Key West Hotels on the Bay Key West, FL
Welcome to our guide to Key West hotels on the bay.
Bayside Key West hotels are located on Roosevelt Blvd in the west side of "New Town".
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Rates shown below are averages. Use Search above to see rates for your dates.
Parrot Key Hotel & Villas Key West
2801 North Roosevelt, Key West, FL 33040
0.2 mile to Bayside, Roosevelt Blvd
Enter Dates
From $189
Check In 16 00
Check Out 11 00
Rated High
Upscale, smoke-free, full-service, bayside hotel
Near Overseas Market
3 floors; 74 rooms and suites, 2 townhomes - no elevator
4 outdoor swimming pools open all year - exercise room
Restaurant - lounge - room service
Valet parking only - $15 per night
Not pet friendly
- no pets allowed. - Oct 2020
Note: This hotel charges a resort fee of $38 per night - includes WiFi.
TripAdvisor Traveler Rating:
Based on 806 reviews
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Capitana Key West Hotel
2401 North Roosevelt Blvd, Key West, FL 33040
0.2 mile to Bayside, Roosevelt Blvd
Enter Dates
From $260
Check In 16 00
Check Out 11 00
Rated Very High
Upscale, smoke-free hotel near Overseas Market
Main hotel - 3 floors, 64 rooms and suites - elevator
Cottages - 2 floors, 11 units - no elevator
Outdoor swimming pool open all year - exercise room
Tiki bar
Microwave and refrigerator in every room
Pet friendly hotel
More >
- allows dogs up to 30 pounds only, 2 dogs per room - $75 per night fee for each dog. - Feb 2021 < Less
Note: This hotel charges a resort fee of $35 per night - includes parking, WiFi, and continental breakfast.
TripAdvisor Traveler Rating:
Based on 275 reviews
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Fairfield Inn & Suites by Marriott Key West
2400 North Roosevelt Blvd, MM 2, Key West, FL 33040
0.2 mile to Bayside, Roosevelt Blvd
Enter Dates
From $271
Check In 1500
Check Out 1100
Rated High
Upper-midscale, smoke-free, bayside motel 2 floors, 106 rooms - elevator Outdoor swimming pool - exercise room Tiki bar Microwave and refrigerator in every room Free hot breakfast buffet Free WiFi Free parking
Not pet friendly
- no pets allowed. - Sep 2015
Most Recent HotelGuides Reviews
Read >
"The motel was nice, clean, and comfortable, and the staff was friendly. Good place to stay.2017-09-03 "
"Hotel was nice and clean.2015-02-19 "
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TripAdvisor Traveler Rating:
Based on 1965 reviews
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Courtyard by Marriott Hotel Waterfront Key West
3031-41 North Roosevelt Blvd, MM 2.5, Key West, FL 33040
0.4 mile to Bayside, Roosevelt Blvd
Enter Dates
From $303
Check In 1600
Check Out 1100
Rated High
Upscale, smoke-free, waterfront hotel 3 floors, 68 rooms and suites - elevator Outdoor swimming pool open in summer - exercise room 2 restaurants - lounge Restaurant open for breakfast and dinner only Free WiFi Free parking
Not pet friendly
- no pets allowed. - Feb 2015
TripAdvisor Traveler Rating:
Based on 1114 reviews
Read Recent Reviews
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Key West Hotels and Reviews
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Pet Friendly Hotels in or near Key West
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Hotels near Me
Hotels near Smathers Beach 0.9 mile SE
Hotels near Key West Airport EYW 1.4 miles SE
Hotels near Casa Marina Key West 1.5 miles SW
Hotels near Key West Express 1.5 miles west
Hotels near Fantasy Fest 1.6 miles west
Hotels near Historic Seaport Boardwalk 1.7 miles west
Hotels near Immigration Key West 1.8 miles west
Hotels near Downtown Key West 1.8 miles SW
Hotels near Hemingway House 1.9 miles SW
Hotels near Southernmost Point 1.9 miles SW
Hotels near Sloppy Joe's Bar 2.0 miles west
Hotels near Duval Street Key West 2.0 miles west
Hotels near Mallory Square, Waterfront 2.1 miles west
Hotels near Truman Waterfront Park Amphitheater 2.3 miles SW
Hotels near Sunset Key 2.4 miles west
Boca Chica Key FL Hotels 5 miles east
Big Coppitt Key FL Hotels 8 miles east
Cudjoe Key FL Hotels 19 miles NE
Summerland Key FL Hotels 22 miles east
Little Palm Island FL Hotels 24 miles east
Big Pine Key FL Hotels 27 miles east
On place pages like this, we order hotels from lowest cost to highest except we list low-rated hotels at the bottom of the page.
Most of our competitors order these same hotels in other ways that make them more money.
To us, motels are smaller lodgings that have rooms you can enter directly from the parking area.
At hotels , on the other hand, you can enter your room only through a hall inside the building.
Beware of non-refundable reservations that could cost you a lot of money if you change or cancel them. + Non-refundable reservations are a gamble that will usually save you less than $10. If you make a $90 non-refundable reservation instead of a $100 refundable booking, you are betting $90 to win $10. Would you do that in Las Vegas? -
Don't assume you can cancel a non-refundable reservation without penalty if you notify the hotel weeks or even months in advance. + Often you cannot because some hotels' profit strategy is to get paid more than once for the same room for the same night. -
Always read cancellation policies carefully before you make a reservation. + When is the latest date and time you can cancel without penalty? - More >
When you make a reservation, you will receive a confirmation email. Take a copy with you to the hotel.
The earlier in the afternoon you check into a hotel, the more likely you will get a room or suite that matches your preferences.
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