See all properties

Grandfathered Unit Weekly Rentals Allowed-Pool View-Duval Street-Beach

Top rated by guests

Nice size pool with plenty of sitting areas and lounge chairs.

Full size kitchen leads to front balcony overlooking the pool.

Nice size pool.

Second private balcony.

Private front balcony.

9.6Outstanding

(128 Ratings)

Great location, clean property, comfortable beds, easy access to amenities and attractions. Responsive and accommodating host. Perfect for families and enjoyable vacations.

From real guest reviews summarized by AI

Don't miss out! Price and availability may change

9.6 / 10.0

Outstanding(128 Ratings)

Apartment in Key West, FL

6 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this apartment rental

This condo has been grandfathered in to allow for weekly rentals. One of only a few with City approval. This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in the Truman Annex, a gated community of private homes and condominiums. Located inside the Truman Annex is Truman's Little White House Museum, Eco-Discovery Center, Water Park for small children and Fort Zachary State Park. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin beds that are easily converted to a king sleeper, a sofa sleeper, full kitchen, living room, washer/dryer and two private balconies one overlooking the swimming pool and the other facing the courtyard. Free assigned parking spot and Free Wi-fi. Steps from famous Duval Street, sunset celebration and all the downtown action one desires. High demand book early.

Amenities at Grandfathered Unit Weekly Rentals Allowed-Pool View-Duval Street-Beach

Family friendly

Map of Key West, FL

city location on map

Nearby attractions

The Key West Butterfly and Nature Conservatory

Southernmost Point of the Continental U.S.A.

The Hemingway Home and Museum

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

$$$$

Top rated by guests

9.6Outstanding

(128 Ratings)

Great location, clean property, comfortable beds, easy access to amenities and attractions. Responsive and accommodating host. Perfect for families and enjoyable vacations.

From real guest reviews summarized by AI

Don't miss out! Price and availability may change

$$$$

9.6 / 10.0

Outstanding(128 Ratings)

Apartment in Key West, FL

6 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Map of Key West, FL

city location on map

Nearby attractions

The Key West Butterfly and Nature Conservatory

Southernmost Point of the Continental U.S.A.

The Hemingway Home and Museum

About this apartment rental

This condo has been grandfathered in to allow for weekly rentals. One of only a few with City approval. This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in the Truman Annex, a gated community of private homes and condominiums. Located inside the Truman Annex is Truman's Little White House Museum, Eco-Discovery Center, Water Park for small children and Fort Zachary State Park. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin beds that are easily converted to a king sleeper, a sofa sleeper, full kitchen, living room, washer/dryer and two private balconies one overlooking the swimming pool and the other facing the courtyard. Free assigned parking spot and Free Wi-fi. Steps from famous Duval Street, sunset celebration and all the downtown action one desires. High demand book early.

Amenities

Family friendly

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

Ratings and reviews

9.6 / 10.0

Outstanding(128 Ratings)

Summary of reviews

Great location, clean property, comfortable beds, easy access to amenities and attractions. Responsive and accommodating host. Perfect for families and enjoyable vacations.

From real guest reviews summarized by AI

10.0 / 10.0

Safe location, great for families! Steps from the community pool. Plus a really nice neighborhood walk to local attractions like the aquarium and museums.

10.0 / 10.0

Just as advertized !

10.0 / 10.0

This property was a wonderful stay. The beds were comfy, the showers were refreshing, the air conditioning was cold. Perfect place to come "home" to after a hot day out on the water. A dip in the pool was greatly enjoyed after getting used to the initial chill of the water, a little colder than previous years, but tolerable. We look forward to more visits to this complex in the coming years!

10.0 / 10.0

Great stay, great unit and great location. Host was great as always

8.0 / 10.0

Several recommendations were sent to property manager - some regarding cleanliness others repairs, fixes. We were without air on holiday when temperature and humidity was high. Air fixed next day. Requested partial refund but have received no response. I sent photos of all issues some of which handyman and others couldn’t find. Do not recommend for older people due to stairs.

10.0 / 10.0

Love Key West and this is a fantastic location in the middle of everything, making all entertainment very walkable if you choose. Great pool and very friendly people.

