Key West Vacation Rentals

Are you looking for Key West rentals that are both luxurious and convenient? Look no further than Last Key Realty! Our properties are strategically located across Key West's most coveted areas, including the historic charm of Old Town, the serene beaches at 1800 Atlantic, the exclusive Truman Annex, and the picturesque Sunset Marina. Plus, we offer rentals near Duval Street, the lively heart of Key West.

Our rentals here in Key West cater to your needs, whether you're planning a quick getaway or an extended stay. Available for nightly, weekly, or monthly stays, our properties offer a range of premium amenities. From fully equipped kitchens for culinary enthusiasts to private pools and outdoor dining spaces for those who love to entertain, we have everything you need to make your stay comfortable.

And for those who can't bear to leave their furry friends behind, our pet-friendly options ensure that no family member misses out on the fun in Key West!

Would you prefer a condo setting? Our vacation condos feature luxurious amenities, including communal pools, spas, and tennis courts.

When planning your stay in Key West, remember that regulations require a transient rental license for short-term stays. As these permits are limited, short-term rental rates may be higher than monthly rentals.

To find the perfect fit for your stay, simply use our user-friendly search bar. Input your travel dates, and our system will show you the most suitable options, including flexible rate options, to ensure you find your ideal Key West rental. At Last Key Realty, we're dedicated to making your stay in Key West genuinely memorable. Don't hesitate to contact our property managers for any help or if you have questions about your booking.

155 properties available

On an island where being unique is embraced and the unusual is quite ordinary, lives a home that embodies that colorful spirit. ANGELA’S ECLECTIC GALLERY is a lovingly restored historic home that has been designed and outfitted to include all the modern conveniences paired with exotic and playful touches throughout. Original local artwork and hand-

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)

Angela's Eclectic Gallery

Private Home

$300^.00 - $925^.00 / per night

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

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.

Elegant Escape

Private Home

$850^.00 - $2,995^.00 / per night

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

Monthly Rental

Dance of the Butterflies

Private Home

$237^.00 - $739^.00 / per night

It is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack dab in the middle of Old Town. SEAPORT SENSATION is one of the newly built breathtaking townhomes at Old Town Vil

Monthly Rental

Seaport Sensation

Townhome

$275^.00 - $846^.00 / per night

It doesn't get any 'sweeter' than vacationing with a large group of your closest friends and family in America's Paradise. As a combination of two side-by-side private homes, SWEET AMERICANA not only offers plenty of comfortable accommodations for the whole crew but is an extremely rare find in the center of Old Town Key West. Located at the end of

Sweet Americana

Compound

$1,300^.00 - $5,825^.00 / per night

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

$599^.00 - $2,840^.00 / per night

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

Monthly Rental

Cayo Calypso

Private Home

$199^.00 - $875^.00 / per night

FOLLOW THE SUN is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own 28-foot balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors. FOLLOW THE SUN is located in an upscale private community within walking or biking distance to all of your f

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.

Follow the Sun

Condo

$200^.00 - $1,230^.00 / per night

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

Dockside Daydreams

Townhome

$200^.00 - $795^.00 / per night

Imagine a home with floor-to-ceiling panoramic views of the Atlantic Ocean from every room. WINDSWEPT PALMS has been thoughtfully decorated and furnished. The modern, upscale furniture is complemented with splashes of color throughout the home. The balcony wraps 270 degrees around the condo, with seating for everyone in your group. WINDSWEPT PALMS

HOT 30

Windswept Palms

Condo

$445^.00 - $2,374^.00 / per night

The moment you arrive at CASA AMARILLA and see the dual rocking chairs beckoning you to the front porch, you’ll feel the weight of the world start to lift from your shoulders as your vacation truly begins. Upon entering this adorable cottage, you’ll see the quaint interior is the perfect place to unwind, offering cozy bedrooms, a fully stocked kitc

HOT 30

Casa Amarilla

Private Home

$425^.00 - $2,897^.00 / per night

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

2026 Changes

Promenade to Paradise

Condo

$415^.00 - $1,497^.00 / per night

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