Nightly & Weekly 4-5 Bedrooms


Properties Available 19 properties available
All year long you dream of a getaway to capture that feeling of Key West's ENDLESS SUMMER - carefree days spent tooling around Old Town on bicycles or wandering the island streets in flip flops with the sun warming your shoulders. No plans, nowhere to be, no deadlines - only a to-do list of making memories with your family and friends and possibly
Hot HOT 32
Endless Summer
Private Home Pet Friendly
$675.00 - $4,052.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (222)
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
Hot HOT 36
Duchess of Catherine
Private Home Pet Friendly
$850.00 - $4,092.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating Rating Rating Rating Rating 5 (16)
SOUTHERNMOST HOSPITALITY V is a luxurious private estate that occupies an entire corner of Old Town's famous Duval Street, just a block from the Southernmost Point. Don't let the address fool you... this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private pool. Privacy also comes in the form
Southernmost Hospitality V
Private Home Pet Friendly
$800.00 - $4,876.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (73)
The vacation opportunity of a lifetime awaits at GRAND KEY OASIS. This breathtaking one-of-a-kind property is the epitome of luxurious island living, featuring two separate homes connected by a covered pavilion that overlooks the exceptional backyard and resort-style private pool. The interior design of this compound will leave you marveling at the
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2026 Changes 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.
Grand Key Oasis
Compound
$850.00 - $3,363.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (10)
Tranquility. Peace. Relaxation. You’ll find these traits are in abundance at GARDEN OF EMMA. The open and airy interior of this exquisite Key West home will keep your group connected and present, while being the perfect complement to the tranquil, tropical exterior. The spacious backyard is your very own private oasis, complete with a lagoon-style
2026 Changes 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.
Garden of Emma
Private Home
$725.00 - $2,740.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (5)
For the ultimate stay in America's Paradise, what could be more perfect for your whole group than AMERICANA TROPICALE? This festive and patriotic home will promise a one-of-a-kind island experience. AMERICANA TROPICALE has 4 spacious bedrooms each complete with its own en-suite bathroom for privacy, a private saltwater pool, a fully equipped kitch
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Americana Tropicale
Private Home Pet Friendly
$625.00 - $3,202.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (316)
For a truly over-the-top Key West stay with your entire group, whether that be the whole family or your closest friends, STAR OF THE SEAPORT has the location, amenities, layout, and extra guest service to help host the island trip you envision. STAR OF THE SEAPORT is a luxurious private estate that occupies an expansive space on an iconic street in
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Star of the Seaport
Private Home Pet Friendly
$1,200.00 - $5,506.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (184)
Key West has a unique way of appealing to anyone and everyone that visits the island, and it's easy to see why: the laid-back way of life, the historic charm and walkability of Old Town, and the overall 'good vibes' that the island has to offer those needing an escape from the day to day hustle and bustle of the real world. These same appealing cha
Good Vibrations
Private Home Pet Friendly
$599.00 - $2,994.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (179)
CONCH CASA GRANDE has been reborn! This majestic home recently underwent a complete renovation, turning an already stunning property into the crown jewel of Truman Annex. As the largest home in the gated community, CONCH CASA GRANDE is one of Key West’s premiere rental properties available.From the moment you set foot in this magnificent home, wit
Hot HOT 28
Conch Casa Grande
Private Home
$1,200.00 - $4,617.00 / per night
Bedrooms 5 bedrooms
Bathrooms 6 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (250)
The vacation opportunity of a lifetime awaits at CASSIE’S PARADISE. A secluded oceanfront experience, this breathtaking home sits on over half an acre and is less than 20 miles from Key West. The 4,300 sq ft interior affords your group plenty of room to spread out. The real showstopper of this home is the backyard - complete with 120 feet of privat
Hot HOT 25
Cassie's Paradise
Estate Pet Friendly
$3,500.00 - $6,553.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (6)
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 Pet Friendly
$560.00 - $3,158.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating Rating Rating Rating Rating 5 (107)
There’s no better way to escape the hustle and bustle of reality than by sneaking off to Key West for a taste of the island life. ELEGANT ESCAPE offers first-class accommodations in a beautiful tropical setting. From the open layout and soaring ceilings of the main house to the enticing private pool and unique guest cottage, ELEGANT ESCAPE has ever
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Elegant Escape
Private Home
$850.00 - $2,992.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (14)

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