Truman Annex Holidays from £1,275

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Your Truman Annex Holiday

Take in everything this neighbourhood has to offer with a customized Truman Annex holiday package. However you imagine spending your time here, you'll find countless opportunities for fun, relaxation and adventure. Wondering what to see and do during your trip to Truman Annex? Nearby attractions such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square are good places to begin. Whatever your travel goals or budget, booking the ultimate Truman Annex holiday is easy with Expedia.

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was £1,883, price is now £1,275 per person
£1,275
per person
13 May - 19 May
found 1 day ago
Return direct flight included
London (LHR) to Key West (EYW)
9.2/10 Wonderful! (1,230 reviews)
Nicely situated. Comfy room. Neat swimming pool(s). Breakfast and bar areas did the job!

Reviewed on 8 Apr 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was £3,148, price is now £1,938 per person
£1,938
per person
11 Jun - 18 Jun
found 1 day ago
Return flight included
London (LON) to Key West (EYW)
9.2/10 Wonderful! (542 reviews)
Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!

Reviewed on 5 Apr 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was £2,313, price is now £1,561 per person
£1,561
per person
11 Jun - 18 Jun
found 1 day ago
Return flight included
London (LON) to Key West (EYW)
9.4/10 Exceptional! (1,011 reviews)
We had a wonderful family vacation there

Reviewed on 8 Apr 2026

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was £1,890, price is now £1,328 per person
£1,328
per person
11 Jun - 18 Jun
found 1 day ago
Return flight included
London (LON) to Key West (EYW)
9/10 Wonderful! (1,848 reviews)
Very family friendly place and the property grounds was beautiful.

Reviewed on 8 Apr 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
Price was £2,333, price is now £1,681 per person
£1,681
per person
13 May - 19 May
found 1 day ago
Return direct flight included
London (LHR) to Key West (EYW)
8.8/10 Excellent! (3,162 reviews)
Enjoyed the resort. We experienced 2 of the pools.

Reviewed on 9 Apr 2026

Where to stay in Truman Annex

Find the best Truman Annex areas and neighborhoods for the activities you enjoy most. Learn more about Truman Annex
Old Town Key West

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 Truman Annex

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
200 Sunset Lane Key West FL
Fully refundable
The price is £335 per night from 12 Apr to 13 Apr
£335
12 Apr - 13 Apr
includes taxes & fees
8.4/10 Very Good! (350 reviews)
When we arrived, we were not told about that there would be no running water. I had to use the bathroom and thereafter could not wash my hands. I did receive a text message later from the resort that the water was back on. The next day, we went jet skiing. Afterwards, we came back to the room and ...

Reviewed on 8 Apr 2026

Hyatt Vacation Club at Sunset Harbor, Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is £191 per night from 10 May to 11 May
£191
10 May - 11 May
includes taxes & fees
8.2/10 Very Good! (2,060 reviews)
Great little hidden gem! Our only issue was never having pool towels and always having to wait for them Property is about 10 minutes outside of town and on a very busy road but other than that it was a great property.

Reviewed on 9 Apr 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is £330 per night from 10 May to 11 May
£330
10 May - 11 May
includes taxes & fees
8.8/10 Excellent! (3,196 reviews)
Great experience

Reviewed on 9 Apr 2026

Southernmost Beach Resort and Guesthouses
See all 2,724 properties in Truman Annex
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.
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Frequently asked questions

How much does a Truman Annex travel package cost?
From just £1,275. Yes, you read that correctly. Our Truman Annex travel packages are a simple way to make your budget stretch further. Combine your flights, hotels and rental car and explore this fabulous destination.
If I'm not able to travel, can I cancel my Truman Annex travel package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can change or cancel your Truman Annex travel package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Truman Annex?
Our Truman Annex travel packages mean plenty of savings for the savvy traveller. For the best deals, simply combine your hotel, flights and rental cars into a neat and tidy package. But impressive bargains are only the start of your next unforgettable adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 hotel options worldwide to choose from. Whatever your style or budget, there's a travel package here just for you.
Does Expedia offer Book Now, Pay Later Truman Annex holidays?
Expedia has partnered with online lender Klarna to make your next getaway easier on your hip pocket. Paying in instalments means you can spread the costs of your next big adventure, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that suits your budget. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that fit all budgets, so you can escape on that well-earned holiday sooner.
  • Pay in instalments holidays: If you'd prefer to pay for your escape across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you spot an awesome deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in Truman Annex?
Most people who visit Truman Annex include both Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens on their to-do lists. Why not reserve a hotel close to one of these fantastic attractions?
What are the top hotels in Truman Annex?
Book a room at The Gates Hotel Key West. It's one of the neighbourhood's most sought-after hotels. Another top-rated option in Truman Annex is Crowne Plaza Key West-La Concha.
How far in advance should I book my Truman Annex holiday?
It's hard to pick the best time for airfares, but we normally say the earlier, the better. Plenty of international flights on Expedia become available up to a year in advance. If you can't book ahead, don't despair. Bargain prices appear from time to time within a few weeks of departure dates.
What does an Expedia Truman Annex travel package include?
Hotels, flights and a cool car for your road trip adventures. Simply pick and choose your preferred bundle and get access to incredible deals. Once you've made your booking, add on a few experiences and tours and watch your savings pile up. When it comes to planning your Truman Annex trip, you're in control!
What should I know before booking a Truman Annex travel package?
A travel package can be cheaper than separately booking all you need for your escape. For example, bundle your flights, hotels and rental cars and save a tidy sum. Whatever your holiday goals are, you're sure to find a package that's right for you.
Can I choose my airline with a Truman Annex Expedia travel package?
Definitely. Expedia has more than 550 airline partners to pick from worldwide. With so much choice, finding the ideal carrier to fly you to Truman Annex will be a snap.

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

£32
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Kayak the mangrove tidal creeks

Key West Mangrove Kayak Eco Tour

£60
per adult
100% of travellers recommend
Key West Mangrove Kayak Eco Tour
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

£42
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
See all activities in Key West

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.