Downtown Key West Holidays

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Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was €1,324, price is now €985 per person
€985
per person
17 Apr - 21 Apr
found 1 day ago
Return direct flight included
Hartford (BDL) to Key West (EYW)
8.8/10 Excellent! (571 reviews)
The staff was very kind!

Reviewed on 1 Mar 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was €2,387, price is now €1,579 per person
€1,579
per person
17 Apr - 21 Apr
found 1 day ago
Return direct flight included
Hartford (BDL) to Key West (EYW)
9.2/10 Wonderful! (532 reviews)
Loved this hotel, immaculate.

Reviewed on 7 Mar 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was €1,817, price is now €1,388 per person
€1,388
per person
17 Apr - 21 Apr
found 1 day ago
Return direct flight included
Hartford (BDL) to Key West (EYW)
8.8/10 Excellent! (3,103 reviews)
The room is nice and clean, we don't really have any view. I would book ocean view next time.

Reviewed on 9 Mar 2026

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was €1,920, price is now €1,491 per person
€1,491
per person
17 Apr - 21 Apr
found 1 day ago
Return direct flight included
Hartford (BDL) to Key West (EYW)
9.4/10 Exceptional! (442 reviews)
From check-in with Dwight (who goes above and beyond!). Breakfast was wonderful, plenty of choices. Pool area is great, sunscreen and towels available. All staff friendly and kind. Thank you for a wonderful stay.

Reviewed on 8 Mar 2026

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was €1,695, price is now €1,331 per person
€1,331
per person
17 Apr - 21 Apr
found 1 day ago
Return direct flight included
Hartford (BDL) to Key West (EYW)
9/10 Wonderful! (903 reviews)
Perfect hotel for the perfect Key West vacation. The location, staff and beautiful blooming orchids made our stay extra special! I loved that Hemmingway’s House was across the street.

Reviewed on 4 Mar 2026

Where to stay in Downtown Key West

Find the best Downtown Key West areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Key West
Key West Historic District

Old Town Key West

4 out of top 10 points of interest in this area
5/5(6 area reviews)

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Find hotels in Old Town Key West

Top hotels in Downtown Key West

Duval House

Duval House

3 out of 5
815 Duval St Key West FL
The price is €347 per night from 11 Mar to 12 Mar
€347
11 Mar - 12 Mar
includes taxes & fees
9.4/10 Exceptional! (1,010 reviews)
First impression with office female staff member was not good. She was extremely robotic and very disinterested. Staff at breakfast were extremely friendly and warm. Rooms are very small. Grounds are well maintained.

Reviewed on 7 Mar 2026

Duval House
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane Key West FL
8.8/10 Excellent! (1,019 reviews)
Location is great for activities. Staff was friendly. Even though Rosters are part of Key West, they are getting out of control with crowing all night out your bedroom window (take ear plugs). There is a hidden hotel amenity fee of $39.99 per night for a couple. I did double-check Expedia advertisement ...

Reviewed on 8 Mar 2026

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The Cabana Inn Key West - Adults Only
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
819 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,008 reviews)
Clean, quiet, close to everything we wanted to do!

Reviewed on 7 Mar 2026

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Paradise Inn Key West - Adults Only
See all 2,751 properties in Downtown Key West
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

How much does a Downtown Key West holiday package cost?
Chart your own course with our Downtown Key West holiday packages, which start from a low €985. Handpick the hotels and flights that fit your travel plans. Then, add on one or two enriching experiences to round off your unique getaway.
How do I get a cheap travel package to Downtown Key West?
Our Downtown Key West holiday packages offer plenty of savings for the savvy explorer. For the best deal, simply bundle your flights, hotels and activities into a convenient package. But impressive bargains are just the beginning of your next amazing adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 hotel options all over the world to pick from. Whatever your style or budget, there's a holiday package here just for you.
Where should I stay in Downtown Key West?
A trip to Downtown Key West has to include Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Book a hotel right nearby for quick access to these impressive sights.
What are the top hotels in Downtown Key West?
If it's your first visit to Downtown Key West, reserve a room at Maya's Secret Treasure @ Duval Private Pool And Balcony Over Duval + Last Key or Southernmost Retreat: 2 Blocks From Duval In Old Town. Both hotels offer comfy beds and are favourites with lots of travellers.
How far in advance should I book my Downtown Key West holiday?
Savvy travellers will likely want to book as early as possible. You can normally browse through international fares on Expedia up to 12 months before your flight. If you're purchasing tickets last minute, don't worry. Cheap prices occasionally become available just weeks before departure dates.
What does an Expedia Downtown Key West travel package include?
Choose from a combination of hotels, rental cars and flights. Once you've made your booking, you can add some experiences and activities. Want to pick your fare class? That's easily done too. The choice is all yours when it comes to putting together your ideal Downtown Key West escape.
What should I know before booking a Downtown Key West travel package?
Whether it's relaxation or adventure you're seeking, a Downtown Key West holiday package lets you organise your escape your way. Plus, you'll score great discounts when you combine your accommodation with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Downtown Key West Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the freedom to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Downtown Key West holiday package?
It's hard to predict what the future holds, so it's good to know that you can change or cancel your Downtown Key West holiday package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.