Find 4 Star Hotels in Old Town Key West, FL from $186

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Compare Old Town Key West 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Southernmost Beach Resort
3 outdoor pools, pool umbrellas, sun loungers
Southernmost Beach Resort
4.0 star property
8.2 out of 10, Very Good, (1906)
"We loved the location of our room with real close access to the pool and beach. We loved the morning breakfast and afternoon snacks. Everybody was extremely friendly."
The price is $305
$406 total
includes taxes & fees
Jun 19 - Jun 20
Southernmost Beach Resort
Opal Key Resort & Marina, Key West
Front of property - evening/night
Opal Key Resort & Marina, Key West
4.0 star property
9.0 out of 10, Wonderful, (1009)
"Walkable to everything, quiet and clean property"
The price is $323
$403 total
includes taxes & fees
Jun 4 - Jun 5
Opal Key Resort & Marina, Key West
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, (626)
"Staff were friendly & helpful. Property was beautiful & close to everything "
The price is $350
$455 total
includes taxes & fees
Jun 11 - Jun 12
The Reach Key West, Curio Collection by Hilton
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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, (736)
"We enjoyed everything, apart from the broken ice machine and the inconvenience of having to buy ice several times a day. The staff is amazing and such hard workers. All friendly and very accommodating, front desk kept up with us via text which was very helpful. Beautiful setting, convenient and walkable. Able to rent a golf cart very easily and not too much trouble parking. Nice pools, not too many children or super crowded. Good enough breakfast, would’ve liked a simple salad and/or raw...
The price is $230
$301 total
includes taxes & fees
Jun 11 - Jun 12
Winslow's Bungalows - Key West Historic Inns
The Gardens Hotel
Gazebo
The Gardens Hotel
4.0 star property
9.6 out of 10, Exceptional, (920)
"Great experience but need a tv cable not roku"
The price is $227
$255 total
includes taxes & fees
Jun 4 - Jun 5
The Gardens Hotel
Santa Maria Suites
Courtyard
Santa Maria Suites
4.0 star property
9.6 out of 10, Exceptional, (1004)
"We loved our stay at Santa Maria Suites! The rooms were nice and clean and had all the amenities you could ask for. The pool was also nice and the surrounding area within walking distance was excellent. We will visit again!"
The price is $449
$550 total
includes taxes & fees
Jun 9 - Jun 10
Santa Maria Suites
The Guesthouses at Southernmost Beach Resort - Adults only
Property entrance
The Guesthouses at Southernmost Beach Resort - Adults only
4.0 star property
9.2 out of 10, Wonderful, (884)
"I liked the adult only "
The price is $279
$399 total
includes taxes & fees
Jun 4 - Jun 5
The Guesthouses at Southernmost Beach Resort - Adults only
The Porch on Frances Inn
Front of property
The Porch on Frances Inn
4.5 star property
9.6 out of 10, Exceptional, (60)
"Great, quiet spot in Old Town Key West. The owner, Jeff, has been renovated the 1860 house to keep all the old charm, but adding modern comforts. First and foremost, the property manager/ concierge Rider is a true delight!! She is knowledgeable of the town and can help arrange just about anything. She's an asset for your trip. Stop by the office in the morning for a cup of coffee, conversation, and adventure suggestions. Our room was spacious with a good-sized bathroom, Keurig coffee...
The price is $186
$220 total
includes taxes & fees
Jun 10 - Jun 11
The Porch on Frances Inn
Bishop Hotel Key West
Room 48 - Signature Room - King Bed | Balcony view
Bishop Hotel Key West
4.0 star property
Bishop Hotel Key West
Suite Dreams Inn by the Beach
Deluxe Apartment, Ensuite, Pool View (Hemingway Retreat) | Exterior
Suite Dreams Inn by the Beach
4.0 star property
8.4 out of 10, Very Good, (48)
"Nice clean room and good location. Michael met us for check in and was very helpful. We enjoyed the delicious fresh nango’s falling from the tree in garden"
Suite Dreams Inn by the Beach
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Interior
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
4.5 star property
10.0 out of 10, Exceptional, (3)
"The unit had fun and stylish decor. Bed was comfy and I’m picky. The steeps are a challenge- always forgetting there is one more step. Was concerned about the noise in the back from a restaurant or bar- but when doors closed you can’t hear it. And there is no noise later in the evening. One suggestion- some nightlights for the night for Safety. We will be back. Great experience "
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Duval Penthouse
Outdoor pool
Duval Penthouse
4.0 star property
Duval Penthouse
Bahamas House
Outdoor pool
Bahamas House
4.0 star property
Bahamas House
6 bdrm Duval Compound -Old Town Key West
Outdoor pool
6 bdrm Duval Compound -Old Town Key West
4.0 star property
6 bdrm Duval Compound -Old Town Key West

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Old Town Key West.
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street, Key West, FL
The price is $319 per night from Jun 10 to Jun 11
$319
$419 total
includes taxes & fees
Jun 10 - Jun 11
6.6/10 (996 reviews)
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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.

Frequently asked questions

What are the best 4-star hotels in Old Town Key West?
Kimpton Winslows Bungalows, an IHG Hotel is one of our travelers’ favorite 4-star hotels around Old Town Key West. Concierge services and a swimming pool are only the start of its many conveniences. Another option that receives great reviews for its unforgettable guest experience is Santa Maria Suites. Book your stay here and enjoy access to a pillowtop mattress and a terrace.
How much does it cost to stay in a 4-star hotel in Old Town Key West?
Expedia can help you quickly track down the ideal 4-star hotel for your getaway in Old Town Key West. Use our handy filter tool to tailor your search by things like price, amenities and star rating and get access to fantastic deals in a couple of clicks.

  • Search for the lowest price from $319

What's the difference between 5-star and 4-star hotels in Old Town Key West?
Offering a friendly traveler experience and upmarket surroundings, 4-star hotels are a fabulous option for your Old Town Key West break. These types of stays generally feature loads of useful amenities that make it a breeze to kick back and relax — think pillowtop mattresses, gyms and restaurants. Or live the high life at a 5-star hotel designed to indulge you in luxury perks and amenities. 24-hour front desk, complimentary toiletries and gourmet dining are typically featured at these plush properties.
Does Old Town Key West have any 4-star all-inclusive resorts?
Our handy “All inclusive” filter makes it easy to search for your perfect resort. You’ll also find other standard 4-star properties such as Santa Maria Suites and Kimpton Winslows Bungalows, an IHG Hotel. Offering the same level of luxury and comfort, they are fantastic options for your Old Town Key West getaway.
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 handy filter to narrow your search. Offering resort-style amenities and an upmarket level of service, staying in a 4-star casino hotel is a sure bet for a good time.

Recent reviews of Old Town Key West hotels
Expedia verified reviews

Southernmost Beach Resort

Southernmost Beach Resort

5/5 Excellent
"We loved the location of our room with real close access to the pool and beach. We loved the morning breakfast and afternoon snacks. Everybody was extremely friendly."
A verified traveler stayed at Southernmost Beach Resort
Posted 2 days ago
Southernmost Beach Resort