Book Direct & Save

At Last Key Realty, located in Key West, we work directly with homeowners to ensure you receive the best possible rental rate on your vacation rental property! Search our wide inventory of Key West Home Rentals, Condo Rentals, Rentals With Pools, Luxury Rentals, and more!

WHAT ARE THE BENEFITS?

When you book directly through a Vacation Rental Management Company like Last Key Realty, you not only get the best rate possible, but you also receive local assistance before and during your vacation! Cut out the middleman and book directly at the source. There are a lot of vacation rentals located in Key West, FL, and we can guarantee all of the vacation rentals in our program are well-managed and properly maintained. With a variety of amenities to select from, you are sure to find something for every member of your vacation crew.

NO ADDITIONAL FEES

Online Travel Agencies (OTA's) like VRBO, Tripadvisor, Airbnb and Expedia now charge you a service fee to book on their sites. Fees up to 20% are added to the cost of your reservation when you book through a third-party site. Save yourself those fees and book direct!

LOCAL SERVICE & EXPERTISE

To book at the lowest possible rate and get local knowledge and expertise, reserve online today or call us at 305.292.6266. Our staff is here to provide you with the highest level of customer service. We look forward to having you stay with us soon!

156 properties available

You can skip Key Largo and Montego and go straight to Kokomo! The KOKOMO SUITE at the Seaport Inn that is. Just as suggested by the song's lyrics, you can get there fast since it is close to all of the action Duval Street, Old Town, and the Historic Seaport have to offer. You can also take it take it slow, which many residents and visitors of the i

Kokomo Suite

Condo

$210^.00 - $738^.00 / per night

1 bedrooms

1 baths

2 guests

There’s no doubt you’ve heard of Duval Street; phenomenal restaurants, eclectic shops and legendary nightlife. This immaculate condo is just a half block away, giving you access to everything Duval Street has to offer while still allowing you to get a restful night’s sleep. SOUL OF DUVAL truly captures the essence of what makes Key West so special,

Soul of Duval

Condo

$240^.00 - $1,243^.00 / per night

You have many choices when choosing where to stay in Key West, but the most unique way to get an authentic Key West experience is by spending your vacation in a classic conch cottage smack dab in the heart of Old Town. You know what they say - “In a world full of apples, be a pineapple.” Whether you’re on a writer’s retreat or simply need an escap

Monthly Rental

A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)

The Poetic Pineapple

Private Home

$175^.00 - $550^.00 / per night

COLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking distance of all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to a prime location, COLORS OF THE

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.

Colors of the Keys

Townhome

$350^.00 - $1,220^.00 / per night

In the Historic Seaport area of Old Town, there is a house that will behold your eye. At first glance you'll see that HEAVENLY ZEN is beautifully maintained with carefully tended landscaping; however, nothing will prepare you for what is inside. As you walk in, you will feel an immediate sense of peace and relaxation. All of the spaces in this meti

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Monthly Rental

Heavenly Zen

Private Home

$345^.00 - $1,243^.00 / per night

This renovated Old Town estate is designed for the real downtown experience in the Conch Republic, but in a large home-base all your own. SWEET HOME ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. You couldn't be any closer to the late-night scene and attractions

Sweet Home Angelita

Private Home

$560^.00 - $3,158^.00 / per night

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 - $971^.00 / per night

If your idea of a vacation includes pampering yourself and indulging in the finer things in life, then a stay at the DUCHESS OF CATHERINE will be your cup of tea. This newly built, professionally designed home is fit for a King and offers plenty of space for all the members of your court. Located on Catherine Street, just steps from Duval Street, y

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Duchess of Catherine

Private Home

$850^.00 - $4,092^.00 / per night

A highlight of any Key West vacation is exploring the island and discovering for yourself Old Town's most treasured restaurants and attractions. The newest discovery awaiting you is a precious ‘gem’ of a home tucked away in a quiet enclave within Truman Annex, Key West’s most exclusive gated community. SALTWATER SAPPHIRE is a newly renovated two-st

2026 Changes

Saltwater Sapphire

Private Home

$475^.00 - $1,437^.00 / per night

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

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 - $1,544^.00 / per night

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

CASA VICTORIA, located in the heart of Old Town just two blocks from Duval Street, is a large 5 bedroom home built with the charm and quirkiness of early 20th century Key West. Dating back to the Cigar Manufacturers' era, CASA VICTORIA exudes the classic Old Town style that makes Key West such a unique vacation experience. This authentic Conch Hous

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Casa Victoria

Private Home

$995^.00 - $5,007^.00 / per night

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