Key West 1-2 Bedrooms Homes & Condos Rentals

Are you looking for a 1-2 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, near 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're looking for something smaller, we even have luxurious fully stocked condo rentals in various locations throughout Key West. Our condos have resort-style amenities, including access to onsite pools, spas, tennis courts, and more! Vacation rentals in Key West are our specialty. If you have any questions please feel free to contact one of our vacation specialists today!

2 BEDROOM NIGHTLY/WEEKLY RENTALS

2 BEDROOM MONTHLY RENTALS

50 properties available

SERENITY ON SOUTHARD is a beautifully renovated 1 bedroom second floor condo with a full kitchen and washer and dryer. This condo is located in the Truman Annex, a gated community located in the heart of the island - just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have a peaceful retreat withi

POOL CLOSURE

POOL CLOSED - AUGUST 2026

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)

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

Monthly Rental

A stay at the DUKE OF CATHERINE is fit for a Queen to bring her King! From the crisp, clean decor to the large hot tub and the spacious master bedroom, the DUKE OF CATHERINE has everything his Majesty could desire. This freshly built, professionally designed home is the perfect size for a weekend rendezvous or an extended stay with the royal family

The sound of steel drums, the warm breeze off the water, the palm trees rustling in the sky… the essence of the Caribbean awaits in Key West for your next private vacation. This classic island townhome is located within Truman Annex, Key West's most exclusive gated community. From the Tommy Bahama furnishings and island inspired décor to the tropic

Monthly Rental

SEA BREEZE VILLA is an elegant two-story townhome located in the quiet residential community of Grinnell Gardens, a quaint and intimate community in the middle of Old Town. From this location, you’ll be only a handful of blocks from world famous Duval Street in one direction, and a handful of blocks from Higgs Beach in the other direction. SEA BREE

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Located across the street from Blue Heaven, above the delicious La Creperie French Cafe, sits THE PIRATE’S PENTHOUSE. This hidden gem is ideally located in the heart of Bahama Village and within walking distance to everything Duval has to offer. THE PIRATE’S PENTHOUSE has touches of maritime decor sprinkled throughout this spacious condo, complete

The Pirate's Penthouse

As soon as you enter, you'll feel like you stepped into a dream. Welcome to DEEP BLUE DREAMS, a modern coastal retreat in the heart of Truman Annex, Key West’s most exclusive neighborhood. This freshly updated 2 bedroom, 2.5 bathroom condo brings a new level of style to island living — sleek and modern, yet relaxed and inviting, with subtle touches

Monthly Rental

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

Monthly Rental

Promenade to Paradise

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,

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

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DOCKSIDE DAYDREAMS is a tastefully decorated villa located in the Coconut Mallory Resort & Marina with two large community pools with plenty of chaises. There are also boat slips available on-site for rent if you want to bring your boat.THE LIVING AREA...This modern home has just undergone a complete renovation to a very high standard. No expen

Hunting for the perfect Key West vacation home can feel like a daunting task. However, once you discover TRUMAN’S TROVE, you’ll know that you’ve struck gold! This two-story private home has been beautifully furnished and designed to the highest standard. In addition, TRUMAN’S TROVE offers an ideal location within Truman Annex, Key West’s most exclu

Monthly Rental

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