Nightly & Weekly 1-2 Bedrooms
47 properties available
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...S
2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Sea Captain's Haven
Townhome
$315.00 - $1,206.00 / per night
2
bedrooms
2
baths
1
half-baths
6
guests
5
(117)
TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of the Florida Keys and the home com
Turtle Cove Views
Cottage
$222.00 - $756.00 / per night
2
bedrooms
2
baths
6
guests
5
(151)
What could be better than spending your tropical vacation in a newly built waterfront home that offers spectacular views and easy access to the beautiful waters of the Florida Keys. POSTCARD POINT is an elevated 2 bedroom home that allows you to enjoy the luxury of brand-new construction in the waterfront location you've been searching for. Picture
Postcard Point
Private Home
$244.00 - $1,019.00 / per night
2
bedrooms
2
baths
4
guests
5
(48)
FOLLOW THE SUN is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own 28-foot balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors. FOLLOW THE SUN is located in an upscale private community within walking or biking distance to all of your f
Construction Notice
Construction Notice
There will be concrete restoration of every balcony in this complex through Summer 2026. This construction WILL impact your stay. Call us at 305-292-6266 prior to making a reservation.
Follow the Sun
Condo
$200.00 - $1,257.00 / per night
2
bedrooms
2
baths
6
guests
5
(240)
GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two spacious balconies as well.Compliance with Truman Annex Community Rules & Regulations is expected of all
Gulfside Vistas
Condo
$430.00 - $1,550.00 / per night
2
bedrooms
2
baths
1
half-baths
6
guests
5
(264)
When you think of Key West, you think of spending relaxing days with your toes in the sand under the palm trees, and fun-filled nights walking through the Streets of Old Town on your way to catch the sunset at Mallory Square. Experience these kinds of days (and nights) at SOUTHERNMOST PALMS, a beautifully renovated townhome, located at The Foundry
2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Southernmost Palms
Townhome
$399.00 - $1,064.00 / per night
2
bedrooms
2
baths
1
half-baths
6
guests
5
(102)
SUITE SANCTUARY is a luxurious penthouse condo that overlooks the ocean and is certain to be your haven from everyday life. This newly renovated condo features many delights throughout, from the vaulted ceilings to the fresh tile floors reminiscent of a walk on the beach. The large balcony offers a place to relax and enjoy the warm Florida weather
Construction Notice
Construction Notice
There will be concrete restoration of every balcony in this complex through Summer 2026. This construction WILL impact your stay. Call us at 305-292-6266 prior to making a reservation.
Suite Sanctuary
Condo
$299.00 - $1,546.00 / per night
2
bedrooms
2
baths
6
guests
5
(28)
If you dream of waking up to expansive water views and island breezes, and walking out your front door right onto the streets of Old Town Key West in the center of it all - PROMENADE TO PARADISE is everything you are looking for. With a spacious layout, relaxed island-style furnishings, a semi-private gated pool, and three private balconies all you
2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Promenade to Paradise
Condo
$415.00 - $1,546.00 / per night
2
bedrooms
2
baths
5
guests
5
(160)
Want to be in Key West, have access to all the fun, but not be in the middle of the crowd at the end of the day? Then step away from the hustle and bustle and come roost at… THE OSPREY’S NEST. Boasting views from your private balcony on the top floor of Sunrise Suites, 2-Bedrooms, 2-Bathrooms, and a full kitchen; THE OSPREY’s NEST has all the neces
The Osprey's Nest
Condo
$215.00 - $788.00 / per night
2
bedrooms
2
baths
6
guests
5
(39)
This freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll be able to enjoy quiet afternoons at CONCH IN THE TREETOPS with those balmy Key West breezes wafting through the floor-to-ceiling glass doors, while sitting on your private balcony surrounded by the palm tree tops. CON
Construction Notice
Construction Notice
There will be concrete restoration of every balcony in this complex through Summer 2026. This construction WILL impact your stay. Call us at 305-292-6266 prior to making a reservation.
Conch in the Treetops
Condo
$200.00 - $1,263.00 / per night
2
bedrooms
2
baths
6
guests
5
(350)
SET SAIL celebrates the experiences of the Keys, both on the water and on land. The ideal complementary home base for your water-based excursions awaits in this condo just steps from the marina. SET SAIL is a well-appointed first floor condo located in the waterfront community of Coconut Mallory Resort & Marina, which offers two large community
Set Sail
Condo
$200.00 - $760.00 / per night
2
bedrooms
2
baths
6
guests
5
(143)
Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a two-story private home that not only transcends island living at its finest but also offers an ideal location for e
2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Jasmine Jewel
Private Home
$600.00 - $2,402.00 / per night
2
bedrooms
2
baths
1
half-baths
6
guests
5
(95)
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