, Key West

4.0 star property
9.2 out of 10, Wonderful, (1000)
"We had a great time! We were even given an upgrade. It was an amazing trip!"
The price is CA $599
CA $730 total
includes taxes & fees
Jan 26 - Jan 27
Opal Key Resort & Marina, Key West
Seashell Motel & Key West Hostel
Free WiFi, bed sheets

Seashell Motel & Key West Hostel

1.5 star property
7.8 out of 10, Good, (1000)
"Time for ME, doing what I Want, my pace, my needs"
The price is CA $203
CA $228 total
includes taxes & fees
Jan 23 - Jan 24
Seashell Motel & Key West Hostel
Casa Marina Key West, Curio Collection by Hilton
Fireplace

Casa Marina Key West, Curio Collection by Hilton

4.0 star property
7.0 out of 10, Good, (1003)
"Good nice place, friendly. But to expensive "
The price is CA $862
CA $1,060 total
includes taxes & fees
Feb 2 - Feb 3
Casa Marina Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton
Outdoor pool, pool umbrellas, sun loungers

The Reach Key West, Curio Collection by Hilton

4.0 star property
8.4 out of 10, Very good, (854)
"They charged me abunch of extra for I have no idea why "
The price is CA $685
CA $861 total
includes taxes & fees
Jan 29 - Jan 30
The Reach Key West, Curio Collection by Hilton
Lighthouse Hotel - Key West Historic Inns
Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

Lighthouse Hotel - Key West Historic Inns

3.5 star property
9.0 out of 10, Wonderful, (660)
"The rooms were so unique and different. We loved area. It was small and wonderfully staffed. The area is very clean. The breakfast was very fresh and good. Bar had good drinks and a lounge place to hang out and visit with friends. The location was great and walkable to restaurants. Parking was a bit of a challenege with only 4 spots. We got lucky, had to pay for it but its Key West. The only complaint was the super thin walls. Everyday we heard the neighbor yelling at his kids. Ugh!...
The price is CA $549
CA $678 total
includes taxes & fees
Jan 28 - Jan 29
Lighthouse Hotel - Key West Historic Inns
Southwinds Motel
Exterior

Southwinds Motel

2.0 star property
8.8 out of 10, Excellent, (1053)
"Wonderful property. Very reasonable price. Definitely would stay here again."
The price is CA $359
CA $444 total
includes taxes & fees
Jan 27 - Jan 28
Southwinds Motel
Heron House - Adult Only
Exterior

Heron House - Adult Only

3.5 star property
9.0 out of 10, Wonderful, (1067)
"the pool was lovely, and the house cat Mary was so sweet came and visited us. breakfast was very nice with lots of options."
The price is CA $372
CA $465 total
includes taxes & fees
Jan 27 - Jan 28
Heron House - Adult Only
The Southernmost Inn - Adults Only
Courtyard

The Southernmost Inn - Adults Only

3.0 star property
8.0 out of 10, Very good, (1002)
"First time in Key West, found hotel to be warm, welcoming, well appointed and reasonably priced. Thank you for a great experience !!!"
The price is CA $471
CA $594 total
includes taxes & fees
Jan 29 - Jan 30
The Southernmost Inn - Adults Only
Duval House
View from property

Duval House

3.0 star property
9.4 out of 10, Exceptional, (1002)
"Loved the location on Duval street. We could walk to all the fun spots. The room was a bit small but clean and bed was comfy. The free breakfast was good. We will stay again. "
The price is CA $418
CA $502 total
includes taxes & fees
Jan 22 - Jan 23
Duval House
Wicker Guesthouse
Porch

Wicker Guesthouse

3.5 star property
8.6 out of 10, Excellent, (1000)
"Very close to everything. "
The price is CA $569
CA $640 total
includes taxes & fees
Feb 11 - Feb 12
Wicker Guesthouse
Caribbean House
Terrace/patio

Caribbean House

3.0 star property
9.0 out of 10, Wonderful, (170)
"Perfect location. Right in the middle of everything. "
The price is CA $433
CA $523 total
includes taxes & fees
Jan 26 - Jan 27
Caribbean House
Silver Palms Inn
Outdoor pool

Silver Palms Inn

3.5 star property
9.2 out of 10, Wonderful, (1007)
"Great place to stay "
The price is CA $411
CA $558 total
includes taxes & fees
Feb 4 - Feb 5
Silver Palms Inn
The Palms Hotel
Deluxe King Room (Not Pet Friendly)

