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Sun and Fun at Truman Annex Townhome with pool near Duval Street

Bedrooms 2
Half Baths1
Property type condo
Minimum Stay 7 - 8 nights

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Half Baths
Minimum Stay
7 - 8 nights


Truman Annex Condo Rental Photos and Description

2 Bedrooms, 2.5 baths. One of the few homes with half bath downstairs.

The 45 5 Star Reviews say it all. Our guests love to spend a week or a month at our sunny, leafy green vacation townhome. We have no application fee, no extra cleaning fee for our non smoking home away from home- and your free reserved parking space in your secure lot.

Flip Flop Retreat is in Old Town Truman Annex within walking distance of live music, entertainment, shopping, restaurants, and outdoor activities. Return home to the pool at your back gate. You will think you are deep in the Caribbean... and you are! You don't even need a passport.

We have two bedrooms, each with a bath ensuite. A pullout sofa downstairs can accommodate a fifth guest. The half-bath downstairs, rare in Truman Annex townhomes, provides extra convenience and privacy.

As a guest in Flip Flop Retreat you have all conveniences you need to relax and entertain in style and comfort. Free parking space in secure lot close to your front door. BBQ on the landscaped terrace with the large new Weber grill, dine outdoors on the deck under the ceiling fan below the balcony or in air conditioned comfort indoors.

Secure wireless internet in a Non Smoking environment lets you relax with all the entertainment you need: Sony 46' TV with BluRay/DVD. You could even telework if you can tear yourself away from the attractions of Key West.

From the comfortable Adirondack chairs on the master bedroom balcony you might watch the moon rise over the pool in the evening or enjoy the sunrise with a cup of coffee. Our favorite way to start the day is to walk down Caroline Street to the Cuban Coffee Queen and drink their wonderful iced coffee on the balcony at Flip Flop.

Easy booking flat fee with no add ons... except tax.

More Details
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible

Ward Anderson
Member since: 2012
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
December 1, 2016
Call Owner

About Ward Anderson

We were frequent visitors to Key West while serving in the Navy. Later we vacationed in Key West with our children and found Truman Annex to be the best location on the island. We plan to retire here because of the magnificent weather, the entertainment, and range of outdoor activities. We live in Annapolis and visit frequently to keep Flip Flop in great shape.

Ward Anderson purchased this condo in 2011

Why Ward Anderson chose Key West

We wanted to be in Truman Annex because it is quiet and yet close to everything. We can walk or ride bikes anywhere we want to go. This townhome is one of the few with a half bath downstairs. We like the fact that Flip Flop is steps away from the pool and has a tranquil tropical terrace. French doors open directly to our outside dining area, the BBQ and gate to the pool. Our reserved parking space is conveniently near the front door.

After many vacations in Key West having fun and doing research, we found the perfect spot to put our feet up. FlipFlop Retreat is quiet despite the festive atmosphere in town.

What makes this condo unique

Knowing Flip Flop would be our retirement home we started making renovations right away. We have added high efficiency air conditioning, washer and dryer, ceramic top range, and tropical landscaping, and have renovated the upstairs ensuite bathrooms and the downstairs powder room.

Plantation shutters throughout put you in the Caribbean.

We love coming to Key West from Annapolis to vacation at Flop Flop Retreat.


Exceptional! 5/5 -
(48 traveler reviews)

Sun and Fun at Truman Annex Townhome with pool near Duval Street
average rating of 5.0 based on 48 reviews

#1 Best of The Best in Key West

  • 5 of 5

This was our second time renting this beautiful condo from Ward. Ward is easy to work with and is attentive to your needs or questions and he is always updating his condo. Beautiful, clean and amazing location ever! Pool is right behind fence in backyard. This pool is cleaned daily a few times a day. Shower and bathrooms are also available. Chairs are comfortable plus pool is heated, nice! We met many of the owners in the complex in our late afternoon happy hours. Beautiful furnishings, soft sheets/towels and very well maintained. This is huge since most rentals have thin towels. Each of the bedrooms have updated bathrooms. Each bedroom have large closets. We always seem to have laundry detergent and other items available. New fridge and dishwasher coming in the next couple of weeks. Just love the location to beach, a short walk or 2 blocks to Duval street which are the two main places we visit daily. Trust me, you will not find a condo like this nor will you be disappointed!

Rent early to ensure you get the week you want.

  • Submitted: Nov 23, 2016
  • Stayed: Nov 2016
  • Source: HomeAway
Owner's Response: We are so pleased with this excellent review. Our prime location next to the pool and also a short walk to Duvall Street, attractive decor and built in entertainment center, and all new appliances distinguish us from others. Our guests become family and we try to make them feel at home.
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1 0
Waverly, OH

Always the perfect rental!!!

