Key West Vacation Rentals

Discover the best Key West vacation rentals with Last Key Realty. Whether you're looking for a private home with a pool, a cozy condo near Duval Street, or a beachfront villa, we have options for every group and budget. Browse our complete inventory and experience Key West like a local.

Our Key West vacation rentals are hand-selected for comfort, convenience, and style. Guests enjoy private pools, spacious outdoor areas, fully equipped kitchens, and easy access to the island's top attractions. Whether you're planning a romantic getaway, a family reunion, or a group trip with friends, you'll find a perfect fit in our collection of homes and condos throughout Old Town, the Casa Marina district, and other sought-after neighborhoods.

Browse Vacation Rentals by Type

Private pool and patio area at a Key West vacation rental. The pool is surrounded by a wooden deck with lounge chairs and a table with chairs. Tropical plants and palm trees provide shade and privacy.

Private Homes 

Find your perfect home-away-from-home in Key West! Choose from cozy cottages, spacious family homes, and luxurious estates with private pools and stunning views.

Balcony with a table and chairs overlooking tropical foliage at a Key West vacation rental.

Condo Rentals 

Experience Key West living in a stylish condo! Enjoy modern amenities, breathtaking waterfront views, and easy access to the island's best attractions.

Two kayaks on a dock at a waterfront Key West vacation rental. Palm trees and boats are visible in the background.

Waterfront Rentals 

Indulge in the ultimate Key West escape with a luxurious waterfront rental. Wake up to stunning sunrises and enjoy unparalleled access to the crystal-clear waters.

Private pool and patio area at a Key West vacation rental. The pool is surrounded by a wooden deck with lounge chairs and a table with chairs. Tropical plants and palm trees provide shade and privacy.

Pet Friendly Rentals 

Bring your furry friend along and find the perfect pet-friendly getaway in Key West! Choose from charming cottages, spacious family homes, and upscale estates with room to relax and enjoy, plus features like fenced yards, private pools, and nearby pet-friendly parks and beaches.

Balcony with a table and chairs overlooking tropical foliage at a Key West vacation rental.

Beachfront Rentals 

Wake up to ocean breezes in a beachfront Key West rental! Enjoy stunning waterfront views, direct beach access, and all the modern comforts you need for a relaxing island escape — just minutes from top attractions, dining, and nightlife.

Two kayaks on a dock at a waterfront Key West vacation rental. Palm trees and boats are visible in the background.

Lower Keys Rentals 

Unplug and unwind with a Lower Keys vacation rental. From tranquil waterfront homes to secluded island retreats, enjoy peaceful mornings, vibrant wildlife, and easy access to snorkeling, kayaking, and the unspoiled beauty of the Lower Florida Keys.

