Monthly Rentals


Properties Available 49 properties available
Coordinating the entire gang for a dream Key West wedding, reunion, or simply a vacation of a lifetime is hard enough... let Last Key Realty make the accommodations easy for you. ALL TOGETHER NOW is an entire block of private homes just steps from Duval Street, all yours to enjoy and with everything needed for a large group getaway: a total of thir
All Together Now
Compound Pet Friendly
$2,185.00 - $9,513.00 / per night
Bedrooms 13 bedrooms
Bathrooms 13 baths
Half-Bathroom 2 half-baths
Guests 32 guests
Rating Rating Rating Rating Rating 5 (9)
Imagine a traditional conch home in the Solares Hill section of Old Town. MAISON TROPICALE is stunningly restored then decorated in a post-modern style with vivid colors and sophisticated decor. Every room is adorned with colorful art and has been furnished with unique show pieces. This brilliant decor is set against a backdrop of original Dade Cou
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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)
Maison Tropicale
Private Home Pet Friendly
$250.00 - $825.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (18)
Get ready to reel in Last Key Realty’s newest vacation home! THE WICKED TUNA is a classic Key West home located in one of the most desirable areas of Old Town. This tastefully restored home features a historic appearance and charm, while offering all the modern conveniences one could desire. Located just down the street from the historic seaport, y
Hot HOT 31
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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 Wicked Tuna
Private Home Pet Friendly
$250.00 - $699.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Travelers from around the world would agree spending a month in Key West is truly a magical experience, especially when you find two classic conch homes made into one. This cozy compound perfectly captures the magic of the island, with its beautiful Dade County Pine walls, tropical decor, and the plunge pool waiting just outside. MARGARET’S MAGIC
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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)
Margaret's Magic Compound
Compound Pet Friendly
$333.00 - $1,104.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
PERFECT HARMONY is a unique one-story home that features an ideal balance between modern touches and tropical styling. With its high ceilings, spacious kitchen, and outdoor lounge beside the pool; PERFECT HARMONY has everything you could desire in a vacation rental. Most importantly, this stylish home includes full-time guest services from Last Key
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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)
Perfect Harmony
Private Home Pet Friendly
$222.00 - $646.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (3)
In the same way that the island of Key West has captured the hearts of so many, this charming monthly vacation home will capture yours. ISLAND INSPIRATION combines the appearance and charm of a historic Keys home, with all of the modern conveniences you have come to appreciate. This special home is situated on Margaret Street at the edge of where O
Hot HOT 65
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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)
Island Inspiration
Private Home
$275.00 - $913.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (11)
Escape the “changing tides” of your day-to-day routine by spending a month in the Keys. MARINER’S HIDDEN HAVEN provides an ideal island setting for re-centering your compass by way of your own private waterfront retreat. Picture mornings sipping coffee on the dock, lazy days by the pool, and beautiful sunsets on your boat. The home’s open layout an
Hot HOT 30
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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)
Mariner's Hidden Haven
Private Home Pet Friendly
$175.00 - $551.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (4)
For a month in Key West it is ideal to harness the comforts of new construction similar to the luxuries of your own home, but keeping the true spirit of Old Town Key West and the magical surprises around every corner. This brand newly constructed home, located a stone's throw from the Southernmost Point, also backs up to the famous Butterfly Museum
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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)
Dance of the Butterflies
Private Home Pet Friendly
$250.00 - $755.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (6)
Upscale island living is epitomized with this beautiful home, CAYO CALYPSO. This modern home is well appointed, spacious and comfortable. CAYO CALYPSO offers a relaxing tropical theme and prime location near the Beach. Enjoy easy walks to Higgs Beach and pier, community playgrounds, Salute Ristorante or Smathers Beach. Comfortable accommodations in
Hot HOT 30
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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)
Cayo Calypso
Private Home Pet Friendly
$215.00 - $875.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (27)
MODERN MAJESTY is a stunning, freshly renovated three-bedroom condo that checks every box for the perfect vacation rental. This large unit is laid out over one floor, meaning you don’t have to worry about stairs. The three bedrooms are luxuriously appointed suites, each with their own en-suite bathroom. The kitchen is as functional as it is beautif
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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)
Modern Majesty
Condo
$325.00 - $935.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (4)
THE POLYNESIAN HOUSE is an extraordinarily unique and whimsical home, designed to capture the culture and experience of island life in an upscale private home. Viewing this home from the street, you'll know immediately how the name THE POLYNESIAN HOUSE came to be; The Polynesian-style curved roofs of the two rooms sitting atop this home are the fir
Hot HOT 42
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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 Polynesian House
Private Home
$500.00 - $1,370.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (3)
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
Cassie's Paradise
Estate Pet Friendly
$3,500.00 - $6,645.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (6)

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