Discover a selection of 1,500 vacation rentals in Truman Annex, Key West that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $217 per night, and houses and condos are popular options for a stay in Truman Annex. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — Truman Annex
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

What are the top vacation rentals in or near Truman Annex?

Whatever you're looking for in a getaway, you'll find a rental property in or around Truman Annex that's a match made in heaven. Why not try these on for size?:

  • Around 1 mile from the center of Truman Annex, you'll find it hard to resist "Key West Oasis, Seperate Cottage". It has 2 bedrooms and handy features including a kitchen island and a nearby hospital.
  • Another great option is "Cloud 9 ~ It's Heaven On Earth In This 3b", which is around 1 mile from Truman Annex. With 3 bedrooms, golf and nearby ecotour services, it has everything you need to make your stay comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Truman Annex vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Truman Annex?

Your working week will be easier to get through if you've got something awesome lined up for the weekend. Give yourself something nice to look forward to by arranging a stay at one of these top weekend getaways in or near Truman Annex:

  • Located around 4 miles to the east of Truman Annex, "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach" has all you need and more for a quick weekend escape, including an outdoor pool and a microwave oven. When it's time to venture out, there are plenty of outdoor attractions to see like Florida Keys Eco-Discovery Center and Nancy Forrester's Secret Garden.
  • Also consider "Starfish - Sunny Townhome In Quiet Truman Annex Two Blocks From Duval St", which is around 0.1 miles east of Truman Annex. After a day of discovering nearby natural attractions like Upper Sugarloaf Sound and Florida Keys Eco-Discovery Center, kick back in your rental and make use of a barbecue grill, a nearby marina and more.

Can I find studio apartments for rent in and around Truman Annex?

Discover the culture and lifestyle of Truman Annex from the privacy and comfort of a studio apartment. Whether you're planning to kick back on your own or have a good time with friends, we'll help you find the ideal studio apartment for rent in and around Truman Annex:

  • Unpack your suitcase at "Condo In Old Town Key West's Truman Annex". Amenities including an oven and free WiFi will make you feel right at home here.
  • Another excellent option is "Your Condo By The Beach With Ocean View". Make use of an oven, WiFi and other amenities during your vacation.

When it's time to step out of your studio apartment and explore the highlights, there's lots to keep you on the move around Truman Annex. Passionate about culture? Swing by City Zoo Gallery and Red Barn Theatre.

Can I find short term rentals in or near Truman Annex?

Now and then, you just need to take a well-earned breather, even if it's only for a few short days. Enjoy the ideal combination of rest and recreation at one of these short-term rentals in or around Truman Annex:

  • If you want to be close to the action, "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach" will suit your style. It's within reach of the center of Truman Annex and a great base to explore sights like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens.
  • Eat, sleep and discover your surroundings from "Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location", another popular option. Smathers Beach and Southernmost Point should be on your must-do list when you're ready to see the sights.

What are the best romantic weekend getaways in or near Truman Annex?

Nothing says "I love you" quite like a romantic weekend escape. If you want to spend a couple of evenings away with your beloved, we've got some romantic getaways in and around Truman Annex that will whisk you off your feet:

  • Put on some relaxing music and slow dance the nights away at "Key West Oasis, Seperate Cottage". Around 1 mile from Truman Annex, this property has everything you could want for a romantic weekend away, including beauty services and shopping facilities.
  • Another place where you can spend a few precious days together is "Cloud 9 ~ It's Heaven On Earth In This 3b". Around 1 mile from Truman Annex, a nearby marina and air conditioning add to the atmosphere here.

Are there mansions for rent in or near Truman Annex?

Nothing says "Best. Vacation. Evvv-er." like staying in a mansion. Spoil your loved ones with a truly unforgettable getaway at one of these mansions for rent in or near Truman Annex:

  • Located around 0.1 miles to the southeast of Truman Annex, "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" is the place to go to put your feet up in the lap of luxury. Amenities offered here include a swimming pool and golf.
  • Another top pick is "Captiva" ~ , Historic Mansion Suite With Community Pool". Around 1 mile to the east of Truman Annex, this opulent vacation rental gives you a taste of high-class living and comes with concierge services, a swimming pool and more.

What are the best large group vacation rentals in or near Truman Annex?

Big groups mean gigantic fun. They also mean finding someplace that'll comfortably fit your entire crew. Check out our large group vacation rentals in or around Truman Annex and get your favorite people together under one roof:

  • A nice range of amenities including a garden and a chef make "New Photos: Drive To Your Getaway" a winner. This popular retreat has 5 bedrooms and accommodates up to 12 guests. From Truman Annex's center, it's around 1 mile away to the southeast.
  • Nothing is more important than spending time with the people you love, and "William Skelton Home - Heart Of Key West" is the ideal place to do that. Located around 1 mile to the northeast of Truman Annex, as many as 14 people can stay in this vacation rental which has 6 bedrooms. A swimming pool and a garden are among the various amenities here.

What are the best houses for rent with a pool in or near Truman Annex?

Having access to a swimming space is always a bonus when you're on vacation, especially if you're traveling with youngsters. Splish splash the days away at one of these houses with a pool in or near Truman Annex:

  • Top on our list of cool pool escapes is "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". Vacationing families will feel right at home here, with useful amenities like a toaster and cable/satellite TV services also at hand.
  • Alternatively, make a reservation at "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach" and spend lazy days poolside. A nearby laundromat and free toiletries are other things your fam will love about this rental.

What are the best large family vacation rentals in or near Truman Annex?

Whether your perfect escape is up in the mountains or by the ocean, you'll have a lot more fun if you share it with family and friends. Choose one of these large family vacation rentals in or near Truman Annex and bring along the whole gang:

  • Located around 1 mile to the east of Truman Annex, "Cloud 9 ~ It's Heaven On Earth In This 3b" has 3 bedrooms and sleeps up to 7 guests. It's equipped with a range of amenities, including a dishwasher and a toaster.
  • Another popular choice is "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach". This vacation rental is 4 miles east of Truman Annex and comes with a smart TV, cable/satellite TV services and more. With 3 bedrooms accommodating up to 8 people, don't worry about leaving anyone off your guest list.

If you're in the mood to sightsee, there are loads of family-friendly attractions close by to add to your to-do list. Duval Street, Key West Aquarium and Key West Wildlife Center are fine places to start.

Can I find family cabin rentals in or near Truman Annex?

Nothing's more important than family, which is why we'll help you find a place where you can truly connect. Stay in one of these family cabin rentals in or near Truman Annex and make memories with the ones you love the most:

  • "Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval" - This sought-after getaway offers a dishwasher and a TV and is located around 1 mile east of central Truman Annex.
  • "Cabin - Hidden Treasure - 2 Bedroom 2 Bath With Shared Pool" - Another superb option, this rental comes with a microwave oven, cable/satellite TV services and more. You'll find it around 1 mile to the east of Truman Annex.

For more options, use the search bar at the top of the page and adjust the filters to find the Truman Annex vacation rental that's perfect for your needs.