Find 4 Star Hotels in Old Town Key West, FL from $242

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Check availability on Old Town Key West 4 Star Hotels

Tonight
Aug 28 - Aug 29
Tomorrow
Aug 29 - Aug 30
This weekend
Aug 29 - Aug 31
Next weekend
Sep 5 - Sep 7

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

Our top choices for Old Town Key West 4-star hotels

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

Southernmost Beach Resort and Guesthouses

4.0 star property
8.6 out of 10, Excellent, (2712)
"Great stay awesome staff we will definitely stay here again. "
$229 nightly
The price is $258
Sep 11 - Sep 12
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
Casa Marina Key West, Curio Collection by Hilton
Fireplace

Casa Marina Key West, Curio Collection by Hilton

4.0 star property
8.4 out of 10, Very Good, (312)
"Amazing hotel, beautiful areas and lovely rooms. "
$261 nightly
The price is $293
Sep 7 - Sep 8
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
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, (1013)
"Great stay! "
$294 nightly
The price is $331
Sep 1 - Sep 2
Total with taxes and fees
Opal Key Resort & Marina, Key West
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
9.2 out of 10, Wonderful, (1008)
"Loved Our Stay"
$227 nightly
The price is $255
Sep 2 - Sep 3
Total with taxes and fees
Winslow's Bungalows - Key West Historic Inns
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, (1013)
"great location for our trip "
$295 nightly
The price is $332
Sep 7 - Sep 8
Total with taxes and fees
The Reach Key West, Curio Collection by Hilton
Bishop Hotel Key West
Room 27C - Economy - Queen Bed | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

Bishop Hotel Key West

4.0 star property
9.8 out of 10, Exceptional, (229)
"Great stay all the way around. "
Bishop Hotel Key West
Santa Maria Suites
Courtyard

Santa Maria Suites

4.0 star property
9.6 out of 10, Exceptional, (1002)
"Best place to stay great staff and the rooms are beautiful "
$274 nightly
The price is $309
Sep 2 - Sep 3
Total with taxes and fees
Santa Maria Suites
The Gardens Hotel
Carriage House | Terrace/patio

The Gardens Hotel

4.0 star property
9.8 out of 10, Exceptional, (1002)
"What a fantastic place this is, very clean and classy. I would stay here again!"
$215 nightly
The price is $242
Sep 10 - Sep 11
Total with taxes and fees
The Gardens Hotel
Southernmost House
Mansion Room #201 - Ocean View with private balcony - Adults Only | Terrace/patio

Southernmost House

4.0 star property
9.4 out of 10, Exceptional, (1007)
"This hotel is beautiful, love the history Bed comfortable Would definitely come and stay here again"
$266 nightly
The price is $299
Sep 11 - Sep 12
Total with taxes and fees
Southernmost House
The Porch on Frances Inn
Front of property

The Porch on Frances Inn

4.5 star property
9.6 out of 10, Exceptional, (91)
"Awesome stay with great service. "
The Porch on Frances Inn
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, (921)
"Hotel was great and Kasey the activities direct was so fun and helpful"
Duval Gardens at Southernmost Beach Resort – Adults Only
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
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Top Old Town Key West Hotel Reviews

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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 $242

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.