4-5 Bedroom Key West Vacation Rentals

Are you looking for a 4-5 bedroom rental in Key West, FL? Last Key Realty has you covered! We have vacation homes that are private homes in the most desirable locations in all of Key West Florida. Whether it is located on Duval St, a block off Duval Street, 1800 Atlantic, Truman Annex, or a location in the heart of Historic Old Town we have something for everyone. Many of our homes have private pools, full baths, and a front porch for you to enjoy the seasonally warm weather we have year-round. In addition, our homes come fully stocked with all of the appliances, linens, and comforts you can expect in a luxury vacation home in the whole Key West area. Each home is tastefully decorated to show the unique conch flavor of the area.

If you have any questions please feel free to contact one of our vacation specialists today!


Properties Available 42 properties available
If you’re looking for a Florida Keys home that rivals the seaside homes found in ‘Coastal Living’ magazine, look no further! COASTAL LOVING is an inviting two-story private home that offers a relaxing vacation setting and comfortable accommodations. This easy living home combines a classic Key West design with the finest modern updates and convenie
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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)
Coastal Loving
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (5)
Key West is known for having amazing properties, but one home stands tall above the rest with its six majestic Royal Palm trees. HOUSE OF THE ROYAL PALMS features a spacious exterior that will make even the most high-end influencer envious. You’ll be spoiled with multiple seating areas, an oversized covered porch, and a swimming pool, all set under
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House of the Royal Palms
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (10)
If the rhythm of the islands has been calling and you're ready for a taste of the good life, then a stay at HALFWAY TO HAVANA is just what your soul is craving! Situated between the calm waters of the Florida Bay and the vibrant nightlife of Cuba's capital City, this unique vacation home blends the laid-back island vibes with all of the modern conv
Halfway to Havana
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating Rating Rating Rating 4.6 (3)
This ultimate Key West dream home is nestled in the highly desirable residential Old Town neighborhood of Solares Hill, just a quick walk from Duval Street and the Historic Seaport areas. No expense has been spared in upgrading and furnishing VILLA OLIVIETTA; the most up-to-date appliances and technology can be found in each room. The comfortable a
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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)
Villa Olivietta
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (3)
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
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating 4.9 (133)
Think back to being a kid in the middle of summer — when the days stretched out long and golden, your biggest worry was whether the ice cream would melt before you finished it, and the whole world smelled like sunscreen and warm grass? That's DREAMSICLE BY DUVAL. From the moment you spot that nostalgic orange front door, something inside you slows
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New Property New Property
New Property
Dreamsicle by Duval
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 10 guests
WATERFRONT WHISPERS captures the essence of island living within a private gated community situated on the water where you can’t hear a whisper. This 4 bedroom premium waterfront home blends total tranquility with easy access to the waters of the Florida Keys via a private boat dock. Spend your days relaxing in the pool or out on the boat, and your
Monthly Rental Monthly Rental
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)
Waterfront Whispers
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 8 guests
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
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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
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (2)
Imagine your whole group staying in one home, with everyone having their own private bedroom suite. At CASA SUITE CASA, all four bedrooms are laid out as suites; each with an en-suite bathroom and flat screen TV. And that's just the beginning! A large private pool surrounded by tropical gardens, an expansive living area, and an ideal location close
Monthly Rental Monthly Rental
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)
Casa Suite Casa
Private Home
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (13)
Life in the Florida Keys is all about spending time outdoors, indulging in the things you love with the ones you love; and BLUE HORIZON is the perfect vacation home to experience Keys living for yourself. Whether your ideal day is floating around the large pool with a cold drink in hand, cruising the waters of the Lower Keys in your boat, or gather
Monthly Rental Monthly Rental
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)
Blue Horizon
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (2)
Nestled in the heart of Old Town Key West, BLUE HERON’S HIDEOUT is a newly renovated ranch-style home that perfectly blends historic charm with modern luxury. Featuring 4 bedrooms each with an en-suite bathroom, a heated pool, home office, and off-street parking, this exquisite home is a private oasis for discerning travelers seeking both convenien
Monthly Rental Monthly Rental
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)
Blue Heron's Hideout
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Like many highlights of Key West, THE ADMIRAL'S ESTATE celebrates a rich history of the island while embracing a modern restoration. THE ADMIRAL'S ESTATE is a true historic Key West home, originally built for a high-ranking Naval Officer in the early 1900s. This impressive estate is armed with two living areas, a top-of-the-line gourmet kitchen, cl
Monthly Rental Monthly Rental
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 Admiral's Estate
Private Home
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (2)

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