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**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...

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Tropical resort complex with swimming pool, hot tub, and colorful colonial-style buildings surrounded by palm trees.
Unwind in your coastal-inspired living space featuring an ocean-blue accent wall, tropical touches, and comfortable seating for ultimate relaxation.
Your fully equipped kitchen awaits with crisp white cabinetry, granite counters, and stainless appliances—perfect for cooking memorable meals together.
Sink into plush seating while ocean breezes from your ceiling fan keep you cool in this coastal-themed living space.
Unwind in your bright living room with coastal décor, comfy seating, and entertainment center—perfect for relaxing evenings.

Reviews

9.8 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 696.2 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View map
Key West, FL
  • Place, Harry S. Truman Little White House
    ‪3 min walk‬
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Mallory Square
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Master Bedroom

1 King Bed

Second Bedroom

1 King Bed

2 bathrooms, 1 half bathroom

Master Bath

Powder Room

Second Floor Bath

Spaces

Deck or patio
Kitchen

About this property

**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

SEA CAPTAIN'S HAVEN is an immaculately furnished villa at the Porter Court Complex in Truman Annex, Key West's most desirable gated community, right in the middle of Old Town. At SEA CAPTAIN'S HAVEN, you'll be close to all of Key West's best restaurants and attractions, including Mallory Square and Fort Zachary Taylor State Park.

THE LIVING AREA...

SEA CAPTAIN'S HAVEN has been meticulously designed to make the most of every square foot of space. The walls are rich with the art you might expect to see in a sea captain's home. There is plenty of seating for the whole crew, and while you might not expect a large flat screen TV in a sea captain's house, it's there nonetheless. French doors open to a very private deck with chaises and outdoor dining. If you prefer to eat indoors, there is a dining area situated comfortably in the bay window, with seating for six. The gourmet kitchen is a model of efficiency, with every appliance a good chef would need. The sofa converts to a queen bed, and there is a powder room for the convenience of your guests.

THE POOL and JACUZZI...

The pool area is spacious, and is furnished with plenty of chaises, chairs, and dining tables with umbrellas. The pool itself is large enough to swim laps, and there is a large Jacuzzi, too. If you want to feel the sand between your toes, Fort Zachary Taylor Park is just down the block, with the prettiest beach in Key West.

Compliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.

THE ACCOMMODATIONS...

• Master Bedroom: Located on the Second Floor with a King bed, a flat screen TV, double closets, and an en-suite bathroom with a walk-in shower.

• Second Bedroom: Located on the Second Floor with Two Twins OR One King bed, a flat screen TV, a closet, and access to the full bathroom in the hall.

ALL LAST KEY VACATION HOMES INCLUDE:

• Washer and Dryer
• Central Heat and A/C
• Ceiling Fans
• Flat Screen TVs in Living Room & All Bedrooms
• Fully Equipped Kitchen
• Basic stock of spices
• Starter supply of paper products
• Starter set of cleaning products
• Linens and Towels provided
• Wireless high-speed Internet access & full cable included

In addition, this fully stocked home also includes, but is not limited to the amenities on this list:

• Fully Fenced and Landscaped Private Yard
• Community Pool Access
• Community Jacuzzi Spa
• Assigned off-street carport for 1 car (with vehicle restrictions - no vehicle over 18’ long or 80’’ wide)
• Propane BBQ Grill

Other notes:

• Interim housekeeping provided upon request
• This property will accommodate up to 5 adults
• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Key West

Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Harry S. Truman Little White House - 3 min walk - 0.3 km
  • Duval Street - 5 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 6 min walk - 0.6 km
  • Mallory Square - 8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.8 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 15 min drive

Restaurants

  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Margaritaville - ‬6 min walk
  • ‪Caroline's Cafe - ‬9 min walk
  • ‪La Concha Bar - ‬6 min walk
  • ‪First Flight Island Restaurant & Brewery - ‬7 min walk

Frequently asked questions

Does **SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES... have a pool?

Yes, this property has a pool.

How much does it cost to stay at **SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...?

As of 11 April 2026, prices found for a 1-night stay for 2 adults at **SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES... on 11 June 2026 start from NZ$357, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is **SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES... pet-friendly?

No, pets are not allowed at this property.

How much is parking at **SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...?

On-site parking is available at the property.

What time is check-in at **SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...?

Check-in begins at 4:00 PM.

What time is check-out at **SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...?

Checkout is at 10:00 AM.

