Truman Annex Holidays from £1,063

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was £1,574, price is now £1,063 per person
£1,063
per person
1 Nov - 8 Nov
found 24 hours ago
Return flight included
London (LON) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Fantastic staff, always smiling. Great amenities, super clean, fantastic location.

Reviewed on 25 Aug 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was £2,247, price is now £1,415 per person
£1,415
per person
1 Nov - 8 Nov
found 24 hours ago
Return flight included
London (LON) to Key West (EYW)
9.4/10 Exceptional! (366 reviews)
everything was easy and staff was very helpful!

Reviewed on 18 Aug 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was £1,839, price is now £1,177 per person
£1,177
per person
1 Nov - 8 Nov
found 24 hours ago
Return flight included
London (LON) to Key West (EYW)
9/10 Wonderful! (775 reviews)
it’s a great location but quiet. Love the free breakfast, pool and rooms! staff was great too!

Reviewed on 23 Aug 2025

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 £1,881, price is now £1,231 per person
£1,231
per person
1 Nov - 8 Nov
found 24 hours ago
Return flight included
London (LON) to Key West (EYW)
9.2/10 Wonderful! (1,006 reviews)
Beautiful property with several private pools. The front desk was very helpful in helping us get bikes delivered. They were always helping people and answering questions.The breakfast is perfect to get your day started. We will definitely return.

Reviewed on 22 Aug 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was £2,191, price is now £1,500 per person
£1,500
per person
1 Nov - 8 Nov
found 24 hours ago
Return flight included
London (LON) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
It's a really nice property next to a marina. Quiet at night much livelier during the day. There is a shuttle from property to get to down town if you don't have a rental car. Rental car is needed and necessary in my opinion. The pool was great and there are three places to eat in the immediate area. Our first time here and we will be returning in the future.

Reviewed on 25 Aug 2025

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
Default Image

Old Town Key West

3 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 Saint Mary Star of the Sea.

Find hotels in Old Town Key West

Top hotels in Truman Annex

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St, Key West, FL
The price is £141 per night from 27 Aug to 28 Aug
£141
27 Aug - 28 Aug
includes taxes & fees
9.2/10 Wonderful! (947 reviews)
nice property
"nice property with friendly staff in a beautiful, off-the-beaten-path location. will definitely stay again."

Reviewed on 7 Aug 2025

Weatherstation Inn
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 £234 per night from 27 Aug to 28 Aug
£234
27 Aug - 28 Aug
includes taxes & fees
8.4/10 Very Good! (312 reviews)
"Nice and quite"

Reviewed on 21 Aug 2025

Hyatt Vacation Club at Sunset Harbor, Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is £141 per night from 26 Aug to 27 Aug
£141
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very Good! (1,480 reviews)
"The property was excellent, located in the heart of everything!! 😍"

Reviewed on 23 Aug 2025

Beachside Resort & Residences
See all 2,759 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Truman Annex travel package cost?
From just £1,063. 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

Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

£40
per adult
84% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
Key West Jet Ski Tour – High-Speed Adventure Around the Island

Ultimate 90 minute Sea Doo Jet Ski Tour of Key West -Additional Rider Free!

£125
per traveller
94% of travellers recommend
Ultimate 90 minute Sea Doo Jet Ski Tour of Key West -Additional Rider Free!
Crew member guiding mother and daughter parasailing in Key West

Parasailing in Key West – Soar Above the Island Paradise

£63
per traveller
86% of travellers recommend
Parasailing in Key West – Soar Above the Island Paradise
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.