Find 4 Star Hotels in Old Town Key West, FL from $263

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Check availability on Old Town Key West 4 Star Hotels

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
8.6 out of 10, Excellent, (2791)
"Top notch resort."
$234 nightly
The price is $264
Oct 29 - Oct 30
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
Fireplace
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton
4.0 star property
8.4 out of 10, Very Good, (396)
"The location at the water is great. The restaurant on the beach with amazing live music was marvelous."
$304 nightly
The price is $343
Oct 23 - Oct 24
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
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
9.2 out of 10, Wonderful, (1023)
"The room was clean and the facilities lovely. We enjoyed our stay."
$234 nightly
The price is $263
Oct 29 - Oct 30
Total with taxes and fees
Winslow's Bungalows - Key West Historic Inns
Front of property - evening/night
Opal Key Resort & Marina, Key West
Opal Key Resort & Marina, Key West
4.0 star property
9.2 out of 10, Wonderful, (1008)
"Staff was tremendous and location is perfect!! "
$284 nightly
The price is $320
Oct 16 - Oct 17
Total with taxes and fees
Opal Key Resort & Marina, Key West
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
8.4 out of 10, Very Good, (1009)
"Great staff, view and food!"
$241 nightly
The price is $271
Oct 29 - Oct 30
Total with taxes and fees
The Reach Key West, Curio Collection by Hilton
Courtyard
Santa Maria Suites
Santa Maria Suites
4.0 star property
9.6 out of 10, Exceptional, (1006)
"We really enjoyed the hotel, and especially the receptionist named Azul — she helped us a lot with everything we needed"
$393 nightly
The price is $443
Oct 19 - Oct 20
Total with taxes and fees
Santa Maria Suites
Room 27C - Economy - Queen Bed | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds
Bishop Hotel Key West
Bishop Hotel Key West
4.0 star property
9.8 out of 10, Exceptional, (266)
"A fantastic property and staff, made my first visit to Key West amazing!"
Bishop Hotel Key West
Carriage House | Terrace/patio
The Gardens Hotel
The Gardens Hotel
4.0 star property
9.8 out of 10, Exceptional, (1007)
"Great location and rooms. Lovely gardens and pool. "
$249 nightly
The price is $280
Oct 16 - Oct 17
Total with taxes and fees
The Gardens Hotel
Mansion Room #201 - Ocean View with private balcony - Adults Only | Terrace/patio
Southernmost House
Southernmost House
4.0 star property
9.4 out of 10, Exceptional, (1008)
"Loved this hotel so much! I really loved the atmosphere of this hotel and how close to the water you were. We will definitely be staying here again."
$266 nightly
The price is $299
Oct 30 - Oct 31
Total with taxes and fees
Southernmost House
Front of property
The Porch on Frances Inn
The Porch on Frances Inn
4.5 star property
9.6 out of 10, Exceptional, (93)
"It was amazing..... Great people . Great place. "
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
9.2 out of 10, Wonderful, (922)
"Hotel was great and Kasey the activities direct was so fun and helpful"
Duval Gardens at Southernmost Beach Resort – Adults Only
Outdoor pool
Bahamas House
Bahamas House
4.0 star property
Bahamas House
Outdoor pool
Duval Penthouse
Duval Penthouse
4.0 star property
Duval Penthouse
Outdoor pool
6 bdrm Duval Compound -Old Town Key West
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"The balcony was not private it was outside our front door located outside. Other then that it was a great stay!"
Danielle 4-night trip
Posted 2 days ago
Southernmost Beach Resort and Guesthouses

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 $263

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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