10.0 / 10.0

This property checked every box. The place was clean, and just the right size. Everything we needed for a two week stay was there from beach towels, linens, pans, dishes, even hand soap and dish soap was provided. The few questions I had were answered immediately. The location is absolutely perfect. Within walking distance to everything. The pool was cleaned daily and the grounds were immaculate. I highly recommend this place.

10.0 / 10.0

Roberta was wonderful to work with. Extremely responsive. The unit was spectacularly clean. We could not have asked for a better location.

10.0 / 10.0

Great location, close to the action on Duval St as well as the water front.

10.0 / 10.0

We had an amazing time at this condo. The place had everything we needed. Having two balconies and one that overlooked the pool was a plus. We walked everywhere, this condo was right in the middle of town. You just needed to decide everyday go right or left. Take a Sunset cruise!!! Visit Hemingway house and Butterfly Exhibit. Oh yeah and Irish Kevin’s on Duvall St. Thank you Roberta.

10.0 / 10.0

We had a great stay… loved being overlooking the pool as it was quiet and pretty. Lots of Key West chickens about and nice to hear the national anthem at 8 am every morning from the nearby military base. Many good restaurants within walking distance and the parking for a car/golf cart was really handy. The unit is cute and clean. Everything you need is available. Loved the two porches although they were being painted for much of our stay. The unit could do with a spot of paint but overall it was wonderful.

10.0 / 10.0

This was a great vacation and this unit/location was amazing!!! Literally walk to everything and in the complex the pool was just outside the door, 2 balconies so you could always find shade and relax

10.0 / 10.0

You can't beat this location. It is quiet, safe, and within walking distance from nearly everything you want to do in Key West. We saw a manatee at the waterfront right next to the complex the second night we were there. We also spent several days at Fort Zachary Taylor State Park, which is walking distance from the property if you don't have a lot of items to carry. This is a great spot for families. Despite the heat, we also spent a lot of time reading on the balcony overlooking the pool. The pool is clean and very quiet during this time of year. There were several points during our 10 day trip when we had the pool to ourselves. The complex property is immaculate and everyone was very friendly. Property manager was responsive and helpful.

6.0 / 10.0

I wasn't really thrilled with this particular property. There were a lot of rules for the pool, the interior stairs were narrow and steep, the condo itself was kind of small. However, and huge however, Roberta, the property manager is amazing and will make everything right for you. She quickly put us somewhere larger and nicer when the tv and internet were not working correctly and the new place was AMAZING! We will definitely be back with Roberta again, she is awesome and caring.

10.0 / 10.0

Property is exactly as described. Easy check in/out. Walking distance to Duval.

10.0 / 10.0

The stay at the Truman Annex was great. The location, facilities available and the staff are all commented for the nice appearance and wonderful environment.....

4.0 / 10.0

The Truman complex is lovely, great location and very well maintained. But the property is very tired (as per other reviews) and needs a major overhaul to bring it up to a reasonable standard. The experience was pretty awful. From getting the dates on our booking messed up (and host was no help to get this resolved - had to escalate through to Directors at VRBO to get help), through to broken floor tiles in every room, fridge door held on by sticky tape, dirty and discoloured kitchen sink, dangerous looking electrics, wall tile hanging off the wall in the bathroom, dirty bottom bed sheet in the master bedroom, sofa bed that you cannot sleep on as the mattress is so bad and the springs make it totally impossible to sleep on. Made the host aware of all these issues and she did nothing.

10.0 / 10.0

Roberta was great ! Communicated Exceeded what we expected. Made our holiday very relaxing Can’t wait to come back!

10.0 / 10.0

It was clean, spacious for a 2 bedroom. It had 2 balconies which we loved. Had breakfast every morning outside over looking the pool. The beds were comfortable. The unit came with a washer and dryer which I think is a bonus. Roberta was very easy to get a hold of and responded very quickly no matter what or when I asked questions. The property was well maintained and quiet. Great location for us since we prefer that side of Key West.