Where is **SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES... located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of Truman Waterfront Park and Duval Street. Mallory Square and Ernest Hemingway Home and Museum are also within 15 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 45 out of 53 reviews
Rating 8 - Good. 7 out of 53 reviews
Rating 6 - Okay. 0 out of 53 reviews
Rating 4 - Poor. 1 out of 53 reviews
Rating 2 - Terrible. 0 out of 53 reviews

10/10

Cleanliness

10/10

Check-in

9.6/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Susan d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful everything

From the location to the amenities to the customer service…everything was first class! Five stars all around!!!!
Stayed 7 nights in May 2023
Verified

10/10 Excellent

Dirlam F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fishing and Lobster Trip

Awesome house and grounds equipped with everything we needed. Property manager, Brian, was fantastic and extremely helpful. Loved the patio space for morning coffee, and the pool was refreshing after long days on the boat. Location is perfect for walking to night life and waterfront areas. Would definitely stay again.
Stayed 6 nights in Jul 2023
Archival

10/10 Excellent

Pam P.

Lovely

We enjoyed our stay and I feel confident I picked the right place. Great location, quiet neighborhood, clean, well equipped, nicely appointed home. I would definitely come back and would have loved to have stayed longer. Nothing beats having the space of a condo for the cost of a luxury hotel room.
Response from VrboOwner on 22 March 2020
We definitely agree that nothing beats being able to spread out with the space of a condo instead of holing up in a hotel room. The perks of having a kitchen, only sharing the pool with a few other guests, and still enjoying the fabulous location. The wording in this review describing Sea Captain's Haven as "nicely appointed" is certainly true - anything you could need can be found in this home, or will be brought to you by your Guest Services Coordinator immediately upon request.
Verified

10/10 Excellent

Mike K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location for a relaxing vacation

Our family of four had the best week enjoying all Key West had to offer. The ease of walking to attractions, restaurants and shopping was perfect while being secluded from the crowds of tourists. This home was extremely well maintained, stylish and comfortable. All the appliances were in working order and the kitchen had everything we needed to make a few meals on the evenings we stayed in. The neighbors were helpful and kind. We always love our time in The Truman Annex.
Stayed 8 nights in Mar 2024
Verified

10/10 Excellent

Ken M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sea Captain’s Haven

It was very clean and spacious. Also, it was one of the only places with multiple bathrooms. The last key rentals personnel were great! We had a Kermit’s key lime pie awaiting in our refrigerator, which was amazing. The pool and the outdoor shared common area was very clean. The location was perfect as we were right in the middle of Duval street. It was only a 5 min walk to get there and it brought us out to a Starbucks!!!! I’d def go back!
Stayed 6 nights in Jun 2023
Verified

10/10 Excellent

Cori B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful place

The townhouse was very clean and beautiful. They left a key lime pie in the refrigerator for us when we arrived. We were 2 blocks from duval street and very close to everything. My very large Yukon XL SUV was able to park in the parking spot very easily even though the description for the property said it needed to be a certain size. The townhouse sits on the backside of the pool 2 homes down from Fleming St. The pool was clean and refreshing from a long day of walking around Key West. The neighbors were all very nice and always said Hi when we walked up. If we ever get to go back to Key West we will be staying here again.
Stayed 6 nights in Apr 2023
Verified

8/10 Good

Jodi K.

Liked: Cleanliness, check-in, location
Disliked: Communication

Convenient property

Place was very walkable for alot of places. Only had to uber once for a kayaking excursion. No internet when we arrived on fri and didn't get fixed until Sunday afternoon. It was known that internet was very spotty there and it should have been checked before the arrival of guests. Especially when they know it's an issue and not wait for guests to complain numerous times.
Stayed 7 nights in Apr 2022
Response from VrboOwner on 24 May 2022
We were quite disappointed to see this review as we were on top of the issue the moment it happened and Jodi was quite understanding, even grateful, while staying with us. The problem was Truman Annex, the neighborhood this property is located in, decided to upgrade everyone's internet service (whether we wanted them to or not) when Jodi arrived. Our hands were tied as this was not our choice, it was forced upon the neighborhood by the HOA. For the inconvenience, we issued Jodi a partial refund and provided her with a wireless hotspot so she still had wireless access. We explained this, at length, to Jodi when we provided the hotspot and the partial refund. The good news is, this issue was fixed early in Jodi's stay and has been working as it should ever since.
Archival

8/10 Good

Edward T.

