Find 4 Star Hotels in Old Town Key West, FL from $269

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Dec 4 - Dec 5
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Dec 5 - Dec 6
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Dec 5 - Dec 7
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Dec 12 - Dec 14

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

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

Southernmost Beach Resort and Guesthouses

4.0 star property
Old Town Key West
8.6 out of 10, Excellent, (2910)
"Room was great, the pools and beach were great"
United States
Tina
$294 nightly
The price is $330
Dec 18 - Dec 19
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1057)
"Great staff, beautiful grounds, clean. "
United States
David
$284 nightly
The price is $320
Dec 16 - Dec 17
Total with taxes and fees
Winslow's Bungalows - Key West Historic Inns
Fireplace
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4.0 star property
Old Town Key West
8.4 out of 10, Very Good, (455)
"beautiful Hotel! "
Mexico
iria
$299 nightly
The price is $336
Dec 15 - Dec 16
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
Outdoor pool, pool umbrellas, sun loungers
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4.0 star property
Old Town Key West
8.4 out of 10, Very Good, (1000)
"The friendly and helpful staff, beautiful private beach, and location of the property wowed us beyond expectations! "
United States
Julie
$239 nightly
The price is $269
Dec 14 - Dec 15
Total with taxes and fees
The Reach Key West, Curio Collection by Hilton
Front of property - evening/night
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4.0 star property
Old Town Key West
9.0 out of 10, Wonderful, (1014)
"Great location and accommodations… great all around"
United States
Jose
$284 nightly
The price is $320
Dec 14 - Dec 15
Total with taxes and fees
Opal Key Resort & Marina, Key West
Courtyard
Santa Maria Suites

Santa Maria Suites

4.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (1007)
"Awesome place we loved it"
United States
Josh
$367 nightly
The price is $413
Dec 10 - Dec 11
Total with taxes and fees
Santa Maria Suites
Mansion Room #201 - Ocean View with private balcony - Adults Only | Terrace/patio
Southernmost House

Southernmost House

4.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1000)
"Great place with excellent staff. "
United States
Willie
$370 nightly
The price is $416
Dec 21 - Dec 22
Total with taxes and fees
Southernmost House
Room 27C - Economy - Queen Bed - Adults Only 21+ | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
Bishop Hotel Key West

Bishop Hotel Key West

4.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (310)
"Excellent staff, clean property and walkable location to everything"
United States
Phyllis S
Bishop Hotel Key West
Carriage House | Terrace/patio
The Gardens Hotel

The Gardens Hotel

4.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (1000)
"Amazing hotel, the perfect Key West vibe. Clean rooms, delicious breakfast. We will come back again"
United States
Isis
$324 nightly
The price is $364
Dec 7 - Dec 8
Total with taxes and fees
The Gardens Hotel
Front of property
The Porch on Frances Inn

The Porch on Frances Inn

4.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (101)
"Very nice room, spacious bathroom, quiet area, clean. Short walk to Duval street, marina, convenience store and coffee shop/bakeries. Staff was friendly and helpful. Will definitely stay there again!"
United States
David
The Porch on Frances Inn
Front of property
Duval Gardens at Southernmost Beach Resort – Adults Only

Duval Gardens at Southernmost Beach Resort – Adults Only

4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (924)
"Thank you!"
United States
Renee
Duval Gardens at Southernmost Beach Resort – Adults Only
Outdoor pool
Duval Penthouse

Duval Penthouse

4.0 star property
Old Town Key West
Duval Penthouse
Outdoor pool
6 bdrm Duval Compound -Old Town Key West

6 bdrm Duval Compound -Old Town Key West

4.0 star property
Old Town Key West
6 bdrm Duval Compound -Old Town Key West
Outdoor pool
Bahamas House

Bahamas House

4.0 star property
Old Town Key West
Bahamas House
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Top Old Town Key West Hotel Reviews

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Excellent"
Sandhya 3-night trip
Posted 3 days ago
Opal Key Resort & Marina, Key West

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 $269

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.

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