10.0 / 10.0

great location and close to all the activities we were interested in

10.0 / 10.0

The unit is more dated than others I’ve stayed in, but met all of our needs. Well equipped, plenty of towels and extra bedding. We loved having two balconies to relax on. The location is great within the complex, right next to the pool, it was easy to look out and see how busy it was. It’s an end until which makes it quieter, and the bedrooms are on the outside wall thankfully because the walls are thin and our neighbors were loud talkers. Super quiet at night. Thank you!

10.0 / 10.0

Enjoyed the closeness of the unit to all things downtown and proximity to pool with so many friendly people

10.0 / 10.0

We loved the architecture and location of the Shipyard Condos. We were revisiting Key West after 30 years and wanted to do it on foot. This sweet place was central to all Old Town had to offer: we walked to the beach at Fort Zachary Taylor, to the great old aquarium, sat on benches across from the Green Parrot listening to their live music, had Cuban lunch with the roosters. We caught the air-conditioned Duval Loop free bus when it got too hot to enjoy walking. We appreciated Roberta making it possible for an early arrival to the condo; were grateful to be close to the pool and enjoyed both verandas at dusk and dawn. Our stay was too short and we intend to do it again!

10.0 / 10.0

Love the location, couldn’t ask for a better place!

10.0 / 10.0

Loved the place and can’t beat the price. Excellent location, walking distance to almost everything and easy for kids. Loved the pool and the fun community at Truman Annex.

10.0 / 10.0

We had a great time at this property. It is conveniently located to Duval, Mallory Square, Fort Zachery, and the beach. Nice view of the pool from the balcony and overall comfortable stay.

10.0 / 10.0

This is a very nice place in a very good location close to everything. Beaches are close by (walkable, less than 1 mile). Higgs beach was probably the best one. Plenty of shopping and restaurants on Duval St. Overall, it was a great Key West vacation.

10.0 / 10.0

Awesome location, property as described in listing.

10.0 / 10.0

The condo and property were clean and well equipped, the pool was great and well maintained. The property is in a quiet park like setting that is well manicured and beautiful and is only 2 blocks away from Duval St. We also met several residents that are condo owners and make long-term stays in the facility, they were very pleasant and hospitable and offered many great suggestions for food and entertainment. We knew from the start of our second day that we will return to this property again!

10.0 / 10.0

This is a great property. The host was informative and was easy to access. Great location and very clean.

10.0 / 10.0

Would absolutely rent this condo again. It is perfect !

10.0 / 10.0

A wonderful location, close to town yet away to be able to relax. Like the secured gate and parking. The host was excellent.

10.0 / 10.0

Everything was as it appeared. Nice place.

10.0 / 10.0

Our family of 6 had a lot of fun in Key West over Thanksgiving! Condo is in a great location at the Truman Annex. Easy walking distance to Duval Street and close to Ft Zachary. Condo slept all 6 of us but was a little crowded. Would be perfect for 4 people but it suited us ok because we didn't spend much time at the condo. We had to contact the manager on Thanksgiving night and no problem she answered promptly. We appreciated that! I would stay at this property again! We loved our time in Key West & hope to be back next year!

10.0 / 10.0

Best location on Key West. Condo was exactly as described. Smack in the middle of everything, dining, the best restaurants shopping, nightlife and Mallory Square. Short walking distance to everything. No need for a car. In my opinion Fort Zachary Taylor beach is one of the most beautiful beaches I’ve ever seen. (You will need water shoes.. lots of coral!). We’ve stayed in Truman Annex the 4 times we’ve come to key west and wouldn’t stay anywhere else.

10.0 / 10.0

Property manager was helpful when needed. Great location.

10.0 / 10.0

Great location . We have stayed in KW 4 times, 3 times in Truman Annex. Very convenient to all of downtown. Unit was equipped well. No issues at all

10.0 / 10.0

We had a wonderful time at the house…Very roomy and clean and the kitchen had everything we needed..We were also right next to the pool..Will definitely stay here on our next visit..Thanks for making our visit so enjoyable…

10.0 / 10.0

Fishing with 4 Brothers good fishing and enjoyed the food and night life of Keywest weathered the hurricane great location to stay

10.0 / 10.0

Only dissatisfied that the pool closed on us for maintenance half way through the week!