Wonderful vacation

My husband and I, my daughter, son in law, my son and 2yr old grandson spent a week at sea captains haven. The openness of the condo was perfect for us. Very comfortable with lovely furnishings. We really loved being on porter court with pool right outside our door. Being in Truman Annex is the best way to experience Key West. Although we rented a car we never used it. We walked to everything we wanted to see and do because the location was so perfect. The only negative thing I would have to say is that my son ended up using the pull out couch in living room and it was very uncomfortable. I think he had a pretty sore back by end of week. That being said, we would definitely rent here again as it was nearly perfect for us. Everything went smoothly with rental company and wouldn't hesitate to use them in the future
Stayed 7 nights in Mar 2016
Response from VrboOwner on 22 March 2020
We are sorry to see this feedback come through after this guest departed, as the sofa bed comfort could have easily been resolved during this guest's stay. The sofa bed typically has a foam mattress topper on it when made up, but after this guest's departure the foam mattress pad was found underneath the upstairs master bed - clearly not being put to its best use under there! We always encourage our guests to call their Guest Services Coordinator when there is ANYTHING we can improve for your stay, because often times there is a solution right there in the home! And if not, we will find a way to resolve the issue as quickly as possible.
Verified

10/10 Excellent

Patrice C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect

The property was lovely, clean and charming. The concierge service was top-notch. We had a problem with the a/c, which was handled immediately. The location is great - close to beach and Duval St. Thoroughly enjoyed our stay.
Stayed 6 nights in May 2022
Verified

10/10 Excellent

Jessica L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous Spring Break

My family stayed here over spring break. Great location - super close to Duval. The accommodations were as described. Equipped kitchen. Nice space. Great neighborhood. Loved the pool area, privacy of the back patio. Safe and secure. Hope to stay again!
Stayed 6 nights in Mar 2022
Verified

10/10 Excellent

James S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful!

The property was delightful.....We especially enjoyed the large outside deck. The kitchen was stocked with everything needed to have a cookout and celebrate birthdays and our family reunion. We loved the pool. Also, the owners in Porter Court were VERY pleasant and welcoming . Lost Key provided excellent service
Stayed 7 nights in Nov 2021
Verified

8/10 Good

Shirley M.

Liked: Cleanliness, check-in, communication, listing accuracy

Nice but noisy.

The condo was wonderful, but neighborhood was noisy with garbage trucks, street cleaning and landscape crews. Was good location to walk everywhere. Nice and private back patio. Kendra was very accommodating and kind.
Stayed 6 nights in Nov 2021
Verified

10/10 Excellent

David P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Fast and easy
Stayed 6 nights in Oct 2021
Verified

10/10 Excellent

Linda Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

This property is very close to many attractions and restaurants yet it is a in nice quiet location. Beautiful pool. Comfortable for 4. The VRBO description was accurate. The concierge service was very friendly and helpful. We would absolutely consider staying here again.
Stayed 6 nights in Oct 2021
Verified

10/10 Excellent

Michael O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West

This was a great place to stay. Within easy walking distance of everything. The rental floorplan worked great for our family and fully equipped and very nicely decorated. Absolutley stay here again in the future.
Verified

10/10 Excellent

Jobn F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and excellent service!!

Greg with Last Key Realty was great! The location of our home was excellent and the chilled pool was a nice touch. Thanks
Stayed 6 nights in Jun 2019
Verified

10/10 Excellent

Melissa B.

Relaxing getaway

We had a wonderful time at Sea Captains Haven. It was clean and well furnished. The location is perfect, quiet and relaxing but so convenient to all the excitement of Old Town. We are already looking forward to our next visit!
Stayed 6 nights in Mar 2019
Verified

4/10 Poor

Susan D.

