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

45 Reviews
Bedrooms 2
Separate WC's1
Property type condo
Minimum Stay 7 - 8 nights

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Minimum Stay
7 - 8 nights


Photos and Description of this 2 bedroom holiday condo in Truman Annex - FlipFlop Retreat Truman Annex

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

The 5 Star Reviews say it all. Our guests love to spend a week or a month at our sunny, leafy green vacation townhome.

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:
25 October, 2016
Call Owner

About Ward Anderson

We were frequent visitors to Key West while serving in the Navy. 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 two upstairs ensuite bathrooms and the downstairs powder room.

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


based on 45 holidaymaker reviews

Sun and Fun at Truman Annex Townhome with pool near Duval Street
average rating of 5.0 based on 45 reviews

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.

  • Review Submitted: Oct 21, 2016
  • Date of Stay: 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!

  • Review Submitted: Aug 2, 2016
  • Date of Stay: 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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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.

  • Review Submitted: Jun 22, 2016
  • Date of Stay: 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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Great Week at Flip Flop

  • 5 of 5

My wife and I, plus two other friends, stayed at Flip Flop for our second time in May/June 2016. Great place!! Close to pool, and the walk to the local bars on Duval is just a few minutes. Ward is great to work with directly, and he is constantly upgrading the Condo. We plan on returning in 2017.

  • Review Submitted: Jun 6, 2016
  • Date of Stay: May 2016
  • Source: VRBO, from HomeAway
Owner's Response: We are so grateful for this kind review! Our goal is to exceed expectations. Thank you for choosing Flip Flop Retreat again and being such great guests! See you next year, Ward
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Nice property, great location

  • 5 of 5

We (wife & I) spent a week at Flip Flop, May 2016.

The property is immaculate with everything you would need. Quiet pool area, easy access to Duval St., Mallory Square and other areas that are all walkable, with a very comfortable condo to return to.

The rental process with Ward was very easy and everything was as advertised and more.

We enjoyed ourselves and would recommend Flip Flop.

  • Review Submitted: May 28, 2016
  • Date of Stay: May 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you! Our 41st 5 Star Review- we are thrilled. Early in the booking process through check out.we treat our guests like they are 5 Stars.
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Perfect location for family vacation

  • 5 of 5

Rented Flip Flop Retreat with another couple and we will return! There are many good properties in KW and the website helped find them. After talking with Ward we liked his because of the downstairs half bath and his newly renovated bathrooms. Flip Flop Retreat met all our BBQ needs, entertainment wishes, and the beds are regularly replaced. The eastern exposure of the balcony and deck was nice for early sun but not the heat of the afternoon.

Already booked for next year.

  • Review Submitted: Apr 28, 2016
  • Date of Stay: Jan 2016
  • Source: HomeAway
Owner's Response: This is our 40th 5 Star Review and we have worked hard to keep our guests delighted with their stay at Flip Flop Retreat. Thank you.
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Key West Kayak Fishing & Eco-Tours
"Kayak in the day Duval Street tonight!"
Mallory Square
"Entertainers just like San Francisco Fisherman's Wharf. Get your camera and catch the green ..."
Duval Street
"Oh yes! Day time Night time... be there for fine dining, live music, great shopping. "
Hemingway House
"This is a must. Get there at 8:50 in the morning and beat the crowd. "
Conch Tour Train
"Excellent tour guides will share locals knowledge of Key West."
Key West Lighthouse Museum
"Climb to the top and see the whole Island, the channels, and beaches."
Fort Zachary Taylor State Park
"10 minutes walk to the entrance and then you may enjoy the beach, snorkel at the artificial ..."
Red Barn Theatre
"Plan ahead and get your tickets to plays and these high caliber actors and actresses. "
Tropic Cinema
"5 excellent movies showing every day. Very comfortable seats, super popcorn and even enjoy a..."
Mile Marker 0
"Take a selfie at this one of a kind sign"
Green Parrot Bar
"Sound Check at 5:30 Friday. Free popcorn and meet the locals."
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: http://web.keywestchamber.org/events

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.


Prices & Availability

Prices for this holiday condo in Truman Annex, Key West

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

Additional pricing information

Tax Rate 12.5%

In addition to winter weeks, certain festival/event weeks are higher- please inquire. Base rates do not include taxes and cleaning/booking fees.
Initial $500 is non refundable deposit as noted on the contract. Add $50 if sofa bed used.
See sample contract on this website.

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


Accommodation and facilities for this holiday condo in Truman Annex in Lower Florida Keys

Property Type:
  • condo
Building Type:
  • building
  • Self-catering
  • Housekeeper Included
Floor Area:
  • 1026 sq. ft.
Location Type:
  • beach ...
  • city centre ...
  • near the sea ...
  • 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 ...
  • Hob ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • 1 Separate WC
  • Downstairs - Toilet , Powder room fully remodeled 2016. Great for 5th guest.
    Master - Toilet , Shower Enclosure , Remodeled in 2016. Hair dryer, makeup mirror.
    Queen Bedroom - Toilet , Bath with 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 Large Double Bed , Closet with plenty of storage
    Master Bedroom - 1 Extra Lg. Double Bed , 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 ...
  • Terrace ...
  • Deck Furniture
  • Fully Fenced Property
  • Gated Community
  • Golf ...
  • Kayak / Canoe ...
  • Garden ...
  • Outdoor Furniture
  • Barbecue ...
  • Outdoor Grill Gas
  • Patio
  • Veranda ...
  • Porch Furniture
  • Small Cooler
  • Tennis ...
  • veranda
  • Walkway to Water
  • Water Sports Gear ...
  • Wood Decking
  • 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
  • botanical garden
  • churches
  • cinemas
  • laundrette - not serviced
  • festivals
  • library
  • live theatre
  • marina
  • museums
  • playground
  • recreation centre
  • reefs
  • restaurants
  • ruins
  • synagogues
Leisure Activities:
  • antique hunting
  • beachcombing
  • bird watching
  • eco tourism
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • Basketball Court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf pass optional
  • hiking
  • jet skiing
  • paragliding
  • pier fishing
  • roller blading
  • sailing
  • diving
  • ski pass optional
  • snorkelling
  • 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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