  • 5 of 5

As we have come to expect from this property, it was perfect! After staying at various properties in KW, this remains our favorite! Ward is fantastic to work with and we would highly recommend this rental to others!

Thank you Ward and we will "see" you on our next visit!

  • Submitted: Nov 16, 2016
  • Stayed: Nov 2016
  • Source: VRBO, from HomeAway
Owner's Response: 5 Star Reviews make our day! We are most grateful for this concise review. Thank you for returning to Paradise at Flip Flop Retreat. We love our repeat guests- they promote Flip Flop Retreat and we have benefited from their many referrals. Our goal is to exceed expectations.
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0 0

A relaxing and wonderful place to stay

  • 5 of 5

The place was beautiful. Have stayed in many units in the Annex. This tops them all. So convenient to everything.

  • Submitted: Nov 15, 2016
  • Stayed: Oct 2016
  • Source: HomeAway
Owner's Response: Another 5 Star Review is most appreciated. We are dedicated to keeping Flip Flop Retreat perfect in every way that we can. We vacation there nearly every month and every detail of our townhome is looked at closely and put as good as it gets. As our guest, now part of our extended family, notes we are better than other units in the annex because of location, cleanliness, decor, modern appliances, and our respectful communications. Thank you
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0 0

Perfect on Porter Lane

  • 5 of 5

My family and I just returned from our yearly Key West visit and I am so glad that we have finally found the perfect vacation rental. Everything was clean and well taken care of as well as quite comfortable. It was a plus that each bedroom had its own full bath so that we didn't have to share as most other rentals in the Annex do and the back deck was our favorite spot to sit and unwind. The location was perfect, close to the beach, Ft. Zachary Taylor, the pool and Duval Street but far enough away from the noise and activity. Ward also made the rental process easy and answered any questions that we had in a timely manner. We have stayed at four different places in the Annex but from here on out we will only stay at Flip Flop Retreat. I can't wait to go back next year.

  • Submitted: Oct 21, 2016
  • Stayed: Oct 2016
  • Source: HomeAway
Owner's Response: Our 45th 5 Star Review- Thank you. Flip Flop Retreat is in mint condition and perfectly located for a wonderful family vacation. Long time Key West vacationers recognize that we are superior to other locations and recommend us to their friends. Most of our bookings are repeat guests and we welcome them to our extended family.
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  • 5 of 5

Even better than it looks on the photos. Feels so at home. Immaculately kept with everything you could need. Ward arranges everything to ensure your stay goes smoothly. Handy for the lovely pool. Garden area great for a bbq and the air con is quiet and keeps it comfortable inside. Quiet location yet a few minutes from all the action of Duval Street. It has to be a five star rating!

  • Submitted: Aug 2, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Owner's Response: Our guests are the best. We stay in touch enough to make sure their vacation is perfect. We will finish our third bathroom remodel this summer and the pictures will really show off Flip Flop Retreat. Thank you for this 5 Star! Ward
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0 0
Flowood, Ms

Perfect location, everything you could ever need!

  • 5 of 5

Ward was great to work with and we found Flip Flop to be everything we needed and more. Most importantly was it's location. You can walk or bike anywhere. Do use Eaton Bikes by the way. They deliver and pick up free right to your door. The pool being right out the back door was fantastic and made a quick dip an option we used several times a day. The additional lower bathroom was very handy. The washer and dryer are over and under but not the small size that I've seen in other similar condos. The kitchen appliances and cookware were top notch. I cook a lot and was happy to see Calphalon which I have at home. TV channel choices we plentiful and wireless internet worked fine. The back patio is great and the grill was nice to have. Our car was parked just outside the front door so loading and unloading was very easy. Do go to Fort Zachary beach! It's a couple hundred yards away and has everything, shady places under palms to hang a hammock, sun bleached beaches for laying out and snorkeling (plenty of fish to see) as well as refreshments sold on site.

All in all, if I go back, I will want to stay here again. The Truman Annex is the only place I'd want to stay and Flip Flop is in my opinion, one of the best in the Annex.

  • Submitted: Jun 22, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: Another 5 Star Review that describes why we purchased Flip Flop Retreat: Location, amenities, first floor bathroom and more. We appreciate our guests and work to meet all their needs with good communication. Thank you, Ward
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Nearest Airport
2 Miles
Key West International Airport
Nearest Barpub
0.05 Miles
Green Parrot, great bands & free popcorn!
Nearest Ferry
0.3 Miles
Terminal for ferry to Ft. Myers and Marco Island
Nearest Golf
4 Miles
Key West Golf Club
Nearest Train
0.3 Miles
Conch Train, guided tour of Old Town
Nearest Motorway
0.1 Miles
Mile 0, Highway 1- end of Florida Keys Highway
Nearest Restaurant
0.05 Miles
Blue Heaven, best Key Lime Pie Ever!
Nearest Ski
0.2 Miles
Fury water ski at the pier
Nearest Beach
0.1 Miles
Fort Zachary Taylor Park and beach
Car: not necessary