The Palms Hotel

3.0 star property
8.6 out of 10, Excellent, (1001)
"Perfect location, Although it does not have enough parking"
The price is CA $357
CA $430 total
includes taxes & fees
Jan 22 - Jan 23
The Palms Hotel
Ella's Cottages - Key West Historic Inns
Business centre

Ella's Cottages - Key West Historic Inns

3.5 star property
9.2 out of 10, Wonderful, (260)
"Excellent property close to Duval street. Parking on site. Staff was friendly and excellent hosts. Breakfast was delicious and delivered right to our room. Would definitely recommend "
The price is CA $718
CA $867 total
includes taxes & fees
Jan 27 - Jan 28
Ella's Cottages - Key West Historic Inns
Authors of Key West Guest House
Sundeck

Authors of Key West Guest House

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Nice place"
The price is CA $285
CA $352 total
includes taxes & fees
Jan 26 - Jan 27
Authors of Key West Guest House
The Mansion on the Sea - Southernmost House in the USA
Mansion Room #201 - Ocean View with private balcony - Adults Only | Terrace/patio

The Mansion on the Sea - Southernmost House in the USA

3.0 star property
9.4 out of 10, Exceptional, (1000)
"Beautiful, unique experience. "
The price is CA $785
CA $927 total
includes taxes & fees
Jan 22 - Jan 23
The Mansion on the Sea - Southernmost House in the USA
Duval Gardens at Southernmost Beach Resort – Adults Only
Front of property

Duval Gardens at Southernmost Beach Resort – Adults Only

4.0 star property
9.2 out of 10, Wonderful, (908)
"We decided to ask for an upgrade to our original reservation We did not stay at Duval Gardens.We stayed in king room with balcony and pool and ocean view. It was recently updated and beautiful. We couldn’t have made a better decision. "
The price is CA $655
CA $866 total
includes taxes & fees
Jan 28 - Jan 29
Duval Gardens at Southernmost Beach Resort – Adults Only
Almond Tree Inn Hotel - Adults Only
Queen Deluxe ADA

Almond Tree Inn Hotel - Adults Only

3.5 star property
10.0 out of 10, Exceptional, (1001)
"The hotel is a little gem. It is just off of Duval on Truman which is a great location. We could enjoy our breakfast and walk off into town. The hotel is surprisingly quiet. The staff is lovely and very, very, helpful. Beds were great! We want to come back. "
The price is CA $619
CA $696 total
includes taxes & fees
Jan 27 - Jan 28
Almond Tree Inn Hotel - Adults Only
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Frequently asked questions

What are the best 4-star hotels in Old Town Key West?
Relax in the quality and comfort of Winslows Bungalows. This 4-star hotel around Old Town Key West is ranked highly by many Expedia guests and includes concierge services and designer toiletries. Another in-demand property in or close to this neighborhood is Santa Maria Suites. Designer toiletries and a swimming pool are two amenities you can expect here.
How much does it cost to stay in a 4-star hotel in Old Town Key West?
To find a 4-star hotel in Old Town Key West that fits your budget, make use of Expedia’s handy filters. Check out the available options during your chosen dates and use our pricing filter to set your limit. You can also list your results by the cheapest escape first.

  • Search for the lowest price from CA $571

What's the difference between 5-star and 4-star hotels in Old Town Key West?
Offering a welcoming guest experience and upmarket surroundings, 4-star hotels are a wonderful option for your Old Town Key West escape. These kinds of accommodations generally come with lots of useful amenities that make it easy to unpack and recharge — think complimentary bathrobes, pools and gyms. Or enjoy even more lavishness at a 5-star hotel designed to indulge you in exclusive perks and amenities. Concierge assistance, premium toiletries and world-class dining are typically included at these plush properties.
Does Old Town Key West have any 4-star all-inclusive resorts?
Use our “All inclusive” filter to find properties that take care of your room, meals, drinks and daily activities. Old Town Key West also has other terrific options for travelers seeking someplace comfortable and upmarket. Santa Maria Suites and Winslows Bungalows are a couple of the most popular 4-star stays here.
Are there any 4-star casino hotels in Old Town Key West?
To find your perfect getaway in Old Town Key West, simply use our convenient filter tools to narrow down your search. Boasting resort-style amenities and a level of service that’s hard to beat, staying in a 4-star casino hotel is a sure bet for a good time.