Poor location within Truman Annex

The location alone is why I would never rent this condo again. It backs up to the US post office parking lot and it is incredibly noisy. You could not sleep with the windows open and during the day it was too loud to go out and enjoy the patio at the back. Also, the pool was supposed to be heated but was only 78°. The owners association controls that, not your rental agent. One resident told me it’s usually 88° but someone had turned off the heat… go figure, but we never swam the whole week because of the cool temperature and the fact that the pool is shaded at least half of the day . Bbbrrrrrt. Before you rent in Truman Annex, get a map of the area and avoid renting next to the post office parking lot or the county parking lot. There are some lovely locations within Truman Annex but not those who border these two areas.
Stayed 7 nights in Mar 2018
Response from VrboOwner on 22 March 2020
What a disappointing review to receive, for multiple reasons. First off, we wish Susan had brought the pool temperature issue to our attention while she was here in residence because while we do not physically control the temperature we certainly have the ability to get involved with the HOA Management company to have the temperature changed - but we can only do that if we are notified by our guest that this is needed. As far as the post office noise, we are in process of implementing a solution to this issue: sound proof windows and panels are being installed in this home to alleviate the noise from the post office that has been reported by this and other guests. After 6 years of renting with no complaints this situation has only arisen this winter since Amazon started working through the post office now, with 24/7 activity. Future guests should not experience the same noise level and are encouraged to call us immediately if an issue such as the pool temperature arises so we may address while you are here versus responding to an after the fact review. We will always do everything in our power to resolve your issues so you can enjoy your time in Key West!
Verified

10/10 Excellent

Joan B.

Great expectations met in Key West Home

Lovely town house in private enclave in the Truman Annex. Great place to escape the bad weather and winter blues. Exceeded our expectations.
Stayed 14 nights in Jan 2018
Archival

8/10 Good

Roger F.

Exactly as advertised!

The property was exactly as pictured and had most everything we needed. Our concierge was on the spot with anything we requested. Totally happy with the property, Amanda and John. Only 4 stars due to the early morning rumble from the post office carts next door. Was not aware of that and was the only flaw in our stay. 5 stars for the property itself!
Stayed 7 nights in Dec 2017
Response from VrboOwner on 22 March 2020
Thank you for this review and we are so happy to hear your stay met your expectations. We are in process of implementing a solution to the post office noise issue: sound proof windows and panels are being installed in this home to alleviate the noise from the post office that has been reported by this and other guests. Future guests should not experience the same noise level.
Archival

8/10 Good

Christy K.

Amazing property...but..

The property is just beautiful and immaculate!! Amanda could not have done more to make our stay just amazing and worry free!! She took care of everything and answered calls immediately whenever we had any concerns or issues. She even had a birthday celebration all laid out for our friend Jeff! We love Key West and the Truman Annex. The USPS facility for the lower Keys is right over the fence from the deck. So, so noisy early in the am to about 9 or 10. If you’re an early riser, you might be ok. The other issue is the neighbors. They clearly DO NOT want renters in their lovely enclave. Several folks were down right rude!! Way too much time on their hands. But overall, we had a great Key West experience!
Response from VrboOwner on 22 March 2020
We love to hear that Amanda took great care of these guests and made their Key West vacation extra special. As far as the post office noise, we are in process of implementing a solution to this issue: sound proof windows and panels are being installed in this home to alleviate the noise from the post office that has been reported by this and other guests. Future guests should not experience the same noise level. We are disappointed to hear there was negative interaction with the neighbors and have brought this to the HOA's attention in hopes of preventing this type of issue in the future, but any guest staying with us is encouraged to tell Amanda (or any Guest Services Coordinator on our team) about an interaction like this with a neighbor and we will do whatever is within our power to resolve the issue while you are in residence.
Archival

10/10 Excellent

Teresa L.

Perfect Getaway

Very pretty setting, tasteful and well appointed, stocked kitchen and baths. Thoughtful and delicious welcoming gifts and even our favorite wine. Well maintained and very prompt attention to any needs. Concierge and hostess were right on with reservations and recommendations. Weather was perfect and the patio retreat was hard to leave. Short walk to Duval St and the whole downtown, museums and attractions-only used our car 3 times and once was to pick up family at the airport. Our week flew by and look forward to returning. Highly recommend this charming place.
Archival

10/10 Excellent

Daniel O.

Very nice! Great location!

Condo was very nice, well-equipped and having a pool right outside your door was excellent. Would stay here again in a minute.
Stayed 7 nights in Aug 2017
Archival

10/10 Excellent

Heather B.

Beautiful, spacious property that is close to everything!

Lovely home with pool outside front door. Super quiet but close location to all the action.
Stayed 7 nights in Apr 2017
Archival

10/10 Excellent

Ben G.

Nice Condo, Great Location

In Truman Annex, the only gated community in Key West, the condo is close to the beach and close to downtown Key West (but in a quiet area). Nice pool right outside your door. Very good service from the rental company. Lot of beach towels, good kitchen, some beach chairs and pool/beach toys available on property. Grill on nice private patio out back. We stayed with our 2 daughters, wife, and myself and had a great time, no complaints at all about the property. Would highly recommend staying here.

About the host

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