Explore similar stays in Key West

Explore all rentals in Key West

10.0 / 10.0

Outstanding(27 Ratings)

**OLD TOWN OASIS @ THE ANNEX** Oceanside Condo & Pool + LAST KEY SERVICES…

6 guests · 2 bedrooms · 2 baths

Family friendly

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Key West, at $326 per night for your next great vacation.

10.0 / 10.0

Outstanding(27 Ratings)

**OLD TOWN OASIS @ THE ANNEX** Oceanside Condo & Pool + LAST KEY SERVICES…

6 guests · 2 bedrooms · 2 baths

Family friendly

Apartment in Key West, for $326 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

8.4 / 10.0

Excellent(317 Ratings)

Hyatt Vacation Club at Sunset Harbor, Key West

2 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Key West at Hyatt Vacation Club at Sunset Harbor, Key West for $300 for your next trip.

Key West Found by AvantStay | Close to Shops w/ Patio & Shared Pool! | Week Long Stays Only

6 guests · 2 bedrooms

Pool · Kitchen or Kitchenette · Air conditioner

Indulge in a peaceful retreat at Key West Found by AvantStay | Close to Shops w/ Patio & Shared Pool! | Week Long Stays Only, our elegant House in Key West. Enjoy amenities including Internet / Wifi, Pool and Dishwasher, and more.

10.0 / 10.0

Outstanding

The Southernmost Comfort House

10 guests · 4 bedrooms · 3 baths

Pool · Kitchen or Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Key West, at $286 per night for your next great vacation.

8.2 / 10.0

Excellent(310 Ratings)

Hyatt Vacation Club at Sunset Harbor, Key West

2 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

Nestled in Key West, this Apartment is perfect for your next vacation. Enjoy Hyatt Vacation Club at Sunset Harbor, Key West's top-rated amenities, including Air conditioner, Internet / Wifi and Kitchen or Kitchenette, and more.

10.0 / 10.0

Outstanding(37 Ratings)

**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE

6 guests · 2 bedrooms · 2 baths

Family friendly

This inviting House in Key West can fit your needs for many types of vacations, at $349 per night.

10.0 / 10.0

Outstanding(37 Ratings)

**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE

6 guests · 2 bedrooms · 2 baths

Family friendly

This House in Key West, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

You can save with One Key

9.6 / 10.0

Outstanding(88 Ratings)

~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!

6 guests · 2 bedrooms · 2 baths

Family friendly

This Apartment in Key West, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

8.0 / 10.0

Excellent(2 Ratings)

Last Minute

6 guests · 3 bedrooms · 2 baths

Pool · Kitchen or Kitchenette · Air conditioner

The best choice in Key West for House, for $286 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(101 Ratings)

**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...

6 guests · 2 bedrooms · 2 baths

Family friendly

Soak up the beauty of Key West in our House, **VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES.... With a range of amenities such as Family friendly, you'll feel right at home.

You can save with One Key

9.9 / 10.0

Outstanding(100 Ratings)

**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...

6 guests · 2 bedrooms · 2 baths

Family friendly

Business stays, family stays, couples stay, getaway vacation, and rental in Key West at **VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES... for $330 for your next trip.

10.0 / 10.0

Outstanding(82 Ratings)

PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!

6 guests · 2 bedrooms · 1 bath

Family friendly

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Key West, at $348 per night for your next great vacation.

9.9 / 10.0

Outstanding(82 Ratings)

PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!

6 guests · 2 bedrooms · 1 bath

Family friendly

This House for $348 in Key West, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

Gulf Getaway

6 guests · 1 bedroom

Pool · Pets allowed · Kitchen or Kitchenette

Looking for the perfect place to call home during your trip to Key West? This House offers a comfort and style with top-notch amenities, including Pets allowed, Pool and Air conditioner, and more.

9.8 / 10.0

Outstanding(8 Ratings)

Gulf Getaway | Condo w/Pool!

