Key West Luxury Rentals

Welcome to Elegance in Key West: Choose Your Luxury Rental and Book Today!

Experience the pinnacle of opulence with Key West luxury rentals that feature unmatched amenities such as private pools, hot tubs, captivating views, and gourmet kitchens. Every stay with us grants you access to a complimentary concierge, ensuring your Key West vacation is a seamless blend of comfort and indulgence.

Group travels become unforgettable with our Key West Compound Rentals, offering two or more adjoining properties. If you're journeying with a furry companion, our pet-friendly Key West luxury house rentals are a perfect match.


Properties Available 156 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
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.
Serenity on Southard
Condo
$200.00 - $917.00 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating Rating Rating Rating Rating 5 (50)
ATLANTIC REFLECTIONS is a newly renovated water view condo that has been meticulously furnished with a modern tropical feel, with spectacular views of the neighboring nature preserve and the ocean beyond, with no end in sight. You'll be able to enjoy those famous Key West sunsets from the living room, and sunrise shadows from your bedroom balconies
Construction Notice Construction Notice
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.
Atlantic Reflections
Condo
$300.00 - $1,482.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (232)
Traveling to Key West with a group deserves the ultimate vacation rental home: plenty of space to stretch out and enjoy time together, separate rooms and bathrooms to enjoy privacy, a private saltwater pool and outdoor lounge area, and off street parking for scooters, and of course, bicycles. THE CONTENTED CRANE checks all of these boxes, and more.
The Contented Crane
Townhome Pet Friendly
$400.00 - $2,518.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (209)
You have many choices when choosing where to stay in Key West, but the most unique way to get an authentic Key West experience is by spending your vacation in a classic conch cottage smack dab in the heart of Old Town. You know what they say - “In a world full of apples, be a pineapple.” Whether you’re on a writer’s retreat or simply need an escap
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 Poetic Pineapple
Private Home Pet Friendly
$175.00 - $550.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (4)
Get the gang together for the ultimate Key West Beach Vacation in a one-of-a-kind giant of an island beach house, BEAUTY OF THE BEACH. Fully renovated to exceed the highest level of quality and comfort as a large family vacation home, this private estate occupies an entire corner lot, just a block from Smathers Beach. This stilted home allows for a
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)
Beauty of the Beach
Private Home Pet Friendly
$333.00 - $1,050.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half-Bathroom 1 half-baths
Guests 12 guests
Located in Truman Annex, a gated community with some of the most impressive homes in Key West, this exceptional home stands out from all the rest. NOONA'S MANSION is nestled in a quiet cul-de-sac facing the ocean on a beautifully landscaped piece of property. This impressive home features six spacious bedrooms, a fully equipped kitchen, a stunning
Hot HOT 39
Noona's Mansion
Private Home
$1,500.00 - $5,878.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (275)
Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a two-story private home that not only transcends island living at its finest but also offers an ideal location for e
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.
Jasmine Jewel
Private Home
$600.00 - $2,330.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (97)
ISLAND BLISS is a classic Old Town Key West home, complete with delicate gingerbread accents, a classic Southern front porch with rocking chairs, and lush, tropical foliage tastefully surrounding the property. This beautiful, historic two-story home has been lovingly cared for and restored with a mix of modern touches and traditional Key West influ
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 Bliss
Private Home Pet Friendly
$225.00 - $760.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
TIDEWATER VIEWS is a cozy 820 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out, a residential community with a heated 80-foot pool with large Jacuzzi and Kiddie Pool, tennis courts
Tidewater Views
Cottage Pet Friendly
$200.00 - $744.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (309)
Finding high-end accommodations for a large group vacation can be a challenge... let Last Key Realty make it easy for you with this one-of-a-kind compound. A ROYAL AFFAIR is the combination of three homes that offer everything a large group could desire in a Key West vacation home - a total of eleven bedrooms, twelve full bathrooms, three open livi
A Royal Affair
Compound Pet Friendly
$1,800.00 - $9,330.00 / per night
Bedrooms 11 bedrooms
Bathrooms 12 baths
Guests 34 guests
SUNFLOWER MELODIES captures the feeling of a childhood summer, like your bare feet on freshly cut grass, the summer sun gently kissing your skin or the sweet, subtle scent of a field of wildflowers in bloom. A month in Key West is defined by a simpler way of life, with low stress, high fun, and heaps of relaxation - which SUNFLOWER MELODIES provide
Hot HOT 29
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)
Sunflower Melodies
Private Home Pet Friendly
$222.00 - $765.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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