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
Nestled in the heart of Old Town, HEMINGWAY’S HAVEN is just the spot for anyone dreaming of what Key West was like during its golden days when Ernest, Sloppy Joe, and Harry T roamed the island. This welcoming, two-story private home has been lovingly renovated and decorated, showcasing a delightful mix of classic conch style with a modern, fresh tw
Hot HOT 31
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)
Hemingway's Haven
Hemingway's Haven 2
Hemingway's Haven 3
Hemingway's Haven 4
Hemingway's Haven 5
Hemingway's Haven 6
Hemingway's Haven 7
Hemingway's Haven 8
Hemingway's Haven 9
Hemingway's Haven 10
Prev
Next
Hemingway's Haven
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (1)
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
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)
Modern Majesty
Modern Majesty 2
Modern Majesty 3
Modern Majesty 4
Modern Majesty 5
Modern Majesty 6
Modern Majesty 7
Modern Majesty 8
Modern Majesty 9
Modern Majesty 10
Prev
Next
Modern Majesty
Condo
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (4)
Like the mystical flower this home is named after, THE ENCHANTED ROSE is a breathtaking monthly vacation home that stands out from the rest. Situated on Rose Street, in the Beachside district of Key West, just a couple blocks from Smathers Beach, this recently renovated one-story home provides a magical setting for vacationers looking to experience
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 Enchanted Rose
The Enchanted Rose 2
The Enchanted Rose 3
The Enchanted Rose 4
The Enchanted Rose 5
The Enchanted Rose 6
The Enchanted Rose 7
The Enchanted Rose 8
The Enchanted Rose 9
The Enchanted Rose 10
Prev
Next
The Enchanted Rose
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (12)
This freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the Atlantic Ocean and sand in your toes. Enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling sliding glass doors, or while sitting on your private balcony surrounded by the palm tree tops. DRIFTWOOD DREAMS is locate
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)
Driftwood Dreams
Driftwood Dreams 2
Driftwood Dreams 3
Driftwood Dreams 4
Driftwood Dreams 5
Driftwood Dreams 6
Driftwood Dreams 7
Driftwood Dreams 8
Driftwood Dreams 9
Driftwood Dreams 10
Prev
Next
Driftwood Dreams
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (6)
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
Dockside Daydreams 2
Dockside Daydreams 3
Dockside Daydreams 4
Dockside Daydreams 5
Dockside Daydreams 6
Dockside Daydreams 7
Dockside Daydreams 8
Dockside Daydreams 9
Dockside Daydreams 10
Prev
Next
Dockside Daydreams
Townhome
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating Rating Rating Rating 4.8 (152)
Finally, a large vacation home where every member of the family will be happy. From the vaulted living room with three couches and a giant 60-inch TV, to the kitchen large enough for a whole team of chefs to prepare dinner, CASA OLIVIANA has it all.THE LIVING AREA...The aforementioned living room is truly big enough for the whole family. The only d
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 Oliviana
Casa Oliviana 2
Casa Oliviana 3
Casa Oliviana 4
Casa Oliviana 5
Casa Oliviana 6
Casa Oliviana 7
Casa Oliviana 8
Casa Oliviana 9
Casa Oliviana 10
Prev
Next
Casa Oliviana
Private Home Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (14)
THE COZY STARFISH is a newly furnished and decorated first floor condo located in the Truman Annex, a private gated community situated in the heart of the island. Despite being only steps away from all that Old Town Key West has to offer, THE COZY STARFISH is a peaceful retreat within a private gated community that offers access to a large, shared
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 Cozy Starfish
The Cozy Starfish 2
The Cozy Starfish 3
The Cozy Starfish 4
The Cozy Starfish 5
The Cozy Starfish 6
The Cozy Starfish 7
The Cozy Starfish 8
The Cozy Starfish 9
The Cozy Starfish 10
Prev
Next
The Cozy Starfish
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating Rating Rating Rating 4.8 (15)
Seals & Crofts said it best: ‘Diamond Girl, you sure do shine.’ Formerly known as Seventh Heaven, DIAMOND GIRL is a stunning two-story private home that epitomizes island living, with its’ distinct exterior eyebrow design, ample indoor and outdoor living space, and comfortable accommodations. Once here you’ll quickly realize this peaceful oasis
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)
Diamond Girl
Diamond Girl 2
Diamond Girl 3
Diamond Girl 4
Diamond Girl 5
Diamond Girl 6
Diamond Girl 7
Diamond Girl 8
Diamond Girl 9
Diamond Girl 10
Prev
Next
Diamond Girl
Private Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (22)
If your idea of a vacation includes pampering yourself and indulging in the finer things in life, then a stay at the DUCHESS OF CATHERINE will be your cup of tea. This newly built, professionally designed home is fit for a King and offers plenty of space for all the members of your court. Located on Catherine Street, just steps from Duval Street, y
Duchess of Catherine
Duchess of Catherine 2
Duchess of Catherine 3
Duchess of Catherine 4
Duchess of Catherine 5
Duchess of Catherine 6
Duchess of Catherine 7
Duchess of Catherine 8
Duchess of Catherine 9
Duchess of Catherine 10
Prev
Next
Duchess of Catherine
Private Home Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating Rating Rating Rating Rating 5 (45)
All year long you dream of a getaway to capture that feeling of Key West's ENDLESS SUMMER - carefree days spent tooling around Old Town on bicycles or wandering the island streets in flip flops with the sun warming your shoulders. No plans, nowhere to be, no deadlines - only a to-do list of making memories with your family and friends and possibly
Endless Summer
Endless Summer 2
Endless Summer 3
Endless Summer 4
Endless Summer 5
Endless Summer 6
Endless Summer 7
Endless Summer 8
Endless Summer 9
Endless Summer 10
Prev
Next
Endless Summer
Private Home Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating Rating Rating Rating 4.9 (144)
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 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)
Cayo Calypso
Cayo Calypso 2
Cayo Calypso 3
Cayo Calypso 4
Cayo Calypso 5
Cayo Calypso 6
Cayo Calypso 7
Cayo Calypso 8
Cayo Calypso 9
Cayo Calypso 10
Prev
Next
Cayo Calypso
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (11)
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
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)
Serenity on Southard
Serenity on Southard 2
Serenity on Southard 3
Serenity on Southard 4
Serenity on Southard 5
Serenity on Southard 6
Serenity on Southard 7
Serenity on Southard 8
Serenity on Southard 9
Serenity on Southard 10
Prev
Next
Serenity on Southard
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating Rating Rating Rating 4.9 (47)

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

I agree

Copyright © 2026 • Last Key Realty

All Rights Reserved.