Truman Annex beach rentals
We found 366 beach rentals — enter your dates for availability
Explore Truman Annex beach rentals
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
290 reviews(290 reviews)
Upscale end unit home @ Truman Annex close to Duval St
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
116 reviews(116 reviews)
BOOKING SMOKING HOT 2025 DEALS NOW!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
200 reviews(200 reviews)
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Sleeps 8 · 2 bedrooms · 2+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Location, Location, Location!!! Downtown Key West - Truman Annex!!!
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
CONCH RETREAT Truman Annex Condo - 2 decks, pool, 2 Bikes, Free parking and WIFI
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
231 reviews(231 reviews)
Top rated beach rentals - Truman Annex
Excellent
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Fabulous
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Key West week
1010 out of 10
Exceptionalexceptional
193 reviews(193 reviews)
Truman Annex in Key West is the best
1010 out of 10
Exceptionalexceptional
166 reviews(166 reviews)
Nice Condo
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Perfection!!
1010 out of 10
Exceptionalexceptional
207 reviews(207 reviews)
Spring Break in Key West
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Great Visit
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any beach vacation rentals in Truman Annex?
You can select from 366 beach vacation rentals in Truman Annex. With top-rated attractions such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Smathers Beach within close reach, this is a great neighborhood to base yourself in.
How much does it cost to stay in a beach vacation rental in Truman Annex?
If you're planning to stick around a while and want to save on your beach vacation rental, use our "Discounts" filter. This will bring up any properties in Truman Annex that offer deals for longer breaks, such as a weekly or monthly discount. You can also tailor your search by entering your maximum budget. While a range of factors will impact how much you pay, we'll help you find a seaside getaway at a wallet-friendly price.
When is the best time to book a beach vacation rental in Truman Annex?
You'll have a wonderful time whenever you visit Truman Annex. If you're looking to experience this destination at its liveliest, March is when most guests stay in a beach vacation rental here.
Where can I book a Truman Annex beach vacation rental with great views?
The best way to book your ultimate escape with amazing views is to apply some filters after your initial search. For example, "Location" will list all the properties in scenic areas or with particular outlooks. You can also check "Guest rating" to find stays other Vrbo guests rave about. From dawn to dusk, you can experience the best of seaside living in Truman Annex at our beach vacation rentals.
What are the most popular beaches in Truman Annex?
When it's time to explore the most popular beaches in Truman Annex, Smathers Beach should be at the top of your list. Then, find your way to South Beach and finish your day with a relaxing sunset stroll.
What are the top things to do in Truman Annex?
When you're not having adventures by the sea, drop in on well-known sights like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Smathers Beach is also a great addition to any family-friendly travel plans here. Once you've made yourself at home in your Truman Annex beach vacation rental, you'll have no shortage of experiences to enjoy.
Why should I book my beach vacation rental with Vrbo?
When you select a Vrbo beach vacation rental, the only people you have to share your space with are those you bring along. It will just be you, family or friends and the whole property to yourselves. Our flexible cancellation policies also mean you can book your rental house with peace of mind if you need to change your plans. And remember, if you're a member of our One Key™ rewards program, you'll be able to earn and use OneKeyCash™* on all eligible bookings on Vrbo, Hotels.com and Expedia. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo, Hotels.com and Expedia.