6 guests · 2 bedrooms · 2 baths

Pets allowed · Family friendly

Looking for a memorable stay in Key West? Our House might just be what you're looking for. Enjoy amenities including Pets allowed and Family friendly, and more during your stay.

10.0 / 10.0

Outstanding(8 Ratings)

Gulf Getaway | Condo w/Pool!

6 guests · 2 bedrooms · 2 baths

Pets allowed · Family friendly

Enjoy the best of Key West in our House, Gulf Getaway | Condo w/Pool!. A stunning property with amenities including Pets allowed and Family friendly, and more.

9.4 / 10.0

Outstanding(204 Ratings)

HOLIDAY SPECIALS BOOKING NOW!

6 guests · 2 bedrooms · 1 bath

This inviting Apartment in Key West can fit your needs for many types of vacations, at $390 per night.

9.2 / 10.0

Outstanding(205 Ratings)

HOLIDAY SPECIALS BOOKING NOW!

6 guests · 2 bedrooms · 1 bath

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Key West, at $390 per night for your next great vacation.

10.0 / 10.0

Outstanding(34 Ratings)

OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!

6 guests · 2 bedrooms · 2 baths

Family friendly

Experience the best of Key West with this House available for $350. This property is equipped with amenities including Family friendly, and more.

Blanco Luxury Villa

8 guests · 1 bedroom · 4 baths

Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Key West? Look no further than our House, Blanco Luxury Villa. Enjoy top-rated amenities including Parking, Laundry and Free parking, and more.

10.0 / 10.0

Outstanding(34 Ratings)

OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!

6 guests · 2 bedrooms · 2 baths

Family friendly

Looking for a House in Key West, this House for $350 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

8.8 / 10.0

Excellent(14 Ratings)

Snowbird-friendly condo with private balcony, garden views, W/D, on-site pool

6 guests · 2 bedrooms · 2 baths

Family friendly

Indulge in a peaceful retreat at Snowbird-friendly condo with private balcony, garden views, W/D, on-site pool, our elegant Apartment in Key West. Enjoy amenities including Family friendly, and more.

You can save with One Key

8.8 / 10.0

Excellent(14 Ratings)

Snowbird-friendly condo with private balcony, garden views, W/D, on-site pool

6 guests · 2 bedrooms · 2 baths

Family friendly

Business stays, family stays, couples stay, getaway vacation, and rental in Key West at Snowbird-friendly condo with private balcony, garden views, W/D, on-site pool for $275 for your next trip.

9.6 / 10.0

Outstanding(131 Ratings)

Grandfathered Unit Weekly Rentals Allowed-Pool View-Duval Street-Beach

6 guests · 2 bedrooms · 1 bath

Family friendly

Experience the best of Key West with this Apartment available for $344. This property is equipped with amenities including Family friendly, and more.

Takeover at the Grand Maloney

16 guests · 6 bedrooms · 7 baths

Pool · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Key West? This House offers a comfort and style with top-notch amenities, including Parking, Garden and Free parking, and more.

You can save with One Key

9.6 / 10.0

Outstanding(22 Ratings)

Latitude Adjustment @ Truman Annex Shipyard

6 guests · 2 bedrooms · 1 bath

Family friendly

Nestled in Key West, this Apartment is perfect for your next vacation. Enjoy Latitude Adjustment @ Truman Annex Shipyard's top-rated amenities, including Family friendly, and more.

9.8 / 10.0

Outstanding(22 Ratings)

Latitude Adjustment @ Truman Annex Shipyard

6 guests · 2 bedrooms · 1 bath

Family friendly

Apartment in Key West, for $386 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

9.4 / 10.0

Outstanding(6 Ratings)

Key West Cabana-Old Town Key West- Steps to Duval Street w/ Pool & Tiki Bar

6 guests · 2 bedrooms · 2 baths

Family friendly

This attractive House in Key West, $333 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

9.4 / 10.0

Outstanding(6 Ratings)

Key West Cabana-Old Town Key West- Steps to Duval Street w/ Pool & Tiki Bar

6 guests · 2 bedrooms · 2 baths

Family friendly

This House for $333 in Key West, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)