Properties Available 156 properties available
If you’ve recently heard the Siren’s call beckoning you to Key West, it might be because you were drawn by the SIREN’S SERENADE luxurious interior, lush private backyard, and dream-like location. The moment you enter the gate, you’ll meet the Siren posed in her tropical garden. You’ll come around the lavish and very private pool area to enter this
Hot HOT 31
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.
Siren's Serenade
Siren's Serenade 2
Siren's Serenade 3
Siren's Serenade 4
Siren's Serenade 5
Siren's Serenade 6
Siren's Serenade 7
Siren's Serenade 8
Siren's Serenade 9
Siren's Serenade 10
Prev
Next
Siren's Serenade
Private Home
$999.00 - $3,449.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (13)
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
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)
Island Inspiration
Island Inspiration 2
Island Inspiration 3
Island Inspiration 4
Island Inspiration 5
Island Inspiration 6
Island Inspiration 7
Island Inspiration 8
Island Inspiration 9
Island Inspiration 10
Prev
Next
Island Inspiration
Private Home
$240.00 - $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)
Get out of the turtle pond and make a splash in the ocean with your month stay at TORTUGA SUITE at the Seaport Inn! Within in quick walk to great sunsets, food, drinks, and attractions, you can still move at a “tortuga’s” pace and see it all! You can relax with ease as you will have access to Last Key Realty’s Five-Star Guest Services and Complimen
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)
Tortuga Suite
Tortuga Suite 2
Tortuga Suite 3
Tortuga Suite 4
Tortuga Suite 5
Tortuga Suite 6
Tortuga Suite 7
Tortuga Suite 8
Tortuga Suite 9
Tortuga Suite 10
Prev
Next
Tortuga Suite
Condo
$165.00 - $524.00 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (2)
A highlight of any Key West vacation is exploring the island and discovering for yourself Old Town's most treasured restaurants and attractions. The newest discovery awaiting you is a precious ‘gem’ of a home tucked away in a quiet enclave within Truman Annex, Key West’s most exclusive gated community. SALTWATER SAPPHIRE is a newly renovated two-st
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.
Saltwater Sapphire
Saltwater Sapphire 2
Saltwater Sapphire 3
Saltwater Sapphire 4
Saltwater Sapphire 5
Saltwater Sapphire 6
Saltwater Sapphire 7
Saltwater Sapphire 8
Saltwater Sapphire 9
Saltwater Sapphire 10
Prev
Next
Saltwater Sapphire
Private Home
$475.00 - $1,437.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 2 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (62)
SOUTHERNMOST VISTAS has everything you’re looking for to spend an unforgettable month in Key West. This recently built multi-story home plus rooftop sun deck exudes a wonderful blend of modern and island vibes. Featuring an open living plan, a lovely heated pool, and a spacious rooftop sundeck with incredible views of the Atlantic Ocean and histori
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)
Southernmost Vistas
Southernmost Vistas 2
Southernmost Vistas 3
Southernmost Vistas 4
Southernmost Vistas 5
Southernmost Vistas 6
Southernmost Vistas 7
Southernmost Vistas 8
Southernmost Vistas 9
Southernmost Vistas 10
Prev
Next
Southernmost Vistas
Private Home Pet Friendly
$300.00 - $1,150.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (2)
GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two spacious balconies as well.Compliance with Truman Annex Community Rules & Regulations is expected of all
Hot HOT 35
Gulfside Vistas
Gulfside Vistas 2
Gulfside Vistas 3
Gulfside Vistas 4
Gulfside Vistas 5
Gulfside Vistas 6
Gulfside Vistas 7
Gulfside Vistas 8
Gulfside Vistas 9
Gulfside Vistas 10
Prev
Next
Gulfside Vistas
Condo
$430.00 - $1,550.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (264)
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
Hot HOT 25
Truman's Trove
Truman's Trove 2
Truman's Trove 3
Truman's Trove 4
Truman's Trove 5
Truman's Trove 6
Truman's Trove 7
Truman's Trove 8
Truman's Trove 9
Truman's Trove 10
Prev
Next
Truman's Trove
Private Home
$475.00 - $1,531.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (5)
Resembling a French Plantation, PLANTATION TROPICALE is an impressive island estate that occupies an entire corner block of the desirable Casa East neighborhood of Key West. This expansive property features nearly 3,000 square feet of indoor living space, a separate Guest House, beautifully maintained gardens, and a large private pool and cabana –
Hot HOT 26
Plantation Tropicale
Plantation Tropicale 2
Plantation Tropicale 3
Plantation Tropicale 4
Plantation Tropicale 5
Plantation Tropicale 6
Plantation Tropicale 7
Plantation Tropicale 8
Plantation Tropicale 9
Plantation Tropicale 10
Prev
Next
Plantation Tropicale
Compound
$1,045.00 - $5,148.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (82)
This Old Town condo is perfect for anyone who can't get enough of Key West's famous nightlife scene. CASITA 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 of downtown. Fair warning... It can get
Hot HOT 30
Casita Angelita
Casita Angelita 2
Casita Angelita 3
Casita Angelita 4
Casita Angelita 5
Casita Angelita 6
Casita Angelita 7
Casita Angelita 8
Casita Angelita 9
Casita Angelita 10
Prev
Next
Casita Angelita
Condo Pet Friendly
$220.00 - $1,552.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (250)
Walking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West. Perched above Duval Street, this beautifully modern condo offers
Hot HOT 41
Maya's Secret Treasure
Maya's Secret Treasure 2
Maya's Secret Treasure 3
Maya's Secret Treasure 4
Maya's Secret Treasure 5
Maya's Secret Treasure 6
Maya's Secret Treasure 7
Maya's Secret Treasure 8
Maya's Secret Treasure 9
Maya's Secret Treasure 10
Prev
Next
Maya's Secret Treasure
Condo Pet Friendly
$599.00 - $3,303.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (151)
THE DUKE & THE DUCHESS is a compound fit for a Queen, her King, and their whole court! These newly built, professionally designed side-by-side homes have everything you could desire for a large group vacation - a prime location, coveted amenities, and plenty of space. Your stay at the THE DUKE & THE DUCHESS also includes Last Key Realty's F
The Duke & The Duchess
The Duke & The Duchess 2
The Duke & The Duchess 3
The Duke & The Duchess 4
The Duke & The Duchess 5
The Duke & The Duchess 6
The Duke & The Duchess 7
The Duke & The Duchess 8
The Duke & The Duchess 9
The Duke & The Duchess 10
Prev
Next
The Duke & The Duchess
Compound Pet Friendly
$1,200.00 - $6,063.00 / per night
Bedrooms 7 bedrooms
Bathrooms 8 baths
Guests 22 guests
Rating Rating Rating Rating Rating 5 (1)
Key West is known for all things lime: Key Lime Pies, Margaritas, and now, THE ZESTY LIME, a rare gem in the heart of Old Town Key West that captures the essence of classic Key West in a completely renovated modern design. THE ZESTY LIME includes all of the coveted amenities of a vacation home: a spacious living area, an ideal bedroom and bathroom
Hot HOT 28
The Zesty Lime
The Zesty Lime 2
The Zesty Lime 3
The Zesty Lime 4
The Zesty Lime 5
The Zesty Lime 6
The Zesty Lime 7
The Zesty Lime 8
The Zesty Lime 9
The Zesty Lime 10
Prev
Next
The Zesty Lime
Private Home Pet Friendly
$500.00 - $2,606.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (158)

Tell us what you're looking for and someone will contact you with available options.

I agree

Copyright © 2025 • Last Key Realty

All Rights Reserved.