Truman Annex is a gated quiet neighborhood within walking distance of the beach, pool, adventure tours, restaurants, entertainment, and historic sites. In addition, special events are always happening in Key West like Pirate Week, Fishing Tournament, Fantasy Fest, Powerboat Race Week, Bike Week, and Sailboat Race Week. Check out the city calendar:

Nearly every water sport is available in Key West- deep sea fishing, bone fishing, snorkeling, diving, parasail, sailing, and more. Try online searches to arrange for activities you plan during your stay. Make reservations in advance for your bike or scooter or any daily plans you might have.


Rates & Availability

Truman Annex Condo Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
December Holidays 2016
Dec 24 2016 - Jan 1 2017
7 night minimum stay
Winter in the Keys 2017
Jan 2 2017 - Mar 24 2017
7 night minimum stay
March 25
Mar 25 2017 - Mar 31 2017
7 night minimum stay
Spring in the Keys 2017
Apr 1 2017 - Apr 29 2017
7 night minimum stay
Fantasy Fest 2017
Oct 21 2017 - Oct 28 2017
7 night minimum stay
Powerboat Races 2017
Nov 4 2017 - Nov 11 2017
7 night minimum stay
Powerboat 2nd week
Nov 11 2017 - Nov 17 2017
7 night minimum stay
Flat fee
December Holidays 2017
Dec 23 2017 - Jan 5 2018
7 night minimum stay
Fantasy Fest
Oct 13 2018 - Oct 29 2018
8 night minimum stay
My Standard Rate
7 night minimum stay

Additional information about rental rates

Tax Rate 12.5%

In addition to winter weeks, certain festival/event weeks are higher- please inquire. Base rates do not include taxes.
Initial $500 is non refundable deposit as noted on the website.
See sample contract on this website in the booking process.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing
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Available arrival
Available stay (no arrival)


Truman Annex Condo Accommodation and Amenities

Property Type:
  • condo
Building Type:
  • building
  • Guests provide their own meals
  • Housekeeper Included
Floor Area:
  • 1026 sq. ft.
Location Type:
  • Beach ...
  • Downtown ...
  • Near The Ocean ...
  • Resort ...
  • Town ...
  • Water View ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer ...
  • Garage ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Local Maps
  • Paper Towels
  • Parking ...
  • Parking Off Street ...
  • Sofa Bed
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Coffee Maker
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Freezer
  • Garbage Disposal
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • 1 Half Bath
  • Downstairs - toilet , Powder room fully remodeled 2016. Great for 5th guest.
    Master - toilet , shower , Remodeled in 2016. Hair dryer, makeup mirror.
    Queen Bedroom - toilet , combination tub/shower , Remodeled in 2016. Hair dryer and make up mirror.
  • Hair dryer, makeup mirror, available in each upstairs bathroom with lots of towels available and storage under counter top.
  • 2 Bedrooms, Sleeps 5
  • Queen bedroom - 1 queen , Closet with plenty of storage
    Master Bedroom - 1 king , or two twins
  • Each bedroom has cable flat screen TV, plenty of storage, and towels for the pool and beach. The bedrooms are on the second floor so there are no worries about noisy upstairs neighbors. Iron and ironing board. The first floor sofa converts to a bed.
  • Books ...
  • DVD Player ...
  • Games ...
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • Video Library ...
  • Balcony ...
  • Barbecue
  • Beach Towels
  • Boat ...
  • Deck / Patio ...
  • Deck Furniture
  • Fully Fenced Property
  • Gated Community
  • Golf ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Furniture
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda ...
  • Porch Furniture
  • Small Cooler
  • Tennis ...
  • Unscreened Porch / Veranda
  • Walkway to Water
  • Water Sports Gear ...
  • Wood Deck
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible
Pool / Spa:
  • Communal Pool ...
  • arboretum
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • coin laundry
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • reefs
  • restaurants
  • ruins
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf privileges optional
  • hiking
  • jet skiing
  • paragliding
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • ski privileges optional
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Flip Flop Retreat is in the gated community of Truman Annex, within walking distance of restaurants, art and antiques galleries, Mallory Square, Southernmost Point, Duval Street, Fort Zachary Taylor, scooter and bike rental and more. The bright kitchen is fully equipped whether for a week or the entire winter. Ceiling fans in every room and on deck allow open air living, A wide screen TV in the living room and flat screen TVs in the bedrooms offer full entertainment capability, Built in cabinets contain books for every taste (but specializing in beach reading, of course), puzzles and board games. Double French doors open to the outdoor deck with dining table set under the balcony, and new plantation shutters make the home clean and bright.

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